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12.03.2026 06:36
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📍 Hosting bi-monthly livestreams about everything Craft, Career, Calling for designers, sign up to get the written recap live.uxplaybook.org
📺 For a better streaming experience, go to YouTube (recorded): youtube.com/live/bLOygHa...
Together with Dazl
A designer’s best prototyping friend.
→ Show your ideas (in real code)
→ Edit on the canvas, visually
→ Close the comms gap
The workspace for modern product teams: dazl.dev
🙋🏻 Drop your questions in the comments: www.linkedin.com/events/howto...
🎙️ We’ll answer them next Wednesday, Mar 18th!
Ryan is the founder of CDO School, author of Business Thinking for Designers, and works 1:1 with senior design leaders on how to be strategic at work.
If you've been wondering what your career looks like in an AI-first world…
This one's for you.
That's why I'm bringing Ryan Rumsey on to speak about How To Build A Personal OS With AI
We're diving into how to turn your expertise into something AI can actually use
1. The context layer
2. How to codify your expertise
3. How to build AI agents with your judgment
And all of your Qs!
Most designers think AI is coming for their job.
Actually, AI is coming for the execution part of their job.
Which means your value shifts to:
→ Your judgment
→ Your frameworks
→ Your way of thinking
The problem? It's all stuck in their head.
📍 I go super deep on UX management tactics here: uxplaybook.org/senior
This transparency does two things:
1. Shows you're being intentional, not just bossy
2. Teaches them when speed trumps learning
💡 Pro tip: When you switch from coaching to directing, SAY IT OUT LOUD.
"Usually I'd coach you through this, but we're 2 hours from the client presentation. Here's exactly what needs to change and why."
• Legal/accessibility requirements are non-negotiable
• The same mistake keeps happening (they're not learning)
𝟰. 𝗞𝗻𝗼𝘄 𝘄𝗵𝗲𝗻 𝘁𝗼 𝗷𝘂𝘀𝘁 𝗳*𝗰𝗸𝗶𝗻𝗴 𝘁𝗲𝗹𝗹 𝘁𝗵𝗲𝗺
Sometimes coaching is the wrong move.
Just tell them when:
• Client presentation is in 2 hours
• They're about to make a career-limiting mistake
What this does:
- Builds trust (you're not micromanaging)
- Creates psychological safety to experiment
- Lets them learn from experience, not lecture
- Sets clear boundaries so failure doesn't affect timelines
Pro tip:
Use the "safety net" approach:
"I think approach A might have issues, but let's try it. Here's the constraint: if we don't see progress in 2 days, we pivot to approach B."
3/ Let them fail (safely)
This is the hardest one for new managers.
You KNOW their approach won't work.
You've seen it fail before.
But sometimes they need to learn it themselves.
One designer told me: "I realized I wasn't actually stuck. I just wanted validation."
Exactly.
Pro tip:
Set a time limit: Spend 30 minutes exploring this, then let's sync.
Why this works:
Time constraints prevent overthinking
Stops them from waiting for you to solve everything
Forces decision-making under pressure (real-world skill)
2/ Make them do the heavy lifting
Designer: "I'm stuck on this interaction"
Bad response: "Try a bottom sheet instead"
Good response: "Show me 3 solutions by end of day. Pick your favorite and tell me why."
This does 3 things:
Shifts them from defensive to reflective mode
Reveals their thought process (or lack of it)
Makes them justify decisions like they will in stakeholder meetings
They’ll learn to critique their own work before you do.
Pro tip:
Add "Help me understand..." before giving feedback.
→ Help me understand why you chose this UI pattern over something already existing in our design system?
1/ Ask, don’t tell
When a designer shows you work, resist the urge to fix it.
Ask instead:
→ What alternatives did you explore?
→ What user problem does this solve?
→ What would you change if you had more time?
So if you’re a UX manager doing this right now — stop.
Here’s the framework I wish I had back then:
1. Ask, don't tell
2. Make them do the heavy lifting
3. Let them fail (safely)
4. Know when to just f-ing tell them
Full deets below ↓
Know why?
They weren't learning HOW to think.
They were learning how to wait:
For my fixes
For my opinion
For me to save the day
That’s when I realized the problem was me.
I wasn’t building designers.
I was building dependents.
When I was Head of Design, I made one massive mistake.
My team would bring me work. I'd rework it in front of them.
They’d nod
They’d take notes
They’d say, “Got it”
What happened next time?
They brought me the same (poor) quality of work.
How to be a UX manager (part 3)
The Stop-Doing-Their-Work Framework:
📰 Senior, here’s my weekly writeup, about the work behind the design work: newsletter.uxplaybook.org
The company had a problem.
They believed I could solve it.
I get promoted.
That's it.
If you're waiting for your turn for a promotion. There is no turn. Seniority doesn't get you promoted.
Solving the right problem does.
🫳🎤
P.S. Still telling yourself "next year" or you finally doing this?
↓
I lived this experience.
I wasn’t the most talented designer by any means. Somehow I got to Head of Design in 4 years.
It wasn’t my reward for time served
It wasn’t a given for my seniority
It wasn’t about my “turn"
Promotions are business decisions.
↓
3. Being there longer ≠ mattering more
The question isn’t:
“How long have you been here?”
It’s actually:
“Where can this person create the leverage?”
Sometimes that’s:
∙ As a domain expert
∙ As a Staff / Principal IC
∙ As a cross-team problem solver
Not a manager.
↓
2. Leadership is a different skill set
Design excellence ≠ people leadership.
Managing designers means:
∙ Navigating politics
∙ Hiring, firing, feedback
∙ Protecting team morale
• Handling business pressures
∙ Coaching underperformance
Many strong designers don’t want this. And that’s okay.