Think leadership is something you earn with a promotion? I used to think that too.

Last month, I had the opportunity to share some thoughts on leadership with Tokyo Design. The session was filled with ICs and managers asking the same kinds of questions I have heard throughout my career:

How do I build more influence?

Shouldn’t my work speak for itself?

How do I get a seat at the table?

Why doesn’t my impact always show up in reviews?

What I shared with them, and what I want to share here, is that leadership is not just for people with titles. It’s a set of habits that anyone can practice.

I had a turning point early in my career as a manager. I focused on supporting my team and executing well. I thought that was enough. But I wasn’t seeing the growth I wanted. I wasn’t getting pulled into the conversations that mattered.

Something was missing.

It wasn’t until I started practicing these three habits that things shifted. I began asking better questions in my 1:1s with leadership. I closed every meeting with clarity on next steps. I volunteered ways forward when we hit uncertainty. Slowly, I built the context I needed to make better decisions. I earned the trust that gave me more autonomy. And I moved from supporting the team to driving decisions as a senior manager.

These habits didn’t just change my trajectory. They changed how I showed up. And I’ve seen the same shift in managers and ICs I’ve worked with. The difference between someone doing just enough and someone showing traits of a high performer often comes down to practicing these small, repeatable habits.

Habit 1: Help your manager show up well

As an IC, one of the most impactful ways to lead is by helping your manager represent the team effectively in rooms you may not be in.

Your manager carries the voice of the team into leadership discussions. How clearly they can advocate for your work often depends on how much context you give them about what’s happening and what matters most.

1:1s are a great opportunity to not just to share updates, but to understand what’s top of mind for your manager so you can tailor your work and communication around it. The next time a big meeting or milestone comes up try asking questions like:

“What’s most important for you going into this conversation?”

“How can I help make our work easier to represent?”

“What parts of this are getting the most attention from leadership?”

“Was there anything that landed well last time? Why?”

Every question you ask gives you more context and helps your manager show up with clarity and confidence.

Why it works:

• Builds awareness of what your manager values and how they think.

• Positions you as a thoughtful partner, not just an executor.

• Ensures your team’s work aligns with broader priorities and is represented consistently.

For ICs, this is about understanding the bigger picture and amplifying your team’s impact. For managers, it’s about creating psychological safety so team members feel empowered to take ownership and understand how thier work might contribute to the bigger picture.

A strong partnership here makes both of you look good and builds trust that lasts beyond individual projects.

I found this to be a key unlock of situational awareness for me to understand some of the in’s and out’s of roles that I aspired to have.

Habit 2: Close with clarity

Too often, meetings end with a vague “sounds good.” Then, a week later, there is confusion, rework, or the dreaded “I thought you meant…”

A simple fix: end every meeting by repeating next steps and owners. This is also known as active listening.

If things are not clear, extend the meeting or schedule a follow-up.

Clarity is one of the most underrated ways to build trust and increase velocity of decision-making.

Why it works:

• Reinforces accountability.

• Strengthens memory and team alignment.

• Reduces rework and friction down the road.

For ICs, it builds your reputation as dependable. For managers, it ensures alignment sticks.

Habit 3: Have a bias for action

When ambiguity stalls progress, leaders do not wait. They offer a way forward.

Try this:

“Here is how I would approach this, and why. What could I do on my part to help move this forward?”

Setting this can also drive ownership and accountability of others in the room.

Progress beats polish. Momentum matters more than perfection.

Sometimes getting the point across means you don’t need a polished pixel-perfect design, maybe something you’ve scribbled on a marker board, or vibe coded can do the trick.

Why it works:

• Keeps momentum alive, even in uncertainty.

• Demonstrates ownership and a leadership mindset.

• Builds trust by showing initiative instead of waiting.

For ICs, this proves you can lead without authority. For managers, it sets the tone for how the team moves.

Leadership is everywhere

We often think about organizations in terms of hierarchy. But leadership is not a box on an org chart.

It’s is multidirectional: up, down, and across. The impact of influence can show up at every level: your team, your organization, your product, your customers, and your career.

Put some thought into where you want to see yourself and where you want to drive impact.

What’s your next move?

Here’s what I want you to try this week:

Pick one habit. Just one.

Maybe it’s asking your manager a better question in your next 1:1. Maybe it’s closing your next meeting by repeating the next steps out loud. Maybe it’s volunteering a way forward when the team hits a wall.

Start small. See what shifts.

Leadership isn’t something you wait for permission to practice. It’s not granted when you get the title or the promotion. It’s built in the everyday moments when you choose to help your team move forward with clarity, confidence, and momentum.

The question isn’t whether you have the authority to lead.

The question is: what leadership habit will you practice today?

Technically Speaking is where I share reflections, insights, and conversations to help you lead with confidence, clarity, and community.

Early on in my career as a manager, I assumed those behind-closed-doors conversations about business shifts, roadmap changes, and performance were meant to stay at the leadership level. My job was to cascade information if and when it became necessary.

But here's what I learned the hard way: when your team operates in the dark, everything becomes a “design emergency.” Priorities shift without warning. Deadlines move overnight. Work gets scrapped after weeks of effort.

My thinking changed when I understood that sharing business context can be a multiplier.

The more your team understands why something is happening, not just what, the better they can adapt, prioritize, and lead from where they sit.

As a middle manager, you're often caught waiting for someone to give you the green light to share information—but that permission might never come. The difference between sharing context early versus waiting until decisions are final changes everything about how your team shows up, and how you show up as their leader.

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Information that’s often discussed at the leadership level might include:

• Business direction or shifting priorities

• Planning tradeoffs and roadmap changes

• Progress toward adoption or revenue goals

• Headcount changes or org reshuffles

• Timing for reviews and performance cycles

• Compensation decisions

The “Protecting the team” trap

On the surface, it’s easy to say: “ICs don’t need to worry about that.” And it’s even more common to fall back on the well meaning cliché of “protecting my design team from the politics.”

But let’s be real; most of these decisions do trickle down—sometimes in the form of unclear priorities, shifting deadlines, or changes in focus due to market dynamics or business need. Protecting your team from politics doesn’t mean shielding them from context. It means giving them the clarity and tools to navigate the organization with confidence.

Many times I saw this information held back until two or three weeks after the decisions were made because a manager was uncertain if there would be a clear yes or no to distribute this information. In some cases, adjacent teams like marketing, product, or engineering were already operating under the new context, while design teams were still executing against the old directives.

It was almost like waiting for the train wreck to happen.

By the time ICs learned what had changed, it was often a surprise met with confusion, frustration, and anxiety. The work they’d poured hours into suddenly no longer aligned, and they had to pivot without warning.

The feedback would show up to the dismay to managers once performance review season comes around because their directs felt blind-sided and unsupported.

This is a patten that happens all to often when design functions are often the last the receive information.

If you’re already in the room, you have a choice; you can wait to react, or you can use that context to lead.

Practical ways to share context

A few practical examples:

• Business direction: If something is deprioritized until next quarter, let your team know early. It helps them recalibrate expectations and energy.

• Review season: Even if the company is sending broad comms, your team wants to hear from you. Remind them of timelines and expectations.

• Roadmap shifts: If you sense a change coming that may be disruptive, give them a heads-up. Don’t wait for confusion to set in.

• Adoption goals: If you're hearing about progress toward growth, adoption, or revenue targets, work with your team to connect the dots to their experiments or design focus.

Some rules of the road:

• Confirm primary sourced information before you communicate (hearsay helps no one).

• Don’t share sensitive or confidential information.

• Frame context as an enablement tool, not a stressor (more on this below).

The strategic advantage: Better upward communication

When your team understands the broader business context, something powerful happens, they start spotting risks and opportunities that you might miss from your higher-altitude view.

For example, when your designers understand both the business timeline and the user research findings, they might flag that a proposed launch date conflicts with critical usability testing phases. Instead of discovering this conflict during a tense stakeholder meeting, you have weeks to negotiate realistic expectations and propose alternative approaches.

This early risk identification creates what I call "strategic leverage", the ability to influence decisions while there's still time to course-correct. Being the manager who surfaces problems early, complete with potential solutions, positions you as a strategic partner rather than someone who just executes directives.

The timing of when you raise concerns fundamentally changes your influence. Flagging a resource constraint three months out opens up conversations about priorities, scope, and creative solutions. Raising the same concern three days before a deadline only creates panic and blame.

When your team has context, they help you understand how leadership decisions will actually play out in practice. They might point out that the "simple UI change" being discussed in strategy meetings actually requires a fundamental rethinking of the user flow, or that the aggressive timeline being proposed conflicts with known technical constraints they've encountered in previous projects.

This creates a valuable feedback loop: you share context downward, and your informed team helps you communicate more strategically upward. You're not just passing along information, you're building a network of informed contributors who can help you lead more effectively.

Richer 1:1s and stronger partnerships

When your team has context, they don’t just execute, they own.

They start connecting the dots between their work and the broader business. They begin to anticipate needs rather than react to change. They operate with more clarity, trust, and confidence.

Additionally, you may be able to communicate any risks that may arise from these things and communicate them upstream that’s much more timely and ultimately when you have more chips to bargain.

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You’re not just giving them information.

You’re putting yourself and your team closer to the driver’s seat when it comes to strategy, influence, and outcomes.

And here’s something else: your 1:1s get a lot more interesting.

With empowered designers who understand the bigger picture, you’re not just reviewing tasks, you’re exchanging ideas. You gain a thought partner on the ground, ready to drive new thinking from within the work and context of the organization.

Technically Speaking is where I share reflections, insights, and conversations to help you lead with confidence, clarity, and community. Are you looking to level up your design leadership and management craft? Schedule a free intro call for 1:1 coaching to help you thrive in your role.

It's been over two months since I left the United States to take a break from corporate life. I'm writing this from a coffee shop in Tokyo, reflecting on the journey that brought us here.

A quick replay:

I left LinkedIn as a Director on the Marketing Solutions team after eight years in May and I often think of most roles in season. Those seasons saw me through major organizational shifts, each shaping my experience in different ways:

• I joined not long after the Microsoft acquisition

• Managed through the chaos of a global pandemic

• Helped build a functioning hybrid team

• Navigated major shifts across the org during the rise of AI

Balancing those professional challenges, life outside of work unfolded in big ways: I bought a home, got married, lost my mother, and survived a near-death experience that completely shifted my perspective.

Reflecting on it all, to say these eight years shaped me would be an understatement. I’ve grown tremendously both personally and professionally and wanted to share a few reflections I’m carrying into this next chapter.

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Lessons and reflections

Health is wealth. Without it, milestones and impact mean little. Guard yours and be proactive.

Prioritize what you can control. Otherwise you’ll live in a constant loop of disappointment, discontent, and frustration.

Managing is selfless. You can guide and support, but you can't control people's decisions. Take care of yourself just as fiercely.

You won't always be right. Choose environments that value learning, people who challenge you, and recognize your wins.

Reframing is a powerful unlock. Win or lose, pause and reframe. Reflection leads to growth and renewed energy on the long game.

Burnout is a clarity problem. If you’re leading others or yourself and things feel murky, that friction adds up fast. Do the work to close the gap or create the clarity you need to move forward.

Make time for your parents and loved ones. We’re at a stage in life where our parents are getting older and that reality can feel at odds with ambition, growth, and opportunity.

The truth is, you can’t get that time back once it’s gone. And sometimes, the people around you; your peers, your manager may not fully understand, especially if they haven’t gone through it themselves.

But if you have the chance, take the time. Be present. Prioritize what matters. You won’t regret it — the work will always be there.

