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It is imperative that sales managers challenge their team to confront reality when reviewing their opportunities. If you are without a sales manager, you need to challenge yourself when it comes to reviewing the opportunities on which you are working.

Some sales organizations struggle to challenge people over opportunities, believing that their challenges might come across as negative, and that the conversations might turn into protracted arguments. Friction is good. It brings out issues that need resolved. If your intentions are right, it doesn’t have to be negative.

The intention has to be to expose any weaknesses in the strategy for pursuing and winning the opportunity while still retaining the optimism that allows the salesperson to pursue opportunities—even against long odds.

Getting this right means your intention must be to help your sales team (or yourself), to confront reality—and then to do something about it.

The Devil in Your Deal

What are the obstacles on the path to deal? What obstacles must be overcome in order to win? What is your plan to overcome them?

What are the competitive threats that might derail this opportunity? What internal threats are you going to have to deal with if you are to win?

A good opportunity review might begin with questions about whether or not the prospect is even qualified. Sometimes the opportunity isn’t qualified, and sometimes just the challenge of defending it and talking through why it is a real opportunity strengthens the value proposition.

Winning deals requires that you identify the devil in the deal. Once you have identifies the risks, the threats, and the obstacles, you can decide what you can do to about them. You can face the reality that is your devil.

Facing Reality

Often, the reality is that there are issues that are going to have to be dealt with if you want to win your opportunity.

Ignoring the obstacles, the threats, and the risks to an opportunity doesn’t mean that they’ll go away, and it doesn’t mean that they won’t cost you the deal. The longer they go unaddressed, the more likely they will cost you your opportunity and the more difficult they are to solve. The earlier you face reality, the better.

This is why challenging the opportunity early and often is so effective in sharpening your approach.

Maybe your competitor is perceived as having a better solution in one area that’s important to your client and where you are not as strong as you need to be. Or, maybe a key contact has a long relationship with your competitor, a relationship that could derail your opportunity?

Maybe your dream client needs something that would require a major exception to how you do business. That exception might require approval from someone at the executive level of your company, and it might be something difficult to obtain.

Maybe you are missing information, missing consensus from end users and stakeholders, or maybe you missed key components of your sales process.

The obstacles, the risks, and the threats are many. But they are your reality. Facing that reality improves your chances of winning.

A Thoughtful Group Approach

You don’t have to address all of these issues alone. Even if you are a sales manager, you don’t have to have all of the answers. In fact, it’s more important to have the right questions and a group to answer them.

If you are without a sales manager, you don’t have to go it alone either. (Go it alone together).

Your resourcefulness is massively improved when combined with the resourcefulness of others. You can assemble a group of salespeople or people on your team and talk through the issues. Someone else within your organization may have already successfully resolved what might be a difficult challenge for you. Or someone with a different view might have an out of the box idea that just might work.

The great benefit of challenging opportunities and facing reality is that it improves your odds of winning. The benefit in doing so in a group is the increased learning, the teamwork, and the building of a sales team that brings their initiative and resourcefulness to their game.


Why do we tend to avoid the unpleasant realities of an opportunity?

How do you develop a culture that welcomes a little friction, a little give and take, around opportunities and deals?

How do you deal with an obstacle to an opportunity when you are late in the sales process?

Who can you employ to help you walk through your opportunities and identify your blindspots?

Sales 2011
Post by Anthony Iannarino on November 30, 2011
Anthony Iannarino
Anthony Iannarino is a writer, an author of four books on the modern sales approach, an international speaker, and an entrepreneur. Anthony posts here daily.
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