Four years ago, I wrote my thoughts on what makes a good design lead. I thought it would be a good time to revisit it as I recently hired a lead for our largest design teams at Automattic. During the process, I made an important shift inspired by a conversation with Matt. (Happy Birthday!)

Instead of hiring someone who I think would be a great person that could work for me, I looked for someone that I would be excited to work for. Someone I can learn and grow from, along with the team they will lead. We won’t improve our products, our designs, our organization, or ourselves, if we aren’t hiring and surrounding ourselves by people who are markedly better.

There’s also the very real fact of keeping great people. We now know that, by in large, people don’t leave bad jobs, they leave bad managers. A great lead is someone you are excited to work for. Regardless if that person works for you or you work for them.

A great design lead:

• Leads by example.
• Clearly articulates and upholds a bar for quality.
• Stays close to the customer and the product.
• Is focused on the work.
• Regularly moves through altitudes, from setting design direction to details like widows & orphans.
• Knows the strengths & weaknesses of each designer (including themselves!) and provides opportunities that are compatible yet challenging in order to facilitate growth and product excellent results.
• Is resilient and can lead through change.
• Gives ample feedback, both praise and constructive.
• Is always learning.
• Is someone you want to work for.

Getting feedback on a design iteration is an important part of the job. Sometimes it can result in a spiraling, often unproductive discussion. Over time, this leads to more time talking and less time doing. The user will not benefit from these discussions – they will only see and interact with your design. Focus on the design. Next time, instead of replying to feedback with an explanation: take it in, thank the person, and then reply with a design.

I’ve had this loose idea forming around what it takes to be a highly effective lead. It has to do with altitude. Specifically, the ability to quickly and consistently travel between the really high level to deep down in the details. Staying too long in either place causes you to be out of touch in some way – you can’t see the big picture, connect dots across areas, or ensure goals are carried through to quality output.

Designers are often hesitant to receive feedback on their designs from someone who is not close to the project.

“But they don’t have the context!”

This has always confused me. When I present a design flow, I find the people who are furthest away from the project gave really valuable feedback. They see things I don’t. And if I find myself having to explain things in order to figure out how to interact with my prototype, something is up.

After all, when this ships, the user won’t have been part of any of the project meetings, be aware of the research, any technical constraints, or otherwise. The design and implementation of it will need to stand on its own.

Of course I stole the title for this talk from George Orwell. One reason I stole it was that I like the sound of the words: Why I Write. There you have three short unambiguous words that share a sound, and the sound they share is this:

I

I

I

In many ways, writing is the act of saying I, of imposing oneself upon other people, of saying listen to me, see it my way, change your mind. It’s an aggressive, even a hostile act. You can disguise its aggressiveness all you want with veils of subordinate clauses and qualifiers and tentative subjunctives, with ellipses and evasions—with the whole manner of intimating rather than claiming, of alluding rather than stating—but there’s no getting around the fact that setting words on paper is the tactic of a secret bully, an invasion, an imposition of the writer’s sensibility on the reader’s most private space.

–Joan Didion, Why I Write

We’ve been doing the NYT crossword together every night for the past several months, which is a lovely way to end the day. This week, we started playing Wordle after seeing half the internet playing it. It’s so good. Here are the first four results, which are just fun to share. Can’t tell if we have beginner’s luck or if the crossword playing is helping. Probably a bit of both.

I’m still listening to books with the only exception being the physical books I bring along with me on camping trips in the van.

The books that have stayed with me
Ones I couldn’t stop thinking and/or talking about.

Ones I revisited

Getting Unstuck & From Fear to Fearlessness are recordings of Pema Chödrön giving talks on weekend retreats. I love listening to her and went back to both of these several times throughout the year.

Full list
with a ★ next to books I’d recommend to most anyone who asked.

And the books I’m in the middle of that I’ll carry into 2022 are Dune, Outline, and Hidden Valley Road.