Win/Loss? I'd rather "Win/Win!"

Updated: Apr 26, 2020

I recently worked with a client trying to walk them through the win/loss prediction quandary – how to tell if we are going to win an opportunity or lose it and when? The truth is that even the most sophisticated analysis tool in the world is incapable of predicting that outcome – it can only identify some of the likely factors to influence it.



If you step into a pipeline review and tell your boss “the deal is in the bag”, you should prepare yourself for the follow-up on how you can guarantee that outcome. If a manager tells a tenacious salesperson they don’t have a chance to win a deal, “stop chasing it”, depending on how stubborn the sales person is, they might spend the next three months trying to prove their manager wrong – even at the expense of ten better opportunities.


A single unpredictable factor such as bias, preference or timing can convert any deal into a win or a loss at any point. So let’s spend less money and cycles trying to predict the outcome, and rather focus our efforts on better management of the pipeline and the tangible factors we can influence, to win the deals that matter most.


The experienced sales professional knows most of the factors that influence the outcome of a deal. Is there a real problem to solve here? Does the client have a compelling reason to buy? Is there an impending event? Do they have the budget? I’ll stop here as most of you know the drill.


Don’t guess, make predictions or rely on gut-feelings. Look at all the deals in the pipeline and stack-rank them without bias, and leverage well-known industry factors that will tell the sales team and their leadership what deals should be worked first and aggressively, and which deals should be nurtured and worked at a later time.


More importantly, because most of these factors are known, the actions that the team needs to take in order to improve the likelihood of a win are also known. There is the secret sauce; accurate prioritization, manage the risk and influence the win. It is not just win/lose, it is more about what are the actions that need to be taken and when, so that you end up with a win/win on the deals that make the most difference for your organization.


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