16 Jul 2014

Tricky Business: Awkwardness

By Paul Miller

If you make the choice to go into startup life there’s something you should know – things are going to get awkward.

You’ll have to have lots of awkward conversations as a team. You’ll have to talk about money, about who gets the credit, about whether people are doing a good job or not. You’ll think it’s easier to avoid these conversations but don’t – short term awkward is better than long term resentment.

You’ll have awkward conversations with friends who just don’t get why you’re going it alone. They’ll nod politely and then there will be an awkward silence as they ponder their nice secure salary and pension. You’ll get things wrong with approaching investors, customers or journalists. You might bum dial them and then realise later, address the email to the wrong name, sign off with ‘love and hugs’ by mistake.

And then at some point in the future there will be a bunch of people who you find it difficult to talk to, people who are annoyed with you, people that you are annoyed with, people you’ve effectively fallen out with. Things not working out is an inherent part of startup life and it generally leads to things getting awkward.

It’s hard to do but life wil be a lot easier if you embrace the awkwardness. Recognise it, celebrate it, laugh about it and then resolve it. Make awkwardness your friend.

[Finally it turns out after a bit of Googling that we’re not the first to think about this, which is awkward. Here’s our friend Banks Benitez of the Unreasonable Institute getting *really* awkward.]