You might wonder: why make such a big change now?

Early in our relationship, my wife and I made a commitment:
We wanted to live abroad for at least a year before starting a family.

This year, we decided to honor that promise.

Professionally, I’d hit an inflection point.

At LinkedIn, the cogs of change in a company that size require immense, sustained effort—and with layoffs, reorgs, growing anxiety, and the internal politics of shaping an AI strategy, it felt like the right moment to step away.

Is it an exciting time to be in Silicon Valley? No doubt. But I could feel the start of another two- to three-year cycle, and I wasn’t ready to sign up for that.

This was the perfect time for us.

In January, we committed to making it real. We began the process of unwinding the life we had built: leaving our jobs, downsizing (hello, Facebook Marketplace), selling our cars, packing up our home, hiring a property manager, and renting out our place.

Behind the scenes, we checked off more than 60 tasks, each a step toward a bigger leap.

There were a few bumps along the way, but nothing a little extra time, patience, and trust in the process couldn’t carry us through.

Saying goodbye wasn’t easy. There were long nights, moments of doubt, and the kind of anxiety that comes with stepping into the unknown.

But once we boarded that plane, there was peace in the finality—no looking back.

Where we are now

We spent May through July in Korea exploring Seoul, Busan, and Jeju Island. We will be based in Tokyo until October, after which we plan to travel through Southeast Asia later this fall, with the intention of returning to Japan in the spring.

Along the way, it has been energizing to connect with local design communities, share stories, and soak up new creative inspiration. Exploring has become second nature—we often find ourselves walking over 15,000 steps daily.

What I’m up to

Here's how I'm spending my time these days:

Work-wise:

• I’m coaching product and design leaders. You can set up a free intro call here.

• Writing and recording to unpack the nuance of design management the messy middle, the mindset shifts, and the moments that shape leadership. If you’re reading this article you’ve likely subscribed, if not then hit the button!

• My wife just launched her tea business, Thi Time.

Not-work-wise:

• Reading - send me your recs

• Running - aiming for sub-8 min miles

• Prioritizing sleep - my WHOOP band is now one of my favorite pieces of tech

• Exploring - always on the lookout for new cafés, coffee spots, and restaurants

Let's connect

If you're new here, welcome! I invite you to share your thoughts on these reflections and let me know what topics would most benefit you in the future.

Your input drives these conversations, so please reach out.

If we haven't talked in a while, I encourage you to hit reply. I'd love to reconnect and hear your updates.

If you're in Japan, Vietnam, Singapore, or Australia, and in VC, product, or design space, book some time.

Thanks for reading—and here's to whatever season you're in.

Harrison

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P.S. Special shout out goes to Andrew Seok and SanHyo Lee for hosting me in Seoul and connecting me with Hiroki Tan in Japan.

P.P.S. Appreciate Emmanual Michael and Jesutofunmi Oluwatosin from Sections for inviting me to be a guest of their group that connects designers from Lagos and London to share experiences, build connections, and collaborate with professionals from diverse sectors. You can check out the replay here.

Design maturity has become the holy grail for design leaders. It's the idea that as organizations grow, their design capabilities should evolve from basic execution to strategic influence—moving from "make it look good" to "help us build the right thing."

But here's the problem: Most organizations measure design maturity completely wrong. They focus on operational improvements: expanding design teams, implementing processes, securing leadership representation—while missing what actually creates strategic impact.

Check those boxes and you’re done, right?

Your team has reached some irreversible, mythical level of design maturity.

The reality: Teams can achieve all traditional maturity markers while remaining strategically irrelevant.

Real maturity isn't about how many designers you have or whether you're in the room when decisions get made. It's about whether you can actually change the trajectory of the product and business.

This comes down to understanding two fundamental dimensions: Adoption (how much your organization invests in design) and Efficacy (whether your work actually shapes outcomes).

Most leaders obsess over the first dimension and completely ignore the second. The best ones build systems that deliver both.

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1. Adoption: How much your org is willing to invest in design

Adoption reflects organizational willingness to invest in design and research functions—the obvious operational markers:

• Are you funded for the right tools and team investment?

• Is headcount growing alongside the company?

• Is design represented in roadmap and strategy conversations?

Many teams stop here. If you've got decent budget and meeting invitations, it feels like maturity. You might even have design ops rituals and a strong research function.

Its understandable because it takes a lot to achieve the above and even more effort to maintain it.

But adoption alone doesn't mean impact.

You can have high investment and still see low impact. Dozens of designers might ship mockups daily, research may have in-depth share-outs while having almost no influence over product direction. The culture becomes top-down and reactive, burning through budget with incremental gain (which may not always be a bad thing, but if there’s room to do better than why not?).

Meanwhile, scrappy startup teams with two to three designers can become some of the most influential voices in the company, directly impacting growth and strategy.

Resource investment is just one piece of the puzzle—it doesn't tell the full story about return on design investment.

2. Efficacy: How much your design work actually matters

The other piece—and honestly, the more important one for your business—is efficacy.

Efficacy measures how much your design team's work actually matters to organizational success:

• Are you enabling them to influence what gets built?

• Are you positioning them to shape strategy early, not just execute after decisions are made?

• Are you helping them connect their work clearly to measurable business outcomes?

Without leadership creating efficacy, teams get stuck in triage mode—constantly reacting to requests, measuring success by output volume, optimizing for efficiency over influence.

High-efficacy teams operate differently

They're in the room before decisions get made because you've secured their access. They shape your roadmap because you've empowered them to contribute. They know when and where to intervene because you've given them strategic context.

Most importantly, their contributions show up in your growth metrics, conversion rates, and product direction because you've connected their work to business outcomes.

A strategic framework for design investment

If you want to understand where your design organization really stands, evaluate both dimensions:

Organizations move across these quadrants constantly due to leadership changes, market dynamics, business focus shifts, and economic pressures. But the key insight is: Maturity isn't about headcount. It's about your ability to create impact through your team.

Teams with strong efficacy can adapt, pivot, and thrive—even under resource constraints—because you've built their strategic value. Their worth isn't defined by size or output, but by influence and strategic contribution. This creates organizational resilience.

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Leading in leaner times

Right now, design teams are being challenged to operate leaner and faster. This is especially difficult for leaders who equated maturity with scale.

Many teams are being asked to do more with less, blurring lines of ownership and responsibility. If your team is thriving in this environment, that's a strong signal you've built high efficacy. But if their roles are becoming overly specialized or narrowed, it's a warning sign that key decisions are being made without design input—and critically, without your voice advocating for design's role.

This is a critical moment to assess: Are you losing influence, and by extension, is your team losing relevance?

Your action plan

As a leader, don't get caught chasing headcount ratios and resource benchmarks—those can all change during the next budget cycle.

Instead, focus on building efficacy through your leadership. But here's the key: you need to be in the room first. Your team can't influence decisions they don't know about, and they can't attend meetings you're not invited to yourself.

This week:

• Audit your own meeting access - Are you in the room for strategic planning, roadmap setting, and budget discussions? If not, your design team has no chance of being upstream.

• Review your last 3 major product decisions - How many included design input before the direction was set? If it's less than 2, you failed to position your team properly.

• Ask your design lead for their top 3 business concerns - Not design concerns, business concerns. If they can't articulate them, it's because you haven't given them visibility into what you're seeing.

Next 30 days:

• Get yourself included in higher-level strategic conversations - If you're not in the room for executive planning, your design team will always be playing catch-up.

• Connect one design project to a business metric - Pick your most important current design initiative and define how you'll measure its business impact.

• Share executive context with your designers - What business pressures are you hearing about? What's keeping other department heads up at night?

This quarter:

• Establish design KPIs that matter to executives - Move beyond "shipped designs" to metrics like conversion improvement, user satisfaction, or feature adoption. If you don’t have access to these types of dashboards then it may be time to prioritize this instead!

• Create a design roadmap tied to business goals - If your design team doesn't have visibility into next quarter's business priorities, first ask yourself: do you have that visibility?

• Position yourself as the design advocate in leadership - When strategic decisions are being made, you need to be the voice asking "What's the impact on the design team" before it gets to your team.

Real design maturity isn't about being seen or having the biggest team. It's about your ability as a leader to create measurable impact through your design organization.

The question isn't whether you can afford to invest in design. It's whether you can afford not to develop your leadership skills and lean-in to maximize that investment.

Technically Speaking is where I share reflections, insights, and conversations to help you lead with confidence, clarity, and community. Are you looking to level up your design leadership and management craft? Spend an hour with me for personalized 1:1 coaching to help you thrive in your role.

Lenny Rachitsky released findings from a sweeping survey of over 8,200 tech professionals. It covered everything from roles and remote work to seniority and satisfaction. One stat in particular hit home for the design community:

Designers and researchers, integral roles in the tech industry, are among the most severely affected by burnout.

It's not surprising. But it is validating—especially for those of us who've felt the weight of burnout creeping in for a while, even if we couldn't always name it. This shared experience in the design community is a powerful validation of our feelings.

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Why creative work burns you out

Creative work isn't just about solving problems; it's about solving ambiguous ones. Design teams are often expected to navigate constant critique, justify decisions, align with shifting business goals, and get stakeholder buy-in—all while meeting compressed timelines.

It's a role built on uncertainty. And when the target is constantly moving, it becomes hard to feel grounded. That ambiguity, when left unmanaged, creates a low-grade anxiety that designers often carry silently.

Studies suggest that creative professionals often experience higher levels of cognitive strain due to the inherent complexity of their work and the continuous demand to reframe problems and produce novel solutions. This type of mental load can accumulate over time, contributing to burnout and fatigue.

The pressure of perfection

On top of the ambiguity, there's the relentless pressure to be perfect within their peergroup. Design, more than most functions, ties professional worth to a single dimension: craft.

We glorify polish. We celebrate aesthetic brilliance or create a rabbit hole of polarizing hot takes (looking at you, Liquid Glass). And we place unspoken expectations on ourselves and each other to measure up. But at some point, you have to ask: What does chasing perfection get us?

Sometimes, an obsession with craft can lead to toxic behaviors. We gaslight each other under the guise of "standards." We might discredit good work if it doesn't present itself in a certain way in a portfolio. We often forget that context and constraints can shape outcomes more significantly than talent alone.

Truth is, there are many ways to drive impact—and not all of them look shiny and result in a high-fidelity mock or prototype.

The enterprise wasn't built with modern design organizations in mind

Unlike our PM, engineer, and marketing counterparts, designers often don't have a clear educational or career track with a built-in reward system. PM and engineers teams often inherently own headcount budgets, IC levels are directly tied to clearly defined charters. Many come from structured programs with MBAs and CS degrees—that provide them with access to networks, playbooks, and startup capital.

Design doesn't have that (although there is a growing movement for design-founders). Even with a seat at the table, our role is still widely misinterpreted by our peers.

So what happens? We see PMs and engineers get promoted or publicly recognized for work that we directly contributed to. And unless we're willing to step up and tell that story ourselves, our role gets written out of it.

This can have a significant impact on morale, as well as compensation, rewards, and career growth.

Leadership matters more than we think

Here's where leadership becomes mission-critical.

According to Lenny's survey:

• People with ineffective leadership are 4.3x more likely to be at risk of leaving.

• Those with extremely effective leaders are 8.2x more likely to be committed to their role.

• Folks "actively looking" for new jobs? They're 5x more likely to rate their manager poorly.

That's not fluff. That's a hard signal.

If you're leading a team, the environment you create matters—probably more than you realize. The way you recognize your team, set the pace, share credit, and define "good" has a direct impact on how people feel—and whether they stay.

