How to Celebrate the Small Wins in a Startup

By Dave Bailey

Acknowledging your team’s hard work can have a powerful effect on morale and output. But when there’s nothing obvious to celebrate, recognizing the small wins can make all the difference.

It took six months and more than a pound of flesh, but finally our seed round was closed. We’d done it! Obviously, a celebration was in order, so the whole team and our new investors gathered in a private room at a trendy restaurant in London. The atmosphere was electric.

One of the investors got up to say a few words. After expressing his excitement about the future, he offered some words of advice: ‘celebrate the small wins.’ The whole team looked around, nodding and smiling at each other. This was the kind of advice that’s easy to hear.

Fast forward six months, and we hadn’t celebrated anything. Closing the fundraising had been clear-cut, concrete, definitive. In contrast, the slow progress in building our business was far from concrete.

Sure, we’d closed a marketing partnership . . . but it wasn’t clear whether it would generate results. Yes, we’d released some cool features this sprint . . . but none seemed big enough to warrant a celebration. So we waited . . . and waited.

Whenever I thought about celebrating, I quickly talked myself out of it. By their very nature, startups are unfinished and uncertain. Something about celebrating felt scary. What if we celebrated something today and it fell apart tomorrow? I didn’t want that egg on my face.

So, the easiest thing to do was avoid it altogether.

When you’re so focused on the peak of the mountain, it’s easy to lose sight of how far you’ve come. The art of celebrating the small wins isn’t about setting smaller goals — it’s about being grateful in the midst of uncertainty.

Practising gratitude is hard, but the rewards are great. I reflected on the previous six months and realised that there was an abundance of things to celebrate sitting right under my nose. We’d made significant progress on our product, hired some incredible people, and set up some great partnerships.

The best way to ensure that you celebrate every chance you get is to plan it into your calendar. Here are a few ways that leading companies celebrate proactively:

On Friday afternoons, teammates take it in turns to show off what they’re working on and what’s gone well. Engineers might show new features, sales might talk about new deals, customer services might share a client success story.

I’ve heard it called many things: ‘Friday Wins’, ‘Beers and Cheers’, ‘Wine and Winners’. But it’s fast becoming a staple of many fast-growth startups, as a way to end each week on a high note.

Staff retreats aren’t only for big corporates. Small companies can reap massive benefits by investing in quality time as a team. You might not be able to send everyone to Courchevel for a ski trip, but a little planning and effort can make a small budget go a long way.

Travel is powerful because it creates distance between the team and the company, literally and figuratively. And with distance comes perspective. Games, awards, meals together, and unscheduled time play an important role in team cohesion and connection.

If you really look for them, you can find dozens of milestones that are worthy of celebration. The trick is thinking them through in advance, so you can spot them when they happen. You can find celebration milestones in every part of your business:

  • Funding — receiving a term sheet, closing the deal
  • Growth — acquiring the next paying client, the 100th paying user, etc.
  • Revenue — selling £1K in MRR, £5K, £10K, etc.
  • Team — becoming a team of 10 people, 20, 50, etc.
  • Product — releasing version 1 of the product, version 2, etc.
  • Business development — closing a big account or a big partnership
  • Time milestones — reaching the next anniversary, calendar events

What milestones will you be looking out for?

Have you ever noticed how spontaneous parties are often better than planned ones? The truth is there’s always something to be grateful for. If you’re conscious that it’s been a while since you’ve had a celebration, why not find any old reason and make it happen!

Celebration has a powerful impact on team morale and collaboration. It increases inclusion and has a knock-on effect on innovation and resilience. And most of all, it shows people that you care about them and appreciate their work.

If you want to celebrate more, you need to adopt the ‘gratitude mindset’. What are you grateful for? What have you been making slow progress with? What do you take for granted? And as for how often you should celebrate — if it feels like a long time, a celebration is long overdue.

I’m Dave and I coach CEOs of Series A+ tech companies. Over the last 10 years, I’ve co-founded three VC-backed tech companies, invested in dozens of early-stage startups as a VC and Angel investor, and mentored hundreds of startups as a Lead Mentor for Google. For more info, visit Dave-Bailey.com.