Member preview

How To Be a Better Startup Mentor

What improv actors can teach the startup community

Photo: rawpixel

One thing I’ve learned from being involved with startups, is that people love to tell you that an idea won’t work, that it’s already been done, and/or that they can think of various problems with it.

These people need to try their hand at improvisational theatre/comedy.

In improv, there is something called the ‘Yes, and…’ rule. It is one of the most important rules of the genre and helps to ensure its very survival.

The rule is that regardless of which premise someone puts to you, you have to accept the premise and build on it. You can never flatly reject a proposition or the whole sketch will fall flat too.

A ‘yes, and…’ dynamic is key to good on-stage chemistry. The moment that someone rejects a premise is the moment that the beating heart of the sketch fails. Done for. Dead in the water.

It is not possible to generate momentum when someone is constantly hitting the brakes. What’s more, it’s exhausting and frustrating to work with someone like that. Imagine being an actor who constantly has their ideas shot down by another. You would never want to work with them again.

This rule applies to the startup community—and particularly mentors — just as much as it does to the theatre community. We’re all in this together, and the ‘Yes, and…’ rule will not only improve your interpersonal chemistry, but also your personal value and reputation.

Sure, some entrepreneurs may need to hear the ‘hard truth,’ particularly those who risk personal ruin by trying to force a solution through. But many do not.

Entrepreneurs got in the game already knowing that they were embarking on a big, risky idea. That’s part of what defines a startup. They also know that at some point they may need to pivot, or even fold up entirely.

The whole premise of the lean startup method is that a startup should be treated an experiment. Founders start by hypothesising about which type of business model will be desirable, feasible, and viable, and then test and adjust their hypotheses as they go. It’s about exploring the possibilities and responding to the evidence in an agile way.

Photo: David Travis

Mentors should let the entrepreneur make the decision to persist or pivot based on the evidence. Negative ‘advice’ helps nobody. Not to mention that unless you are pointing to evidentiary proof, your advice is just a contrary hypothesis.

This means if you have been approached for mentorship, or even are just someone having a chat with an entrepreneur, you should apply the ‘Yes, and…’ rule.

This means accepting what the entrepreneur wants to achieve and building on it. It means saying ‘Yeah, I get what you’re aiming for, and…

…this is how someone else did it,’

…here’s another idea,’ or

…I know someone who you can talk to.’

If you apply this approach you will instantly become an above-average mentor, because you will be a valuable team member. You will be somebody who brings solutions rather than problems — ideally without even being asked. That is the kind of value-adding that earns you equity.

Sure, sometimes you are going to disagree with the entrepreneur about their strategy. In that case though, simply ensure they stick to the lean startup method by saying ‘Yeah I get what you’re aiming for, and…

…you should test that hypothesis in case it’s flawed,’

…here’s a way to test that assumption,’ or

…if that fails you can try pivoting to this.’

Photo: Keenan Constance

Telling somebody ‘Let’s test it,’ is a clear, useful message. But if it’s not landing and you really want to drive the point home, you might even challenge them to a friendly bet. Betting is a great way to make somebody think on a deeper level. It’s an indirect challenge, so it won’t be taken personally, but it’s also cause for consideration. What do they know that I don’t? Why do they think they have the upper hand?

Finally, if you foresee a problem but are unsure how to test or fix it, well then it’s OK to say that. At least that is being as helpful you can possibly can be at the time. No entrepreneur will hold that against you.

But just throwing up obstacles, problems, and criticisms means the entrepreneur is unlikely to talk to you again. Because you’re literally useless to them. They already knew the journey was going to be tough; they prepared themselves for that. They want to meet people who are able to help them succeed.