I've always held onto a quote from Bill Walsh, legendary 49ers coach:

"For members of your team, you determine what their inner voice says. The leader, at least a good one, teaches the team how to talk to themselves. An effective leader has a profound influence on what that inner voice will say."

I think about that quote often—especially when interviewing design leaders. Many present polished portfolios showcasing what their teams built, but few speak to how they created the conditions for that work to thrive. It leads me to believe this is a muscle that design leaders haven’t quite mastered in the stories that we tell or value.

The environment is the product.

No one out-grinds burnout

Life happens. Burnout isn't something you hustle through. It's not a rite of passage. It's not a badge of honor.

You don't do your best work when you're depleted. You do it when you have the clarity, space, and energy to think creatively. And sometimes, that means taking a hard look at your environment.

Burnout isn't always about the work itself. It can be shaped by what's happening outside of it: the political climate, economic pressure, grief, depression. Sometimes it's family stress it might be the feeling of being underpaid or overlooked.

That's why it's so important for managers to identify it early and notice when something is shifting. Burnout doesn't always announce itself, and when it does, it's often been building for a while. You don't need to be a therapist, but you do need to be aware. Know what support and benefits are available. Sometimes, all it takes is a thoughtful check-in or a simple nudge in the right direction.

Clarity can reduce the weight of burnout

Building clarity is one of the most effective ways to prevent burnout. When people understand what is expected of them, how their work contributes to the larger vision, and how they'll be evaluated, they feel more confident and less anxious. Here's a quick checklist to help create that clarity:

• Have you talked about what's expected from the team? Clarity on expectations helps reduce uncertainty and ensures everyone is on the same page.

• Are goals clear, and do people know how their work connects to them? Reinforcing team priorities ensures that everyone is clear about their focus.

• Is the focus for this quarter front and center so the team can prioritize what's immediate? Clear, actionable goals enable the team to focus on what is most urgent.

• Have you reinforced OKRs or team priorities more than once and made them readily accessible? Repetition and easy access help people stay aligned and create accountability.

• Is there clarity around how performance is evaluated. Specifically, how their deliverables are assessed? Knowing how you'll be evaluated reduces anxiety and ensures everyone is focused on the right metrics.

• Have you created regular space for alignment, questions, and feedback? Regular check-ins and feedback loops help teams stay agile and responsive.

Burnout thrives in ambiguity. Offering clarity consistently and accessible helps people move with more confidence and less mental load.

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Building morale and awareness

Burnout doesn't have to be the norm. I've been there, feeling the weight of deadlines, expectations, and constant pressure. Over time, I've learned that leadership isn't just about driving results; it's about creating an environment where people feel seen, heard, and valued. Here are a few things that have worked for me:

• Recognizing wins, big and small: I've made it a habit to highlight my team's wins, even the small ones. It's easy to get caught up in what's next, but celebrating progress; whether it's completing a high-visibility project or resolving a complex edge case. If your team doesn't know what good looks like, how can they model it?

• 1:1s beyond delivery: Early on, I learned that 1:1s shouldn't just be about checking off tasks. I make sure to check in on well-being, too. It's about creating space to talk openly about stress, challenges, and how everyone's really doing, not just what's on their to-do list.

• Modeling healthy work habits: I started modeling rest, clarity, and thoughtful decision-making myself. I realized that if I'm always pushing through without taking breaks or slowing down, my team will do the same. Now, I prioritize balance and encourage the team to do the same.

• Fostering open dialogue: I've worked hard to build an environment where team members feel comfortable speaking up and providing feedback. It's not just about being receptive; it's about following up and making sure they know their voices matter.

• Following through on support: When my team needs help, I make it a priority to follow through on their requests. It's not just about offering support; it's about delivering the proper support and being consistent in providing the resources they need to succeed. Also remember, its OK to say “I don’t know” if you are uncertain about something.

Design is demanding work. It requires emotional labor, creative stamina, and constant context-switching. But burnout isn’t inevitable. It’s often a symptom of what’s missing: clarity, recognition, support, and psychological safety.

You don’t need to solve everything overnight. But small actions add up. Create space for honest conversations. Be clear about expectations. Celebrate the effort, not just the outcomes. And when someone’s struggling, don’t wait for them to raise their hand—check in early, check in often.

Because over time, the environment you shape becomes the voice your team carries with them. Their inner dialogue, the one that says “I’m supported here,” or “I’m on my own” is influenced by what you do, and what you choose not to.

When people feel seen, supported, and steady, they do their best work.

And they’ll want to keep doing it—with you.

Let’s not wait for burnout to show up loud. Let’s lead in a way that helps people thrive from the inside out.

Technically Speaking is where I share reflections, insights, and conversations to help you lead with confidence, clarity, and community. Are you looking to level up your design leadership and management craft? Spend an hour with me for personalized 1:1 coaching to help you thrive in your role.

One of the toughest transitions in a design leadership career is the move from manager to senior manager—and it’s not just about scope, it’s about mindset.

As a manager, your job is clear: keep the team running smoothly. You’re focused on planning, assigning work, unblocking people, and translating top-down guidance into execution. You’re close to the work and in sync with your team.

But as a senior manager, things get messier—and more ambiguous.

Now you’re expected to create clarity, not wait for it. Your manager is likely focused on a broader set of challenges, meaning you won’t get the same level of direction you once did. It’s your responsibility to step up, shape direction, and lead your team forward—even when no one’s asking for it.

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Here’s where a lot of folks get stuck:

They stay in reactive mode. They maintain. They wait.

But maintenance isn’t growth.

Managing to operating

In many ways, a senior manager operates like a mini-director—not in title, but in practice. You’re expected to:

• Spot opportunities before they become problems

• Develop a point of view on product direction

• Motivate and elevate your senior talent

• Build a culture where top performers thrive

If you lose that connection to your “messy middle”—those senior designers and emerging leaders—you risk losing the soul of your team. They may start taking all their cues from product or engineering, and while work will still ship, it may lack vision, quality, or depth.

Gut-check

If your manager needed a product vision tomorrow—could you deliver it clearly, confidently, and without derailing your team?

Most people say, “I don’t know if I could say it eloquently.” But the truth is, that’s not about skill—it’s about preparation.

Craft your vision

Block out time to think intentionally about the space your product plays in:

• How does it differentiate in the market?

• Where can design elevate it?

• What’s the long-term opportunity—and how can each of your teams contribute?

Timebox your campaign

Treat vision-building like any other project. Three to six-month cycles.
Mid-cycle and annual checkpoints let you:

• Validate assumptions with feedback loops.

• Spot gaps early and adjust initiatives.

• Reflect and measure progress when review season hits.

Act

Proactive thinking is what unlocks real leadership.

• It can create clarity in terms of the next steps that you take.

• You start having work beyond delivering work but contributing the conversation and welcome new points of view with product leaders

• Intentionality tied to exploration of ideas

• Your team can speak to how their work ladders up.

You make your manager look good.

Your team makes you look good.

And more importantly—you’re not just reacting to what’s next.

You’re building it.

This is how you grow. Not just into a senior title, but into a leader that drives the future forward.

Technically Speaking is where I share reflections, insights, and conversations to help you lead with confidence, clarity, and community. Are you looking to level up your design leadership and management craft? Spend an hour with me for personalized 1:1 coaching to help you thrive in your role.

Technically Speaking is where I share reflections, insights, and conversations to help you lead with confidence, clarity, and community. Are you looking to level up your design leadership and management craft? Spend an hour with me for personalized 1:1 coaching to help you thrive in your role.

If you’ve been in a leadership role long enough, you’ve probably found yourself in a room where something didn’t sit right.

Maybe it was a decision, a direction, or something that was said that didn’t reflect your experience. You felt it in your gut that this was your moment to speak up, but the moment passed.

Maybe you deferred to someone more senior. Perhaps you were waiting to be called on, or maybe you told yourself your perspective didn’t carry enough weight.

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Later, you replay the meeting, wishing you had said something because it could have moved the needle. And now, that decision impacts your work or team—and you must live with it.

It happens more than you think. You know, that Zoom meeting with 20 windows but only 2-3 talking heads?

It’s a recurring theme I come across in conversations with managers. I’ll ask why they didn’t speak up, and the reasons tend to follow a familiar script:

“It just didn’t feel like the right time.”
“I wasn’t sure how it would land.”
“It felt uncomfortable.”

Here’s the truth: discomfort is baked into the job. Not every room will feel safe, but tough conversations are where change starts. Healthy discourse is a leadership obligation, it advances the work, sharpens the thinking, and, when done well, builds trust.

Confrontation ≠ combat

Challenging ideas doesn’t mean challenging people. However, it’s important to ensure that the tone in which they are delivered isn’t perceived as combative.

Some phrases I lean on:

• “From my experience…”

• “On my team, we’ve found…”

• “I feel like there’s something we may be missing…”

They’re anchors rooted in your perspective in lived and anecdotal experience, and they invite others to engage rather than shut down and invite discussion.

Of course it’s important to be prepared to speak to the reasons as to why and be able to back it up.

One thing to note is that not everyone receives critique or divergent points of view gracefully. That’s their work, not yours. Stay curious, stay professional, keep the conversation on the work.

Share context

There’s no one-size-fits-all playbook. The way you manage might look different than someone else, and that’s the at the core of diverse teams. Build context around how your team works. Share what’s worked for you and the kinds of results you’ve seen.

A few examples:

How you navigate prioritization:

“On our team, we noticed designers were being pulled into too many low-priority asks. We created a shared intake doc with product partners to align early and cut down on fire drills. Within a quarter, team velocity improved and designers felt more ownership.”

Bringing clarity during ambiguity:

“We were handed a really broad AI initiative with no clear brief. Instead of jumping into solutions, we spent a week mapping user jobs and technical constraints. That helped us align across disciplines and honestly, saved us months of back and forth.”

When you tried something new that paid off:

“One of our newer designers was nervous about speaking in cross-functional reviews. We ran a dry run the day before and had her present a small section. The next meeting, she led the whole thing. Now it’s just part of our rhythm.”

Sharing insight and context can be the difference between someone shutting down or being open to trying something new.

The point isn’t to say this is the only way.
It’s to say: this is what we’ve seen work.

Ultimately, we all want to build great things. And that means being open to trying different tactics, even when they feel uncomfortable at first.

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Silence has a cost

When context that can shape or guide a discussion stays in your head, the team may risk committing to a solve for the wrong problem.

If you’re not speaking up whether to flag a concern or spotlight your team’s impact you’re leaving both trust and visibility on the table. If no one knows you were behind it, how can you be recognized for your impact and expertise?

Staying silent cannot only hinder your team but also prevent you from having opportunities to lead and grow.

See something? Say something and support

All this to say, these habits take practice.

Speaking up, navigating nuance, and shaping ideas in the moment isn’t always easy. Sometimes people just need a nudge. Here are a few ways you can support your team or peers on your next call in building that muscle:

Let’s say someone has more context than you but hasn’t jumped in, backchannel and shoot them a quick DM on the side in Slack or Teams.

“Hey, weren’t you working on X? Might be worth chiming in.”

If louder voices are dominating the room, create space for others. Say your piece, then pass the mic:

“Actually, Alex has been closer to this—want to share your take?”

And afterward, reinforce it:

“Loved what you shared in the meeting.”

If someone didn’t take feedback well, bring it up 1:1 and reframe it:

“I heard it as X—how did you take it?”

These might seem like small moments, but they compound. That’s how confidence builds and how culture shifts.

