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.

In this episode of Technically Speaking, I'm joined by Jermaine Murray also known as The Jobfather. He's a career coach and founder of Jupiter HR, who's vision is to help 500 Black professionals land jobs in tech (he’s currently at 448).

We get into the state of today's job market from employer indifference toward DEI to the rise of AI, and what it actually takes to future-proof your career. Jermaine shares his approach to identifying green flags when evaluating companies, how to avoid burnout while doing meaningful work, and why now is the time to invest in yourself even when the odds feel stacked against many.

This one's part motivation, part strategy, and packed with sharp insights for anyone navigating change. We also had a few moments of laugh out loud laughter from his stories.

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Key Takeaways

• Leverage Your Past Skills: Don't abandon previous experience when transitioning to tech - assess what you're good at, what you like, and what you've had success with to find the right tech role

• Job Market Reality Check: Current tech job searches take 9-18 months (vs. 2-3 months previously) due to increased competition and fewer opportunities - timing and referrals are crucial

• DEI Shift: Companies have moved from active diversity requirements to "indifference" - focus on finding places where you're appreciated, not just tolerated

• Embrace AI as a Tool: You won't be replaced by AI, but by someone leveraging AI better than you - adapt and use it as a productivity multiplier rather than fear it

• Ask the Hard Questions: Always interview to know your market value, and directly ask about things that make you anxious (company stability, layoff history, diversity support) - how they respond matters more than what they say

Notable Quotes

"Ask them the most awkward things. The things that make you feel anxious. Ask them... what happens with disruptions or new technologies."

"Taking an interview is not the same as job hopping... you should always be interviewing so that you know what your real time value is and whatever decision that you make is an informed decision."

"You can't be scared of AI... you will be replaced by somebody that is leveraging AI rather than AI itself."

"Why do you think that your employer owns the skills that you carry with you in your body? They own the time that you work for them, but all the skills you carry with you."

Resources

• Follow Jermaine on LinkedIn, Twitter, Instagram, TikTok

• JupiterHR

• Harrison on LinkedIn, Instagram

Timestamps

00:00 Introduction

00:30 Meet Jermaine Murray "The job father"

00:47 Jermaine's mission and success stories

02:05 Balancing work and health

03:01 Gaming talk: from Final Fantasy to Nvidia

04:30 Current obsessions: fitness journey

07:41 Unusual jobs and memorable stories

11:59 The origin of 'The job father'

17:54 Defining tech and career advice

24:29 Understanding career motivations

25:10 Leveraging past skills in new roles

27:35 Recruitment strategies and market trends

30:51 The impact of DEI in the workplace

35:02 Navigating AI and technological advancements

40:18 Identifying green flags in job opportunities

47:25 Final thoughts and contact information

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.

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We get into:

• Why she left Google to build Right AI

• The risks no one’s talking about in AI product development

• What MoviePass, the Black Death, and Silicon Valley have in common

• The real environmental and economic costs of running LLMs

• What design leaders need to unlearn now

• Her “Mindful AI” framework for building responsible, people-first experiences

• Why systems thinking beats wireframes, and what it really takes to design for the future

Ovetta breaks it all the way down, history, economics, tech, and the human cost of innovation. This one’s part philosophy lesson, part design critique, part wake-up call.

Timestamps

02:09 Origins of Ovetta's company Right AI

05:15 Moving fast and breaking things...again

10:20 The risks of funding with no business models

18:56 Enviornmental sustainability

30:18 Principles of building a responsible experience

34:01 What's top of mind for design leaders?

43:24 Closing

Mentions

• Right AI

• LinkedIn - Follow her on LinkedIn for hot takes and sharp truths

• The Philosopher’s Zone (Podcast) – She references a philosophy podcast about the Dark Ages

• Gutenberg & the Printing Press – Used as a metaphor for today’s AI hype

• MoviePass – Referenced extensively as an analogy for unsustainable business models

• Black Death / Plague – Referenced in historical parallel to today's societal reset

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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.

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We get into:

• Why he shifted from music to design, and now from design to building AI tools

• How he used AI to build a Figma plugin without any coding background

• The tools in his AI stack and how he actually uses them (Claude, Cursor, Lovable, Vercel, and more)

• What MCPs are and how they help Claude "remember" his context across chats

• Why rapid prototyping now beats hours in Figma

• His framework of “Software as a Gift,” building custom apps just for friends

• A look at the Jeopardy-inspired app he built for his trivia-loving best friend

Kyle brings curiosity, technical scrappiness, and real heart to everything he builds. Whether you’re a designer figuring out how to start with AI or just looking to rekindle some joy in your craft, this one’s for you.

