Small tasks, big picture

“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: 

  1. A main board and the only board that is “active”.
  2. A board we use just for archive purposes.
My (filtered) Trello view one week. Apparently I had a ton of reviews to do.

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. 

The output

At the end of the week, the person assigned to the Woo Week in Design Trello card, does the following:

  1. Collects the cards in the Done column that week and writes up a post titled Woo Week in Design: [Month Day-Day].
  2. 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.
  3. 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.
  4. Renames the To Do column to include the current week. 
  5. Adds a new Dones! column with the current week referenced. 
  6. 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.

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).


g+gWhen 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.

Twenty minutes with your customers


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.


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.

This was originally posted on

Little corners

“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.

All together now

The WooCommerce design team is five people strong. At any given time, we have at least that many projects in development. As you may guess, this means that all designers aren’t working together on a single area of WooCommerce. Instead, we each lead a product or project and meet frequently as a team to discuss, share, and give feedback. This ensures we are all aware of each other’s work and that our overall customer experience is cohesive.

There’s a team outside of the WooCommerce division at Automattic working with the greater WordPress community to make a new post and page building experience called Gutenburg. The goal with Gutenburg is to make writing rich posts effortless so you don’t have to know any code at all. Progress on the new editor is moving along really fast. It’s full featured and intuitive, but there hadn’t been any work done into how this will integrate with WooCommerce.

How do you handle adding a high priority item to everyone’s already full schedule without burning your team out or lowering morale? There’s probably many ways, but here’s what we did:

Instead of discussing it separately with each member of the team, I brought it up in one of our team’s twice weekly video calls. This allowed us to discuss it openly as a team. We all ended up agreeing it was part of our responsibility, was of importance, and was worth putting our time into. Time-boxing was brought up as a great way to approach something like this. Since it was summer and there were a few vacations coming up, we decided to have the due date be in one month.

I put up a sticky post on our team’s internal blog and tagged each person on the team so they were all notified. A day before the due date, we each commented on the post with our ideas. That was yesterday 🙂 Today we all met on a video chat. We all started by sharing our experiences we had testing out Gutenburg. For many of us, it was our first time using it.

Then we took turns presenting our ideas. To do this, we simply “went around the room” and took turns sharing our screens so we could walk though our thought process behind our sketches and flows. We didn’t specify a deliverable so we saw pen and paper sketches, Mural boards, high fidelity screenshots, and clickable prototypes. We then gave feedback to each person before we moved on to the next.

At the end of the call, we remarked on how this was such a treat that we all got to work on the same thing together. It was really fun to see how my teammates approached the same problem and it made me excited to go back and iterate. My goal is make these group time-boxed design problems a more regular occurrence on our team.

This post was originally published on

Should designers API?

There’s plenty of discussions on the internet about whether or not designers should code, but what about API’s? Hear me out. I’m going to tell you about a project I’m working on and how I went from knowing almost nothing about API’s to knowing a little more than nothing and along the way, discovered how we could use the data in our design sketches.

This post was originally a talk given at AIGA West Michigan’s Design Week.Continue reading “Should designers API?”


Every year our entire company gets together and one of the things we all have to do is give a four minute talk on any subject. In the past, this has always made me super nervous, and this was the first year that I wasn’t shaking in my boots. Progress!

The slides aren’t exactly synced up, but if you have ever wanted to learn more about cyclocross or have no idea what it is, your wait is over!

Two things I want to work on for next time:

  1. Look at the audience instead of the slides
  2. Less “um”s and “yeah”s

Looking forward

One year turning into the next is exciting. I feel filled with hope and reenergized. It’s not about resolutions; I don’t really make goals. If I want to do something, I’ll just do it. It’s more about the feeling of knowing there’ll be new places to explore, relationships to grow, things to make, ideas to form, and lessons to learn.

Cheers 🎊

Sketch notes from WordCamp Denver

I went to my first WordCamp this weekend in Denver. What’s a WordCamp?

WordCamps are informal, community-organized events that are put together by WordPress users. Everyone from casual users to core developers participate, share ideas, and get to know each other.

It was a great to see coworkers from far away places and talk to real live users and developers of WordPress and especially WooCommerce. I also sat in on quite a few talks and sketched some notes on my iPad.

Sonja Leix and Meg Delagrange critiqued websites that were submitted by a few brave conference-goers.


eCommerce Townhall
Caleb Burks of WooCommerce and Pippin Williamson of Easy Digital Downloads answered any and all questions the audience had about eCommerce and selling things online.


Accessibility Testing
Robert Jolly gave a great talk about accessibility and testing for WordPress development.


Marketing and Growth Townhall
Tracy Malone and Amber Hinds answered everyone’s marketing questions.


Forms that Don’t Suck
Steve Wells and Jessica Wittmier told us how to engage users with forms that aren’t terrible.


Business Townhall
And Vi Wickam, Miles Kailburn, D’nelle Dowis, and Gordon Seirup ended the first day with a great Q&A about all things business.