Management Values I Didn’t Expect to Learn

Design management is harder (and better) than I thought.

I’ve been a design manager since 2022. Like many others in this role, I’ve been slowly shaping and reshaping my management values. This is where I’m at now. I’ll likely update this over time, or do a part 2.

I was an individual contributor (IC) for over 20 years before moving into management. Even then, I was reluctant to take the job because I enjoyed doing the work so much. So I’m familiar with ICs, how they think, and what sorts of things they think about. Things like craft, product quality, three-month timelines, career development, and recognition.

Now that I’ve been in management for a while, I also see how leadership thinks too. They’re thinking about strategy, year-long roadmaps, revenue, and the overall health of the organization.

I have a foot in both worlds, which will be a common thread in this article. I can help ICs think a little more strategically, and I can help leaders stay closer to the work.

Whether or not “manager” is in my title, I try to be that bridge, and to help everyone around me get just a little bit better.

It All Starts With Team Health

No one does their best work when they’re stressed, burned out, or afraid to speak up. Great collaboration comes from trust and honest feedback that never feels personal or belittling.

I try to build that culture:

  • Giving people both async and live ways to contribute, so it’s not just the loudest voice or one in an optimal timezone that wins.
  • Making it normal to share work early, not just when someone “feels it’s ready for critique.” We’re going to get leadership’s feedback at some point, better to get it early when there’s still time to address it and possibly change direction.
  • Being realistic about bandwidth and not overcommitting folks. I sometimes have to talk someone out of saying “yes” to something when they don’t realistically have time for it.
  • Encouraging experimentation and making room for failure as folks drift into adjacent roles. Especially now as research, design, product, and engineering move closer together.
  • Being vulnerable myself: sharing a past failure with the team, saying “I don’t know the answer”, or admitting when I’m struggling.

With a healthy team culture, everything else gets easier.

Player coach

Some managers are comfortable not doing design anymore. Not me. I prefer being a player-coach, coaching the team and still doing some actual design work myself.

Most of the leaders I respect are close to the craft. Especially now, when AI enables everyone to build more, there’s less room for people who don’t actually do the work. I spend about equal time between people problems and craft problems.

I need real knowledge of the craft to be a useful thought partner. If I drift too far from the work, I stop speaking the same language as my ICs. I miss the little details that matter. Without that context, my input feels generic and surface-level.

Being good at the people side helps me move projects forward by unblocking decisions, aligning folks around a goal, and building momentum.

Getting better at the craft makes meme better at the work itself. The product experience, along with its complexity and details. The thing customers actually experience.

You need both to lead well.

That said, I’m mindful not to take on any large or “critical path” projects. My design contributions usually involve things like designing small features, covering a project when a designer is on PTO, bug fixes and polish, taking “busy work” from my ICs, and starting larger vision work to hand off to someone else.

This keeps me hands-on, but not in the way. That balance is important for me. That balance is important for me.

Delegation is a Sliding Scale

Delegation is often treated like a light switch. You either do the work yourself or you hand it off completely. In reality, it’s more of a sliding scale.

Sometimes you take on the task yourself. Sometimes you work alongside someone. Other times, you let them run with it. The right approach depends on the situation, their experience, and how much I want to check in along the way.

For example, I stay involved in the day-to-day of important projects. For smaller ones, I might delegate fully and just say, “Let me know how it turns out” or “Holler if you need anything from me.”

It’s less about rules and more about knowing my team.

Avoid Becoming a Bottleneck

You may be lying to yourself when you say, “I’m the only one who can do this”. - Wes Kao

Wes’s quote stuck with me because I’ve caught myself doing exactly that. In the past, I've been guilty of “hiding” in the work I’m already good at, keeping it from others. I tell myself no one else can do X, but deep down it’s also pride in being the one who does it well.

It's important to be honest and call myself out in situations like this.

There are going to be new things that are ambiguous and uncertain, and it's going to feel tempting to delay thinking about those and focusing on what I know. There will always be too much on my plate. The job is to decide where I’ll have the most impact, usually not by falling back on what I’m already good at. That might mean passing on a design review I’d normally jump into so I can focus on a hiring decision instead.

An example is HTML email: Every job I’ve had in the last 10 years, I’ve been known as “the email guy” who knows how to code HTML emails. That may be true when I first join, but I make sure to document what I know so others can help themselves. As an example, I created an email design system during my time at Stack Overflow so each product team could build their own emails without being email experts.

Another example is design feedback. I can’t review everything in real-time, and I don’t want that to slow my team down. So I documented what I look for: my taste, established UX conventions, our design system, and the comments I repeat most often, and made a custom GPT for my team to use. I even added some of my boss’s feedback style.

The goal isn’t always to replace me, but to help my team go farther without me.

Clearing the Path

A big part of my job is helping my team focus on the work that matters most. That means filtering out noise before it ever reaches them. Not every request deserves their attention. I’d rather say no early than let distractions pile up. Pushing back is not always comfortable, but protecting the team’s focus is part of my role.

I also spend time clearing fog. Ambiguity slows people down. By sharpening the problem, setting constraints, or filling in missing context, I can help the team move faster and make better decisions.

And then there’s tension. Between what leadership wants, what the team needs, and what the product should become. I absorb that tension so my team doesn’t have to. That might mean telling leadership we need to slow down, or explaining to the team why priorities just shifted.

The team gets the clarity. I carry the weight.

Just Enough Process

Process helps teams stay on track, but too much of it kills creativity and momentum. When checkpoints and approvals pile up, the work starts to feel like factory output. I’ve seen projects where the design review process added more overhead than the design itself. No bueno.

My goal is to have enough structure to guide the work, but allows detours along the way for folks to find the right solution. Like prototyping an unexpected idea.

I teach designers to use their own judgment so they need me less for permission and more for refinement. Figma’s Jonas Downey has a few great prompts to get designers thinking:

  • What would you decide if it was fully up to you?
  • How would you explain this to a user?
  • How does it support our business?
  • How could we simplify it?

I love using these in design reviews to get the discussion going when the group is quiet, and they always spark better conversations than another checklist would. These nudge people toward clearer, stronger work without adding more process.

The Manager’s Quiet Kind of High

I’ve made peace with not getting that daily high from making something with my own hands. I get satisfaction from watching my team build great stuff and grow personally, and knowing I played a part in it.

There’s power in those indirect wins:

  • Clearing the path so someone can ship something they’re proud of.
  • Coaching someone today so their work months from now is stronger.
  • Rejecting the urgent-but-low-impact so the team can focus on what matters.

Like when a designer nails their review with leadership, a coworker compliments one of my reports, or our work moves an important metric.

These moments aren’t always loud or concrete, so I keep a section for them in my brag document so I don’t forget about my wins as a manager.

Don’t Forget Who You Are

Design work is tough, even in the best conditions. As a manager, one of the things I enjoy most is finding ways to take pressure off the team when things get especially stressful.

I still upload unhinged custom emojis to company chat, host silly birthday games over Zoom, and drop funny links in chat.

[cowboy emojis: Cowboy emojis, a tradition started by a former co-worker.]

Don’t get me wrong, I’m mindful of what I say publicly because I realize the weight my words and actions carry as a leader in the company. But it’s important to lighten the mood once in a while That spirit finds its way back into the work and helps people feel psychologically safe.

Everyday is Winding Road

Like I said earlier, I’m still learning and my thoughts are evolving. I’m not a seasoned pro, but after a few years in management I’ve learned a few things worth sharing. I’m pressing publish now… curious to see how this will read a year from today.

Thanks for reading!