Ten Signs That You Need Win-Loss Analysis

Have you ever sat around a conference room table trying to understand why you win and lose? These discussions happen every day in companies large and small, at the executive level and the front-line, yet they often yield little to no results. My guess is that you have also found yourself six months later in a room having the same conversation.

As Einstein said, “Insanity is doing the same thing over and over and expecting a different result.” These speculative conversations are repeated over and over eating up resources and critical time. 

Companies have been trying to figure out why they win and lose forever. But less than 20% of companies actually run win-loss programs according to Pragmatic Marketing.

What do the other 80% do? They share one-off stories and allow volume, influence, and emotion to drive speculative conversations. Here's a real-world example.

The overarching problem is that win-loss discussions tend to be one-off, be anecdote driven, not represent reality, not provide proper perspective on your core business versus growth initiatives, be dominated by the most vocal people, and confine any learnings to the people present in the room.


You should consider implementing a win-loss program if:

  1. Your company has launched a new product and wants to understand buyer reactions.

  2. You are making decisions based on anecdotes from sales reps . . . and you aren't sure if the reps actually know what happened.

  3. You are starting to lose to a new competitor and you don't know why.

  4. You do not have alignment on priorities across the organization.

  5. Your product roadmap doesn’t seem to line up to what customers want.

  6. You struggle to ramp new sales reps and drive sales productivity.

  7. You do not have a method for extracting tribal knowledge from your top performing reps.

  8. You have an idea of what drives buyers’ decisions but don’t know how to weight those factors or whether they are comprehensive.

  9. You have expanded geographically and you want to understand how buyer expectations differ.

  10. You are using a CRM drop-down with win-loss reasons that are speculative at best.


The simple answer to stopping the insanity is to create and run a formal win-loss program through a third party that interviews your buyers, identifies the real reasons why you and lose, and makes those learnings available to your entire organization.