life, work, etc.
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.
Today my coworker Brie asked me,
I think a good design director/boss/manager/leader is someone who:
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:
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.
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:
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.
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.
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.
At the end of this cycle, mentors and mentees will write a post detailing what they learned in their respective ends of the process.
Soon after I started managing managers, I promoted a few designers to a Design Director role, meaning they went from designing to managing designers. I had a few conversations with some who were very eager to get started and “make their mark”. One particular high achiever wanted to “do” something in their first few weeks as a manager and asked for my advice. I thought for a moment and said:
“I wouldn’t _do_ anything.”
Focus on being a human first. Build real relationships. Listen. Look for patterns. Be yourself instead of an exact replica your boss or someone you think is super awesome. After all, you were promoted because of your unique qualities. (And if you don’t know why you were promoted, ask!) If you focus first on forming a genuine working relationship with each of your direct reports, trust will form. Then your real work can begin.
When I took on a new role, it was in addition to running a product design team. In order to do both jobs well, I decided to take a good look at what I was currently doing on my product design team. Turns out, there were things that had crept into my routine that were not truly necessary.
While being in a managerial role comes with some admin and process-related tasks, I’ve seen it overtake people’s job to the point where they start think and then act as if its their primary job. And this can leak through to the team. Process becomes the proxy for productivity.
I decided I needed to be pretty ruthless with how I approached my days in order to carve out the space to do my new job really well. So, if it didn’t directly effect the quality of my designer’s output, I cut it out of my job description. Some things I delegated the things that still needed to get done to the Design Directors below me, and others I stopped doing all together.
I sort of came to the realization that: at the end of the day, the final output is all our customers sees; they aren’t there for the planning, the research, the iterations; they only see and use what we ship. While everything leading up to it is imperative and directly effects the final output, I didn’t want the process of it to become my main focus. I hired and built an awesome team, so I trust my design directors and designers (along with their project teams) to do that! I decided to focus in on the design output and giving feedback on each design iteration until it was something I knew we would be proud to ship to our customers.
I did trimming down and refocusing exercise because of a major change and role shift, but I think I would benefit from doing this more regularly, even without such a big event. Things creep in and can really add up over time if you don’t take the time to look and reassess.
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!
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:
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.
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.
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.
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:
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.