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.
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.
As the Design Director for WooCommerce at Automattic, I manage a large team of designers. Automattic is distributed company and everyone works from home (or wherever they happen to be). Our team is spread out across Europe, the US, and Australia.
The WooCommerce design team has grown and changed over time. As new people join, we try new things and the things that work, stick. One of those things that has organically evolved over time has been our twice-weekly team meetings.
Why meetings? Why two a week?
We are a team of designers. A designer’s job primarily is to identify and solve problems. But the end result is making a thing. Whether it’s a design, landing page, flow, or insights from research, we are all making something. And great design needs a short feedback loop. Since we are all remote, we have to be more intentional about meeting than we would if we were all together in an office.
The purpose of our meetings:
To form a tight feedback loop so our product is consistent and the best it can be.
To get to know each other, bond as a team, build trust. In a remote setting, virtual face-to-face time is key.
To discuss thoughts, ideas, and changes to make as a team.
How we run them: logistics and tools
Our team chats are very casual, but over time a general flow and process has evolved. I’ll walk you through how a typical meeting goes, including the tools we use.
Reminding and alerting An hour before the call, a recurring slackbot reminder that I set up goes out. (“Team X” is the name of our team.)
Agenda The link leads you to the running meeting agenda in Google Docs. For efficiency, we keep the same doc for every meeting. It contains the following information:
The header, which stays on top of the agenda, has the title of the doc with everyone’s name.
Below that is the note taker and call leader, the blog post title with date, and a list of who was present/not the previous meeting.
Before the meeting
Whoever is the first person to click on the link that day is the one who updates the agenda. To update the agenda, you simply copy and pasting the portion below the line. Then change the date to today’s date, update the leader and note taker (we go in order of colored names up top) so its all ready to go for the meeting.
If you have work in progress to share, you add it to that section. If you have something else to discuss, you make a new section and add it below.
When the meeting starts, I drop the Zoom link in our public Slack channel (it’s also in the channel description) and everyone starts filtering in. We chit-chat and say hi until everyone joins.
When everyone is on, I usually announce who is the call leader and who is taking notes. The call leader takes over and runs the meeting. Running the meeting involves two things: reading through the agenda topics, facilitating discussion, and making sure we are good on time. This will vary from person to person, depending on their style and personality. Taking notes involves writing down what is discussed and posting the meeting notes to our team’s p2, a private WordPress blog only accessible to people within the company. (The Google doc is formatted in a way where it’s pretty much just a simple copy & paste.)
What we do
The short answer is: Anything anyone wants as it relates back to the purposes of our meetings. The only real rule we’ve made is no status updates. This came about from a quarterly retrospective; someone expressed that our team had a bad case of Status Update Overload. We all agreed they weren’t a productive use of time and wanted to fix it. We all agreed to focus our meetings on three things: Question of the day, show and tell, and topical discussion.
Question of the day
This idea came up after a recent company-wide survey, where we scored low on “Feeling Part of a Team”. Someone on the team suggested we try a Question of the day at the beginning of every Tuesday meeting. It was around the time when three new people joined the team and it was a great way to get to know everyone.
Questions are asked in the beginning of the meeting as an ice breaker and usually take around 20 minutes. Past examples include:
What time of day are you naturally most productive? When are you least productive?
What else is on your desk besides a computer? (Bonus: Stop, take a picture and share on Slack)
If all the computers, electronic gadgets and software on earth disappeared tomorrow, what would you do with your time?
A note: We don’t do these every week anymore as we all feel part of a team now. Instead we do them ad-hoc as questions come up. For example, today we spent our whole meeting on this one question: “What is something you are actively working to improve upon?” This was asked for a variety of reasons, but essentially it was to make a space for people to be vulnerable, share their work struggles openly, and for everyone to see that they aren’t alone. It was sort of like group therapy so we decided to not take notes and keep it in a safe space.
Show and tell
For those who went to design school, you may know this as a Design Critique. Every meeting (give or take), someone from each squad will add an in-progress design they are working on to the agenda. The process varies from here depending on what the design is. If its a:
Idea We try and stick to only sharing designs, even if they are super rough sketches. This way, we’re all seeing the same thing. When you are sharing ideas about a design instead of an actual design, everyone will have a different picture in their head and it can be difficult to get on the same page. That said, it does happen and we’ll listen to the idea(s) and offer feedback on if and how to move forward, usually by asking to see a design 🙂
Sketch/Figma file or other static design
If there’s a piece of UI, a logo, or a landing page that a designer is iterating on, they will share their screen, describe the problem, and show the various solutions they have come up with. They’ll ask for feedback and anyone on the team can comment. The notetaker is responsible for capturing the feedback.