Timestamps

00:00 Introduction

02:07 Kyle's musical interests and background

06:41 Kyle's journey into "vibe coding"

13:02 From an early course to building som ething functional

20:59 Leveraging MCPs to build smarter

26:26 Software as a gift

36:49 Where AI has influenced Kyle's design process

38:59 How can design org incentivize to close the skills gap

41:29 How to get started with AI

43:15 Closing

Follow Kyle

• Website: https://kylezantos.com

• Twitter: https://twitter.com/kylezantos

• LinkedIn:https://www.linkedin.com/in/kylezantos

Mentions

• Jeopardy practice game — Kyle launched (in time for this release)

• Claude (by Anthropic) — AI assistant used throughout Kyle's workflow

• Cursor — AI-first code editor forked from VS Code

• Lovable — No-code AI app builder Kyle uses for software-as-gift experiments

• Vercel — Deployment platform for full-stack apps

• SuperWhisper — Voice-to-text transcription tool

• Ammaar Reshi — Design leader at DeepMind; inspired Kyle's early AI builds

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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.

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We get into:

• The drag-and-drop design challenge no existing tool could solve and how he had to rely on his ingenuity

• Prototyping high-fidelity interactions with ProtoPie to shape engineering scoping

• Why working across time zones requires clarity, collaboration, and great prototypes

• How Canva Sheets makes data visualization, formulas, and mobile editing easier for everyday users

• The principles behind Canva’s “magic” AI features like Magic Insights and Magic Formulas

• Jay’s own side project: an article tracker app built with AI

• What working with AI taught him about the limits of solo building

This episode isn’t about slapping AI on a product. It’s about thoughtful design, real teamwork, and pushing past the hype to deliver something users actually need.

Mentions

• Canva Sheets: Jay’s current product focus

• ProtoPie: Interactive prototyping tool used for high-fidelity handoff

• Claude: Used for early AI prototyping

• Cursor: IDE for building with AI

• Jay Demetillo on LinkedIn: Follow his updates and perspectives

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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.

Subframe isn’t just another no-code platform or AI playground. It’s a visual way to build production-ready software, allowing designers and non-technical teammates to collaborate directly with engineers using code-native components, real-time prototyping, and AI-assisted workflows. Filip calls it “design with code.”

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We unpack what it really means to bridge the gap between design and development, the philosophical shift away from static mockups, and how Subframe puts creative control back into the hands of full product teams. We also get into:

• Why designers should think more like engineers (and vice versa)

• How AI becomes a co-creator, not a replacement

• What makes a good design system “trainable” for AI

• Why stress-testing components in Subframe feels like building your own mini design tool

• What it looks like when prototyping and production merge

If you’re a designer, builder, or curious product leader navigating the messy middle of AI and UI, this episode offers practical insights, creative inspiration, and a glimpse into the future of design tools.

Learn more at subframe.com

Timestamps

00:00 Filip Skrzesinski x Harrison Wheeler: AI Product Builders Series

00:25 Introduction

02:56 Where Subframe sits in the product development process

06:02 The origin story

10:39 The ideal customer profile

21:13 What makes Subframe stand out?

27:11 Where a designers job starts

30:15 Examples of how people are using the platform

34:51 How to get started within minutes

37:26 How organizations can embrace

40:18 Closing and whats next

Mentions

• Subframe.com — Official website

• Filip Skrzesinski on LinkedIn

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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.

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We get into:

• The hilarious and humbling journey of building AI-generated imagery

• Why good taste and team joy matter more than ever

• The pivot moment that saved Lummi.ai

• The surprising power of curating AI outputs

• Why code isn’t the hard part, and how AI is leveling the playing field

• His take on vibe coding, open-source design, and why now is the moment to build

This episode is a reminder that creativity, clarity, and a sense of humor are some of our best tools.

Mentions

• Lummi AI – Pablo’s AI-powered image generation platform

• Blush – His earlier open-source illustration tool

• Another Design Newsletter – Pablo’s newsletter with comics and commentary

• Another Design Newsletter

• Pablo Stanley on LinkedIn and Twitter

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• LinkedIn

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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.

This isn’t another AI hype machine. I’m sitting down with designers and builders who are actually shipping real work. We're digging into:

• Real talk on integrating AI into existing products and worklflows

• Play-by-play stories of launching net-new experiences (minus the vaporware)

• Honest takes on ethics, personalization, and what “future-of-work” really means for design teams.

Meet the line-up:

• Ovetta Sampson — Owner, Right AI: guiding SMBs through safe ML/AI adoption.

• Pablo Stanley — Founder, Lummi.ai: a fresh library of AI-generated imagery.

• Filip Skrzesinski — Co-Founder, Subframe: the UI design tool for the AI era.

• Jason Demetillo — Lead Designer, Canva Sheets: helping the creative workforce closer to getting things done more efficiently and effectively.

• Kyle Zantos — AI design consultant helping teams ship with emerging no-code aka "vibe-coding" tools.

The series drops Monday, May 5th.

You can follow on LinkedIn and subscribe to Technically Speaking on Substack to get access as soon as it’s available.

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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.