Designing next to a founder

I’ve sat on both sides of this one. At Digs I was the founder, the person with the picture in my head that nobody else could quite see yet. At Flow I was the founding product designer and then head of design, working directly with our CEO, Adam Neumann, and my job was to take someone else’s picture and make it real.

Having done both, I think designing next to a founder is the best seat in the company. It’s also the one that asks the most of you.

Why I like the seat

When design reports straight to the person with the vision, nothing gets lost on the way down. You hear the idea in its original form, before it has been turned into a requirements doc. You can ask why. You can show something on Tuesday and have a decision by Wednesday.

That speed is addictive, and it’s a big part of why we were able to design five products from scratch at Flow with a small team.

But the speed comes with a responsibility. If you’re the designer closest to the founder, you’re also the person standing between that vision and everyone who has to build it.

A founder describes a feeling

I know this because I’ve done it to other people.

When I was running Digs, I would describe what I wanted in terms of how it should feel. I knew it when I saw it. That’s a completely reasonable way for a founder to think and a very hard thing for a team to build from.

So the first skill is translation. When a founder says something should feel warmer, or simpler, or more premium, I try to work out what they’re reacting to. Usually there’s a real, specific concern underneath: a customer they talked to, a competitor they saw, a worry about how the company is perceived. Find that, and the feedback stops being a matter of taste and becomes a problem you can solve.

The mistake I see designers make is taking the words literally. They hear “make it pop” and add color. The better move is to ask what would be true if this were working.

Protect the idea and the people

There are two ways this job goes wrong.

One is that the vision gets watered down. Every hard part gets negotiated away until what ships is fine and forgettable. If that happens, the founder was right to be frustrated.

The other is that the vision arrives at the team unfiltered, changing every few days, and people burn out chasing it.

I think a design leader’s job is to refuse both. I hold the bar on the idea, and I also give the team something stable to build on. That means I absorb a lot of the change myself. Not every thought a founder has on a Monday needs to reach the team as a new direction. Some of it needs a day. Some of it needs a prototype before it needs a meeting.

That isn’t hiding things. It’s deciding what is signal, and it’s one of the most useful things I do for a team.

Speed needs a system under it

You can only move at a founder’s pace for long if you’ve built something to stand on.

At Flow that was the design system, and it was the design engineers I hired to keep it honest in code. When the direction shifted, we could rearrange pieces that already worked together and had already shipped, so we never started over.

I think of a system as the thing that lets you say yes more often. Without one, every new idea costs weeks and you end up being the person who says no. With one, you can show a real version quickly and let the work make the argument.

What I’d tell a designer taking this seat

• Show, don’t describe. Founders react to things they can see. Bring the prototype.
• Bring options, with a recommendation. Three directions with no opinion gives them homework. Three directions with a clear favorite gives them a decision to make.
• Disagree early and in private. Then commit in public, fully.
• Learn the business. The founder is thinking about funding, hiring and survival. If you only talk about the interface, you’ll always be the junior voice in the room.
• Look after your team first. They should feel the excitement of the vision and very little of the turbulence.

Why it’s worth it

The reward is that you get to work on things that wouldn’t exist otherwise. A founder with a strong vision will ask for something unreasonable, and an unreasonable ask is sometimes the only way anything new gets made.

My job is to make it buildable without making it ordinary. When that works, it’s the most satisfying work I’ve done.