Prototype or flow
If the designer wants to share a prototype or flow, they’ll first set the stage by explaining the scenario, much like they would if they were testing the flow with a real user. They’ll then ask for a volunteer to run through the flow. The volunteer will then share their screen and run through the prototype, talking out loud as they go. The notetaker takes notes and the rest of the team gives their feedback as well.
Giving and receiving feedback We’ve never set any rules for this, but follow this basic guideline: Focus on the work, not the person. It’s up to receiver to decide which feedback to implement and return with an updated design next meeting, post it to p2 for a wider audience, or start prepping for a usability test.
Whatever topics people want to discuss with the team, they can add them to the agenda. This can be big initiatives in WooCommerce product, the Design org, Automattic, or in the outside world. In the past, examples of this have been:
Research: Demos, tips, tricks, updates to process
Brand strategy: Explanation, thoughts, next steps
Figma: It seems to solve a problem we have with Sketch not being collaborative. Should we investigate further?
The whole design team. On Tuesdays, we invite guests from other teams within the company to learn and share.
When they take place
We meet twice a week at two different times to be inclusive of timezones and not to be too US centric. Tuesdays are at 3pm UTC and Thursdays are at 5pm UTC.
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.
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!
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.
“What’s the best way to see what your team is working on?”
As the head of design for one of the products at Automattic, I get this question a fair bit. I have a good way to respond to that without having to do a ton of legwork. It actually has to do with task management!
Why I prioritized solving task management
As most things go, it wasn’t a big ah-ha moment, it was a bunch of little things that all added up to me thinking I needed to do something. I collected a list of observations and problems I had relating to the general issue around task management:
As a team lead ___
there is no one place to see an accurate and up-to-date snapshot of what the team is currently working on. No single source of truth.
who is nearing a three month sabbatical, I would like an easy way to seamlessly temporarily transfer my role to someone else.
it’s not always clear what everyone’s workload is. Who has too much? Too little? and to re-assign things as needed.
much of my work is “invisible” and behind the scenes and I want to make that more transparent.
with a growing team, I’m not in the weeds with everyone. There’s a lot of work everyone does that is in-progress and not immediately visible, and it would be nice if there was a way to help surface those items. Basically: we need a system that will scale with the team.
I was made aware through one-on-ones that some people were having a hard time managing their own individual task lists.
What tool I went with
I’m not a fan of choosing tools over talking to people, but I decided since we are a remote team and everyone is managing their own tasks, we needed a tool! We chose to use Trello because of its simplicity and familiarity. The tool itself isn’t as important as how everyone uses this day-to-day, so I’ll jump right to that.
How this works in practice
First, I made two Trello boards:
A main board and the only board that is “active”.
A board we use just for archive purposes.
The Trello board has 5 columns: Backlog, To Do, In Progress, In Review, and Done!.
As the team log on at the start of every week, everyone adds their to-do’s for the current week only. They then assign it to themselves.
If something comes up during the week, it’s added to the Backlog column. Ideally, nothing is added to the current week’s to-do’s once the week gets going.
Each Trello card is a task. Tasks should be something that takes no more than a couple days. If it takes longer, it should be broken up into smaller tasks. Meetings shouldn’t be tasks, but brainstorming and decision making should be.
As the week progresses, items are moved from In Progress, In Review (if needed) and then to Done! (Trello has a feature that lets you filter to only see your tasks.) We also have a Blocked column for those tasks that are blocked. Ideally, all tasks should be moved from the To Do to the Done! column by the end of the day on Friday. If there’s a link associated with the finished task, its added to the card so that The Week in Design post can be easily written.
If a task has been sitting there for several weeks, something is wrong and a conversation should take place.
At the end of the week, the person assigned to the Woo Week in Design Trello card, does the following:
Collects the cards in the Done column that week and writes up a post titled Woo Week in Design: [Month Day-Day].
The post is formatted to include everyone’s tasks within the divisions five goals. This is to give greater context and meaning around why everyone is doing a particular task.
Move the Dones! column to the Woo Design Dones! board. This is for a couple reasons: to not clutter the board up and also have a nice history of everything that we’ve accomplished over time.
Renames the To Do column to include the current week.
Adds a new Dones! column with the current week referenced.
Assigns the next person in the list to be the writer of the Week in Design post. They get a notification.
The bigger picture
When you’re heads down working on something for so long, it can be hard to remember what its all for. Taking a moment to look up, and see the bigger picture of your work and the work around you can help put everything in context. It also question tasks that may feel like a priority in the moment but don’t actually fit within the company or product’s goals.
When Grandmother was dying, I had so many thoughts and memories swirling through my head that I had to write them down. I sit here now thinking about Grandfather, who was a man of such few words. I spent almost as much time with him as grandmother but he was more of a presence than someone I interacted with a lot.