Put it into practice

Turn that “I should’ve said something” moment into real‑time courage.

• Separate the idea from the person. Treat every proposal as a draft, not an ego extension. Challenging the work doesn’t equal challenging the teammate.

• Anchor your pushback in lived experience. Start with “In my last launch…” or “When we tested this with X segment…” so people see the data or reasoning behind your viewpoint.

• Surface the missing puzzle pieces. Add the “why”. The user pain, the business constraint, the downstream impact. Shared context grounds discussion with real experiences so the team can learn from the past.

• Model calm curiosity. If tension spikes, don’t mirror it. Ask, “Walk me through how you got there?” Understanding their path lowers defenses and raises the conversation.

• Spotlight silent insight. When you know a teammate has the goods, tee them up: “Alex, you ran point on the prototype, mind sharing what you saw?”

Healthy discourse is essential for building stronger teams. Sharing new approaches doesn’t just shape better outcomes, it also opens doors. It’s how you build influence, demonstrate expertise, and lead in a way that reflects your unique point of view.

Technically Speaking is where I share reflections, insights, and conversations to help you lead with confidence, clarity, and community. Are you looking to level up your design leadership and management craft? Spend an hour with me for personalized 1:1 coaching to help you thrive in your role.

During Config in 2024 Figma, Co-Founder Dylan Field spoke of product taste and more recently the Shopify CEO, Tobi Lütke spoke of "taste" as being positioned as a product differentiator. He says they operate on taste and intuition rather than KPIs. I love that business leaders talks about design and craft like this on large platform that reaches a wide audience of product builders. That's progress, and it's also compelling.

But, like with anything that sounds good, knowing who it is coming from (much easier to say as a CEO than an IC) is essential. Everyone's about to start talking about taste—and I mean taste as if it's some newly discovered cheat code. So, let's pause for a second. What is taste?

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A casual observation

As a millennial, I've experienced growing up before the digital and information age, when things were highly crafted and curated before hitting the masses. The word taste was reserved for those who had an ear for music or an artist before it broke or those in fashion who could see the next trend coming because we were still consuming content on static physical media like magazines, CDs, and network television.

It was a mix of expertise, instinct, style, and swag. Taste wasn't just about knowing something looked good it was about seeing it before anyone else did. There were even people called 'tastemakers,' purveyors of good things…maybe.

On the flip side, it could also be used against people as a lack of refinement or as putting people in their place on the merit of subjective and often questionable critiques. You can only imagine the number of people who didn't get their shot because of this.

It's a perfect mix of prestige and gatekeeping, and since then, it has almost been somewhat democratized with the rise of influencers on platforms like TikTok and Instagram, where trends tend to be set by the public (dancing videos and mashups aside).

We've got to be careful about turning "taste" into just another careless buzzword we throw around in meetings to sound like we know what we're doing because it carries some weight and it might come off as pretentious to people you’re trying to influence.

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Developing intuition

From my experience taste and intuition are closely tied together. Making decisions is all about gathering what I’ve learned, testing ideas in real life, and seeing how they play out. Over time, that process sharpens my intuition and turns it into a solid guide or hunch. But I know my gut feelings aren’t formed in isolation. They come from understanding the situation at hand, leaning on my industry experience, organizational politics, human interactions and doing my research. All of this fuels my confidence when it’s time to act.

That doesn’t mean I rely on intuition alone. I usually float an idea, observe how people respond, and adjust if I need to. If it clicks, I’ll keep going. If it doesn’t, I’ll shift direction, reframe, or pivot. I’ve realized there’s no single formula—it really depends on the situation, and sometimes I just have to carve out my own path.

Ultimately, while we might rely on frameworks and theories, our personal journeys play a huge role in how we make choices. It’s about trusting what resonates, being willing to take calculated chances, and evolving as we see the results.

Balancing taste with practical outcomes

With that said I can't imagine walking into a room of executives and saying, "This direction is better because of taste.” If we’re talking about a better user experience, just say that. If we want a simpler interaction or a more delightful flow, call it out. Clarity builds trust; vague “taste” talk doesn’t.

I don’t have a perfect definition of taste, but I have a hunch about why it’s trending: businesses that get it see it as a differentiator. It’s easier to say in hindsight when there’s success is tied to it, there’s product-market fit, and there's a certain reverence. Users not only enjoy what they’re using, but they’re willing to pay for it and yell to the masses because it brings them real value, it satisfies their jobs to be done in a delightful way.

In the AI era, where anyone can spin up hundreds of variations of anything in seconds, designers who can pinpoint the ones the resonate—who bring instincts, sound judgment, and experience—are going to stand out.

But let’s not go overboard. Don’t throw it around in rooms where design maturity is low and trust is fragile. If the person you’re talking to doesn’t get it, you’ve already lost them. Worse, it can make design feel like a black box, which doesn’t help you build influence or credibility—only confusion and alienation.

Yes, taste matters—just beware of waving it around in rooms where design maturity is low and trust is fragile. Without clarity and real evidence, your secret sauce becomes just another empty buzzword.

Technically Speaking is where I share reflections, insights, and conversations to help you lead with confidence, clarity, and community. Are you looking to level up your design leadership and management craft? Spend an hour with me for personalized 1:1 coaching to help you thrive in your role.

I keep returning to the same principle when it comes to hiring: it's like building a championship team. You need the right players in the right roles, ready to make an impact after a reasonable ramp-up period.

Active involvement in hiring isn't just helpful—it's essential. You need to review portfolios, guide your recruiter on the right standards, and ask the right questions. Ultimately, no one understands your team's needs better than you do.

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One common pitfall in hiring I've seen is rushing the process due to understaffing and high workloads. While decisiveness is essential, hiring without considering relevant skills, business needs, and team dynamics can lead to chronic challenges.

Let's be honest—a mismatched hire is expensive in ways that go far beyond salary. The productivity hit, the team morale issues, the management overhead, and potentially the cost of starting over all add up quickly. Because of this, I've seen and been a part of teams set back by months.

Over years of managing and hiring across organizations, I've found that four qualities drive some of the highest performers I've managed: craft, drive, adaptability, and storytelling. Hiring based on just one of these pillars alone usually isn't enough; it's critical to see how they balance each other out.

In the sections ahead, I'll explain how these qualities show up in interviews, what to look for, and a few follow-up questions you can use to dig deeper. Of course, these aren't foolproof, but they can give you a strong hunch that you're moving in the right direction.

Craft

I believe craft is a non-negotiable aspect of hiring product designers. Design tools and systems are commodities, and it is expected that a designer operates at a high level of comprehension and execution, including interaction and visual design. The ability to articulate design decisions is crucial, as it demonstrates clarity, comprehension, and reasoning (I’ll touch on that more later).

Designers likely won't have the time to be learning the tools on the job; rather, they should come prepared with foundational knowledge and examples of how they apply them.

Beyond mastering design tools, designers must have experience collaborating with engineers to ensure that the final output aligns with initial expectations. High-quality design work does not happen in isolation—it requires an understanding of organizational, process, and team dynamics. Designers who exhibit a high level of craft have likely had to influence or advocate for organizations to prioritize this work.

Drive

Drive is a foundational trait, deeply tied to a growth mindset. It manifests as a sense of purpose and pride in one's work and catalyzes impact. I always like to frame it in "How did this person leave their last organization better than when they started?" This could be demonstrated through mentoring other designers, contributing to a design system, improving product quality, or collaborating with product managers to understand and leverage data.

Drive is the quality that pushes someone toward goals rather than away from challenges and risks. In high-performing organizations, everyone around you has demonstrated a drive to reach their position—those who lack it often get left behind.

Conversely, a lack of drive is equally telling. If someone has been in a role for some time and has identified problems without taking action, that can be a red flag. Individual contributors have a unique vantage point to recognize challenges and opportunities, even if they aren't in leadership roles. At the very least, they should communicate blockers to their managers. The worst-case scenario for any leader is a team full of contributors who have opinions but take no action, quickly leading to a toxic culture.

Adaptability

Adaptability and drive are closely related but serve different functions. While the drive is necessary for long-term growth, adaptability determines how someone navigates changing environments and ambiguous situations. Ideally, there is some self-reflection that the candidate can speak to in terms of identifying growth opportunities.

Potential hires must show examples of how they've adjusted their game to meet the moment. Some examples include.

• Adjusting to shifting priorities and organizational changes.

• Taking feedback constructively and applying it thoughtfully.

• Using problem-solving skills to navigate through ambiguous problem spaces

Adaptability is a two-way street. Sometimes, poor adaptability results from unclear goals, poor feedback, or a lack of organizational structure. Clear communication and defined expectations help maximize an individual's adaptability. When interviewing, it's essential to ask targeted questions to uncover how candidates have demonstrated adaptability in the past and also understand what their support structure looks like.

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Storytelling

Storytelling is a more critical quality than ever, especially as organizations aim to do more with fewer resources and move faster. Designers are uniquely positioned to craft compelling narratives using data, research, and craft expertise. However, effective storytelling depends on understanding the audience.

For example:

• Executives are less concerned with design details and more about business impact and shipping timelines.

• Product managers might focus more on how design investments drive user engagement and retention.

• They want to know how designers will collaborate to hand off assets efficiently, share feedback, to meet committed timelines.

The ability to tailor narratives to different stakeholders is a key marker of a strong designer. Storytelling is not just about presenting a case study; it's about strategically using design artifacts to influence the product development lifecycle.

Designers who excel at communication often see faster career growth because they convey their thinking and rally support around their ideas.

Conclusion

These four qualities—craft, drive, adaptability, and storytelling—don't exist in isolation. They form an interconnected system that enables designers to thrive in dynamic organizations:

• Craft provides the foundation upon which everything else is built — it’s the core competency

• Drive supplies the energy and momentum for improvement and impact

• Adaptability allows navigation through changing conditions and requirements

• Storytelling connects design work to broader organizational goals and stakeholders

When evaluating candidates, consider how these qualities complement each other. A designer with exceptional craft but poor adaptability may struggle in fast-changing environments. Someone with great storytelling skills but mediocre craft might win initial support but fail to deliver quality work.

Hiring the right person for the need of your organization goes beyond just checking boxes for skills. Craft, drive, adaptability, and storytelling are foundational traits that separate good designers from great ones.

By focusing on these qualities, managers can build teams that deliver exceptional work and contribute to a thriving and evolving design culture and, ultimately, better design outcomes for your users and organization.

Of course, it's up to you to determine your negotiables and non-negotiables and ideally evaluate focus areas for your hires to develop once they're on your team.

Technically Speaking is where I share reflections, insights, and conversations to help you lead with confidence, clarity, and community. Looking to level up your design leadership and management craft? Spend an hour with me for personalized 1:1 coaching that will help you thrive in your role.

The transition from being an IC to becoming a manager is one of the most exciting and challenging shifts you can make in your career. The skills that helped you excel as a designer aren’t always the ones that help you thrive as a leader. In fact, holding onto them too tightly can unintentionally hold your team back.

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I wrote this as a reflection for anyone stepping into management (or already there), wrestling with where to lean in, where to step back, and how to lead in a way that builds trust, culture, and long-term impact.

So let’s talk about what that shift actually looks like.

Yeah, it’s great you knew how to build components, contribute to the design systems work, created some of the most thoughtful prototypes, and put in the extra hours to develop your expertise. You thought deeply about user flows and edge cases, and guided your teams to focus on what users actually want while understanding the business. That’s exactly why I thought you’d make a great manager.

