Asking Bigger and Better Questions

Anthony Iannarino
Post by Anthony Iannarino
September 29, 2010

One of the primary reasons salespeople fail to gain the time and attention of C-level executives is because they lack the business acumen and/or the confidence to ask the really tough questions. Instead, they hope that their slick presentation and their well-crafted statements about themselves and their company will be enough to gain their dream client’s attention and differentiate them. It doesn’t.

One: C-level executives don’t want to hear about you or your company outside of the context of their major business challenges and opportunities. They don’t have the time.

Two: C-level aren’t considering hiring you as a salesperson. They are hiring you as a manager and a trusted member of their team. They need to you to help get them a business outcome, to make an improvement.

If you want your dream clients attention, especially at the C-level, the way to differentiate yourself is by asking bigger and better question.

It’s All Business . . . Acumen

Your business acumen has to allow you to quickly discover the essence of their dissatisfaction, and to be able to hold your own in a conversation about what that dissatisfaction means to them and their company, what the implications are, the existing constraints that have prevented them from getting a better results before now, and what they believe needs to happen for there to be an improvement.

Your dream clients, especially at the C-level, are looking for someone with the business acumen, the industry knowledge, and the situational knowledge to know how to help. The easiest way to recognize all of these qualities in a salesperson is by listening to the questions that they ask.

Your dream client C-level executive wants to be asked about the biggest problems and the biggest obstacles to their achieving results. They want to be asked about the obstacles to higher performance.

Asking the questions proves that you know what is important. It also shows that you know how to cut to the chase and to identify the essence of the problem. It shows that you are a value-creator and a real resource. It means that you are there to deal with what must be dealt with.

Bigger and Bolder

Your dream clients at the C-level are hoping that you will ask them the big, bold, value-creating question that allows them share where they need help. They hope that you have the ability to know how to make a difference, and that you aren’t merely playing around the edges. They already have vendors. They are looking for the type of business relationships that they can leverage to produce greater results and a higher level of performance.

C-level executives know that all of the improvement that they seek is found in answering the hard questions—and that it isn’t likely to be found in your standard PowerPoint presentation.

Your value is in asking those questions. And then helping to find the answers.


  1. What are the hard questions about performance and improvement that you need to ask to differentiate yourself and to prove that you have the business acumen and the ability to be a resources for your C-level contact at your dream client?
  2. If you were the C-level executive at your dream client, what would you hope to be asked? What questions would you find most compelling from a salesperson if you were in their position?
  3. What is you ratio of hard-hitting, cut-to-the-chase questions to statements about you and your ability on sales calls with C-level executives?
  4. What are the bigger, bolder, and better questions that you need to ask?

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Sales 2010
Post by Anthony Iannarino on September 29, 2010
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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