Learning from Lost Opportunities

June 17, 2025

Phil Krone, President

Understanding why a prospect didn’t buy from you can go a long way toward to making sales to all future prospects.

No other business development activity is more diverse than how salespeople get leads for the top of their sales funnel.

In our experience, too few salespeople make the effort to learn why they did not win opportunities they compete for. Their tendency is to focus on the next one, which results in them missing out on intelligence that might in fact help them win the next one.


Earlier this year we wrote about “the shot” by Duke in the East Regionals in 1992. We discussed how the Grant Hill to Christian Laettner pass, and the Laettner bucket with 3.9 seconds on the clock helped Duke beat Kentucky and move to the championship game.


In addressing this year’s Duke graduating class on Mother’s Day, Grant Hill described a situation leading up to “the shot.” He described a game two weeks before the Kentucky game: “There is

almost no time on the clock, I throw a pass to Christian Laettner, he catches the pass … but he is out of bounds.” Duke was playing Wake Forest, and Grant was inbounding the ball, but he was

guarded by a six-foot-10-inch defender who forced him to make a bad throw.



The point of telling this story, Hill explained, was that after the game he and Laettner sat down and discussed what went wrong. Nobody was to blame, but they realized if they were ever going to run that play again Hill would have to step back to have more room to throw the pass to Laettner. Knowing the two had determined the cause of failure gave Coach K the confidence to keep the play in the arsenal and call it.


When we are retained to help a company better understand their market, we interview lots of people including management, salespeople, prospects, customers, and lost prospects. We almost always learn the most valuable information from lost prospects. We spend time Interviewing the other groups helps us learn what we should be asking the lost prospects about.



Sometimes firms retain us to learn why they lost. There are several pluses to that approach. One is that we will actually do the work to identify the true issues that led to the loss. In other

words, in any enterprise some items on to-do lists—even important items—will be crowded out or simply stay on the list forever because other, more pressing issues take precedence. Another plus if we do the work is that simply tasking the salesperson to do the post mortem is unlikely to produce the necessary insights.



However, that said, I still think it is best for the salesperson to be tasked with doing the lost-prospect follow-up—but with help. It will reveal a lot about the salesperson to the buyer and probably lead to a better relationship. If it was a really close call, maybe this desire to learn from loss will impress the buyer so that the salesperson will get the next sale.


This usually requires training the salespeople so that they have a really good chance of learning the true reasons behind the loss. Basically, they must learn how to set the stage, then which questions to ask, and, finally, how to ask them. They must make it clear to the lost prospect that they are not using the postmortem to get the prospect to change their mind. I did have a lost prospect once cancel his order with competition following my meeting and give the business to my company, but that is rare and should not be the purpose of the call.


Here is an example of a successful debrief with a lost prospect. Before becoming our client, one of our law firm clients lost an opportunity to handle a major international law matter. We

suggested that they request an in-person meeting where they could ask questions about the decision to go with another firm.



What they learned is that the competition had “out-discovered” them; the competition found a need behind the need to use a law firm to handle the matter. That “hidden” need was to learn just how big the problem was before retaining someone to handle it. The competing law firm had asked the buyer if he had ever experienced project creep where the scope continues to expand and become far more expensive than the initial estimates. (Think of a kitchen project that starts with a new refrigerator and ends up with new cabinets and a new floor).


The issue struck a chord with the prospect who decided to hire our client’s competitor for a phase one project to learn how big their world-wide legal problem was, not to fix it. A year later our client won the business back, which would never have happened if they hadn’t discovered why they lost. The post-loss debrief with the client enabled them to persuade the prospect that they were the best source next time.


To discuss this topic further, please get in touch with me directly either by calling 847-446-0008 Ext. 1 or emailing

pkrone@productivestrategies.com. 


We’re happy to give you our take on what you’re doing now or suggest other ways you might not have tried.


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