The benefits of Win/Loss Analysis are well known and have been documented in the research of independent analysts like Gartner’s Todd Berkowitz.

Those that take a more comprehensive approach [to Win/Loss] have seen a 15% to 30% increase in revenue and up to 50% improvement in win rates.

—Todd Berkowitz, Gartner Group

Yet, little has been written about how these gains are being achieved. In other words, how sales and marketing teams are operationalizing insights from Win/Loss Analysis to generate more leads, cut the sales cycle, and win more deals.

In this post, I share my top five tips for using Win/Loss Analysis to improve conversion throughout the buyer journey.

1. Generate more inbound leads with content marketing that accurately reflect the buyer’s reality

While Buyer Personas are terrifically powerful tools for more effective sales and marketing, they’re quickly outdated in fast moving technology markets, and are often based more on anecdote and high level CRM stats than the drivers and motivators behind buying decisions.

The #1 challenge for organizations is developing content that speaks to the buying audience. Difficult to do when you don’t know who the buying audience is.

—Christina McKeon, SiriusDecisions

By taking you behind the curtain to hear actual decision makers’ thoughts and actions during their sales experience with you, Win/Loss Analysis can bolster your Buyer Personas with insight into the motivations, hesitations, and influences on decision makers in recent deals, and more specifically, which ones are associated with deals you’ve won vs. deals you’ve lost. Or, distinctions between SMB vs enterprise buyers, or between buyers in market segments such as technology vs banking.

  • the problems with the status quo solution or events that trigger the search for a new solution (journey)
  • discovery – go-to sites, blogs, and trade shows
  • influencers decision makers rely on for advice
  • criteria used to evaluate new solutions for a new solution
  • existing habits and switching costs that generate inertia
  • anxieties and fears about switching to a new solution

The end result is more engaging, higher converting customer-facing content that addresses the real problems, criteria, anxieties, and goals of decision makers.

2. Truly target the Ideal Customer

The handful of demographic variables in most Ideal Customer Profiles don’t help much, as Craig Rosenberg at TOPO points out, since “ideal customer fit is typically based on one or two variables and thus not predictive.” Yet, there’s a fear of adding a larger number of variables because it limits the prospect universe.  Tibor Shanto calls this the “‘every prospect is sacred’ phenomenon.”

Win/Loss, by relying simply on the facts of deal outcomes (win, lose), identifies the behavioral and situational variables correlated with won deals, and limits the risk that more variables will filter out good prospects. Several examples:

  • corporate initiative (eg, cloud migration, software quality, higher velocity delivery)
  • organizational bias toward value creation vs. cost cutting
  • ultimate decision making power – dev, operations, finance
  • acceptance of new technologies – visionary early adopter, tech pragmatist in the early majority, or tech conservative in the late majority

3. Qualify harder, earlier, and more often

The in-depth deal profiles Win/Loss interviews yield can improve handling of deals that qualified in, but closed-lost. Todd Berkowitz at Gartner calls this “identify[ing] deals you should win (not just deals you CAN win).” Qualifying out the deals you’re unlikely to win frees up resources to focus on higher propensity deals, but it can require both courage and antacids.

4. Find opportunities to increase pricing, or support for an already premium price

Do decision makers perceive your premium-priced product as a premium product? This sounds like a riddle, but it’s a common and vexing debate between sales reps, sales management, and marketing.

Win/Loss interviews also provide valuable feedback for products priced below competing solutions. For example, how low should you go. When I asked a buyer about my client’s pricing, he replied that “it’s expensive.” But to him that was a good thing because it was cheaper than the alternatives he’d considered, but not too cheap. “These guys take their deal seriously.”

Learn how price is affecting deal outcome, how buyers evaluate price, and the latest pricing offered by alternative solutions.

5. The buyer experience is the foundation of an effective Sales Enablement program

Sales training, coaching, content delivery, and enablement technology – buyer knowledge is essential to 3 of the 4 key components of a Sales Enablement program. The detailed, up-to-date insights Win/Loss interviews yield about prospects, buyers, and competitors make sales training and coaching more effective, and can be used to flesh out and correct mistakes in playbooks, scripts, battle cards, other enablement and customer-facing content.

One thing that most experts agree on is that sales enablement should start with a deep understanding of who the buyer is and what they want

—Scott Albro, TOPO

Training the trainer is built in when sales leadership participates in group analysis/synthesis of the interviews using a technique like affinity diagramming. Plus, this taps the group’s domain experience, and increases uptake of the analysis across the company.

Finally, new SDRs and Account Reps will onboard faster – and with a deeper understanding of their customer – after reading Win/Loss interview transcripts.


Note: As I’m using the term here, Win/Loss Analysis is a two-step process. First, decision makers in recent deals (half Closed/Won, half Closed/Lost) are interviewed. Then, inductive reasoning is used to understand why you win deals, why you lose, how to win more deals, and a bunch of other related insight about the buyer’s perceptions of you and the buying experience.


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