If you’ve ever spent time with an enterprise sales team you’ll understand what a win/loss review is. For those who are unfamiliar, it’s exactly what it sounds like. Typically, when a deal you should have won didn’t close, you review back over the sales execution to see where you failed. This shouldn’t be applied to deals that were never appropriately qualified by your BD reps, but rather genuine qualified opportunities that fit your typical buyer profile. And inversely, you should also analyse why you have won deals instead of just drumming the gong and moving on.

The list is endless but some of the most common reasons for failing to close a deal include:

• Not engaging with (the ultimate decision maker / the end user / IT / etc)
• Not understanding what would need to happen internally at the company (the cost of change is really high and most employees would rather stick with a crappy product that gets the job done O.K. then go through the pain ripping the bandaid off and installing a new system, training people how to use it and change behavior) and walking them through how to effectively manage this process as seen by other companies.
• You didn’t know that they had suspended any new purchases for the year.
• IT blocked you bc they thought they could build it internally
• They decided to go with a competitor who gave them a better deal on pricing.

Whatever, it happens. By my own stats, you will be losing probably up to 50% of your qualified opps anyway. A lot of curveballs get thrown during the sales process so staying on top of your closing process and qualification criteria upfront is important.

So when should you start running win/loss reviews. The answer is immediately. Your sales team (which is probably you as a founder plus 2-4 new inexperienced sales people) have learned how to generate leads, move them through the pipeline, and close your first 10-30 deals, but you don’t realise how you’re doing this. It’s mostly the product selling itself.

Understanding how a lead and an opportunity get passed from one stage of your pipeline to the next is not an art, its science. Just look at where your conversions are failing. I can guarantee you that you are passing too many leads on as qualified opportunities without actually asking them questions around their needs, timeframe, pricing etc. So running a win/loss should help educate you and your sales team on how to keep an eye out for a deal that is just not going to close because of factors outside of your control (IT has a product freeze and can’t implement anything for 3 new quarters). A seasoned sales person will immediately drop that lead and move on to the next one. It will get you better at asking all of the right questions to the right people at the right time in the process (and remember, asking the right questions only works if you’re asking the right people!).

And in case you’ve never run a win/loss, this is the best framework I’ve found online courtesy of Hubspot.