Fewer meetings courtesy of automated check-ins

Illustration of automated check-ins on Basecamp.

With our switch to 4-day work weeks (see also the 4-day work week update) at Wildbit, we’ve made a point to be more deliberate about how we spend our time. While we’re trying to work fewer hours, we’re also trying to achieve the same productivity. With eight fewer hours each week, that means we have to be a little more conscious of things like unnecessary meetings or alternative ways to accomplish the same things in order to shorten meetings or even skip some entirely. One of the ways we’ve done that is by shifting more communication to text-based recurring check-ins, and it’s been a huge improvement in terms of efficiency.

With Postmark, the Front of House team includes both marketing and customer success. With the way we work, the two are closely integrated. However, with eight people and the split between marketing and success, while there’s plenty of overlap, it’s not 100%. As a result, plenty of meetings needed all of us together, but others only needed some of us. To help mitigate this, we shifted from weekly video meetings to frequent automated check-ins through Basecamp and Slack.

This has had a huge impact at reducing meetings while still keeping everybody informed. It’s not a perfect solution, but it’s been a healthy change overall. Especially as a remote team, it fits better with how we work and how we’d like to work.

How does it work?

We have two recurring check-ins that are set up through Basecamp’s automated check-ins. There’s one daily question for the marketing side of the team, and one weekly question at the end of the week for the full front of house team.

  1. Daily question for marketing team only: “What are the 1-3 most important things you want to finish today? (Don't forget to @mention anyone you may need help from today.)”
  2. Weekly question for the full Front of House team: “How's your weekly goal looking? And what's your no-matter-what for next week?”

The daily question is limited to the marketing side because the success half of them spends the majority of their time on customer support. As a result, they don’t have as much to share on a daily basis beyond “helping customers.” On a weekly basis, though, everyone has updates to share.

For us, the “no-matter-what” is the important part of the second question. We’re all juggling a lot of random small tasks that are worth mentioning, but the “no-matter-what” helps us think about the things that we feel are important enough to really focus on and ensure they get across the finish line. It doesn’t always happen, but framing it that way helps us stay focused.

So, now that you see how it works, let’s see how the benefits play out.

Enables asynchronous communication

As a remote team spread across eight hours worth of time zones, the asynchronous nature of the text-based check-ins makes it easier than being forced into regular meetings during an ideal window when everyone is at their desk working. Instead of having one big meeting with everyone in every time zone, we’re able to have smaller more focused meetings where time zone overlap is less of an issue because fewer people are involved.

It’s also more convenient for team members to write their check-in at a time that works with the natural flow of their day. The same goes for reading the check-ins. Everyone can read everyone else’s news when it’s most convenient for them.

Encourages deliberate and focused planning

Checking in and sharing updates during a meeting with other people waiting is a bit of a hurried affair. When you write a text-based check-in, there’s no pressure, and it allows for a more calm and deliberate approach to reflecting on recent accomplishments and thinking about upcoming work and news to share.

Provides historical context and reference

With the text-based check-ins, we also gain the benefit of having historical context and insights. I frequently refer back to my own check-ins if I’m ever struggling to maintain focus or remember what’s most important. This is particularly helpful Monday mornings where I can refer back to the previous week’s check-in to refresh my memory about what I wanted to get done that week.

Enables smaller, more flexible, and more focused meetings

Even though marketing and success are closely related, our day-to-day focuses are different. While the meetings are great for some communication, there were often topics that didn’t apply equally to everyone in a full meeting of eight people. Instead of all eight people meeting by default once each week, we check-in on Slack near meeting time to see if there are any pressing topics. If nobody has anything, we skip it. Because of the text-based check-ins, when we do have meetings, they’re able to be shorter because everyone doesn’t have to go around and say what they’re working on. We all already know because we read the check-ins. That way, we can focus only on topics that need discussion. So when we do have full meetings, they’re more efficient than they’d be otherwise

One drawback: Less seeing each other’s faces

The one drawback that we’ve found is that, as a remote team, these meetings were our primary opportunity to see each other. So there’s definitely some drawbacks from a community and relationship building standpoint. We’ll have to figure something out here, but it’s just one of those tradeoffs. Community is important, but the gains here in terms of enabling more focus work and better meetings are too big to be ignored. We’re still working out how we do it, but maybe we’ll make sure we’re meeting at least once or twice a month just for kicks even if it’s only for 5 or 10 minutes.

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