A design manager's playbook / compass

A battle-tested guide through the chaos & complexity per lessons learned

Sep 15, 2025

After nearly 3.5 years managing a design team at a solar tech startup, I've finally reflected upon and distilled some hard-won personal lessons. They’re admittedly not quite what HBR or McKinsey would say! 😅 They admittedly paint a picture of management as a series of frameworks and processes that, if followed correctly, will somehow make everything work smoothly. Well…the reality? Most of your time is spent in what I call the "messy middle" — that space between strategy & execution where everything is ambiguous, stakeholders have conflicting priorities (and incentives), and your team is looking to you for clarity you don't always have. Yikes.

So here's my field guide. Not another management framework, but a compass for when you're lost in that mess and need to find your way forward.

My core beliefs as a manager

After countless 1:1s, difficult conversations, and late-night Slack threads (with maybe a bourbon or two), I’ve landed on three core beliefs that guided my managerial ethos and practical approach:

Management is an extension of leadership — Your job isn't to make people do things. It's to create and shape the conditions where good design can thrive. Sometimes that means removing blockers. Sometimes it means challenging assumptions. Always, it means caring about the people doing the work — seeing them as humans first — and their work as expressions of personal & professional impact.
Coach ≠ Coddle — This one's borrowed from ‘Radical Candor’ but it's worth repeating: challenging directly while caring personally isn't just proverbial management speak. It's the difference between helping someone grow versus letting them stagnate while you avoid those awkward, uncomfortable conversations. It’s hard but therein lies growth for both you and your direct report.
Process = Rhythms, not a checklist — So many places I've worked at tried to solve culture problems with process documentation, rigorous mandatory protocols, or even scorecards. 🙄 OK here's what works better: supportive, collaborative rituals & cadences that become second nature (which are evolved over time, not mandated overnight), not frustrating bureaucracy that folks try to get around. Think drumbeat, not spreadsheet.

Tactical plays from the trenches

Here’s some specific impactful actions I've learned from managing through product pivots, team growth, and the general zaniness of managing in a startup context:

Reduce uncertainty — Your team doesn't need (or expect) you to have all the answers, but they need you to clarify what we do know and reconfirm what we're aligned on. Do this early, and do it often. Uncertainty can be the enemy of good design, and adversely impact team morale.
Alignment ≠ Consensus — Waiting for everyone to agree is how projects die slowly. Seriously! It’s more effective to act with judgment, by making decisions with the information you have. You’ll virtually never have perfect complete information. You can always iterate — and the vast majority of decisions you make in the realm of software are rarely “one way door”, with dire consequences — but you can't iterate on nothing!
Provoke with a POV — It’s not enough to only facilitate meetings. Show up with a perspective that sparks new ideas or good debate. Challenge your team, by leading with a suggestive design vision, even if it's imperfect. Teams need direction, not just coordination or “blocking & tackling”.
- Of course, doing this with your team necessitates creating a safe space of trust and vulnerability, so folks know it’s not “the boss says”… It can be a tricky balance!
Don't always ask permission — See a gap that needs filling, or opportunity to seize? Go ahead and fill it by rolling up your sleeves and getting into the work! Operate from good intent and move forward with your own best intentions, aligned with the team or project goals. It’s better to ask forgiveness than permission, especially in fast-moving environments.
- Of course, it’s good to “manage up” (and around) and connect accordingly with the proper “head’s up” with others.

The humanity layer

Here's what most management advice misses: you're not managing resources or processing headcount. You're dealing with humans who can have bad days, personal goals that don't always align with company objectives, and different ways of processing feedback. 😔 It’s not easy at all, but a few approaches to help:

Meet people where they are — Coach the individual in front of you, not your idealized version of what they should be. Some people need direct feedback. Others need space & time to process, or some demonstration with role modeling and examples. Flex and adjust your approach accordingly.
Some balls are made of glass — Management is all about juggling! 😆 But not everything is equally important, and not everything that gets dropped will break. Learn to distinguish between the glass balls (that shatter if dropped) and the rubber ones (that bounce back). Your time and your team's energy are finite, and perfection is not realistic to expect. Forgiveness is key.
Time is your scarcest design asset — So you must prioritize ruthlessly. Say “no” to meetings that could be Slack messages or don’t need you unless making decisions or providing critical context. Protect your team's deep work time like it's sacred (because it is), as well as your own time!

Rituals that can build culture

Culture isn't built through company values posters. It's built through consistent practices that reinforce what you truly care about for the betterment of the design org overall:

Design reviews as craft-sharpening — Design reviews shouldn't simply be approval gates. Use them to elevate and clarify everyone's design thinking. Ask those crucial questions borne out of curiosity, to make the work better. Challenge project assumptions to spur new altitudes of perspective around the problem. Make it about the quality of thought & problem framing, not just the output.
1:1s for growth / mentorship — These moments aren't status update meetings. Use them to understand where your people want to grow, what's blocking them, and how you can help. Career development conversations are among the most important meetings you'll have, with long-lasting impact!
On-sites with purpose — Remote work is super awesome and convenient for a million reasons, but humans do need to connect. 🙌🏽 When you get together, make it count. Prioritize on relationship-building, collaborative workshops, and strategic alignment, not presentations you could have done over Zoom.

In sum, design management isn't about having all the answers. It's about helping your team navigate uncertainty while maintaining quality standards and human dignity with a sense of authentic purpose, or presence. Indeed, some days you'll feel like a therapist. Other days you'll feel like a translator between business needs and design principles. Most days you'll feel like you're making it up as you go along! 🙃 But that’s OK, because that's totally normal. And if you care enough to think about it this deeply, you're probably actually doing better than you think.

This manager’s compass doesn't eliminate the mess; it just helps you find your way through it. 🙏🏽

What resonates with you from your own leadership experience? What would you add to the compass? I'd love to hear about the messy middle moments that taught you the most about management.