Favorite books of 2020

I listened to a bunch of books last year. On walks with the dog, on the way to and from mountain biking and snowboarding, and on countless road bike rides around town. These were my favorite:

Ealonor Olyphant Is Completely Fine by Gail Honeyman
This book was hilarious but also wrecked me. I couldn’t stop thinking about it and has stayed with me more than any other book has.

Maybe You Should Talk to Someone by Lori Gottlieb
I mean, who doesn’t want to know what therapists really think, how they work, and what they talk about with their own therapists? Also, it’s hilarious.

Dear Edward by Ann Napolitano
I need a good sad book every once in a while.

Powerful by Patty McCord
Practical and no-nonsense. I listened to this twice and then re-listened to certain bits. I was going through a tough time at work and this book was one of the things that helped me through it.

Daisy Jones & The Six by Taylor Jenkins Reid
Love the format, almost felt like you were listening to a music documentary. Read by a bunch of different actors. Made me start listening to Fleetwood Mac again.

The Seven Husbands of Evelyn Hugo by Taylor Jenkins Reid
Who knew I needed a love story? A full life lived.

Full list:

The Seven Husbands of Evelyn Hugo by Taylor Jenkins Reid, Daisy Jones & The Six by Taylor Jenkins Reid, Powerful by Patti McCord, Dear Edward by Ann Napolitano, Maybe You Should Talk to Someone by Lori Gottlieb, Ealonor Olyphant Is Completely Fine by Gail Honeyman, The Nix by Nathan Hill, Where’d you go Bernadette by Maria Semple, Hard-Boiled Wonderland and the End of the World by Haruki Murakami, The Windup Bird Chronicle by Haruki Murakami, Convenience Store Woman by Sayaka Murata, Strange Weather in Tokyo by Hiromi Kawakami, In the Woods by Tana French, Normal People by Sally Rooney, Conversations with Friends by Sally Rooney, There There by Tommy Orange, A Tale for the Time Being by Ruth Ozeki, Olive, Again by Elizabeth Strout, Self Compassion by Kristin Neff, Nine Perfect Strangers by Liane Moriarty, Such a Fun Age by Kiley Reid, Pieces of Her by Karin Slaughter.

Solution mode

I tend to think about things for a bit before sharing with others. I also really like to fix things. This combination can sometimes lead to jumping into solution mode really fast when I’m discussing with others. This happened yesterday when I realized the person I was having a conversation with didn’t even agree on the same problem I was coming to him with. And I was already talking about potential solutions! Our conversation didn’t get far and I had to back up and start again.

Since a big part of my job is coming up with solutions, I think it’s important to get it right. It’s also important to know when solutions are necessary. I jotted these notes down based on my conversation yesterday and others that I’ve learned from in the past:

When someone is coming to me with a problem:

  1. Listen.
  2. Give them a very quick high level overview of what they are saying so you know you have it right.
  3. Ask if it’s something they want help with solving or if they are just venting. If they are just venting, move on to other topics.
  4. If they want a solution: Agree on the problem(s) they would like to solve. Contribute additional info and suggestions if needed.
  5. Ask them for their thoughts on how to solve. Add your suggestions and agree on a path forward.
  6. Follow though and follow up.

When I’m going to someone with a problem I’m observing that directly effects me:

  1. Clearly communicate the problem from my perspective.
  2. Ask if they understand to get on the same page with them about problem I’m trying to solve.
  3. See if they agree it’s a problem to solve. If it is, ask the other person for their thoughts on how to solve. Add your suggestions.
  4. Agree on a path forward. Make it clear who will do what.
  5. Follow though and follow up.

Not just something to check off

I was recently reviewing a design iteration that wasn’t intuitive and lacked attention to detail. I thought to myself, “You (the designer) did research and checked out how others solve a similar problem. Go back to your research, look at your inspiration, and compare it to yours.”

Research, competitor analysis, or anything that you choose to do as a designer as part of your process to ship amazing things isn’t something just to check off. Refer back to it after every iteration. Ask yourself: Is my design as good as or better than this?

When you’re heads-down designing, it’s easy to get caught up in technical requirements and a million other things. Referring back zooms you out a bit to help you recall the bigger picture.