Not just because you were excellent at execution, but because you set an example. You raised the bar. You showed initiative, elevated the impact of design on the business, and built strong relationships across functional disciplines. People respect you. They ask for you by name to lead work. You are a force and a multiplier.

But stepping into management means something fundamentally shifts.

I know it's hard to say no. I know your instinct is to jump into the details, to extend yourself even more. But doing more of the same work doesn't serve you or your team.

Taking on more execution only creates the illusion of extra design capacity. You know better. You know that design work doesn't end with a series of mockups. It has a long tail of responsibilities: edge cases, bug fixes, stakeholder reviews, and QA cycles.

And here's the thing, it’s not your job to do this anymore.

You won’t be evaluated on how flawless your prototypes are or how fast you can ship. In fact, continuing to do that work may hurt your team. If you're in the room, speaking for them, showing your thought process before they've had a chance to articulate their own—you’re unintentionally robbing them of the opportunity to grow.

This is your new challenge: delegate, show people the way, and help them understand the possibilities and their potential. Because when people are performing their best the products we build benefit.

Hand off the projects you used to lead. Let others take the reins. Let them stretch, make mistakes, and find their own way. Some of it might surprise you. Some of it might not meet your standards. That’s okay. You're building something bigger now: a team culture.

You’ll have to accept that your decisions a year ago may no longer hold weight. Things evolve. What worked yesterday might not work today. You might sit in meetings where people question your past design decisions.

Let go of your ego. Because change is constant, and new ideas may go beyond what you thought of.

Create space for others to lead. Provide feedback, but try not to be prescriptive (although, at times, it's necessary).

Don’t forget what got you here—but now, step back, observe, and support.

In doing so, you might learn a thing or two and be the catalyst to make things go beyond what anyone thought was possible.

I’ll share a more in-depth article later on best practices and some historical context around how our team approaches planning, I want to unpack one key challenge I’ve observed that has broader implications across organizations and perhaps some ways you can address this if you’re seeing the same.

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One of the most significant sources of tension teams face is that product teams often don’t approach their work from a systems-thinking perspective. Many product managers, particularly those focused on shipping specific features, are laser-focused on hitting their OKRs for products that they own. On the surface, there’s nothing inherently wrong with that — after all, shipping things within a specified date range is a standard way to measure impact and performance of a team. The issue arises when these individual goals are misaligned with the incentive structures of design or engineering teams. Let’s see how this might show up:

PM: We need design to work on this project next quarter.

Design Manager: When is it due?

PM: We need it ready at the beginning of the quarter.

Design Manager: That’s not enough time for us to explore the space and deliver something meaningful.

PM: But our engineers are ready to go!

Design Manager: You’re putting us on an extremely tight deadline.

PM: "I know, but we expect to ramp this mid-quarter.  

Chaos ensues, leading to a rushed attempt at resolution often resulting in a suboptimal outcome for all parties.

The Root Cause: Competing Incentives Across Functions

This isn’t about calling out any one role but about recognizing that every function in an organization operates under different incentives, which shape how they approach work and define success. While a lot of design discourse centers around a product’s challenges with strategy and how design can influence or lead in some cases, a commonly overlooked piece is how engineering’s structure and planning process adds complexity.

Engineering teams often report to leadership with distinct metrics, strategic priorities, and timelines. A frequently overlooked thing is that engineering bandwidth becomes a major driver of product timelines.

Here’s how:

PMs rely heavily on the time they have engineering resources allocated for their efforts. This time tends to be limited, and after that, engineers rotate where there are other needs.

As a result, PMs feel intense pressure to ship quickly before they lose engineering support. This creates an urgency that bypasses thoughtful problem-solving and drives a frantic need to ship regardless of whether the work is truly ready. If they don’t ship before funding or resources move on, PMs risk being held accountable for delays, and engineers are blocked from moving forward.

This dynamic creates a double tension. When design enters the picture, PMs are already under the gun. They’re frustrated because they’re trying to deliver something now, not because it’s the right moment to ship but because the process demands it. This creates a chain reaction: design is rushed, engineering is pressured, and product is squeezed in between.

What are we here for if we’re not aiming for the same goal?

The more significant issue is that teams are planning for the process, not the problem.

Process Over Problem-Solving

When the process becomes the priority, nuance falls away. Teams are rewarded for moving things through the system, not stepping back to ask whether they’re solving the right customer problem. As this cycle repeats, backlogs swell with work that no one will ever get to because the process doesn’t leave room for change or course correction. It’s all about throughput.

Eventually, this breaks teams. PMs are evaluated on OKRs for delivery. Engineers are measured on what they ship. And design? Design is often left out of these incentives, treated as an afterthought rather than a strategic partner, simply because no one is directly rewarded for integrating customer experience into the process.

Risk aversion becomes the norm.

This isn’t just frustrating; it’s systemic. And unless you’re willing to rethink how your team plans and prioritizes, the cycle will continue. Planning isn’t about cramming work into a process. It’s about aligning teams around the problem, empowering them to think holistically, and creating space for quality, customer-centric outcomes.

If this sounds familiar then what do you do?

How to Break the Cycle

Breaking the cycle isn’t going to happen overnight. It requires consistent effort and intentional change, especially around how teams plan and collaborate. A critical starting point is ensuring that design is involved in strategic planning as early as possible. This means partnering closely with product managers to identify where work can be consolidated, reducing the number of PMs competing for limited engineering resources, and minimizing the risk of engineering teams being stretched thin.

The upside?

When engineers can stay on a project longer, they gain deeper product knowledge, better understand the users, and are more connected to the value proposition.

Where there is trust and expertise, teams perform better across the board. We see this in medicine, sports, and leadership teams.

Another step is finding ways to align incentives across functions. Many organizations operate in hybrid models, so it’s vital to identify shared goals and, where possible, speak the same language. This might sometimes mean stepping up and being evaluated against the same key results. If those KRs aren’t rooted in user success, that’s a prime opportunity to influence them.

Also, lean into conversations to ensure all stakeholders are consistently engaged. Every function—design, product, engineering—should be at the table in pod or squad models. If someone isn’t regularly attending planning or reviews, they’re likely not as close to the product or the users as they need to be.

Develop an Action Plan

In some organizations, structural challenges are deeply embedded in the culture, making change difficult. If these issues persist or escalate, consider raising them with your manager or skip-level leadership.

Start by engaging with your planning partners and asking critical questions to understand the urgency behind faster project timelines. Why is speed the priority? What constraints are driving this push? Gaining clarity here will help you address the root causes rather than just the symptoms.

Before escalating to leadership, look for patterns. If these challenges appear across multiple teams or functions, it’s a sign that the issue is systemic. When the time is right, bringing the conversation to the executive level can be a powerful catalyst for change. It shifts the focus from simply shipping work to solving the right problem, delivering better user experiences, and something everyone can be proud of.

Looking to level up your design leadership and management skills? Spend an hour with me for personalized 1:1 coaching that will help you thrive in your role.

There’s no doubt that landing a job in 2025 is highly competitive. I write about how organizations are changing, in which design teams are often working with fewer resources. This means that, a strong business case has been made as to why teams are hiring for design roles and are under pressure to hire designers who can meet the expectations for the role.

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As someone who has gone through thousands of applicants over the years, In this post, I’m going to drop some game on what really works, what doesn’t, and how you increase your chances of getting noticed. It starts with understanding the hiring process, who’s on the team, and the critical details that can make or break your application. Paying attention to the small things can make all the difference in getting a foot in the door; many strike out by not delivering on the basics.

The Hiring Team

Each role on the hiring team has a different focus and different levels of context about you, so understanding who does what will help you tailor your approach:

• Sourcer: Scours applications and online profiles to find potential candidates. Usually works hand-in-hand with the recruiter. Might look for minimum requirements, not well versed in the specifics of your role. You likely won’t interact with this person. They may facilitate interviews and scheduling.

• Recruiter: The key point of contact who manages the interview process, talking to both you and the hiring manager to keep everything moving. They may be working with a number of teams can speak broadly about the experience team you’d be embedded with but not too deep on the day to day.

• Hiring Manager: The person who champions the business case for the role and sets the job requirements. Likely your future boss or someone in your reporting chain. Likely has vetted you in regards to qualifications, a quick portfolio and resume skim, and verification of role requirements. Likely equipped to speak more about the role and expectations.

• Hiring Committee: A group of stakeholders who weigh in on whether you’re the right fit. They could be designers, cross-functional partners, or horizontal teams that have some overlap with the role. They will have some influence on the final decision. They may not have as many details about the day-to-day but may be aligned to the business area of the role you’re a candidate for.

Depending on the size of the company, one person might wear multiple hats, or these roles may come into play at different points in the interview process. Regardless, each role has its own perspective on your experience and portfolio, so the better you understand who you’re talking to, the better you can tailor your message.

Understanding the Hiring Process

A recruiter or sourcer is typically responsible for sourcing candidates and reviewing applications. Before that, they will have a conversation to align on the type of candidate they’re looking for when setting up a job requisition with the hiring manger.

This means there will be minimum requirements, such as years of experience, time in role, and specific skills. These are typically non-negotiables due to the high volume of applications that may come in. While some strong candidates may be overlooked, it’s crucial to apply for the correct level for example junior vs. senior, senior vs. staff, principal, etc. Applying outside of your experience level often results in an automatic rejection.

The LinkedIn DM Overload

Once the job application is live, I typically share it on LinkedIn. Due to the network effect of reposts and high demand in the market for these roles, my inbox quickly fills up, anywhere from 50 to 100 DMs within a week.

It can be overwhelming, and I don't recommend messaging a hiring manager. In almost all cases, simply applying is the best approach.

Some DMs can even do more harm than good. For example, I've received cut-and-paste messages addressed to a name other than mine and even with the incorrect company name.

While the enthusiasm is appreciated, many hiring managers don’t have the bandwidth to individually discuss each role. It’s important not to take it personal it’s one of the many things hiring managers are responsible for handling and many simply may not have enough time in the day. We include as much detail as possible in the job description, and these discussions are typically reserved for candidates who progress in the hiring process.

The Biggest Mistake: Not Applying

A surprising number of people message me about a role but never apply. If you’re interested, you must submit an application.

Even if we have a great conversation in DMs or in person, you need to be in the ATS to move forward. The Application Tracking System is the source of truth of candidates who have applied to a position in the company. There’s no backdoor, even if you come in as a referral.

Reviewing Applications: First Impressions Matter

Recruiters typically source top candidates, and review them asynchronously or in weekly check-ins with the hiring manager. First impressions matter.

Here are two things that can help:

Make sure your work is accessible. Include a link to your portfolio on LinkedIn—it can be a Figma file, PDF, or website. You’d be surprised how many people forget this and it can lead to a scavenger hunt. Your LinkedIn should serve as a central hub for your experience and relevant links (please excuse my bias).

Avoid password-protected portfolios whenever possible. Many application sites, don’t allow you to add a username/password for direct access to your work. If your site requires a password, consider providing a dedicated, unlisted link or a shareable Google Drive URL.

For candidates the meet minimum requirements and have strong potential, hiring managers may wait for password credentials, but we can’t wait forever. I’ve seen candidates delay for weeks, and we’ve had to move on. Being prepared is key.

Preparing for the Technical Interview

Many companies have moved away from take home test—if companies still doing this then it might be worth question if the effort is worth it? Instead, candidates are asked to come in with one or two case studies prepared to present.

Here’s a high level of what is generally evaluated and what you should account for:

• Craft & Execution – Even at an entry level, you should have a solid grasp of typography, spacing, sizing, and alignment.

• Components & Systems Thinking – Can you clearly articulate design patterns, components, and use cases?