Whenever I went over their house he would always be in his recliner in the corner of the den. He’d either be napping or reading. On the table that sat between their two chairs there was always a National Geographic and a folded up newspaper with the crossword partially filled out.As a kid, I wondered how someone could take so many naps. When he saw you come in, he would un-recline his chair to say hello. I remember loving to sit on the dimpled leather chair in that room at his desk. I’d rotate around back and forth and it had a little squeak.
If he wasn’t in the den, he’d be at the kitchen table, which was right when you walked in. Always in the same chair. He’d have a small bowl of nuts, a nut cracker, and a small pile of walnut remains. We’d say hello and then run down to the bath house with the green translucent roof, put on our bathing suit, and jump in the pool. We could only come back inside if we were completely dried off and dressed. I remember going into the bathroom and seeing his thin metal comb on the sink. Sometimes I’d comb my hair with it because I thought it was cool.
I knew him and Grandmother as world travelers. After trips we’d go over their house and he’d be the one sitting behind the whirring projector, flipping through each slide. He’d describe some photos, and flip through a couple in a row without saying anything and we’d just stare at the photos. My favorite would be when he’d chuckle recalling some funny incident. There’s over 50 boxes of slides and we still look through them from time to time.
He was generous enough to fund half of our college tuition. Every semester when I added up the cost of school and books, I’d nervously drive over there. Asking him for money felt so awkward and uncomfortable, I dreaded doing it. He never showed any emotion when I’d give him the total and he’d sit at his desk, pull out the binder of checks and write it out. My teenage brain was a mess: “Am I too greedy? Is this too much money? I shouldn’t have included books in that.”
Part of it was that I knew he never seemed to spend any money on himself. I don’t remember seeing him in new clothes, he kept his truck till it was rotted through, and just didn’t seem to like stuff in general. This made gift giving especially hard. I remember when we tried giving him a cell phone for Christmas, it ended up getting returned.
Instead, he chose to treat himself with travel. Him and Grandmother went to places I never heard of and they would even meet us on a couple trips around the country. We went to Garden of the Gods and into the Rockies, Outer Banks in North Carolina and one time they took my sister Jen and I to Oregon.
At Christmas or when his entire family was together, he’d sometimes stand up, pull a small price of paper from his pocket and give a little speech. He’d recite a poem, either one he found or wrote, interesting family stats, or a quote. Four years ago, on his 90th birthday he stood up and recited three poems by memory and a few stats, which included how many days he’d been alive up to that point. One of the poems he recited was one he read back when he was a senior in high school:
Strength for each day, that is all that I ask,
Food for my hunger, Zest for my past.
Health for my body and a roof o’er my head.
When I am weary, a rest and warm bed.
Give me a job and a place in life’s scheme.
Give me a moment in which I can dream.
Give me a glimpse of some beautiful things;
Flower and sunshine and birds on the wing.
Not to have riches, position, or fame;
But to be useful, let that be our aim.
Look not ahead to the future;
But pray just for the things we need day by day.
He said it was his philosophy of life and that it was a good way to live; one day at a time because the days really do fly by. He died on December 4, 2017 having lived 34,309 days.
WooCommerce is the most popular way to run a store on WordPress. Because of the nature of WordPress, we don’t have a way to see how people are using WooCommerce like we could if we were hosting the software, but that’s the beauty of open source. We’ve found the best way to learn more about our customers and the way they use WooCommerce is to actually have a conversation with them.
Last week we held WooConf, our annual conference dedicated to everything WooCommerce. People from all over the world came to Seattle to learn, present, and discuss all things WooCommerce. Being the WooCommerce design team at Automattic, we decided to run a Product Research Lab, lead by our user research wrangler, Maria. Six of us broke up into three groups; in my group, I was the interviewer and Justin was the notetaker.
Conference attendees had the opportunity to sign up for a twenty minute session with us during the conference. Our group met with fourteen people over two days.
We structured our twenty minute session into three parts and for the most part, kept this format the same for each and every session.
When the customer walked in, we introduced ourselves and asked them to take a seat in front of the computer. We then gave them a heads up of how the session would be structured, and said, “Today we’d like to learn more about your experience with WooCommerce. We’ll then ask you to walk through the onboarding wizard, which is the first thing you encounter when activating WooCommerce on your WordPress site. We’ll then wrap up with a few last questions. Sound good?”
Okay, great! Before we get going, can I have your permission to record our session so we can reference after we’re done here?
Okay, we’ve started recording now. We have a few questions to ask to get started.
Justin would then start the timer so we would stay on track. We then asked each of the participants the following questions:
First, can you tell us a little about yourself; who you are and how you work with WooCommerce?
Can you tell us more about your role?
Can you tell us more about the your favorite site you worked on? Why did you list this one as your favorite?
Have you worked with any other eCommerce platforms in the past, if so what was your experience?
