Kelly Hoffman

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?

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:

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

Automattic Thoughts

No question

I said yes to a big job opportunity this week without asking a single question. I had plenty of them, I just knew my own answer regardless. I also believe that when someone asks you to step into a new leadership role, there is going to be some ambiguity and part of your job will be to create clarity.

I said yes to something I was working towards professionally, even though it presented itself much sooner than I thought. I said yes to stepping into a lot of unknowns and the opportunity to make things better. I said yes to something I know I’m capable of. I said yes to trying out a new job alongside a great group of people.

I said yes to being an interim head of design for Automattic. And I’m really excited about it!

Thoughts

🌶Spicy topics

Recently, the design team I lead was going through a period of low morale. I noticed this through conversations in 1-1s, our team Slack channel, and most notably in our team meetings. The designers were all working on some very big product problems and while the work was really challenging, the rewarding aspect seemed to be replaced by a feeling of frustration.

Instead of trying to jump in and fix the actual issues, I tried a different approach. Jay, one of the designers on the team, had been referring to some topics and discussions as “spicy”. It became sort of a fun word that the team started using. On the next team meeting agenda, I added an item called “Spicy topics” and asked if anyone had anything on their minds that they’d like to talk about with the whole team. By this point, everyone knew that “spicy” meant something along the lines of: seemingly unsolvable, slightly controversial, generally frustrating, somewhat confusing, or any combination.

Here’s how it works: Someone on the team will describe the issue, topic, or ask a burning question. As a team, we discuss it for a while until we’ve reached some sort of conclusion. Depending on the topic, this could mean: it just needed to be discussed as a group, we’ve identified a problem that needs further action, or we were able to bring some clarification to something that was once confusing. As the lead, I tend to listen and only jump in when I think I am the best person to provide clarity or perspective on a topic.

We’ve been doing this consistently for a couple months now and I’ve seen a notable difference in the team. The benefits:

Creates a space to bring up challenging product, business, and organizational problems.
Diffuses issues that could become distracting, discouraging, harmful, or even toxic if left unaddressed. (Things that people initially thought were Extra Spicy ended up being not so hot once they said it out loud and talked it through.)
Surfaces things you might miss as the lead who operates at a higher level and is more removed from project work. (For example, I was able to identify and prioritize an entire project that I otherwise wouldn’t have.)

Adding 🌶 Spicy Topics 🌶 to a meeting agenda creates a space to bring up challenging problems and diffuse issues before they boil over. The reason this works so well on our team is because we are a very close knit group and have built up a sense of trust. (One person even described Spicy Topics as group therapy.) I personally love it because it means we can all be open with one another and help each other out. Just because I’m “the boss” doesn’t mean I need to or should seek to fix everything. What I can do in this particular scenario is create the space and empower others.

Thoughts

On sharing mistakes

At the end of every week, my boss asks us to write down a lesson we learned. Mine are usually due to a slip up I made. Here’s how it goes: I make a mistake, apologize to the person, and end up saying something along the lines of: “I should have done x, lesson learned for next time.”

Because we work remotely, this apology is often over text. I did a quick search and found out I ~~make a lot of mistakes~~ learn a lot of lessons.

I don’t think we talk openly enough about the mistakes we make, especially as people in leadership positions. Maybe it’s because we are afraid to let people know we don’t actually have everything together or because being vulnerable feels not great. I just think it makes us more human. With that, I want to share a few of the mistakes I’ve made recently and the lessons that came out of them.

I needed to make a big change that involved a number of people. I assumed one of the people involved was already aware but it turns out, they were not.
Lesson: Talk to every party that is involved in the change.
One of my weekly one-on-one meeting with a direct report got canceled. I was going to bring something up that had the potential to get misinterpreted. I didn’t want to wait until a whole week so I decided to send it to them in a text format. It didn’t go well.
Lesson: Have difficult conversations in person or on the phone.
I was working a three day week but didn’t adjust my to-do list accordingly. I ended up having to ask someone on my team to take over one of my bigger items without much notice.
Lesson: Delegate early and often.
We had a team meeting that overlapped with a monthly company wide meeting. A couple people were excited to have our team meeting and wanted to watch the other one later (it was recorded). I decided to leave it up to everyone to decide what they wanted to do. This caused confusion, especially with new folks on the team.
Lessons: Set expectations and communicate them clearly. Cancel team meetings ahead of time when they overlap with townhalls.
I came back from a three month sabbatical and felt extremely frustrated with myself that I wasn’t fully up and running by the second week back. I beat myself up for being so off my game and letting routine things fall through the cracks.
Lesson: Transitions take time. Give yourself the time and space to make it happen.

