Of course it matters whether you won or lost…


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You’ve probably heard some variation of the saying “it matters not whether you won or lost, but how you played the game”. The modern use of the phrase (in a slightly different form) is attributed to the American sports commentator Grantland Rice, but the principles have their roots in the spirit with which the original Olympic Games were conducted over 2,500 years ago.

For anyone in sales repeatedly playing and losing – no matter how well-intentioned – is hardly likely to form the foundation of a successful career. We want to win, but we want (or should want) to win in an ethical, principled manner that sees our customer as a partner and not a combatant.

Systematically learning what works and what doesn’t – and progressively doing more of the former and less of the latter – ought to be the critical foundation of any successful sales organisation. And yet the essential raw materials – in the form of effective win-loss analysis – are all-too-often missing or flawed…

It’s been my experience that the most effective sales people tend to be particularly adept at learning and applying the lessons of both success and failure. In fact, I believe that these top performer’s capacity to learn and adapt is probably one of their most consistent characteristics.

But all too-often this invaluable learning is neither understood nor applied across the rest of the sales organisation. And even when organisations implement win-loss reports, the underlying analysis and the resulting conclusions (assuming there are any) are often incomplete, flawed, biased and of little practical value.

Self-assessment doesn’t work

This is particularly true when our less-effective sales people are asked to self-analyse their reasons why an opportunity was won or lost. I have never seen (nor do I ever expect to) the reason for loss to be self-assessed as sales incompetence, nor the reason for success to be identified as brilliant marketing.

If they are to be in any way effective, win-loss analyses cannot be “tick the box” exercises. They require thought, reflection and the involvement of an unbiased third party. And they cannot be complete without input from the most important contributor – the prospect or customer.

I’ve conducted independent win-loss analyses on behalf of a number of clients over the years, and these exercises have inevitably yielded invaluable insights into how the prospective customer approached the buying process and how and why they came to their ultimate decision to either buy or stick with the status quo.

Internal, self-conducted win-loss analyses – in addition to being generally incomplete, flawed or biased – also tend to concentrate largely or exclusively on the latter half of the sales cycle and on the sales person’s success or failure in “closing” the opportunity.

Start at the beginning

But it turns out that the most important insights are typically upstream of that point. In fact, many of the most strategically important lessons are to do with what caused the prospective customer to become concerned about the status quo in the first place and how they went about researching and identifying their options at the start of their buying decision journey.

Well-constructed win-loss analyses help us to better understand these all-important early stages of the buying decision process, such as:

  • The trends that most concern senior executives in the organisation
  • The issues, threats and opportunities that are most likely to cause them to start researching their options
  • The common demographic, structural and behavioural characteristics of our most valuable customers
  • The roles that are most likely to become successful change agents within the organisation
  • The specific catalysts or trigger events that are most likely to put the issue on their radar in the first place

These early-buying-stage insights allow us to target the right messages at the right people in the right organisations at the right time.

Understand their journey

And by asking the right questions about their buying decision journey, such as:

  • How and where they started to research their options
  • How they determined which solutions to look at in more detail
  • What key stages they went through in their buying decision process
  • Who else was involved in their internal process, and what roles they played
  • Which solution options they considered and rejected, and why
  • If they decided to buy, how they decided what to buy
  • If they decided not to buy, why they decided to stick with the status quo

We can build up a much clearer picture of what we need to look for, what we need to know, what we need to do, what we need to avoid, and how we ought to qualify potential sales opportunities.

There’s another unexpected benefit from conducting an intelligent win-loss analysis process: we’ll often be in a better position to judge how much future potential this particular customer or former prospect might represent.

Is the effort worth it?

Is this harder to do than adding a few fields to a CRM screen? Yes.

Does disseminating the lessons learned require conscious effort? Undoubtedly, Yes!

Is the effort worthwhile? The last time Gartner looked at the issue, they concluded that the minority of organisations that were doing a half-way decent job of win-loss analysis saw an up to 50% increase in sales win rates compared to their less committed peers.

Republished with author's permission from original post.

Bob Apollo
Bob Apollo is the CEO of UK-based Inflexion-Point Strategy Partners, the B2B sales performance improvement specialists. Following a varied corporate career, Bob now works with a rapidly expanding client base of B2B-focused growth-phase technology companies, helping them to implement systematic sales processes that drive predictable revenue growth.


  1. In sales, it actually does matter if you win or lose! Winning means you got the sale, and losses should be carefully examined so that you can learn from the experience.


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