The good cynic: getting startup stuff done by asking awkward questions

I was recently part of a planning meeting for a hackathon. I love hackathons. The idea of getting everyone together in a room to do awesome stuff to solve big problems is inherently exciting. We put aside our barriers, embrace messiness, and get stuff done.

The meeting went well, but there were a couple of people in the room who seemed to be pretty ready to assume the worst about the event: almost as soon as we started discussing the practicalities, heads were in hands and reasons found for each item to be very nearly a hopeless loss.

It was frustrating. I wanted to say yes — to get stuff done — and here were a lot of reasons to stop, to think, to wait, to delay.

Ugh. And yet. These cynics, while their style isn’t mine, didn’t kill the hackathon. Far from it.

Cynics against meh

There’s a distinction to be drawn here between the apathetic and the cynic; or perhaps between the bad cynic and the good cynic. One of the greatest upsides of working in the startup world is that, in my sector, there’s no space for lazy, uninspired time-markers — the people with open-ended contracts who show up to get paid and like to minimise the amount of work they do, and who spread their lack of care around like an endless flu-season.

Apathetic people are killers of projects, relationships and outcomes; they make the world a big ball of meh and I’m glad that in the startup world they last about as long as a snowflake in a flamethrower, because it makes running a startup that much easier.

But there are still people in this sector who get accused of being cynical; and I think they’re different. In fact I think they’re indispensable.

Rapid Prototyping: Round 0.1

No-one likes the voice of someone asking the difficult question; particularly if they ask them a lot. But there’s something important about people who get accused of being cynical in the startup world: they are in the conversation. In an age where apathy is the default, they are showing up.

In fact, these cynics aren’t as cynical as they might like to seem, and that makes them vital; because they call everyone to embrace the real promise of a project rather than hiding behind wishful thinking.

There’s no-one who defends orthodoxy as much as someone who is secretly scared it isn’t true. A cynic on your team, even if they’re irritating, is the first person who asks whether this crazy dream is going to work — and you need to embrace that person, because they’re the first of many who will ask that question.

If, on some level, they’re willing to be convinced, you need them. You might not like them, but if your project is going to be more than a series of excited phone calls and breathless concept notes — if you’re going to get stuff done — then you need someone around who is unimpressed. Because the first version of your product isn’t ever impressive.

Think of the cynic on your team as round 0.1 of your rapid prototyping process.

The good cynic

The crucial difference between the bad cynic and the good cynic is that the good cynic wants to be convinced. They’ll fight — often ferociously — for the problems they see to be recognised, because they want the solution to be real.

You need a range of emotional styles in a team. You need someone who has the idea and loves the idea and advocates for it so it becomes something people accept as desirable and true. But as well as those people, you need someone who tries to find out whether the idea will really work. And those people usually don’t look or sound like cheerleaders.

Good cynics, whether they know it or not, carry into the conversation a powerful and unspoken assumption: whatever you’re doing, it’s worth complaining about. And that’s an assumption that can’t be spoiled by someone asking an awkward question, because it’s embedded in the awkward question like a Greek soldier in a Trojan horse. As long as they’re there, it’s embedded in your work. And that makes your work better.

So the hackathon will go off well. We got stuff done, and it’s still getting done; and it’s better because some of us had our heads in our hands.