How Are You Going to Lose

There are two questions that will help you win more deals. The first question is, “How am I going to win this deal? The second is the other side of that question, requiring an answer for “How am I going to lose this deal?” The first addresses your strategy, your plan. The second addresses your threats.


You have made a lot of sales calls. You have won your fair share of deals—maybe even more than your fair share. You are following your sales process, and your dream client is deeply engaged in the process. While all of these things are super helpful, what you have to do to win may be something completely different.

Where in your sales process does it tell you that you are going to have to help your dream client come up with the courage to fire their existing provider? Where in your playbook does it address having a conversation about your dream client’s willingness to remove a person they have worked with for years?

Where do you find the guidance to negotiate a deal between the technology owner and the business owner when they come to loggerheads over the solution, the timeline, and the scope of the project? How do you navigate your internal legal review when there is no sense of urgency, and when you can’t agree to terms your dream client wants to change?

Competitive strategy is one thing, and it is part of how you win. But, there is much, much more, and you need a plan that includes want you know to be necessary to winning.


You may have never asked yourself the question, “How do I lose?” It’s an excellent question. It clarifies your thinking, like an impending hanging.

You might know that your competitor is going to be priced a lot lower than you are. You might also know that your dream client’s purchasing manager values his ability to extract value from suppliers, because he has stated that fact on his LinkedIn profile (true story, this one). When you hand in your proposal and your pricing is not the time to start thinking about how you are going to deal with what could cause you to lose your deal.

You might also be aware of the fact that one stakeholder who is essential to your deal worked with your company in the past, when they worked at another company. You weren’t working for your company when it happened, but the way you failed to execute for the stakeholder’s past company is the worst moment in your company’s history. This threat to your deal isn’t going to resolve itself. You do something now, or you take your chances.

A loss review is an autopsy. It’s too late to do anything to save the patient that is your deal.

The time to identify what needs to happen for you to win, and what you need to do to not lose, is while there is still time to do something about it.

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