Braden Kowitz

How to write a great check-in

The subtle art of explaining what you’re doing at work

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The complexity and pace of work just keeps increasing. At times, it can feel like chaos. But you know what holds it all together? The humble status update. And I’m not even kidding.

I could dive into management theory and talk about the amount of context that knowledge workers need to do their job properly, and how that context is harder and harder to form in large matrixed organizations, and how it’s all made worse by the swarms of different tools we all use. But you know this already.

The only way we ever really know what other teams and teammates are doing is with a humble status update. You might hear one in a team meeting, or while you're making espresso, or read one on in your inbox. But chances are, you’ve never thought much about what makes a good status update.

I’ve been thinking about status updates for the better part of 2 years, ever since we started Range. And over that time, I’ve had a chance to work with dozens of organizations, all of which practice status updates in some way. Through that experience, I’ve realized that there’s a huge difference between a mediocre update and a great one. All updates convey information. But great updates align teams, build connectedness, and solve problems.

Unfortunately, this crucial skill is often overlooked. I’ve never seen it mentioned in any company training, and I’ve found it challenging to locate good advice on the topic. So if you’d like to master this seemingly simple art, here are a few tips that should help you along the way:

1. Say something new

Vagueness is the enemy of a great status update. If you’ve caught yourself giving an update that sounds something like, “We’re making good progress on project X”, then you’re veered into the land of the vague.

The problem with repeating the “We’re working on it.” status update several times in a row is that doubt starts to creep in. People will begin to wonder what you or your team is doing, and whether you’re really making progress. A good status update should banish this doubt, and you’ll need to provide detail to do that.

For example, I’ve been working on this blog post for a few days. But in my written daily updates to my team, I never once wrote “Working on a blog post.” Instead, I got specific and showed my work. I wrote “Sketching an outline”, then “Writing a draft”, then “Finishing up copy edits”, etc.

By giving just a little bit more detail, you can show your team that you’re making progress. The right amount of specificity can eliminate doubt on your team, and help open up opportunities for collaboration and feedback.

However, there is such a thing as too much detail. Sometimes people will deliver a laundry list of everything they’re doing. Laundry lists make for a extra boring update. So if you’re feeling the urge to include everything, take a moment to think about what parts of your work are relevant to the team, and how you can be more concise. A simple trick here is to take an editing pass after writing your update, and put the most important items at the top. Often this act of ordering is enough to clarify what’s really important to share.

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2. Explain why the work matters

At the beginning of any project, we often underestimate how important it is to communicate purpose. We tend to jump into the “what” of the work, without first covering the “why.”

For example, I recently did some work to improve commenting in Range. When shared the first round of designs, I got some curious looks from one of my co-founders. At that moment, I realized I hadn’t communicated the “why” well enough. I paused, backed up, and explained that we were getting lots of requests for commenting, even though we already had built the feature. That context was enough to clear up any confusion and set the stage for some great design feedback.

As humans, we tend to think that other people have the same context in their heads as we do in ours. It’s natural. But with status updates, it can cause big problems. When you leave out the “why” behind your work, others might not be able the guess the purpose, and may not even feel comfortable asking.

Without clarity on purpose, teams will drift out of alignment. If you find yourself buried in disagreements about low-level details, take a few steps back. You may have forgot to communicate the project’s purpose.

Communicating purpose doesn’t have to take a lot of time. Consider reading this update: “Moved sharing buttons to the left side of the blog.” That probably has people wondering why the buttons moved. Just a little purpose can help a lot: “Moved sharing buttons to the left side of the blog because no one was clicking on them at the top of the page.”

You don’t need to be a broken record, always repeating the purpose of a project. But in my experience, you probably need to reiterate a purpose 2-3 times more than you’d think. And at the start of any project, getting crystal clear on the purpose is essential.

3. Be honest about what's not going well

It’s normal to want to hide things that are not going well. I personally hate when my projects are going sideways. I feel the strong tug to stay silent, rather than ask for help. I think somewhere deep down, I worry that I’ll look bad.

I realize how silly that sounds. Hiding a failing project won’t make it go better. And the team around you, whether peers or managers, are all there to help you succeed. Any good manager will cherish the opportunity to help you when you’re feeling stuck. And any good team will help you when you run into roadblocks. That’s the whole point of a team!

What’s the key to creating an environment where people will share updates about projects going poorly? You have to deliberately build a culture that reminds people they’re safe.

If you want teammates to share bad news, you need to create an environment that minimizes the fear of looking bad, and reinforces that we’re help each other succeed.

If you’re interested in ways to build this kind of culture, check out the articles we’ve written on how to build trust on your team and how to integrate opening and closing rounds to your meetings.

4. Include outside commitments

There’s so much that goes into a typical day: work, family, taking care of yourself. And there’s even more that can get in the way of any given project. You might need to stay home to take care of a sick toddler, work on an urgent project for another team, or spend some time interviewing candidates.

We often have a tendency to hide all that other work from our teams. You might think that they don’t need to know what’s happening on other projects or in your personal life. Or you might feel guilty that other work has taken precedence over something you wanted to get done.

But if we hide all these other commitments from our teams, they’ll just be left wondering why we haven’t been making progress on the projects that are relevant to them. With a lack of context about your total workload, people may think that you don’t care about a project’s success, even though you do!

The next time you’re making slow progress on a project, consider sharing some of your other commitments with your team. Don’t be embarrassed by outside commitments. They’re real work!

If you’re a manager writing a status update for your team, it’s a good idea to include this extra work in the status update, even if it’s work that others might not consider your team’s core focus. For example, you could write, “We made slower progress on other goals this week because the team was focusing on critical bug fixes, interviews, and quarterly planning.”

5. Stick to a cadence

Writing a status update on a regular cadence is a bit like exercise or meditation. The practice builds on itself, becoming easier at each iteration, and accruing more benefits over time.

Keeping a cadence is less work for you. If you share updates sparsely, you’ll likely be interrupted by people wondering what you’re doing. Your manager, not knowing when the next status update is expected, might swing by your desk to see what you’re doing. By keeping a cadence, I find that it calms down the people around me. When people wonder what I’m doing, they know from experience that they can find out in my next status update.

I also find that a cadence, whether daily or weekly, makes crafting an update easier for me. When I’m dealing with shorter periods of time, it’s easier to remember what happened. And the more practice I have in assembling a status update, the better I get at it.

And finally, as companies grow larger, communication need to transition from something that’s ad-hoc, to something that’s actively designed. Ad-hoc status updates don’t work very well as companies grow, and you’ll likely notice that some people are unintentionally left of the of loop. By sticking to a cadence, it becomes much easier to deliberately design the audience and content of a status update, and make sure that the right information is always being shared to the right people.

Status updates as teams grow

I enjoy talking about what I’m doing in meetings and ad-hoc conversations. But I also know that spoken status updates simply don’t scale as companies grow. Here’s the problem: If I share something in a meeting, you might forget it by the end of the day, and some other person that wasn’t present missed their chance to learn about it.

Verbal status updates don’t connect ideas across large groups of people or large spans of time.

So as your company grows, it becomes essential to transition from spoken to written forms, like Check-ins. And I believe that well written updates are our best hope of building a transparent culture while avoiding meeting overload.

If you’re curious to learn more about a tool that makes it easy to write and share status updates at scale, check out what we’re building at Range. And please do let me know your tips to writing a great update. You can find me on Twitter at @kowitz.

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