• Problem-Solving & Collaboration – Do you present a clear, structured narrative? Can you explain how you worked cross-functionally to achieve results? While teamwork is important, this is the time to focus on your contributions. Many candidates default to a "we over me" mindset, but interviewers want to understand what YOU specifically did. Be clear about your role, decisions, and impact while acknowledging team collaboration.

• Metrics & Research – If applicable, be clear about the key metrics and research that guided your work.

• Resourcefulness & Adaptability – If you had to be scrappy and creative, tell us about it. This helps us understand how you navigate complexity.

Landing a product design interview in 2025 isn’t just about having the skills—it’s about showing you can follow directions, communicate your work clearly, and understand each person on the hiring team. The small details can make be the difference in getting your foot in the door.

Looking to level up your design leadership and management skills? Spend an hour with me for personalized 1:1 coaching that will help you thrive in your role.

Over the last few weeks, multiple designers on platforms like LinkedIn and Reddit, have shared accounts indicating that ADPList allegedly used their content without proper permission or credit. Some also claim they were not compensated for their services. Although ADPList has not publicly addressed all these specific incidents, this is a big disappointment to say the least.

If true, this is a serious breach of trust especially considering that the platform was built on the very foundation of supporting vulnerable professionals. It’s hard to imagine how an organization that at it’s core attracted users rooted in design and user-centered thinking could make such a misstep. Whether it stemmed from a need to drive more engagement, a shift in business strategy, the result is the same: a betrayal of the brand trust that brought ADPList where it is today.

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The Roots of ADPList

ADPList was founded in 2019, emerging during the COVID-19 pandemic as a response to a pressing need: connecting designers with mentorship and career opportunities in an uncertain time. You can hear more about its origins in my Technically Speaking podcast—Felix, the founder, was a guest on episode five. I’ve supported ADPList for years because I’ve seen firsthand how transformative it has been in connecting designers across the world with other industry professionals in ways that didn’t exist before.

For me, I saw ADPList as a lifeline for many through mass layoffs and going through a once-in-a-generation global epidemic (hopefully). We were all stuck in our home offices, staring at laptop screens, unsure of what was next. Yet, this platform gave many hope and a sense of community one that wasn’t tied to a major conference or workplace but rather built organically by designers for designers. It made the world feel smaller and more connected. I was excited to be part of it because I could only imagine how valuable a resource like this would have been when I was coming up as a designer, navigating my career. It was an easy way for me to give back.

The Platform’s Evolution

ADPList began as a simple spreadsheet, connecting laid-off designers with new opportunities. Felix saw a chance to build something greater, and over time, the platform evolved not just in terms of user growth but also in features and impact. It expanded beyond design to include product management, offering courses and gamification to encourage more engagement from mentors, and eventually a large remote annual conference. From what I saw on LinkedIn, it became somewhat of a cultural movement. Designers took pride in being on the platform, showcasing their mentorship hours and contributions. I was one of those people. This happened because of what they associated the brand with.

Mentorship is Complicated

Mentorship can mean many different things to different people, but at its core, it’s about supporting someone’s growth and learning by offering guidance, feedback, and encouragement over time. Ideally, it should be a give-and-take marked by trust, respect, and a commitment to each other’s development.

Big emphasis on ideally…

When I first got involved, that’s what I believed ADPList was all about. As the platform matured, many of these connections started feeling a bit transactional, like something on a checklist rather than a genuine mentorship bond. People have been turned off by that vibe, myself included.

It’s important to note that this isn't a challenge exclusive to the ADPList platform. I’ve had plenty of those types of experiences outside of the platform. At the same time, there are bonds I’ve created from the platform that I still have today. At its best, ADPList can offer meaningful connections that embody what mentorship is really supposed to be.

This situation is deeply conflicting for me. I’m a strong supporter of Felix and want to see him succeed. But at the same time, it’s incredibly disappointing to see my peers’ work stolen and repurposed without credit.

Trust, once broken, is hard to rebuild. Did the platform lose sight of its original mission in pursuit of expansion or monetization? And for those who proudly contributed mentorship hours, does this controversy now tie us to a platform that undermines the designers it was meant to help?

Lessons in Brand Promise

This is a crucial lesson for anyone building a product or community: Brand promise matters. The brand promise is the core expectation people have about what your brand stands for and will consistently deliver. It's the heart of why they choose, trust, and remain loyal to you.

People don't just use a platform; they believe in it. And when that belief is shattered, regaining it is an uphill battle.

I don't think ADPList will go anywhere in the immediate term; it's done far more good than harm. However, I hope Felix and his team acknowledge where they've gone astray and sincerely try to course-correct. Without that, the platform risks losing the very people who helped make it successful in the first place.

Time will tell whether it will hurt the growth of the platform.

Large corporations are often hamstrung by a silent killer of innovation: top-down bureaucracy. It’s one reason the next breakthrough AI tool is unlikely to emerge from a traditional corporate hierarchy. We’ve seen this before, many of today’s most influential productivity tools now seen as standard were born from a product-led growth model. In that model, products are designed to be so intuitive, accessible, and valuable that they attract users organically through free trials, freemium tiers, or simple onboarding, without relying on conventional sales or marketing.

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Think of tools like Notion, Slack, and Figma. These products gained traction with individual users and small teams before making their way into enterprises.

Once a product achieves product-market fit, the race to secure enterprise customers begins, as they represent the most significant revenue opportunities.

I've witnessed this firsthand. At a startup I worked for, we were one of the first enterprise clients to adopt InVision (RIP). It was a no-brainer—it connected our globally distributed team, replacing our old Photoshop-to-Dropbox workflow with a much faster, more iterative process with engineers.

Was it perfect? No. But at the time, it significantly improved our collaboration and development speed. Since we were a smaller company, navigating procurement was relatively simple — accounting was on the other side of the room, and I just needed the CEO's approval to move forward.

The Complexity of Large-Scale Tool Adoption

Fast forward a few years to LinkedIn, where I was now part of a 300+ global design team spread across multiple business lines. The complexity of adopting new tools was exponentially greater. We were among Figma's first large enterprise customers, and it was clear they understood the demands of working with a large-scale operation and the necessary considerations, such as enterprise-scale licensing, security compliance, and change management. I remember that evaluating tools set itself apart from tools like Sketch and more specialized tools like Framer and Principle.

It was a classic buyer committee scenario. We ran a structured exploratory phase, rigorously testing Sketch, Figma, and InVision. Initially, there was some internal resistance, but Figma quickly stood out, especially regarding enterprise readiness.

The AI Tool Adoption Challenge

This experience illustrated how critical enterprise readiness can be. Now, as AI tools emerge, the same issues arise. I tell this story because the same challenges exist today as teams seek AI tools to enhance their workflows. Many companies won't approve these tools for enterprise use due to security, compliance, and procurement hurdles, and when you couple that with data compliance, there is a lot to consider. So, where will the next AI breakthrough come from? Most likely, side projects and grassroots adoption within teams experimenting outside of sanctioned workflows.

This highlights a key opportunity: companies that streamline the approval process for emerging tools will have a competitive advantage. Startups building AI-powered solutions should also consider how they can integrate with larger enterprises from day one. The cycle of enterprise tool adoption needs to move faster. Otherwise, the most innovative solutions will remain stuck in red tape while competitors move ahead.

If This Sounds Familiar:

If you're seeing friction in AI tool adoption at your company, here are some recommendations to consider:

For Individual Contributors & Team Leads:

• Start small – Use AI tools in non-critical workflows to test their value before making a case for adoption.

• Build momentum – Share wins with colleagues and create internal demand before pushing for formal approval.

• Document impact – Track time saved, efficiency improvements, and collaboration benefits to strengthen your argument.

• Find workarounds – If security policies block specific AI tools, look for compliant alternatives or offline versions to test.

For Managers & Decision-Makers:

• Shorten approval cycles. AI moves fast, and companies that take months to approve tools will struggle to keep up.

• Pilot AI tools in controlled environments – Allow teams to run structured trials before committing to full adoption.

• Engage security & compliance early – Address concerns proactively to avoid unnecessary roadblocks.

• Encourage experimentation – Create safe spaces for employees to test AI productivity tools within company guidelines.

The next wave of AI-powered productivity tools is already here. The question is whether your company will embrace them or risk being left behind. Even if your organization doesn’t adopt them, it’s still worthwhile to explore these tools on your own.

Looking to sharpen your design leadership and management skills? Join me for a personalized 1:1 coaching session, and we can work together on strategies that will help you truly thrive in your role.

Cross-functional teams can be a powerful force multiplier, but it can also lead to confusion about who does what.

In cross-functional teams, sometimes it's hard to tell who's responsible for what. For example, when the design team helps out with the PRD, a PM creates wireframes, or an engineer pushes a feature that wasn’t discussed — it can be quite frustrating if this happens repeatedly without clear definition.

Things can get even messier when there are tight deadlines or pressure from the higher-ups. That's why it's important to have a chat with your team members and clear things up before things escalate.

Now, you might think of running to your manager to sort things out, but that can sometimes make matters worse. It might make your teammate feel like they've been slighted and often times they may think they're doing the right thing. So, it's best to have these conversations directly.

Here are some things to consider when doing so:

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Avoid personal accusations

When addressing role-related issues, the first rule is to refrain from making personal comments or attacks. Accusations like "you're being unprofessional" or "stepping out of your role" can be emotionally triggering and shut down productive conversations. Instead, focus on mutual agreements and shared values.

Start with common ground

Begin the conversation by identifying common ground—company missions, product principles, or organizational values that everyone has aligned on. This lays a constructive foundation and signals that you're all in this together. It assumes the best intentions from all parties and acknowledges that mistakes can happen in haste rather than out of malice.

Show empathy

Empathy is key. We've all be there, external factors, such as tight deadlines or workload pressures, might lead to colleagues making decisions that deviate from their usual roles. Sometimes, a seemingly small output may require substantial behind-the-scenes effort. Communicate your understanding of the situation and appreciate the effort invested.

Communicate thought processes

In instances where roles blur, explain your thought processes. Sometimes, while the output may appear different, the thinking behind it might involve considerable effort and consideration. Highlighting this can help clarify your colleague's intentions and bridge the understanding gap.

Take action

After a discussion, ensure that you and your colleague agree on a follow-up action plan. This serves as a reference point in case the issue arises again. It demonstrates a commitment to learning from past experiences and working collaboratively to avoid repeating mistakes.

Looking to level up your design leadership and management skills? Spend an hour with me for personalized 1:1 coaching that will help you thrive in your role.

Part 3/3: Conversations on design leadership

This article is the third article in our series in which I sit down with , a design manager. You can also find the series in her publication, , where she shares her reflections on career growth.

Today, we’re digging into something that’s top of mind for many of us, especially in the wake of all the industry shifts and AI buzz — what does the future of design leadership look like?

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The Changing Face of Design Leadership

Harrison: Leadership isn’t static. It’s seasonal. Think about pre-COVID: leadership looked different, there was a focus on providing stability to teams and bringing about new ways of working in a full-remote workforce. Now, it’s about RTO (return to office), culture-building, and adapting to AI shifts. The job keeps evolving!

Anukriti: Absolutely! I’ve learned that as a leader, I’m an extension of the business—but that doesn’t mean I set aside my own perspective. The key is clarity. My team needs to understand what’s changing, why it’s happening, and how we move forward.

Harrison: That’s the essence of leadership-staying grounded, sharing openly, and letting your team know you’ve got their back. The more we communicate and adapt, the stronger we all become.

