I was recently discussing some of the stupid mistakes I’ve made as a Salesperson with our sales training colleagues in Vancouver, Edmonton, Calgary and Toronto.  While it might seem unusual that a Sales Trainer would admit to it, every experienced Salesperson has made some huge blunders that might now be hilarious, yet at the time were downright embarrassing.  While they tend to occur early in our career, they can happen anytime when we make assumptions and rush too fast.


Stupid Salesperson Mistake #1 – Make sure you have your wallet when you ask a client for lunch 

Years ago, I wanted to take one of my key clients for lunch.  He recently increased his investment with me and was a pleasure to deal with.  Knowing that he was a busy guy I called him and invited him to one of his new trendy restaurants in town.  He was a very successful restaurateur and night club owner.  “My treat – If you can spend money with me, the least I can do is buy you lunch at your place.”   He said, “Sure, let’s get together – how about Thursday at noon?”  I agreed and diarized the meeting.

At the time, my chiropractor wanted me to stop carrying my wallet in my back pocket, so I usually kept it in my briefcase – no big deal.  As the lunch was social in nature, you guessed it, I left my case at the office because I didn’t feel I needed it.  When it came to paying the bill, I reached in my back pocket and had the shock of my life.

I buried my head in my hands and was mortified.  He belly laughed and said, “It’s lucky I know you so well.” Of course, he signed for the bill.  What’s worse is that he had to tip his own waitress I tried to recover by giving him cash back in a card that said, “Thanks for teaching me a lesson that I will be able to tell for years.”


Stupid Salesperson Mistake #2 – Doublecheck your proposals

I had created a unique advertising proposal that was engineered around a client’s very specific needs based on his industry.  After pitching it, the client told me he loved it but unfortunately, he simply didn’t have the budget dollars for it this year.  I explained that because it was built around his business category, it would be tough not to seek another potential sponsor.  In other words, I would have to pitch his leading competitor.  He said while he didn’t like that, he understood that being a 100% commissioned Salesperson, I had to do what I could to make a living.

Off I went to the competitor.  After pitching it to the new potential buyer, he called back and said that he loved it!  He wanted to present it at the next board meeting board – under one condition. He chuckled and said that I probably should remove their competitors’ name from one area in the proposal.  It appears I changed the sponsor name in all areas except for one.

Always get another set of eyes on a proposal and use the Find/Select Option on Word to catch things you might miss.  Luckily, my buyer caught the mistake and got a good laugh out of it.  I took him out for lunch when the Chairperson signed the proposal.  Yes, I took my wallet.


Stupid Salesperson Mistake #3 – Do your research and don’t wing it on a client call

I had a meeting with the senior buyer and the owner of a large successful restaurant chain.  I had been pursuing this account for 6 months and finally managed to book the first call.  This was my chance I had been waiting for!  At the time, I was living in a smaller community next to a large city and wanted to impress the pair by telling them that I often visited their restaurant in my town with my family.

The buyer smiled and asked me what menu items I liked.  With a truly bad memory and lost for words, I said “various Items.”  It was a lame answer – the best I could come up with at the time.  He then passed me a menu with a list of their locations on the back and said “You might want to do your client research before a call.  We don’t have a restaurant in your town.  That’s our competitor.” 

I shut up, looked down and tried to recover from a full-blown blood rush to my face.  The media personality that came on the call with me was a good friend of the owner.  He tried to cover by saying “Yeah, but you were thinking of putting one there, right?”

“Geez, Dave do your homework and don’t make it tougher than it has to be.”  That stuck with me for weeks after the call.  I recovered from that Stupid Salesperson Mistake and fortunately, the client signed up for a 6-month campaign.


Salespeople Make Mistakes

When you’ve been in sales for the bulk of your career, you will make stupid mistakes – you’re only human.  Many years ago, this was how we learned as Professional Salespeople.  Today, we have many sales tools to help us learn from other peoples’ mistakes.  The key is to learn from them and make them only once or better yet, not at all.  The ability to laugh at yourself keeps you humble and allows people to laugh with you – not at you.

Feel free to share your own mistakes in the comments.

Are you looking for sales tools to sharpen your skills and always be at the top of your game?  Check out our book SHUT UP!  Stop Talking and Start Making Money available on Amazon. If you prefer online sales training, check out the free trial of our course The Sales Skills Incubator.



Dave Warawa – PROSALESGUY