Try again. Fail again. Fail Better.

Why ‘perfect’ might be your biggest enemy in a pitch.

David Pullan
The Story Spotters
3 min readAug 31, 2020

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Photo by Larry Crayton on Unsplash

I’d rather fail in front of the client.

Back in 2004 I was coaching a pitch team in London.

It was a Tuesday morning and they were about to do a rehearsal to their leadership in preparation for the final presentation that Friday.

The project manager came running up to me in the corridor.

‘David,’ he said. ‘I’m worried. We’re not ready yet.’

‘No,’ I said. ‘But you will be on Friday. This is all part of the process.’

And this is what I heard in reply.

‘I’d rather fail in front of the client than my colleagues.’

Fail Intelligently

Let me tell you, I didn’t work for that client after they won that pitch.

I had no idea what to do with the information I had heard.

They hadn't grasped the fact that there is huge power in allowing yourself to fail intelligently.

Intelligent failure is about giving yourself the space to learn from your mistakes.

To amend Samuel Beckett, it is about trying again, failing again and failing better.

It is about the journey of discovery to a great final product.

If you want a thorough look at how it works then read Rita Gunther McGrath in the Harvard Business Review.

But in my personal experience I have seen it work on at least three occasions.

  1. When my son learned to walk.
  2. When every theatre company I worked with put on a play.
  3. When every start up I’ve coached created a great product.

They tried. They failed. They failed better.

And they triumphed. (Well most of the plays!)

So why don’t we allow ourselves to fail intelligently when we communicate?

Don’t reject me!

I’ve heard it said that as humans we have three fundamental fears.

  1. Destitution
  2. Physical harm, and
  3. Rejection from the pack

And arguably rejection from the pack is the most frightening.

It feels personal. It is an attack on our ego. And I’m sure it was what drove the comment by that project manager back in 2004.

The poor chap was probably thinking, ‘I have to spend most of my waking hours around the people I am about to rehearse in front of. I may never see the client again. Please David, I beg you, don’t make me look like an idiot in front of my colleagues.’

Understandable. But mad if you want to get a great end result to a pitch.

Celebrate failure until launch day.

So here’s my plea.

Celebrate failure.

Try stuff. Find the possibilities in what you might call the mistakes. Stop trying to be perfect until you have to be.

And even then give yourself some wriggle room. As Voltaire said, ‘Perfect is the enemy of good.’

And if you are giving feedback to a pitch team then remember that you are part of the creative process; a process of intelligent failure that will result in a great product if you handle it correctly.

Oh and if you won’t listen to me then listen to James Brown.

Because nothing beats a try but a fail.

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David Pullan
The Story Spotters

I am Chief Story Spotter at www.mckechnie-pullan.com. I also make improvised films at The Tasmaniacs.