At this point we are about five minutes in and are ready to move on to the user testing portion of the session. We transition to the computer, which is still in front of the interviewee and guide them to the next steps by saying, “Okay great! We’re going to switch gears a bit now, we’d like to learn more about your experience with setting up WooCommerce for the first time on a new site.”
Are you familiar with the WooCommerce wizard?
Scenario: Today we’ve setup a new WordPress site with WooCommerce installed. We’d like to watch you complete the initial setup, which is what we call the wizard and ask that you talk out loud as you are doing that. Tell us what you’re seeing and your thoughts about each step along the way.
Your goal: Your goal is to complete the WooCommerce Wizard setup as if you were building [your site or the last site you built]. Let’s get started.
Once the interviewee has completed the onboarding flow we’d ask:
Now that you’ve completed setup, what would your next step be?
Okay! Thank you for walking through that. That was really helpful and we’ll be able to improve this experience in the future.
At this point we are anywhere from ten to fifteen minutes in. We’d lead into the end of the session by saying, “Looks like we have about a few minutes left, I want to be mindful of time so we can be sure to end on time so you can get back to the conference. We just have a few more questions for you.”
Overall, how would you describe your experience with WooCommerce?
If you could change or add one thing in WooCommerce what would it be and why
Is there anything else you think we should know?
“Thank you very much for taking time to talk to us today, We really appreciate it. If you’re interested we will be sending a follow up email where you can sign up for additional research opportunities with us, so be sure to keep an eye out for that.”
We would then stop the recording, shake the interviewee’s hand, and wait until they left before resetting the site in preparation for the next session!
The take away
I went into this not knowing quite what to expect. Was twenty minutes enough time? Was it too much time? What if the interviewees came into the sessions with a litany of complaints about WooCommerce? Will we learn anything?
Yes! Of course we learned something. We learned so much. Personally, I loved every minute of it and cannot wait to do it again. When we got home, we analyzed our notes for patterns and tracked each issue to be prioritized for a future project cycle. These problems felt real, because they were; we had witnessed it first hand.
There’s something about meeting with customers in real life that is incredibility enlightening. There was this one particular step that tripped almost everyone up. Okay, there was more than one, but the first time I recognized a pattern I remember just cringing after the next person was about to get to it. I just wanted to fix it right then and there! And that’s really the best part of this entire experience. We learned in twenty minute what we’d never learn sitting in our desks at home with our heads down in the code.
“You loved September Issue? I didn’t know you were into fashion.”
I’m not. I just love hearing stories and learning about things I don’t know much about. A documentary about the making of the September issue of Vogue was fascinating to me. I’ve watched it a half dozen times.
I’ve always worked at tech companies and been surrounded by people who think that getting ahead means you have to follow all the cool thought leaders on Twitter, read all the books on how to increase productivity and be a better manager, meditate every day, share all the articles with coworkers, listen to the advice of the Tim Ferris’ of the world, and try all the apps. Keeping up with all that is too much and trying to do so won’t make you better at your job. I think that staying in our own tech little bubble is harmful and it stifles creativity.
Instead, take a look around outside the industry for inspiration. Get a glimpse into a little corner of the world you haven’t ever visited, learn about new sub cultures, or anything new or niche. This can be in the form of physical travel, a non work-related book, or my favorite source: Netflix documentaries. I have a collection of the latter below with a brief summary and how I related to each.
Some of my favorites
September Issue is a documentary about the making of the September issue of Vogue magazine. I love everything about it, especially Anna Wintour and learning about Grace’s job and seeing the amazing photographs she produces. I learned the importance of editing, saying no, and killing your darlings.
Indie Game tells the stories of a few independent video game designers. I don’t play any video games and never really have, but seeing how these people worked and what they had to go through to create and launch their games on their own was really eye opening. I can now relate better to some of my video gamer co-workers 🙂
First Position is a documentary about group ballet dancers from all over the world who are trying to turn their passion into a career that pays money. I learned that ballet clothing companies make clothes that cater to light skinned people and the young woman from Sierra Leone in the film has to make her own modifications. Diversity and inclusion isn’t only a tech issue.
Barkley marathons is this totally bonkers trail running race that takes place in Virginia. The guy that started and “runs” it is a chain smoker and changes the entry fee based on what he needs more of; for example – a white button down shirt. Also, the race is 100 miles long, not marked, the start time is random, and only 16 people have ever finished it. Brutal! But I did learn some things about people and project management, mostly what not to do.
Piece of Work shows a behind the scenes look of the late comedian Joan Rivers. Everyone always focuses on her face and profanity, but this documentary shows her as a real, hilarious, workaholic human. Comedians user test their jokes!
Bonus: Truther Love is a super wild Longreads story about a truther online dating site. There’s someone for everyone.
Balance the thought leader blog posts with something outside the tech realm. Get out and find a new little corner of the world and you just might be surprised.