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Here are some of my favorite screw-ups. Those funny stories that I have seen many of my fellow sales professionals make – me included.


Ever realize how much you can learn from watching other people screw up? Sometimes I think that watching the missteps and wrong moves people make can be even more helpful than watching them do it right.

When it comes to sales I am obsessed, obsessed with learning. To be good at sales I think you have to be. You need to realize that sales skills are something that needs to be continually upgraded and developed. So I am always on the hunt, always observing how I am sold to, how others sell, what works and what doesn’t.

I take notes, keep a journal and catalog the great techniques, the major failures and most importantly, the funny sales people stories. And believe me there are plenty of funny sales people stories.

I thought it would be kind of fun to share them, those funny stories that is. Here are some of my favorite screw-ups. Those funny stories that I have seen many of my fellow sales professionals make – me included.

  1. Talk About Themselves

    A doctor client of mine shared this one with me. He has an impossible schedule seeing more than seventy patients a day. He just never has time to meet with sales reps. He had one rep that was so persistent, and he was actually selling a drug my client was interested in. The doctor carved out thirty minutes from his tight schedule and had his assistant set up the call.

    Now this was this reps big shot, he not only had a meeting with the doctor, but he had a meeting with a doctor who was interested in buying. So what does the rep do? He uses (wastes) that time talking about himself, his company and the many benefits of the drug. He never asked the doctor one thing about himself, the practice, his patients or why he was interested in the drug in the first place.  The doctor tuned out after about ten minutes, and never met with the rep again. He did however purchase the drug, just from someone else.

    Sales Strategy 1:  Build relationship first!  If you want to build life-long customers, invest in learning about your customers before asking them to invest in learning about you. 

  2. Lie To The Gatekeeper

    This one is my favorite!  Lying to the gatekeeper, why do sales people do it?  Here is a great story, sales rep had been calling to get an appointment with the CEO. Note here, the assistant and the CEO’s secretary were very good friends. The rep called twice before he pulled out what he thought was his secret weapon. The CEOs name was Richard, so the sales rep assumed he went by Dick. When the rep called the third time, he told the gatekeeper that “Dick” had told him that he would like to meet.  It was all the gatekeeper could do to not to laugh. She knew that Richard not only never went by “Dick”; she knew he sure as heck never told this sales person to call.  So just to have some fun, she passed this sales rep on to the “other gatekeeper” the CEO’s receptionist (her best friend). The receptionist promptly gave the rep an appointment with “Dick.” When the rep showed up two days later, he was taken to meet with Dick. The problem was the only Dick in the company was the 24-year-old intern they had just hired.

    Sales Strategy Two – never lie to the gatekeeper. Instead of trying to get past them, you need to spend time building relationships with them. “Selling” the gatekeeper is as important as selling the CEO.

  3. Think they’re In Control

    This one happened to me. I was trying to find a new vendor for some assessment tools I use. After about a year of looking, I finally found the perfect vendor. I set up a meeting to discuss the final details and close the deal.  As we reviewed the paperwork, I had just a few more questions and one request. I needed to move my “free” training day from December to January. I had a full schedule in the last quarter, and as much as I wanted to, I could not seem to find the time in December to attend the free training. I noticed they had another training in January so I asked to attend that one. That is where the trouble started. The vendor went on to explain that their “policy” does not allow you take the training in another calendar year.  When she held steadfast to the policy I laughed and asked her if she knew how many company has sold the exact same product her company does?   After a year of working to close that deal, they lost my business over a minor policy.

    Sales Strategy Three – you are not in control. Think hard before you tell a customer no, then think harder if you have to stick to it. Customers in today’s economy have a choices and options; you are not the only person from who they can buy!

  4. Assume You’ll Stay

    After ten years of having my insurance with one company, I decided to get a second opinion. For two reasons, one I had made several changes to my home and property and thought I needed to update my coverage. Two, I could not remember the last time I had laid eyes on my agent.  When I called to get my updated profile, my agent’s assistant became concerned and notified her boss. My agent called me five minutes later, shocked to find out I would even think about changing. “You’ve been a great customer for more than ten years.”

    Sales Strategy Four – never assume just because you do not hear from customers that they are happy, never assume they are not looking around. You need to proactively build and protect those customer relationships that matter.

  5. Don’t Do Their Homework

    This one is so embarrassing (and funny) and it happened to me. Early on in my banking career, I went on a joint-call with one of our fellow bankers. We were calling on an attorney, very high profile in our community and a, good customer to have. We took the customer to lunch and shortly after dessert my fellow banker went in for the ask. He said “Chuck we would really love to have your business, who do you bank with” To which Chuck replied “you”  Now in fairness to us, Chuck at the majority of his relationship at another bank, but the point is we had no idea he had two accounts with us.

    Sales Strategy Five – never assume, always do your research and always do your homework. Being prepared, confident and well informed will put you in a solid position to close the deal.

  6. Forget To Dress The Part

    How do sales people forget sales 101? You need to dress the part. Like it or not people have expectations of how we should look, act and talk when we are selling our products. I was training a sales team whose product was solar energy and solar panels. First day I was touring the facility and the grounds when up drives their sales manager. He gets out of his gas guzzling SUV, smoking a cigarette and drinking a mountain dew. Not exactly how I envision a solar panel and renewable energy sales rep.

    Sales Strategy Six – realize actions speak louder than words. People have expectations of how professionals need to look given their jobs, their roles and what they represent.

So what is the moral of this story? Well that is lesson seven: There is more to sales than just positioning a product or service to be bought. You have develop your skills, build your sales acumen and always remember relationships first!

About the author

Meridith Elliott Powell

Meridith Elliott Powell

Meridith Elliott Powell has been named one of the Top 15 Business Growth Experts…

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