Anukriti: Yes, another thing that’s lately been on my mind is the shift in the design industry—it’s so much faster than I ever expected!

Layoffs in big tech. Shifting business models. Budgets tightening. AI reshaping workflows.

It’s no surprise that designers, managers, and leaders are asking, “Well, What’s next?”

There’s this underlying tension-almost like an identity crisis. And I don’t think this is just a phase we’re in—it is the new reality, and it’s one we need to navigate.

Harrison: It’s true. We came up in a time when things like the “Design Maturity Model” were considered gospel. You could measure a company’s design health by how many designers they had per engineer or how much influence design had on strategy. That made sense back then.

But look around, companies that were considered “design mature” are laying off entire teams. Others are racing to reposition themselves in AI, pivoting products overnight. The frameworks we used to swear by? They don’t fit anymore.

Anukriti: Totally, a lot of those ideal company standards are shifting. And if you’re feeling like you’re not designing the way you “should” be-maybe because your org isn’t the shining example from the books-that’s okay. What this all comes down to is that we need to rethink how we lead.

The Evolution of Design Skills

Anukriti: The phrase “full-stack” has been around forever in engineering. But now I’m hearing that design is also evolving in that direction too. What does it really even mean?

Recently, Tomer Cohen, LinkedIn’s Chief Product Officer, introduced the idea of “full-stack product builders”. The concept is pretty simple:

• Anyone with a great idea can bring it to life.

• Teams can form on the fly to tackle emerging priorities.

• Skills matter more than titles.

How does this translate? For designers, this means expanding beyond craft.

• You’d still own your design skill set including research and problem-solving.

• But you also start incorporating product strategy, business metrics, and prototyping even beyond design tools.

• You’d learn to balance ROI with user-centered design—Are users finding value in your product? How’s the product’s adoption? Are you impacting key business goals?

Harrison: Think of it as a new job description. It’s not just about wireframes and high-fidelity mocks anymore. It’s about being an equal partner in shaping the product, alongside PMs, engineers, and business leaders.

Here’s how the role of design has evolved:

Will PMs Take Over Design?

Harrison: Do you think product managers will take over design?

Anukriti: I don’t think so! PMs play an important role in product building but they have their own role. You could say that the lines between product and design are blurring. Designers who understand product strategy and business impact will survive this shift well.

Harrison: And what about PRDs? Are designers going to start writing them?

Anukriti: Maybe not traditional PRDs, but designers are already documenting strategy and user journeys at a higher level. My team has been creating “design briefs” for a while now. You could also call it a “design-driven product brief” if you want. The goal is the same—bridging business strategy with user experience.

Harrison: And what about managers? Where do they fit in all this?

Anukriti: I think that managers who rely solely on people management might struggle. The future is a player-coach model leader who can both guide teams and roll up their sleeves to navigate some hands-on design.

Anukriti: So, final question-do you think AI will replace design managers?

Harrison: Short answer: No. But AI will change the role of design leadership. The best leaders won’t just manage people; they’ll be hands-on, guiding teams through AI integration, product decisions, and culture shifts.

Some ways AI is already helping design leaders:

• Onboarding: AI-driven companions that help new hires ramp up faster.

• Talent Sourcing: AI-assisted recruiting to identify top candidates.

• Process Automation: Less time on routine tasks, more time for strategy.

Anukriti: But at the end of the day, no AI can replace human judgment, empathy, or innovation, right? That’s still on us.

Harrison Facts!

Final Thoughts

Design maturity ebbs and flows. Today’s stable environment might become tomorrow’s reorg. If there’s anything we’ve learned, it’s that we can’t rely on static definitions of design leadership. Instead, we should focus on:

• Being catalysts for cultural and strategic shifts

• Having conviction in our design vision and the impact it can create

• Telling the full narrative—connecting user value, business outcomes, and the evolving technology landscape (including AI)

That’s it for this issue. Thanks for reading, and I hope you’re walking away with a fresh perspective on where design leadership is headed. Let’s continue to adapt, learn, and shape the future of our craft together.

Stay curious and keep building.

You can now read up on our full three-part series:

• Expectations vs. Reality in Design Leadership

• Day in the Life of a Design Leader

This article is part two of a three-part series in which I sit down with , a design manager, to reflect on our experiences at different phases of our careers. You can also find the series in her publication, , where she shares her reflections on career growth. This series is published weekly, so be sure to subscribe to catch the next one!

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Hi friends! Last week we touched on perception vs realities of a design leader. Today we’re diving deeper into what a design leader does on the day-to-day. Let’s dive in!

Navigating meetings, decisions, and team alignment

Harrison: Yes it’s true managers do have a lot of meetings! But what are these all about? Could they have been a Slack conversation or an email instead? I know there is a big anti-meeting movement, but hear me out, for managers they are very important especially when there is intention around them.

Anukriti: That’s a good way to get the elephant out of the room! Meetings often get a bad rap, but the reality is that they play a critical role in decision-making, alignment, and building relationships. If I could summarize all kind of meetings, we’d be looking at another article, but this is a good overview of most meetings design leaders are involved in:

• Hiring - Reviewing portfolios, conducting technical screens, and making hiring decisions to strengthen the design team.

• Team health - Meeting 1:1 with the designers on their project challenges, performance check-ins, workload discussion, or any decisions they need help with.

• Design reviews - Ensures the solution is refined to a high-quality and often surfaces things that someone may have missed.

• Strategic reviews - Aligning design with broader business goals.

• Cross-functional alignment - Ensure alignment with product, design, engineering and other teams.

• Operational planning - Identifying blockers, improving processes, and creating a space for designers to thrive in the work they do.

Harrison: There are so many things to stay on top of, and switching context can be challenging. How do you manage it all?

Anukriti: I literally have a note doc for every person I talk to! It may sound weird at first, but going unprepared for a meeting, or forgetting action items discussed doesn’t benefit anyone in the meeting, so notes of some kind are essential. I used to rely on memory for every decision made in a meeting, but when you're switching contexts every hour (or even every 30 minutes), keeping notes is a lifesaver for me! Also, with so many AI tools out there, it’s easy to condense the raw notes into simple action items.

Cross-functional stake/holder meetings

Harrison: Every major decision comes down to a discussion. And you can’t solution or design your way out of it and sometimes they may not be actionable immediately! You may need more data, input from a specialist and connections with another team.

Anukriti: Exactly! Sometimes, the biggest way to unlock a problem is simply starting the right conversation with the right people. I think building relationships with stakeholders is super important—as important as the decisions themselves. The way I see it, these meetings can fall under any of these categories:

• Decision making: These meetings often set the direction of a product or initiative. I’m in either 1:1 meetings or design review meetings with stakeholders on a regular basis—in most meetings there are short-term and long-term decisions being made.

• Alignment and Delegation: As leaders, we decide whether more data is needed to inform a decision, or if a decision is ready to be made, or if it's time to delegate.

• Uncovering opportunities: Some of my best ideas have come from these discussions with my PMs, researchers and engineers. This collective act of identifying opportunities is rewarding - it often shapes the work our teams do.

What do you think? Anything to add?

Harrison: Another thing to note is that the stakes vary! Some meetings are low-risk and exploratory, while others are mission-critical. It’s our job to help define what’s at stake, drive the conversation forward, and ensure a decision is made.

Now talking this out sounds easier said than done!

One of the things my executive coach taught me is that it’s always important to focus on the shared purpose and have absolute clarity on the topic of discussion and the desired outcome. That means sometimes it may not be clear within the bounds of discussion and so it's ok if there needs to be some time to put thought into things or regroup at a later time.

Keeping the team aligned & focused

Anukriti: Alignment is everything! This is an area I often find myself spending time on, that’s not to say there’s inefficiency in processes. It is often about over-communicating and bringing everyone on the same page early and often. Harrison, how do you ensure your team stays on track?

Harrison: I think there are a few key areas. We get involved a lot in product/project planning to make sure that product and design and all cross-functional partners are aware of what’s on our plate. This provides focus and clear expectations.

Here’s how we make sure our team stays on track:

• Planning - Knowing what projects are coming down the pipeline and aligning cross-functional efforts accordingly

• Quarterly Kickoffs – Defining the focus areas and team pods so everyone knows what they’re working on on a quarterly basis. This format creates a ton of curiosity into what other designers are working on.

• Deep Dives – Designers present their work to foster collaboration and visibility.

• Ownership & Themes – We set themes for the quarter, reinforcing priorities and showcase how their work drives business impact.

Ownership is also key

Harrison: I like to borrow from sports analogies. My former manager recommended this book called The Score Takes Care of Itself, by Bill Walsh, who was a former coach of the San Francisco 49ers. Walsh emphasizes organizational ethics, a high standard of performance, and the leader as teacher. This book really resonated with me in that regard as a former athlete. I remember when I played at Iowa there was a slogan on the practice field that was:

When I played at Iowa, there was a slogan on the practice field that read “Preparing to be the best.” That meant bringing your best effort to every practice, evaluating your performance, learning how to improve, and repeating that cycle. This same mindset can be brought to the work we do daily, ensuring we’re always striving to deliver our best.

Anukriti: I love that! We hold a high bar for craft. I have a weekly team design crit which is a great way for the designers to give feedback and input on each other’s work. It also gives us an overview of what everyone is working on, which identifies opportunities to collaborate and add ideas to making a high-quality user experience.

Harrison: Yes, and if a deliverable doesn’t meet the standard we’ve promised our users, we should escalate to leadership right away. Regardless of whether it's an MVP or a General Availability (GA), every feature should just work and meet our customers' and members' expectations.

We have the ability to change the environment around us. Let’s not waste time imagining what could be, we can make it a reality ourselves. We know things won’t change unless we do something about them, and who better to start than you? It takes commitment and a willingness to take action in the moment.

Anukriti: I agree, this is also my personal philosophy! Taking initiative and working as a team can completely change how we get things done. It’s not just about doing more, it’s more about doing what actually matters, for our users and each other!

Final thoughts

If there is one thing that you could take from this article, it would be understanding that when it comes to the day-to-day of a design leader, no two days are going to be the same.

Staying organized is super important, but it’s also important to embrace spontaneity, and not losing sight of your creativity. Sometimes we tend to get caught up in all of the structure, but great ideas spark from moments of moments of spontaneity, open dialogue and the energy to work through the unknown.

Or simply put, learn to embrace the chaos!

Stay tuned for next week, when we talk about the future of design leadership and AI. Until then, check out our previous post in this series:

• Issue 1: Expectations vs. Reality in Design Leadership

I recently sat down with Anukriti Verma, a design manager, to reflect on our experiences at different phases of our careers. This conversation is part of a series that will be released over the next three weeks. You can also find the series in her publication, Making Design Make Sense, where she shares her reflections on career growth.

Design leadership can feel like the natural next step for experienced designers looking to expand their impact. But the transition from individual contributor to manager isn’t always as straightforward or glamorous as it seems. While leadership roles bring new opportunities, they also come with unexpected challenges that can reshape how you think about your design career and measure growth.

I sat down with Harrison, a seasoned design leader who’s been in my position and adds more light onto the leadership reality changes at every level. We explore some common expectations vs. the reality of stepping into design management. Let’s get into it!

Quick intros

Harrison: Before we get started, let's do quick intros. I can start, I’m Harrison, I’ve been a director of product design at LinkedIn for two years but I’ve been managing in some capacity for over a decade. I’ve been at LinkedIn for almost 8 years and before that I led a team at a medium-sized startup - where did time go!?

