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How To Make Sure You Can Afford to Lose (and still make quota)

Anthony Iannarino
Post by Anthony Iannarino
January 20, 2010

Salespeople get into trouble when they believe so strongly that they will win a particular deal that they don’t take the requisite steps to prepare for the unimaginable loss.

You Cannot Count on Winning

Sales is a tricky business. Sometimes, even when you have done everything right, and when even when you are the very best choice for your prospect, you still lose. Even though every sign may point to you winning, something happens and you are not chosen. Maybe there is a personnel change. Maybe their needs change. Maybe they sideline the project or pull the budget.  Maybe the company you are selling to is acquired by another company. Maybe there is a decision-influencer that acts as an obstacle.

A prospect chooses always chooses a partner because they believe it is in their best interest. Even when it isn’t in their best interest. Even when you have done everything right. Even when you deserve to win.

You can’t count on winning any new client, regardless of what looks like or feels like now. There are too many variables and too many unknowns to allow you to be absolutely sure that you will win a particular deal.

An Ounce of Prevention

When the deal you were counting on winning falls through, it will almost always be at the end of a quarter. It will fall through when it is the one deal that is essential to making quota. It will be the one deal that you felt most strongly about forecasting as a win. And it will be excruciatingly painful.

Desperately, you will pull out all of the stops and try to get the deal back on track. And you should. There is no reason to leave the battlefield with any weapon left unfired.

There is an old saying: “An ounce of prevention is better than a pound of cure.”

Let me rewrite that for sales: You need a pound of prevention. There is no cure.

The only way to prevent the loss of a deal from disrupting your sales plan is to plan for the loss of the deal in the first place. You should never count on winning any deal, regardless of what it looks like, regardless of what it feels like, and regardless of what the prospect has said that indicates that you will win.

What is the prevention?

For our purposes, prevention is a full pipeline. Prevention is a pipeline with future deals that have been nurtured and matured over time. As I have written about here before, you cannot cram for success, and you cannot cram to win deals at the end of the quarter. All of the prospecting in the world cannot save you in the last two weeks of the quarter; the buying cycle and the normal sales cycle make it too difficult to win deals quickly enough for almost all of us in B2B sales.


In planning to make quota, you need to build in the ability to lose a deal. The only way to do that is to ensure that you have more deals than is necessary to reach quota already developing in your pipeline. This starts with prospecting and working deals through your pipeline.

Make sure you fight like Hell for every deal. Do so knowing still that you can afford to lose any battle and still win the war.


1. Are you counting on winning a deal that will make or exceed your quota? What if something out of your control happens and you lose the deal? Will you still make quota?

2. How many active deals do you need to be pursuing to be able to afford to lose the deal you are counting on winning?

3. How much time do you spend doing something other than prospecting because you believe it is certain that you will win the big deal you are counting on?

4. What do you need to do to ensure that you can lose that deal and still make quota?

Sales 2010
Post by Anthony Iannarino on January 20, 2010

Written and edited by human brains and human hands.

Anthony Iannarino

Anthony Iannarino is an American writer. He has published daily at thesalesblog.com for more than 14 years, amassing over 5,300 articles and making this platform a destination for salespeople and sales leaders. Anthony is also the author of four best-selling books documenting modern sales methodologies and a fifth book for sales leaders seeking revenue growth. His latest book for an even wider audience is titled, The Negativity Fast: Proven Techniques to Increase Positivity, Reduce Fear, and Boost Success.

Anthony speaks to sales organizations worldwide, delivering cutting-edge sales strategies and tactics that work in this ever-evolving B2B landscape. He also provides workshops and seminars. You can reach Anthony at thesalesblog.com or email Beth@b2bsalescoach.com.

Connect with Anthony on LinkedIn, X or Youtube. You can email Anthony at iannarino@gmail.com

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