How I Embarrassed Myself and Botched a Big Sales Opportunity


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When I began working in sales, I was on a mission to get up to speed as fast as possible. I read all the sales books, went to seminars and took everything I learned as the gospel truth.

One of my biggest sales opportunities at the time was a fast-growing construction firm. I’d already gotten my foot in the door and met with Tinsey, a very articulate woman who told me she was making the copier decision for her company.

Not long after our first meeting, however, I read a book that insisted salespeople should work directly with the ultimate decision maker – the person who had the power to say “yes” or “no.” Any communication with underlings was just a waste of time. 

That was a real wake-up call for me. I’d been calling at the wrong level.

Tinsey was simply the administrative assistant to the CEO. Clearly I needed to take some corrective action – fast.

So I immediately called the construction company to set up a meeting with the head honcho about the pending copier decision. When he agreed to get together, I was ecstatic. 

Wanting the meeting to be a smashing success, I spent a lot of time preparing my pitch. As I waited in the lobby, I couldn’t help feeling pleased with how well I’d recovered from the terrible position I’d been in earlier. No more selling to peons for me!

Then Tinsey appeared around the corner. Surprised to see me, she asked, “What are you doing here, Jill?”

“I’m here to see Mr. CEO,” I replied, suddenly not so confident I’d made the right decision.

“What for?” she demanded.

I answered lamely, “I’m here to talk with him about your copier decision.”

Hearing that, she launched into a tirade of such a magnitude that I’d never encountered before.

“I told you,” she raged, “that I was making this decision. Not Mr. CEO! Me. Who do you think you are going around my back to meet with him?”

She was right in my face, shaking her finger about two inches from my nose. I’d never made anyone so mad in my entire life — and it was in my new job that I loved. I was mortified. Embarrassed. And suddenly feeling very faint.

The next thing I remember, I was lying on the floor looking up at a crowd of people. They were all talking at once: “Are you okay? Do you need some water? Should we call a doctor?”

Embarrassed to my core, I kept telling everyone, “I’m all right. I’m all right.” After sitting on the floor for a few moments, I finally felt good enough to stand up again.

As I stood there, still shaky, I apologized to Tinsey. She suggested I leave and not bother to meet with the CEO. I followed her directions explicitly and never returned.

You may laugh at my story and think, “Jill, how dumb can you be?” And you’d be right. 

At its core, selling is about people. It’s not a bunch of cheap tricks and techniques to manipulate someone to buy from you.

If I’d thought for two minutes about how my actions could be perceived by Tinsey, I would never have gone over her head to contact her boss directly. But I didn’t. I simply thought about my own sales goal and how to best accomplish it.

Even if you’d never done anything like this, I bet you’re still doing a whole lot of stupid things. But you’ll never know unless you view your own behavior through a client filter. 

Here are several more important lessons you can learn from my major blunder:

  • Once you’re working with someone it’s never appropriate to go around them without their knowledge. They’ll get mad. Furious. It’s a normal human reaction.
  • Don’t make assumptions about someone’s decision-making power simply based on their title. Check out how decisions are made, who else is involved and what has to be done before they make a change. In my case, Tinsey had full authority to make the choice. Her boss wanted nothing to do with it as long as she stayed with the budget.
  • If you discover you’re at the wrong level, you need to find a valid business reason to get to the right decision maker. Most of all, it needs to make sense from the perspective of your current contact in the account.  If it doesn’t and you go behind their backs, they’ll find a way to sabotage you.
  • Have your current contact bring you to meet their boss or colleague. Go WITH, not around. Think about why they might want to do this. What value could they get from setting up this meeting? They’ll never do it just to be nice for you. Somehow you need to find out how they can come out a winner by arranging this appointment.
  • An ounce of prevention is worth a pound of cure. Often there’s no way to determine the decision maker until you get in. So you need to plan for what you’ll do if you’re not with the right person. I always mention that speaking to the chief sales officer is imperative for the success of the project. Invariably that opens the door to the final decision maker.

Finally, I’d like you to think about your own sales bloopers. Each one of them is a valuable learning experience with the potential to make you a better sales person.

No matter how long you’ve been selling, you’re not immune from making mistakes. The key is to mine the gold in them so you keep getting better.

P.S. That was the only time in my whole life that I ever fainted!

Republished with author's permission from original post.


  1. Hi Jill: what a great story. It sounds very similar to one I related in an article, The Modern Sales Force: Too Male to Fail. Though I’ve committed many errors in sales myself, this gaffe provided a lesson that came at the expense of my competitor, and resuled in a sale for my company. Thank you thank you thank you. Make no mistake – much as we love predictability, such serendipity influences many selling results, both good and bad.

    Your story is important for new salespeople, especially those who are coached early that above all, they must engage with the “final decision maker” – often assumed to be the CXO. While that’s a worthy goal, a positive outcome comes from the how, not in simply marking the checkbox, as your article points out.

    When I managed IT for a small manufacturing company, the IBM salesman I worked with executed this to perfection. He wanted to meet with the president of our company, but he knew he should go through me. I remember him saying, “I’d really like to meet Stanley [the president’s name]. Could you set up a time for all of us to have lunch?”


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