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You Lost a Deal: Here is the Secret to Not Losing the Next One Sellers have an incredible opportunity to learn from their losses by asking their buyers a series of simple questions, in an authentic manner, during the post-mortem process

By Ryan Sorley Edited by Dan Bova

Opinions expressed by Entrepreneur contributors are their own.


So, you just lost the deal you'd been working on for the past six months. Chances are you're upset after hearing this news, but don't pack it in just yet: Sellers have an incredible opportunity to learn from their losses by asking their buyers a series of simple questions, in an authentic manner, during the post-mortem process. In fact, this short conversation can improve your future win rates.

As a buyer-insight expert who interviews executives daily, I've heard my fair share of sales cautionary tales. The stories from these potential buyers are endless and, in some cases, are true examples of jaw-dropping, "Sales 101" process fails. But what always amazes me is that 90 percent of the executives I interview claim not to have shared this feedback with the seller or anyone from the selling company.

The reason, says buyers, is that sellers are way too interested in finding a way to change their minds. Instead of looking for opportunities to learn, they look for opportunities to passionately defend their positions. But this behavior causes buyers to shut down, and the lessons they may have once been were willing to share end up lost to the seller forever. As a result, history repeats itself, and the seller's ability to quickly adapt, learn and grow is stalled.

Related: How to Disrupt Your Sales Funnel for Better Results

The good news is that the fix is easy. A handful of well-thought-out and genuine questions, delivered in the right way, will turn these lost opportunities into ones that offer some of the most valuable personal developmental insight a sales professional could ever ask for. And remember: Feedback is free.

Here are the five questions that I've found work exceptionally well:

If you were my boss, what development advice would you offer to help me improve my effectiveness?

I know what you're thinking: "It sounds a bit odd to begin with, "If you were my boss.'" But rest assured, it's an effective approach for the following three reasons: 1) for just a moment, the wall between buyer and seller comes down, and, as your "boss," the buyer now has a vested interest in helping you improve; 2) asking such a question shows a true interest in learning and improving, and it also expresses a vulnerability that's just too hard to ignore; and 3) your buyer feels bad that they wasted your time and providing useful developmental feedback is their way of making themselves feel better.

What resource influenced you most during your evaluation?

Although many things influence buyers during an evaluation process, my research shows that peer recommendations can influence their decisions more than anything else. A buyer recently told me that, although they were planning on selecting one company, they changed their minds at the last minute after a happenstance hallway discussion with an industry friend at a conference. By asking this simple question, sellers can spend less time second-guessing themselves and more time trying to figure out how to "influence the influencers."

Related: After You Close the Sale -- Stop!

At what point in the process did you have a good sense that we were not the best fit?

I call this the "fail point" question, since it pinpoints the moment in time when things may have gone off the rails. Was it a product demo that fell flat, a poor client reference call or possibly some impressive effort done by your competitor that overshadowed your efforts? Whatever the reason, you now have the opportunity to review that "thing" more closely, make improvements and ensure that it's not a hindrance the next time.

What are our three greatest areas of opportunity to improve?

Questions that require a three-part response always yield great insights, while preventing the buyer from rattling off one thing of no consequence. Although some will quickly share a list of improvement opportunities, others will need time to think. If the buyer feels like they've been put on the spot, give them time to think it through on their own and offer to schedule a brief follow-up call.

What advantages did the winning company have over ours?

Knowing why you lost is one thing but knowing why your competitor won is something different altogether. A better understanding of your competition's perceived strengths will help you hone your talk track to be more competitive the next time. I've found that perceived strengths are not often strengths at all but come as a result of one company doing a better job of marketing a feature than another.

Related: Here Is the Equation for Increasing Your Sales Team's Success

Ryan Sorley

Win-Loss Program Expert

Ryan is the founder of DoubleCheck Research, a Boston-based win-loss analysis firm focused on helping solution providers improve their win rates by turning buyer insights into competitive advantage. 

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