While sharing lessons I’ve learned is great, it really only tells half of the story. I’ve found that being open with people about the situation that lead to the lesson can be very freeing. Being so open also has the added benefit of creating a sense of trust, deeper relationships, and invites others to feel okay making and sharing mistakes of their own.

Thoughts

Changing your own oil

I learned how to change the oil in my car before I could drive. Twenty years later, I still change it myself. Sure, I could have someone else do it in the same amount of time for the same amount of money, but I think its important to get under the hood yourself.

I feel the same way in my career. As I grew into various leadership positions, I stopped designing things in order to focus on my new job of growing and leading a team. This transition was really hard at first because my progress could no longer be measured by the amount of stuff I designed. Instead, I began delegating projects and tasks to the right people so I can focus on more strategic work.

Delegating is a major part of leadership, but I’ve found that doing a small amount of contributor work has huge benefits, even if it only adds up to a week out of the year. For these five reasons:

Empathy. For the team, especially new folks joining.
Humility. No one is too important to pick up trash, change a light bulb, or lend a hand.
Context. Puts your high level decisions in context of implementation.
Support. Volunteering to help out shows support, to the people under you and the team itself.
Perspective. Getting closer to the ground means seeing new things and how everything fits together.

For me, it acts as a refresher for how things work. As a lead, it’s vital for me to know the how so I can properly prioritize and speak the same language as designers, developers, and business folks. Same with my car – getting under the hood for the little stuff helps me know how everything works so that when I do need to bring it into the shop, I have a grasp on the problem and can speak to the mechanic in their language.

Thoughts

Something different

Routines. I develop one for a period of time and then realize I’m in one and feel the urge to shake it up a little. This week, I’m in between trips and noticed that I’d develop a daily pattern of sorts. I woke up and decided to do something different. Different for this week meant something outside of reading, writing, house projects, or snowboarding. Denver Botanical Gardens: a place I would not normally choose to go, which meant it was the perfect choice to break up the week.

Stepping into the bio-dome-like greenhouse was like going to a different country. From snow, dry, below-freezing to green, humid, and warm. My mind wandered. There were plants that looked like the patterns on them were computer generated. And colors that would never be described as “natural” or “earthy” were everywhere. I thought about a podcast I just listened to where a guy made an app that sent him a random Facebook event every day, just so he would be guaranteed to not be stuck in a routine. In the orchid room, I thought of Georgia O’Keeffe and how I want to paint again.

It had a similar effect to traveling. Seeing something new and different inspires me, gets me excited, and also has me looking forward to get back home. Back to my routine.

Thoughts

Stopping along the way

I love old signs. I also love road trips. On every long drive, I’m bound to pass at least one old sign. I think, “I should stop, that would be cool picture.” But I don’t, I keep on driving. And then I feel a tiny bit of regret.

Today, while driving across Wyoming, I decided to listen to myself. I stopped at every cool sign I passed along the way. No regrets!

These were my favorites:

Thoughts

Not convincing

I was having a conversation with someone about the book I was reading. I had mentioned that before I had borrowed the book from the library and started reading it on my Kindle, I had no idea it was over 900 pages! They proceeded to start talking about why they preferred to read actual books. I was about to convince them of why Kindles were actually better, but stopped.

I was reminded of something that happens in my work bubble. As a designer, there’s a lot of software and tools out there. Every day, something new comes out and someone is convincing you to switch. Sketch is better than Photoshop! Figma is better than Sketch! I think that we forget that everyone has different needs. And other people aren’t you, even ones that share the same profession.

When my needs aren’t being met by a certain tool, software, or thing, then I look for something else. For example, before going on a trip, I didn’t get my act together in time to find a book. Kindle allowed me to borrow books from the library as I was packing, without going anywhere. This works for me and while I may share my story with someone, I don’t feel the need to convince, especially if something else is already working great for them.

Colorado

St. Mary’s Glacier

We’ve been meaning to hike St. Mary’s Glacier and we finally made it happen this weekend! It’s a really popular spot so we left pretty early and were on the trail by 9am. The hike up to the lake was super rocky. Once we got to the lake, we could see the glacier. It was cool to see that much up close in July. A few people were skiing and snowboarding down it, which I definitely want to come back and do. (Running/skidding down the snow in hiking boots was pretty fun tho.)

Most of these photo credits go to Anne, who has a really nice camera.

Trailhead directions: Google Maps
Parking fee: $5 cash
When to go: Weekdays or early mornings on weekends to beat the crowd.
Difficulty: Easy. (Kids, dogs, people in sandals)
Length: 1+ miles. (We did 4.6) Its an out-and-back so you can make it as long or as short as you want. You can just hike up to the lake for a short trip, but if you want to make it longer, there’s a ton of options including submitting a 13er (James Peak).