Proposing instead of asking

I recently joined a team of designers to lead. One of the patterns I noticed was a lack of ownership over the product areas some of the designers were working in. This came about in a few ways, but the biggest and most common sign was how someone approached a problem. Some designers propose a solution and others ask how something should be solved.

“Should the settings be in a modal or the sidebar?”

“Where should I show the error message?”

When I see a question like this being asked without an accompanying design, I reach out to the designer to learn more. I go about it differently depending on the person, but overall I remind them that this is their project. They are the lead designer on it and they were put on it for a reason! I ask them to use their experience to first ask the question to themselves and start exploring possible solutions. Then, when they had a good grasp and handle on the problem and many designs that solve it, to propose the best solution (or two) instead of asking others how to.

This is a small shift but I’ve seen it have a big impact over time on my previous teams. It leads to more thought out designs, fruitful collaborations, and a sense of pride and ownership over the final design that gets shipped and used by millions of people.

When you don’t have a Project Manager

The projects the designers on my team are working on are ones that don’t have a person whose full time job it is to Project Manage. This means that the job falls to different people. In the past, this job has fallen onto a designer, often as a second full time job. Over time, I’ve taken steps to make sure that doesn’t happen. After all, designers still need to design. Here’s the current way I’m approaching it.

Starting a project when you don’t have a full time Project Manager:

  1. When a project gets identified as a priority, the designer assigned to it spends some time understanding the problem and fully wrapping their head around it through exploration, research, etc.
  2. The designer writes out a list of user flows: all the things the user will be able to do when the first version of the project ships.
  3. The designer shares this list with the devs and they both iterate on it until everyone is in agreement and feels a shared sense of ownership over the project.
  4. The list then gets posted where everyone can see it and Github issues are made for each item in the flow, along with any corresponding dev tasks that are needed to support the flow. This provides a solid baseline and can help when issues “pop up” in the middle of design and dev cycles. The designers and devs can work together to decide if each one is worth adding to this release or the punting to the next.

Designs get added to issues, are iterated on with dev feedback, PRs are made, and as the product area comes to life, it can be tested. (The original list of user stories also makes for a great test plan.) Repeat a few times and ship it!

Not turning my problems into yours

I recently had a conversation with a design manager that started something like this:

“I want to start having my team to do daily standups.”
“Just so I can easily see what everyone is doing.”

This sort of scenario is pretty common and I’ve actually done this myself in the past. (Standups on their own aren’t the issue here, its any task managers ask their team to do that is strictly for the manager’s benefit only.) I now question every non core-work related task I add on to my team’s workload. Otherwise, it will quickly add up and a designer will spend more time not-designing than designing. It will also send the wrong signal: that I care more about the meta work than the core work.

Back to the original example: If you have trouble seeing what everyone is working on, I bet there’s another problem. Focus on that instead. For me, it was just not being used to working in Github after using another system for so long. I ended up finding a solution that surfaces each team member’s comments with images (designs) attached. That way, I can give design feedback without asking my team to add an additional thing to their to-do list. After all, I want them to focus on their work, not on fixing mine!

It’s not obvious

Note to self:

You have expectations. Don’t make people guess what they are.

Write them down. Share them openly. Refer to them regularly. Put them in context of the work. Let everyone know where they stand on each. Alter the expectations as things change. Repeat.

A good design lead

Today my coworker Brie asked me,

“What do you value most in a design leader?”

I think a good design director/boss/manager/leader is someone who:

  • Leads by example. 
  • Sets and upholds a high bar of design quality.
  • Has an efficient & high performing team.
  • Actively works on growing each designer.
  • Knows the strengths & weaknesses of each designer and assigns them work that is compatible but challenging.
  • Knows the difference between guiding and prescribing. 
  • Is resilient and can lead through change.
  • Knows when to listen and when to instruct.
  • Can manage up as well as down.
  • Gives both praise and critical feedback.

What did I miss?

2019 in books

Last year, I read and listened to 20 books. This was way more than usual. I think its because I didn’t work for three months and because I discovered Libby, an app that I hooked up to my (okay, my sister’s) library card and it just made it super easy to find and download audiobooks to listen to on road trips. (I took a lot of road trips.)

