Even if she doesn’t have much to say about product development and has been known to lick other team members, Happy was an essential part of our recent strategy meeting.
It was held at my house, around one table, where people can talk freely and disagree properly. It is far easier to keep your employees engaged when they are enjoying themselves and Happy, my twelve-year-old Portuguese water dog, helps to do that. That may sound like a soft detail. It isn’t.
I’ve founded six startups and exited two, and one thing I have learned is that boredom is a business risk that founders cannot afford to ignore.
Strategy obsesses over speed, fixating on execution, iteration, and moving before the market moves away from us. But very few founders talk seriously about the silent killer of speed inside a company: boredom.
The slow draining of curiosity. The moment a talented person stops feeling challenged, stops caring quite as much, and starts doing the job with only part of their brain switched on.
It is sad to watch. It is also expensive. Gallup’s recent analysis on employee engagement links higher engagement with better productivity, profitability, retention, and wellbeing.
None of this proves that putting a dog in a strategy meeting will increase ARR. Sadly for Happy, the evidence is not that specific. But it does suggest something founders should take seriously. How people feel at work affects how they perform. And startups in particular don't have time for disengagement.
In a large company, boredom can hide behind process and politics. In a startup, it shows up immediately. One person switches off, and a product timeline slows down. One key hire loses energy and a roadmap starts to wobble. One team stops learning and the company becomes less intelligent than the market around it.
The strange thing is that most startups begin with the opposite of boredom. They begin with curiosity. People join because there is a problem that needs to be solved. They want to build, test, improve, and figure things out in real time.
Keeping employees engaged is the way towards retention. This means recognising that people learn better when they are active, curious and present. Here are some tricks I’ve learned for anybody looking for ways to do things differently.
Develop autonomous humans
An autonomous company doesn’t have to mean AI agents. Instead, surround yourself with people you trust to make decisions when you’re not in the room.
The people I want to work with are curious and looking to solve problems. The ones who learn quickly because they want to, and not because someone told them to.
Trust your employees not to need constant clarification. Allow people to pursue new ideas and learn constantly on the job. Autonomy is a precondition to engagement. It’s an inclination that need to be nurtured from the get go, and it has to keep evolving. Your employees are likely to spot potential problems before you.
Challenge old habits
Startups have a unique advantage. We are not weighed down by decades of institutional inertia. We can design our own work, learning, and culture. We can question the boring things before they harden into habits.
Neuroscience has taught us that the brain sends more signals to the memory centre when it is having fun. That’s why you’re more likely to remember something learned while laughing with a colleague than in a monotonous presentation.
Make things interactive
Replace management reviews with weekly demos where everyone presents what they've built to the whole team, not just a boss. This builds individual ownership, and the team sees progress directly. When people know they'll demo their work to the team every Friday, they move differently. They care more because they're not hiding behind processes, they're showing up.
Small teams thrive on this. There’s no management checking boxes. Just people building, delivering, and standing behind their work in front of colleagues who depend on it.
Which brings me back to my dog…
Dogfood your products
The industry term for using your own product is “dogfooding”. It’s one of the simplest ways to keep a team engaged. Your team are your first users. They will find what is clunky long before the customers. They will see where the product makes sense and where it gets in the way. Most importantly, they stay close to the thing they are building.
This matters because people rarely care about work they only observe from a distance. They care when they use it, test it, break it, improve it, and feel that their fingerprints are on it. In a startup, that closeness is part of the operating system.
Founders often ask how to retain great people. The honest answer is that there isn’t a perfect formula. People leave for all sorts of reasons. But we can control it more than we think.
We can make work less dull. We can keep people closer to the product. We can start treating engagement as infrastructure. Boring rarely announces itself. It just makes smart people a little slower and a little less likely to try the difficult thing.
For a startup, that is a risk. But this one is largely within our control. Keep your people curious, keep the work engaging, and you’ll keep the talent that makes a startup thrive. And, where possible, let the dog attend the strategy meeting.
