Questions I Wish I’d Asked (How to Improve Sales Conversations)

It Stopped Me Cold

Recently, when I was thinking about remodeling my house, a contractor asked me a question that stopped me cold. I’ll never forget it. He asked:

“When you drive up to your remodeled home how do you want to feel?”

The question asked for no specific information about building materials or type of windows—no specifics a contractor could actually work with.

But it opened up a series of conversations between us that eventually produced a plan I would never have dreamt possible had he not asked me that initial question.

Why Ask Thought-Provoking Questions

People in executive sales know they’re supposed to ask questions.

The trouble lies with the kinds of questions they’re in the habit of asking. Too often, they either ask for info that can be found elsewhere or they ask questions that bore or put off their customers.

Consider, for example, the difference between these two questions:

  • “What was your sales growth like last year?”
  • “How do you feel about last year’s sales growth?”

With the second question, you’ll not only find out what sales growth was like but whether your prospect felt good, bad, or indifferent about it.

Why is this critical? Because only when you understand your listener’s mindset can you create value for them.

The key to creating value for your customers is to ask the kinds of thought-provoking questions that will engage them, open up a productive conversation, and provide you the insight to give them what they need.

Are Your Questions Thought-Provoking? 

Fundamentally, thought-provoking questions should uncover perspectives, possibilities, and feelings about various topics, events, or scenarios important to the customer.

How do you know if your questions are thought-provoking? Give this a try.

Imagine you’re planning a first meeting with an executive. Go ahead and quickly brainstorm a list of all the questions you’d typically ask in a meeting like this.

Then evaluate whether each of your questions meets the following criteria:

  1. It can’t be answered with a yes or no.
  2. It can’t be answered by anyone else other than your customer.
  3. It engages the customer’s imagination, e.g., “What if…” or “Imagine…”
  4. It leads the customer to new insights.
  5. It sets you apart from other salespeople.

Before every customer meeting, review and then rewrite your questions based on this checklist. If you do, I think you’ll be pleasantly surprised at how much more productive your conversations become.

Is your sales team struggling to identify executive concerns and priorities?

Can they engage executives in consultative conversations? Find out how Mandel’s The Influential Conversation™ Workshop can help.

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Diane Burgess-Faber

Diane Burgess-Faber

Diane is Senior Vice President, Chief Learning & Design Strategist, at Mandel. With over 20 years’ experience in the training and development industry, she plays an important leadership role on Mandel's Executive Leadership and Strategic Planning Teams. As global head of learning design and client experience, Diane has been at the forefront of Mandel’s AI-driven mobile and semi-synchronous online strategies. These strategies reinforce and complete Mandel’s award-winning suite of live in-person and virtual training solutions. Diane and the Learning Design Team assess, consult with, and support hundreds of clients, both nationally and globally, in designing training that delivers business results. Her Client Experience team then delivers the training that supports learners and drives true behavior change while carefully monitoring the user experience. Before joining Mandel, Diane spent 17 years with Zenger-Miller (later AchieveGlobal). Diane served as the Executive Director, Global Sales and Operations, and built worldwide networks of highly capable affiliate partnerships while crafting products and services that were locally and culturally relevant.