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.
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.
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