5 B2B Sales & Marketing Leaders Share Their Epic Fail Stories in the Spirit of FAILFAST17

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“I’ve missed more than 9,000 shots in my career. I’ve lost almost 300 games. 26 times, I’ve been trusted to take the game winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.” – Michael Jordan

As our sales and marketing event, FAILFAST17, nears closer on June 15th, we thought it’d be fun to share short epic fail stories from other B2B sales and marketing leaders. Because who doesn’t enjoy, and can’t relate with, a good fail?


My most epic fail was early in my career with Miller Heiman. Before I worked with my parents, I was a school teacher. Why does this matter? I had been involved with several text book adoptions and knew the text book business from the buyer side. We had an opportunity with a huge text book company. I was chosen to go out and meet them there. This was before the internet, but I did my research. I had talked to the woman who had called in about the opportunity and I learned about all of the buying influences. I prepared my “Green Sheet” sales call plan and I was ready.

When I arrived I was greeted by 6 or 7 of the top executives in the company, including the CEO who had just flown in from overseas. I used my plan to ask questions and I listened. They all seemed very engaged except for the CEO who had nodded off. I wasn’t too concerned knowing he had jet lag. I wrapped up the meeting by getting commitment to the next steps. They all said a hearty good bye to me.  Not just the usual good bye. They all shook my hand and touched my arm and said thank you and good bye. To keep this short we got the deal. But by the time I flew back to the office, they had called my mother, Diane Heiman, who was running the company and told her that they really wanted to buy the training as long as I would not be involved. I was crushed. I simply couldn’t believe it. I called my contact to try and understand where I failed so that I could improve but she wasn’t completely sure where things broke down. I was too young, too bubbly, too inexperienced. I obviously had failed to see the signs from the other senior executives and they were nice enough to be nice to me on the way out.


In my first year as a consultant, I had put together an amazing panel for a client’s webinar.  We had somehow managed to convince a top industry consultant, the president of the industry’s trade association and one of the company’s most prominent customers to participate.  These were all incredibly busy people and were being very generous with their time.

The webinar was fantastic, better than I could have expected.  Great insights, subtle and authentic endorsements of the client’s technology.  Amazing. I had, of course, forgotten to click “record”.

Thankfully we were able to reassemble all three of them at a later live in-person conference to basically “re-record” the event.  But it took awhile to live that one down.


I had been selling to smaller companies when I got my first crack at selling to a Fortune 500 company. Only problem is, I didn’t adjust my pitch. I gave the same talk track I gave to the smaller accounts something like, “We can really help you gain market momentum” or something dumb like that. Of course, what I heard next made me realize just how dumb it was, “Do you really thing we need help gaining market momentum?” Doh! Hard to recover from that one. Also goes to show you’re better off asking questions than making declarative statements.


Many years ago Rosetta Stone was one of the best clients for our sales training business. They saw a quantifiable improvement in appointments, pipeline, and deals with big ROI. My contact was a sales director who was topped by an EVP of Sales. The Sales Director told me they were going to move forward with the contract for the next round of work. The last step was to meet with the EVP of Sales as a formality.

When I got to the meeting the EVP of Sales said they were evaluating us vs. John Costigan. This was not a formality at all; it was a competitive ‘bake off.’ They asked us for a ton of documentation and to jump through a bunch of hoops. We spent collectively 80 people hours on their requests.

Word came in a few weeks later. We lost. Costigan won. One of the sales managers told me that the EVP of Sales was in the same country club as John Costigan. They were golfing buddies! I went to LinkedIn and typed in the name of the EVP of Sales. We had 3 common connections. One of them was John Costigan. 80 hours wasted on a deal we never had a chance of winning. Epic #salesfail.

The lessons:

  1. Relationships run deep. Know the relationships. If you get out-relationshipped you are going to lose.
  2. Check LinkedIn first to see if your competitors are talking to your prospect as well.
  3. Only put in a lot of work if you are in column A on the vendor evaluation sheet. If you are in column B either re-engineer the evaluation criteria or walk away.


I was part of a team that made the mistake of pushing a product to market simply to hit an arbitrary launch date and having it epically fail in the market.  After months of careful research and requirements planning, we had defined what we believed to be a unique and highly desirable product.  As we moved closer and closer to the launch date, it became obvious that all of the features we had defined wouldn’t be ready in time.  Rather than going back to the executive team with a new proposal for launch, we started taking out features so we could hit the launch date.  We thought we could get away with a “version 1” product that would be “ok” and then launch a “version 2” shortly thereafter that would have all of the features we had defined in the market requirements phase.  We launched ‘version 1” on time, without not only differentiated features, but barely even some baseline features.  The product failed in the market and the whole program was canceled before a second version ever had a chance to make it.  Within 12 months, competitors came to market with products like the one we had defined originally, and they were very successful.  We missed the market opportunity because we were afraid to delay our product launch by a few months.

All of these stories are proof that failure can be one of the healthiest steps towards success. So join the sales and marketing event, FAILFAST17, dedicated to learning from our failures! It will be held on June 15th at the Eleve Event Center in Pleasant Grove, UT.


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