Sales Leadership: Why Celebrating Losses Wins!

Oct 12, 2023 | Blog

Sales Leadership: Why Celebrating Losses Wins!

“Celebrate the losses!”

A few months back, I was keynoting a revenue leadership summit for one of the largest technology companies on the planet. I said those three words…celebrate-the-losses. One leader immediately spoke up…

“I don’t know about that…we don’t want to create a culture of losers.”

This company was founded in the 1970s. The culture of “expect to win every deal” was certainly admirable…and they had done it really well!

However, have you ever been in a company where, when a deal moved to “Closed Lost” in the CRM, the entire executive team would receive a notification? As I joined one company, that was the process. And even worse, a rep who had recently moved a deal to “Closed Lost” was soon to encounter an executive, with a message of “You must have gotten outsold.”

As I sat observing my new team’s reaction to this environment, two behaviors became pervasive:

  1. The close date on deals would move out months or even years…“Wait, I thought we lost that deal?” “No…they just delayed their decision a decade or two.” “Oh”
  2. Deals would miraculously be moved to an unqualified stage in our CRM”Wait, we filled out RFPs and had multiple demos and engagements with them.” “Well, they weren’t really ever qualified.” “Oh”

…so, best case, the environment where losing a deal was a punishable offense created a wholly inaccurate forecast. Hiding a loss > reality.

But the worst consequence of a culture where losing?

We were losing deals for the same reasons over and over, and had no way of knowing it!

Change the Culture

I had to make a dramatic change. The first step was obviously to remove the “Closed Lost” notifications. The first person who should know a deal has been lost was the rep’s direct manager, and that shouldn’t come in the form of a CRM notification. 

But second, I had to go extreme. A champagne toast for the rep who lost a deal!

“What? We don’t even do that for the wins, Todd!”

We obviously celebrated the wins. The reps were rewarded handsomely, too, in the form of quota attainment, bonuses, top performers’ designations, and variable compensation.

But for the losses? They were already getting hit in the wallet and their quota attainment.

Celebrating the loss meant celebrating their effort, but even more importantly, the lessons that can be learned! They’ll never get that time back…let’s maximize the ROI on it! And, we’d celebrate even more emphatically when the rep was willing to self-actualize their own involvement in the deal’s result.

  • If you could turn back the clock, what do you wish you had seen earlier?
  • What would you have done differently?
  • What about their environment wasn’t a good fit?
  • When did you know, in your gut, that this deal was at risk, and you felt raised odds of losing?

Collect the answers. Categorize them. And celebrate! There’s an ROI (Return on Investment) still to be had from that time. An ROI that will pay for itself over and over again in the form of focusing on the opportunities you’re bound to win, in the form of losing quickly so your time can be invested in opportunities where our fit is clear, in the form of not losing again for the same reason!

Our role is to be a partner to our customers…to help them achieve optimal outcomes, or in many cases, help them achieve outcomes they didn’t know were even possible. As a service professional, our role should be to help our customers achieve those outcomes, whether it’s with us, or via another route…quickly!

That goal becomes considerably more challenging when the only lessons you learn are only from yourself. And, how can you possibly be an asset to a customer when you can’t truly empathize to their situation, based on additional evidence from like situations, like environments, like challenges, and like companies? When the leadership environments we create frown upon the loss, the subconscious bias of those who are out on the front lines turns to it always being the customer’s fault. They made a bad decision!

We lose more often. We lose slowly. We waste both our own time and our customer’s time. We burn dollars…

The Outcomes

The results from the simple shift to a celebration of losses? 

Forecast accuracy would improve: The deals in our pipeline and forecast represented reality, not a hope that nobody would notice

A higher win rate: Partially because we’d use the lessons learned to qualify in and out more effectively. Partially because we’d avoid making the same mistakes again. And in a big way…because we became better partners to our customers!

A reduction in sales cycle lengths: For all the reasons above – remember, we don’t buy when we’re convinced, we buy when we can predict! Your reps become better able to empathize and help your customers to predict their outcomes. Confidence is contagious, and the confidence of knowing that an opportunity that isn’t a fit can be owned and shared without repercussions, where you’re not afraid to tell your customers the truth, helps your customers to predict faster! 

And in the end, your entire sales team culture improves…your reps will stay, bring their best every day, perform, and become advocates for you and your organization – resulting in lower turnover and faster time to recruit A+ talent!

(here’s a little YouTube Short to give this more context… 52 seconds!)

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I speak and teach revenue organizations on how to leverage transparency and decision science to maximize their revenue capacity. It’s what I do…teach sellers, their leaders, and really entire revenue organizations the how we as human beings make decisions, then how to use that knowledge for good (not evil) in their messaging (informal and formal), negotiations and revenue leadership. I wrote a 3x award-winning book (𝘛𝘩𝘦 𝘛𝘳𝘢𝘯𝘴𝘱𝘢𝘳𝘦𝘯𝘤𝘺 𝘚𝘢𝘭𝘦), and have a newish book out (𝘛𝘩𝘦 𝘛𝘳𝘢𝘯𝘴𝘱𝘢𝘳𝘦𝘯𝘵 𝘚𝘢𝘭𝘦𝘴 𝘓𝘦𝘢𝘥𝘦𝘳) now that just won its first award!

Reach out if you want to discuss The Transparency Sale sales methodology, or really…anything else (sales kickoffs, workshopskeynotes, the economy, history, etc.)! Email or call 847-999-0420.

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(Header picture is from 1927…a group of salespeople celebrating victories during a sales contest)





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