I use Goodreads to keep track, which also tells me I read 6,225 pages across 20 books. They were, in no particular order:

  1. Yes, Please by Amy Poehler
  2. Annihilation by Jeff VanderMeer
  3. Blue Nights by Joan Didion
  4. Bossypants by Tina Fey
  5. The Circle by Dave Eggers
  6. Commonwealth by Anne Patchett
  7. Dark Places by Gillian Flynn
  8. Everything I Never Told You by Celeste Ng
  9. My Brilliant Friend by Elena Ferrante
  10. Heartburn by Nora Ephron
  11. Hunger by Roxane Gay
  12. 1Q84 by Haruki Murakami
  13. The Year of Magical Thinking by Joan Didion
  14. The Making of a Manager by Julie Zhuo
  15. Let’s Explore Diabetes with Owls by David Sedaris
  16. What I Talk About When I Talk About Running by Haruki Murakami
  17. Sorry I’m Late, I Didn’t Want to Come by Jessica Pan
  18. The Summer of Naked Swim Parties by Jessica Anya Blau
  19. Go Set A Watchman by Harper Lee
  20. Wishful Drinking by Carrie Fisher

I bolded ones I would recommend to anyone reading this. Personal highlights include: finally reading a Joan Didion book after watching her documentary, discovering Murakami, and reading only one management/work-related book. (I find them mostly to be not great and too long/repetitive.) I’m excited to read more Didion and Murakami in 2020.

Starting a mentorship program

After co-leading the design org for a few months, we decided it was time to start a mentorship program. We had heard from several people that they wanted to learn from others within design, especially people they don’t get a chance to work with day-to-day. We decided to take a more informal and lightweight approach so we could test this out without too much overhead. Here’s where we landed and how we announced this to the designers:

Mentorship Pilot Program

We are proposing trial running a volunteer-based mentoring program for designers, where people can sign up as either mentors or mentees. Each cycle will run for three months and each pairing will be structured around a goal determined by the mentee (eg. “I want to prepare for giving a talk at a conference,” “I want to develop my prototyping skills,” “I want to be a better manager,” “I want to gain subject-matter knowledge about CMS systems”). How often the mentor and mentee meet will be up to the pair, but 1:1s twice a month are recommended.

At the end of the cycle, mentees and mentors will post a short, internal write-up detailing what each side learned during their time working together. You may also consider posting this publicly on our site automattic.design. The mentor/mentee pairing can choose to continue together for additional cycles if they mutually desire to do so.

If this pilot program is successful, we will open it up to the rest of the company. 

Why a mentoring program?

One of the difficulties a distributed work environment presents is that it becomes hard to understand where skill and subject matter expertise lies in an org for designers to go to when they want to learn from others. This lightly formalized structure allows us to match up people across all the design teams at the company with one another to encourage collaboration and growth in ways that might not happen organically.

Kicking off

A call for volunteers for both those wishing to be mentored, and those wishing to be mentors is now open for January – March (Q1) of /YEAR. Please submit by /DATE. 

First, talk to your Design Director or team lead. Let them know about your interest in the program, and if you’re going to proceed, keep them informed about the cadence you decide upon once you’re paired with a mentor/mentee. (Choose whether you’d like to be a mentor or a mentee, not both.)

Mentees will be asked to outline what they want their focus for the quarter to be centered on, so an appropriate mentor can be matched to them. If a good mentor match isn’t found from volunteers, we will approach designers in the org who might have the needed experience and interests to be a strong mentor for the mentee.

Notes for Mentors

  • Being a mentor doesn’t mean you have all the answers all the time. Be open to guiding mentees through challenges that might be new to you as well, and use it as an opportunity to develop your own skills at the same time.
  • Don’t spread yourself too thin. Make sure you can devote the necessary time to a mentee on top of your other work/management duties, and clearly communicate your availability with your mentee.

Notes for Mentees

  • Have a focus in mind. Timeboxing and having a clear achievement for the end of your cycle will make it easier for you relationship with your mentor to be focused and productive. Help them help you. 
  • Think of your mentor as your guide to help you reach one particular goal. They are not your manager.

Wrapping up each round

At the end of this cycle, mentors and mentees will write a post detailing what they learned in their respective ends of the process.