The Biggest Mistake I’ve Ever Made in a Sales Meeting

by Mar 26, 2019Articles0 comments

“Success is a lousy teacher. It seduces smart people into thinking they can’t lose.” – Bill Gates

It was a bright Tuesday morning. I was a senior AE at a tech startup selling networking software to investors. I came into the office at 8am, fired up and ready to start prospecting my target list.

Little did I know that a cold email I sent that morning would end up catching the interest of a senior executive of one of the largest asset managers in the world. Up to this point, it had proven nearly impossible for me to gain the attention of people like him — Managing Directors investing up to $100 million in deals. So when he invited me to his office the next day, it would be an understatement to say I was excited.

The next morning, I walked in with a positive attitude. The first thing he told me was that he only had 30 minutes but was looking forward to learning more.

I was ready to go and eager to pack as much as I could into the short timeframe. I quickly thanked him for his time, sat down, opened up my laptop, and jumped right into a demo. I spent 15 minutes showing him the product, closed my laptop, sat back, and said, “So, what are your thoughts?”

As I waited for him to answer, I silently congratulated myself. I was speaking to one of the most senior people at the firm and to my mind, I’d done everything right: been efficient with his time and direct in my communication during the demo.

I certainly didn’t expect to hear the words that came out of his mouth a few seconds later.

He stared at me and said, “Charles, you taught me nothing today.”

I was momentarily stunned.

But when I quickly replayed the last few minutes, my overwhelming reaction was pure embarrassment.

I had spent 15 minutes telling him how our product worked — but had provided him with zero insight into the problems we’d uncovered in the market and how we were addressing those problems for our clients. I hadn’t asked him a single question to see whether or not he felt those problems were relevant to his firm.

After all that flashed by me, I looked back at him and said, “You know what? You’re right. I made a mistake. Can I start again?”

Mercifully, he responded, “Yes.”

I took a deep breath and began to tell him what I should have started the meeting with: the problems we’d found in the marketplace, and how our service had helped other firms like his solve for those problems.

I followed up with: “Do these problems surprise you at all?”

“No, they don’t surprise me one bit,” he said. “In fact, they sound like problems we’re also dealing with and which we should be concerned about.”

And just like that, my meeting did an about-face. He ultimately signed up as a client — and I learned a big lesson. Two of them, in fact.

The first is that admitting your mistakes is key. It’s genuine. It’s real. It wasn’t easy for me to tell my prospect that I’d screwed up, but by doing it — and asking for permission to make it right — I began to turn the meeting around (something that would never have happened if I had refused to admit failure). I began to gain his trust.

The second, most important lesson I learned is that selling a service is not about detailing features. The demo is important to an initial sales conversation, but it should never be the star of the show. I realized that day how crucial it is to provide insight to prospective clients into what challenges their competitors are facing and how your service fits into the landscape they’re operating in. You want to prove — without necessarily saying explicitly — that you understand the market your prospects work in just as well and maybe even better than they do. And you want to provide them with at least one a-ha moment — a perspective they haven’t considered, a solution they’re not aware of, a data point they haven’t seen, an insight they couldn’t come up with on their own. This is a nearly infallible strategy to gain your prospect’s respect and lower their level of resistance to your ideas.

So I would ask you, what are you teaching your prospect?

Feel free to reach Charles Muhlbauer with any questions at

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