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:
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.
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.Â
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.
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.
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.Â
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).
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.
The structure
We structured our twenty minute session into three parts and for the most part, kept this format the same for each and every session.
Intro
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?
[Start recording]
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?
User test
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.
Wrap up
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.
When Grandmother was dying, I had so many thoughts and memories swirling through my head that 