• October 23, 2018

My Big Sales Pitch Fail (And How to Avoid the Same Fate)

If you spend long enough in sales, you’ll realize that not every pitch is going to be a winner, no matter how good you are at your job. When your pitch does flop, it’s easy to feel defeated and alone. Let me assure you however, that you are not alone. Here’s the story of my big pitch fail (and how to avoid the same fate).

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The Pitch

Let me preface this story by saying that I was actually quite prepared for the pitch itself. My team had been planning the trip to Michigan for weeks, and I was feeling pretty confident in what I had prepared. But, when you are working on a big pitch for a multimillion-dollar deal, it’s impossible to feel completely at ease.

When we arrived to Michigan, and arrived at the company’s headquarters to pitch the deal, we realized that we weren’t the only company they were interested in working with. They had invited three other companies to deliver their pitches as well.

Normally, I’d be excited to be the last group to, since there’s a not-insignificant advantage to being the freshest on everyone’s minds before making a decision. In this case though, my nerves were starting to get the best of me. I could see heads of sales from our competitors entering and exiting the room, and it seemed like everyone was confident as they exited.

Where it Went Wrong

Since I was delivering my big pitch after lunch, I thought it might be a good idea to start with a bit of humor to wake everyone up. As I delivered what I still considered some pretty killer jokes, they just rolled off of everyone, creating an awkward silence in the room. I tried all the usual tactics to engage my listeners, and elicit a response from them, and.. crickets.

But, I knew I still had one tried and true joke in my arsenal. If you know me, you know that I love to talk about my “no-jerks hiring policy,” that I have used at every company I’ve owned. This has literally always been a winner. But, in this case it was the completely wrong audience.

I was pitching to a financial service company, and they seemed to have a completely different perspective on the matter, joke or no joke. I.e., they were fine with hiring jerks as long as they were good at their job, and saw the policy as weakness. After a few more painstakingly awkward minutes, my team and I said our goodbyes, knowing that there was no way in H-E-double-hockey-sticks that we were going to close that deal.

The Lesson

The main takeaway from this fail is to read your audience, and if something isn’t working, stop doing it! I should have known that the people I was pitching to were no B.S. kinds of guys, which isn’t exactly my forte. The best idea would have actually been to send another member of my team in my place. Also, never let your competition fluster you. If you are confident in yourself and your product, there’s no reason to be nervous.