The BIG Deal About Small Wins

Co-founders are busy people. At my company, AirShr, it’s no different. My co-founders and I run hard to cover the many bases needed to build a great company.

However, we’ve noticed that the speed at which we run can be a double-edged sword.

Sure, we value the productivity, focus and quick decision making that comes from working in a small, high calibre team. In fact, there have been days when we’ve been so mission-focused that we’ve forgotten to check-in to see how each other is holding up! Although this behaviour can be attributed to the ‘nature of startups’, it introduces two risks that, if left unchecked, can irreparably damage the founding team.

The first risk is that you lose sight of achievements (and more importantly how your team interprets achievement – what it is and what it’s not). The second risk is that a very important question doesn’t get asked: What keeps you awake at night?

Anyone who has founded (or co-founded) a company will almost certainly characterise the experience as a roller coaster ride. When the going is good, achievements and what keeps people awake at night seem less important because everyone is upbeat. But when the pendulum swings in the other direction, sometimes at a moments notice, achievements can get lost in the flurry of activity needed to remedy issues. Not surprisingly, a by-product of times like these is not sleeping!

To help manage these risks, I recently instituted a simple weekly ritual. Every Thursday afternoon I send our team an email with this subject: Small Wins of This Week.

I dot-point the wins I think we’ve achieved in the past week and directly below this list I ask (and provide my answer): What keeps you awake at night?

The final and most important part of the email is this request: As soon as you read this email, please add additional wins and what keeps you up at night.

Our team is now in the habit of rapidly responding to this email and by Friday morning we have a very clear understanding of how much has been achieved and the issues that concern the team.

The big deal about small wins (and our weekly ritual) is that it helps us celebrate success and reflect on progress. It also shines a light on important issues that might otherwise linger in the shadows.

I introduced this technique to my company eight months ago and we haven’t missed a week. The impact it has had is incredible. I don’t think we really understood how much this small act would benefit our culture. It’s one of the best steps we’ve taken as a team.

Have you tried it with your team? What does your team consider to be last week’s wins? And do you know what keeps them up at night?