Organizations that adapt and thrive ask themselves the tough questions. They are confrontational with each other, but not in a negative way. They are confrontational in a positive way, a way that allows them to face reality, to test their assumptions, to identify their weaknesses, and to improve their actions.

Sales organizations that are comfortable being confronted and challenged perform better than those that avoid the difficult questions.

Ask the Question and Make It Hurt

Avoiding problems doesn’t make them go away. When it comes to sales, avoiding the difficult questions is a recipe for losing opportunities and missing your numbers. Some organizations, some salespeople, and even some in management and leadership, don’t like asking or being asked the toughest of questions. Hard questions reveal weaknesses, some weaknesses that it are painful to have exposed.

The tough questions sound like this:

“What is the compelling event that makes you believe that you can close this deal by the date you forecasted?”

“Why should this prospective client buy from us when our value proposition isn’t right for them?”

“How do we expect to win this opportunity from here, when we can’t address one of the critical factors the prospective client has identified as being necessary to a solution?”

The first question forces you to address the fact that you have no compelling event that indicates that you can close the opportunity by the forecasted date. You can either address the forecasted date, or you can work with the client to determine a date that works for you both. Either is better than not asking the question.

The second question addresses the fact that the prospective client doesn’t fit your sweet spot. Even though they may spend an extraordinarily significant amount of money in your space, you aren’t the right people to serve them. If you are customer intimacy and they need operational excellence (lowest price), then it’s almost certain the prospective client should have been disqualified. Asking the question brings this to light. You either defend the decision to sell to them, or you disqualify the prospect and move on to the deals you should be working.

The third question addresses a capabilities gap. You are selling, and the client needs something that you aren’t prepared to deliver. They asked whether you had the capabilities, you said you didn’t, and they dropped the subject. Asking the question gives you a chance to address the issue instead of ignoring it and hoping it isn’t held against you (Note: It is going to be held against you!). You can find a way to give them the outcome they need and build the capability. You can find a partner to shore up that part of your offering. Or you can sit down and work with your dream client to find a substitute. Asking the question prevents you from taking the awful decision of doing absolutely nothing.

All of these question sting. Especially if you are the one being asked.

Facing Unfortunate Realities

The reason these questions are so powerful is because they force you to confront the gaps. You know that gap exists. Your sales manager knows the gap exists. Your Vice President of Sales knows the gap exists. Hell, even your prospective clients know that the gap exists. The question forces you to do something about the gap, and in that, you find new power.

You find in the answers to the tough question the power to change something. You can find a new path to the outcome that you need. The tough questions draw out your resourcefulness, and that of your team. The answers to the tough questions also provide you with the power to change your course—or to abandon it altogether.

More still, asking and answering the tough questions makes you a professional, someone that can be counted on to unflinchingly tackle even the most difficult issues.

To improve your performance, ask and answer the questions that you most dread. By confronting these questions, you will find a path to improved performance.


Why do we seek to avoid the most difficult and challenging questions?

What are the implications of avoiding these questions?

What are the benefits of confronting your weaknesses when it comes to your sales strategy, your offerings, or your opportunities?

How can you help be confrontational with being confrontational in a negative and non-beneficial way?

Why are true professionals comfortable dealing with difficult, root cause issues and weaknesses?

Sales 2011
Post by Anthony Iannarino on October 17, 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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