Win/Loss Analysis – By Employee

Conducting a sales win/loss analysis for your entire team is kind of like making a blanket statement – even if most of what you’re saying or seeing might be true, it certainly doesn’t apply to every individual that comprises your team. This is why the best analytical sales managers often conduct their win/loss analysis by looking at how individual employees or sales reps do.

This is Part 3 of our blog series on the importance and best practices of a sales win/loss analysis. We previously touched on conducting this analysis by looking at lead sources, as well as lost reasons. Now, we’ll dive into a win/loss analysis by employee.

Why look at individual sales reps?

Each of your sales reps are unique, with their own personal motivations and work habits. As a sales manager, it is your job to know each of them and what buttons to push in order to maximize each individual rep performance. This is why conducting a win/loss analysis of the entire team will provide an incomplete picture – what works (or doesn’t work) for one rep will not necessarily apply to all the other reps, or maybe even none of them at all.

Conducting a win/loss analysis by employees allows you to ask – and answer – several key questions:

  • Who on my sales team has the best win rates?

  • Which employees are struggling to win opportunities?

Those questions are two sides of the same coin, framed differently. In asking those questions, you’re really trying to figure out one thing: how can we be better as a team?

Studying your best-performing employees might reveal learnings or best practices that could be shared with the rest of the team. Focus on those employees to unearth secrets to better sales performances. Are those top-performing reps dominating their demos? Are they simply qualifying opportunities more stringently than their peers? Are they lights-out closers? More importantly, can what leads them to succeed be bottled up and distributed to other reps?

Similarly, analyzing your weaker employees can also be incredibly revelatory, only this time, instead of looking for strengths to replicate, you’re trying to find weaknesses to snuff out. Once you have identified your worst employees, you can drill in deeper to figure out what those weaknesses are. Studying their individual sales funnels, for example, would reveal which specific stages that rep struggled with. Or the sales manager could simply opt to spend more time shadowing that rep on calls.

Who needs more opportunities?

Conducting this win/loss analysis will also reveal which reps are most efficient at winning opportunities. This means not necessarily winning the most opportunities, by having the highest win rate. Look at this example below:

Nancy Olson has won the most opportunities in the past year, having closed 75 of them at a win rate of 30% – all in all, pretty sterling results. But two other sales reps – Lauren Bacall and Robert Vaughn – have significantly higher win rates, at 40% and 71% respectively.

As a sales manager, you have to look at this data and make some tough decisions. Are these high win rates merely a function of working within a small sample size, i.e. these are relatively new reps who happened to get off to a blazing hot start in their selling careers. Or are Lauren and Robert both exceptional reps who should have a far more robust pipeline with more opportunities to work on? If the latter is the case, it is imperative that you, as a sales manager, provide these sterling reps with the opportunities they need.


The role of a sales manager often requires asking tough questions of your sales team, and conducting a win/loss analysis by employee will certainly open up many of those difficult queries. However, this type of analysis can also be a tremendous boon in finding the answers and actionable insights from those questions. Find the answers you need to maximize your sales team performance by conducting a win/loss analysis by employee.