My dad often told me he could see me going into sales and I’d often reply with a scoff. I wanted to build things, solve real problems, turn chaos into something that actually worked. Sales was for people who didn’t want to create something. I had a plan, and it did not involve a quota.
Years later, deep into a career centered around craft, I had to reckon with something. The part of my job I had grown the most in and the part I looked forward to the most, was the part where I walk into a room, shine a spotlight on the work, and convince people. Convince them this idea is Worth pursuing. Worth fighting for. Worth making real. My work never saw the light of day if I couldn't get people excited enough to build it with me.
My dad was right. Turns out I went into sales after all.
I was terrible at selling ideas for longer than I'd like to admit. I remember a client meeting that went sideways from the first slide. I had everything: research, polish, a narrative that felt airtight. They questioned every single choice. I walked out deflated and went straight to my mentor. He heard me out, and told me: "You're approaching it like a lawyer. Trying to win. But your clients don't need to submit to you. They need to be on your side.”
That advice landed. I'd been designing with empathy for users and then walking into client rooms like I was there to prosecute them. The empathy just switched off.
So I changed my intent. Instead of trying to deliver a conclusion, I started trying to guide the room to one together. The simplest tool I found for doing that was to stop saying how things ought to be and start asking “what if we did it differently?”
What if it looked like this?
What would that mean for your users?
What would it take to get there?
Not "the data says we must do this."
Not "this is the right answer."
Just: what if...
If I ask you to picture a castle, yours won't look anything like mine. Different towers, different stones, different sky. And I don't need you to want my castle. I need you to want yours. When I open with mine, I've narrowed your imagination to fit around my vision, and something gets lost. ‘What if’ keeps the image open long enough for you to fill it in yourself.
It’s worked for me when leading teams towards change, too. But I want to be honest about how it actually works in practice, because organizational change doesn't happen because someone asked a good question in a meeting or an e-mail.
At one agency I worked at, the design team rarely shared work in progress. Unforgiving processes favored polished files, scheduled reviews, and work that had already calcified into something that felt difficult to challenge. Feedback became cautious. Revisions felt like admissions of failure. The work that made it to clients was fine, but it was rarely surprising, because we had optimized away the freedom to reach.
I didn't call a meeting and announce that we were doing things differently. That's not how people change.
Instead I started having individual conversations:
With designers, I asked what it felt like to get feedback on finished work. Most of them, when given the space to be honest, admitted it felt like a verdict.
With project managers, I asked what they thought they were actually seeing in those reviews, and whether they felt like they had any real influence on the outcome.
With creative directors, I asked what it would mean for the quality of the work if they were seeing it three weeks earlier.
Nobody disagreed with the diagnosis. They just hadn't been asked to look at it directly.
From there it was incremental: A casual share here, an informal gut-check there. I framed early sharing not as a new process but as a favor: I'd love a quick gut-check before this goes too far in one direction. When it worked, people noticed. When a project came out stronger because a creative director had caught something early, I made sure that story got told.
Eventually it wasn't my idea anymore. That's how you know it worked.
The team trusted each other more because people had been invited into the work before it was finished, and that changed how we felt about it. Reviewers stopped feeling like judges. Designers stopped performing. The work got better, but the more lasting shift was that the team started thinking out loud together instead of presenting conclusions at each other.
Collaboration that happens in the open is how work moves forward.
The most useful thing I can bring into a room usually isn't an answer. It's a question that makes the answer belong to everyone.