Anukriti: Hiya! I’m Anukriti, and I’ve been managing designers for almost 3 years now. Before that, I spent a decade as a product designer, working in both India and the U.S.

Something I’ve noticed is that there aren’t many folks with my background openly sharing their leadership journey. I’ve been mentoring for a while and often get questions from mentees about leveling up in their career—and I know how valuable those insights can be!

Harrison: I’m excited for this catch-up because I’ve been exactly in your position at some point, I’m also curious to learn more about your perspectives.

Expectation: Leadership is the next step after mastering design craft.

Reality: Leadership requires an entirely new skill set beyond design expertise.

Harrison: I’m curious what made you get into management?

Anukriti: As an IC, I loved crafting experiences. Meanwhile, I’d also observed that beyond the pixels, there were bigger decisions that shaped the direction of a product. I wanted to go beyond designing products to creating a space where design is in the driver seat, where designers can thrive. For me, moving into management was not about stepping away from design; it was about scaling my influence and impact, and helping others do their best work.

Harrison: I must say, that resonates with me a lot. I’ve always been an entrepreneur at heart and there’s some great crossover in what you’re describing.

Anukriti: As a senior designer, I was so focused on my craft and growing it. If I’m honest, I thought moving into management would feel like the natural next step after years of refining my craft. But right now, it’s like I’m learning an entirely new job. Now, I’m navigating a design escalation, a change in priority, an upcoming project review all in the same day–it’s about processes and people all day.

Harrison: Exactly! And it’s even more apparent as you climb higher. As a director, I’m not just managing people or projects, I’m managing up, down, and sideways!

Anukriti: Managing up, down and sideways sounds like another topic of discussion!

Harrison: lol I’m making a note of that!

Anukriti: An ex-manager told me how they’d write their updates for their manager structured by people, process and product. That stuck with me, and now, I constantly find myself thinking about design management in those three pillars.

• People: Supporting my team, clearing roadblocks, and making sure they have the right opportunities to grow.

• Process: Ensuring collaboration is smooth, setting up feedback loops, and helping designers work effectively with cross-functional teams.

• Product: Advocating for design at a strategic level, influencing roadmaps, and identifying the right problems to solve (not just the right solutions).

So to summarize, my overall priority is solving problems for my team so they can focus on their work, simplifying product problems to actionable strategic ideas so we can impact the business, and distilling leadership feedback into actionable steps.

How’s it different for you at the director level?

Harrison: When I speak of managing up, down and sideways, I think of it similarly: I have directors, managers/leadership (up), I have peer groups (sideways). It’s important that we all stay aligned. The detail based on who they are and what’s top of mind of them is where the delivery of that message is different because one may be to inform, act, or influence.

On processes, I think it’s important not to get too caught up on processes. I once had a skip report tell me they couldn't connect with their manager because there was too much process, the order of things almost felt too rigid to talk about real things. Never forget there are people on the other end of things.

Here are things top of mind for me…

• Are we clear on our objectives?

• Are the right people working on the right projects?

• Are there opportunities to consolidate duplicate efforts

• When we get feedback from the team - how do we act on it, how can we equip managers to up level their team.

Expectation: You’ll be less hands-on with design work.

Reality: You’ll still engage with design—but differently.

Anukriti: If I’m honest! There are days when I do miss getting into the zone, designing hands-on. How did you navigate the transition into being hands-off?

Harrison: It’s a common feeling to miss the execution part of design. But remember, your design sensibility is still critical, just in a different way. So while it’s no longer about delivering the work; you’re guiding the team’s vision, giving meaningful feedback, and ensuring alignment with broader goals. It’s still creative work, just at a higher level.

I see no difference in facing some of the unexpected challenges we face as an opportunity to ideate. All organizations need some level of design to them, you’re just not necessarily doing it in the same tools necessarily.

Anukriti: Yeah, I’ve noticed that even though I’m not actively designing, my craft knowledge still plays a huge role in how I’m involved in shaping the design strategy. I often jump in to create a presentation or even mock some strategic concept mocks, especially when I can’t stop thinking about a member problem our team is solving for! Other than that, facilitating cross-functional discussions, leading workshops or helping the team think about new ways to approach a problem, I’m still flexing my creative muscle - just differently!

Harrison: That’s spot on. It’s not about letting go of design, it’s about engaging with it in a more strategic way. An added thing about managing is that you also see what's happening in other parts of the business so there's a real opportunity to connect the dots in a way that you may not see if you’re in IC. In the long run this can create meaningful impact in an organization.

Expectation: You’ll have more control over decisions.

Reality: Design leadership is about finding the best path

Anukriti: I assumed that with leadership would come the ability to set the direction and make key decisions. Well I do influence decisions, but most days it feels like I’m balancing conflicting priorities—business goals, stakeholder expectations, and my team’s needs—all while navigating shifting deadlines and resources–that stuff is hard for real! One thing I’ve realized is, being authentic and transparent with my team helps– so even when things don’t go exactly as planned they understand why decisions are being made and feel empowered to contribute to the best possible outcome.

Harrison: Welcome to the club! Management isn’t about total control. It’s about navigating ambiguity. You’re advocating for your team, balancing business goals, and managing stakeholder expectations, and there’s rarely a perfect solution. It’s about finding the best path forward, whether it means pushing for a design-led approach, aligning with product priorities, or making trade-offs based on engineering constraints. There may be times when there are top down decisions get made where you don’t have much say in. There's never a dull moment.

It’s a bit like navigating the sea, some times the waters will be calm, other days it might get choppy. Hopefully you've got that rain coat ready, otherwise you'll learn to bring it next time.

Anukriti: hmm..So it’s not just me then.

Harrison: Not at all! My focus is always on creating clarity for my team, ensuring they have what they need to succeed, and helping them navigate uncertainty. Sometimes that means making tough calls or compromising on certain aspects, but it’s all part of the role.

Expectation: AI will replace designers/design leaders.

Reality: Designers are expected to be full-stack builders.

Anukriti: Honestly, I feel like the industry is moving so fast. AI is a whole other layer and I wonder if we’re preparing ourselves to keep up with it. The best thing to do is stay curious–keep learning and evolving ourselves. I think it’s less about AI replacing us and more about how we integrate it into our work to make us even better at what we do.

Harrison: You’re right. Staying connected to your craft and fostering a growth mindset are essential. The expectation for designers, especially senior ones, has evolved–we’re no longer just visual or UX designers. We’re systems thinkers, problem solvers, and business enablers. The most successful designers blend their craft, strategy, and soft skills seamlessly while balancing business goals. I think this will be essential for designers to stay relevant in a very competitive market.

Anukriti: And I’ve also noticed there’s an increasing expectation for designers to be proactive, not just reactive—to anticipate problems, propose experiments, and think about long-term impact to the product or business. I see more designers influencing roadmaps, making business cases for their ideas, and even driving growth strategies. It’s a shift, and it’s exciting!

Harrison: Exactly! I believe that design is more poised than ever to lead product strategy. That may just be my bias. I’ve often heard or observed teams that think of design as a part of the waterfall process–where it means they are the last ones expected to execute details on decisions that were already made.

The best-performing teams, though, share early and often. They integrate design from the start. Also PMs aren’t some all-knowing oracles of information, they have a supporting cast that they work with. The most successful designers are ones that have functional and business knowledge, and are also able to craft compelling narratives to shape decision-making. Really think, are you leveraging the supporting cast? If not, start making those connections today, regardless of what level you’re at. There's no reason why this should not be happening more. In fact maybe the role of strategic lead can shift to different disciplines over time!

Anukriti: That’s so true. While core design craft will always be important, design is no longer just about execution; it’s about strategy, systems thinking, and rapid iteration. And with AI accelerating things even further, the best designers will be the ones who adapt, learn, and who drive change rather than waiting for it to happen. In fact, I think we’re going to see the role of a strategic design leader evolve even further—maybe we’ll see an era of super-design-leaders?!

Harrison: Super-design-leaders? Let’s hope that isn’t the title, but I do think the job description is due for a much needed update. The organizations that still see design as an afterthought need a wake-up call because the pace of innovation/iteration is speeding up. The role of a designer is changing fast, and those who embrace that shift will thrive. I’ve got design founders riffing with ideas in their heads on conversations we had, that move into a tool that can create a functioning prototype the same day, and can build in integrated customer feedback cycles within the week!

Anukriti: The way I see it, AI isn’t here to take our jobs—it’s here to take away the mundane, repetitive tasks so we can focus on the work that really matters. The thinking, the strategy, the storytelling—designers who embrace that will be the ones shaping the future, not fearing it.

Final thoughts

Anukriti: Thanks, Harrison! This conversation has reinforced what I’ve been learning leadership isn’t about having all the answers. It’s about guiding your team through uncertainty, making sense of ambiguity, and creating an environment where great work can happen. It’s about showing up, listening, and leading by example.

For all the aspiring design leaders out there, here are some key takeaways:

• Lead beyond titles: Leadership isn’t about a job title; it’s about how you show up, support others, and drive impact. I’ve also written about this here

• Develop a bias for action: Don’t wait for permission, take initiative, when you see something broken, raise your hand and propose solutions proactively.

• Embrace ambiguity: Design and leadership both require navigating the unknown. Get comfortable with not always having clear answers.

• Stay connected to your craft: As a design leader, understanding the nuances of design is critical in advocating for your team and making informed decisions.

• Be curious: The best leaders never stop learning, about their industry, their team, and Resources:

Book recommendations:

• Radical Candor – Kim Scott

• The Making of a Manager – Julie Zhuo

• Dare to Lead – Brené Brown

• Creative Confidence – Tom Kelley & David Kelley

• Leaders Eat Last – Simon Sinek

Design leadership is evolving, and so are we. What are your biggest takeaways from your design leadership experience? What trends are you seeing? Drop them in the comments!

Stay tuned for the next article in the series, Day in the Life of a Design Leader, which drops next Wednesday.

Celebrating Five Years

Technically Speaking will turn five in March. What a ride it has been! We launched during the pandemic, hosted live sessions on Clubhouse, produced 80 episodes, and held in-person events in San Francisco, Oakland, Brooklyn, and Lisbon. It has been an incredible journey.

Building Global Community

From the start, Technically Speaking felt like the right thing to do, something the world truly needed. We have been able to create a platform and foster a global community. The show has been downloaded in over 100 countries. I still receive messages from people who have found inspiration, hope and insightful new perspectives and approaches through the diverse voices we have featured.

Reflections on 2024

This past year was one of highs and lows. I celebrated seven years at LinkedIn, a decade of living in California, and I got married over the summer. However, just eight days after my wedding, my mother passed away. It was devastating. She had been relentless in her support.

Her passing led me to re-evaluate many things, including the future of this project. After careful thought, I have decided to pause production on new episodes in their current format. We have had a great run, but the time investment has become too large to continue at this scale.

A New Chapter: Pivoting to Written Content

Technically Speaking will now pivot to written content with a focus on management, organizations and design leadership in this new era of AI. I believe we need fresh, actionable approaches to leading teams, both for individual contributors and managers. As someone who has been building teams and products for over a decade, I see this as a unique moment that demands an evolution in how we think and talk about leadership.

I plan to share best practices, experiences, and perspectives I have gained in hopes that they will inspire and guide you on your own journey. While select articles will be free, I will introduce a paid tier for deeper, and more comprehensive insights.

Looking Ahead

Do not worry, you can still access all previous Technically Speaking episodes for free. I also have a few unreleased episodes from last year that will be coming out this month, so stay tuned.

Thank you for being part of this incredible journey. I am excited for what comes next, and I hope you will join me for the ride.