Big Picture

In Sales, the Second-Best Thing to Winning Is Losing Quickly

Todd Caponi

In the world of sales, pursuing quality leads over quantity is often expressed, but rarely practiced. Unfortunately, traditional approaches to what actions are measured and enforced by sales leaders disincentivize sellers from quickly qualifying out of opportunities they’re likely to lose.  

So often, sales leaders prioritize the volume, or quantity, of leads over their quality. They figure that more leads equal more qualified prospects, and more qualified prospects lead to more sales. It’s simple math! They measure the volume at the top of the funnel as a measure of the expected results to come out of the bottom. While the math is correct, the logic isn’t.  

Ask yourself: Would you rather have a pipeline of prospects that only represents two times your team’s quota, but is made up entirely of highly qualified opportunities, or a pipeline representing four times their quota, but much of which is likely garbage?   

Sales leaders and their team members know that the most important asset they have to convert to revenue is time. This means that, as a sales leader, you must lead your team to use its time wisely, to spend less time on losers, and more time finding, developing and winning the winners.  

Encourage your sales team to quickly discern if there’s something off with the fit early on so that they can lose quickly using these guidelines:   

  1. Lead with transparency.
    I advocate for leading with transparency. Transparency qualifies inor out quickly and firmly. This can mean saying, “Based on our initial understanding of your environment and desired outcomes, there are a couple of areas where we have a bit of concern around our fit. Can we address those first? If those are going to be showstoppers for you, best we both know that up front versus three months down the road, right?” Or “Given our understanding of your environment, the investment is likely to be between $X and $Y. If that’s way off from your expectations, let’s address that upfront, so we don’t waste your valuable time, either.” It helps the buyer predict their experience faster, with the side effect of a faster sales cycle. If there’s something off about the fit, the customer will find out either during the cycle or after they’ve purchased. Either way, it’s not good. And setting up the price conversation early keeps your salespeople from investing time taking about a seven-figure deal with a four-figure buyer. 
  2. Avoid the sunk-cost fallacy.
    The “sunk-cost fallacy” refers to a greater tendency to continue an endeavor once an investment in time, effort, or money has been made. It’s an inherent bias we all have, causing us to ignore the ongoing cost of working on something we’ve already invested time, resources, and dollars into, even though we know there’s unlikely to be a reward for doing so. We keep investing that valuable time. Occasionally, it turns out you were right, and you could salvage the opportunity. However, those rare wins of a mismatched opportunity are the exceptions. Realize that your time is spent more wisely prospecting and developing opportunities with a higher propensity for both short-term and long-term benefit. 
  3. Celebrate the losses.
    Yes. Seriously! We can flip tradition by empathically celebrating the losses for the effort and the lessons learned. This not only reinforces pipeline integrity and forecast accuracy, but you will also quickly hone your team’s focus on better identifying the warning signs earlier in their prospecting efforts. The reps are already getting punished in their wallets. When losses occur, raise team members’ morale and engagement by creating learning experiences from the losses — debriefing without casting blame —  and see your team’s transparency with their pipeline blossom. 

Losing deals comes with the role of sales. Yet no salesperson would prefer to work an entire sales cycle before finding out that the deal is lost. Losing slowly equates to wasted time and effort. Finding out at the beginning that the deal won’t likely go down is the next-best thing to winning it. 


Written by Todd Caponi.
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Todd Caponi
Todd Caponi is an acclaimed author, speaker and sales leadership professional. He is CEO and founder of Sales Melon LLC, teaching companies’ salespeople and leaders. His expertise is in building the revenue capacity for technology companies, having served in senior leadership roles and helping one organization to a successful IPO followed by an exit valued at almost $3B. He won the American Business “Stevie” Award for VP of WW Sales of the Year. His new book, The Transparent Sales Leader (IdeaPress Publishing, July 5, 2022), challenges long-held sales leadership standards and provides an easy-to-implement framework for today’s sales leaders.


Todd Caponi is an opinion columnist for the CEOWORLD magazine. Connect with him through LinkedIn. For more information, visit the author’s website.