At Sunsama, our goal is to help our customers be thoughtful and intentional as they plan their day. It turns out, the best way to build a product that resonates with this mission is for us to be thoughtful and intentional with how we think about our work as a whole. One specific area we've thought a lot about is how to effectively run a small remote and asynchronous team with minimal process. I want to share with you the five rituals we use to run our team.
We decided to go remote about a year before COVID-19 in the spring of 2019 after finishing YC and raising our seed round. Over the past several months, I've shared the following weekly and daily rituals with a number of YC founders from my batch as they've navigated the transition to remote. While companies like Gitlab and Zapier are well known for their large-scale remote operating procedures, I hope this helps folks on smaller teams like ours at Sunsama (5 people full time).
Before we jump into the process we implemented, I want to share the principles we wanted to achieve in our remote operating system.
Asynchronous First
It was critical for us to be primarily asynchronous. If we worked asynchronously, we realized we could recruit the best engineers regardless of timezones. Asynchronous work also supports deep work and large stretches of "maker time," which is a must if we aim to build an ambitious product with a small team. The final advantage of async and remote over synchronous and remote is that working async forces clarity of thought. If you choose to work async, high-quality written communication becomes an expectation. One of the side effects of writing is that it forces clarity of thought in everything you do as a company.
Iteration Speed
Any process we implemented needed to keep us accountable and shipping on a daily and weekly cadence. In our early days, we learned the importance of small and frequent iteration cycles as an effective way to converge towards a product people love. We built the initial version of Sunsama using two-day sprints. Small iterations are a super power for a pre-product market fit company. They give you more chances to learn from your customers, more forgiveness when you start building something people don't want, and force you to find creative ways to turn hard problems into ones you can chip away one day at a time.
Collective Momentum
Before we decided to go remote, Travis and I had spent years coding in the same room. Seeing things get built and shipped, even if it's by someone else on the team, is incredibly energizing and inspiring. We wanted to replicate this feeling of collective momentum and to end each day feeling amazed by what our colleagues are building.
We eventually settled on three weekly rituals and two daily rituals that give us the structure we need to operate effectively asynchronously while reducing the "work about work".
Daily Rituals
We start each day by sharing our plan for the day and end the day with a short writeup of how the day went. These daily rituals keep us accountable, help coordinate with one another, and serve as a way to mark the start and stop of the work day.
Daily Plan
We use Sunsama to plan our work day and then post our daily plan to a Slack channel. It's an async version of a daily standup meeting. Sharing our daily plan keep us focused, calm, and helps us realize when a teammate might need help.
The unexpected side effect of committing to work publicly is that it forces you to balance ambition and feasibility since no one wants a colleague who consistently fails to follow through on their word or delivers less than they're capable of. If you can find a balance between what you want to accomplish and what you actually can accomplish at the start of the day, you'll end your day with a feeling of satisfaction, which is a simple way to sustain motivation in the long run.
Daily Review
At the end of the day, we share a write up of what we did, what we learned and how we felt along with a video demo of what we built.
The act of writing and publishing our daily review marks the end of our workdays. Since we work from home and don't physically leave an office, it's useful to have a digital routine that represents the end of the day. Once I write my daily review, I feel good about shutting down my computer and stepping away from work.
Personally, I've found that writing a daily review increases the satisfaction I feel about my work. When I can see everything I did in a day, it makes it easier to feel like it was a day well spent, and I can shut down and step away more easily. And on the days where I don't do my best work or feel a bit unfocused, the review helps me recognize how I fell short and where I should focus tomorrow.
If you'd like to implement daily reviews in Sunsama, create a daily repeating task called "Daily Check In."
Weekly Rituals
Our weekly rituals include a single meeting, a weekly review of the company's progress, and a weekly 1:1 email between each employee and their manager.
Weekly Review
On Sundays, I write a "Weekly Update" that highlights our KPIs, what's going well, what's not going well, and what got built. This is directly inspired by Mathilde Colin's weekly updates at Front. In order to better support our async team, we've also added a section where each person can list their goals for the week ahead.
The "What's going well" and "What do we need to figure out" sections are our internal feedback and correction mechanisms. The power of a weekly reflection process means we rarely go more than one week before we fix and identify serious problems with our business, product, or processes.
The KPIs and "What got built" section keeps us accountable to our goals. By starting each week seeing if we're hitting our targets, we make better decisions about what to work on that week. The "What got built" section also creates a shared sense of momentum and a chance to learn about the progress our teammates are making on adjacent projects. This is my favorite part, it's motivating to see everything that got done in one week in the same place.
Writing the update can take one to two hours, but once it's written, I feel confident that I know what what's going well, what's not, and what the most important things to work on the next week are. Writing this weekly update is the most effective strategy I've found to make sure everyone on the team is always working on the right things.
Monday Meeting
On Monday mornings, we have our only team meeting of the week where the majority of our time is spent enjoying each other's company and chatting about what we did over the weekend. This meeting lasts about one hour. The other rituals I've described take care of the operational work which is why this meeting can focus entirely on building relationships. If the bulk of your "work about work" happens during video calls, you might need to reconsider your async processes.
Weekly 1:1
We also do our 1:1 meetings asynchronously! Each person sends their manager an email with their answers to the following questions as the last thing they do on Fridays.
1. What was exciting this week?
2. What wasn’t exciting this week?
3. Did I have a clear idea of how I could make meaningful contributions to Sunsama this week? And did I feel like I was enabled to do meaningful work?
4. Is there anything you could have done to make my job easier this week, unblock me, or better support me?
Their manager responds to the points raised there and tacks on their answers to the following:
5. What did I do this week that got you excited?
6. What did I (not) do this week that got you concerned?
7. Was there something you'd hoped I'd work on that I didn't?
The weekly 1:1 email is the weekly analog to our daily reflection. It symbolically marks the end of the work week and start of the weekend.
When approached thoughtfully, working remotely and asynchronously can be calmer, simpler, and have less overhead (and meetings) than traditional in person work. I hope our processes can be an inspiration for you to be thoughtful and intentional about your own remote practices.
