Strong–and Weak–Questions to Win the Sale

By Andrew Sobel

Advice abounds on "asking good questions" during the sales process. I believe much of it is confusing or even misleading.

My clients and readers have enjoyed Power Questions, but have asked for more detailed guidance about the use of questions specifically in sales and business development. In response, I have published a short ebook entitled Power Questions to Win the Sale 

Here are some examples of what I mean by misleading advice about asking questions:

Some Misconceptions

"Inquiry-based sales is dead"

Really? What they mean is that a sales approach that relies entirely on asking questions doesn't work. That's true. But it's a strawman, because we always knew you couldn't  just walk into a prospect's office and ask them 30 questions and expect to walk away with a contract!

"You must provoke your customer"

That's great–but only when you have a truly provocative idea and only once you've built some rapport and trust! That's like a career strategy founded on becoming a professional basketball player or a supermodel. You need a broader set of value-added conversational strategies than having a breakthrough, provocative idea for every meeting.

"Ask only open-ended questions. Don't ask closed-ended questions"

Well, if I never asked any informational questions I would be rather ignorant about my client's business. You almost always need to ask a few closed-ended questions, especially at the beginning of a relationship.

"Always start with a few general questions about the client's business"

Maybe. It depends. "How's business?" is OK for someone you know pretty well, but if you walk into a Senior Vice President's office and ask such casual, jaunty questions, it will most likely communicate a complete lack of prepara

There are many others like these. But let's move on to a review of Strong and Weak questions that work/don't work during the sales process.

Strong and Weak Questions

Strong: Questions that access emotions not just rational or analytical thinking. For example:

"As you look ahead in your business, what are you most excited about?" Or, "In looking at your implementation plan for this new program, what are you most concerned about?"

Strong: Questions that help the other person reach his or her own conclusions or get committed to a course of action. For example:

"What do you think is your strongest option right now?" Or, "How would you assess your team's effectiveness? How aligned are they, and how well do they collaborate?"

Strong: Questions that inherently build your credibility early on in the relationship. I call these "credibility-building questions." For example:

"Like you, all of our clients in the industry are grappling with pressure to reduce costs and reallocate investment to emerging markets. How is your own organization reacting?" Or, "I was struck by your CEO's speech at the investors' conference, when he talked about realigning your organization to customers rather than geography. How will this impact your area? What changes will you need to consider?"

Strong: Questions that challenge a client's definition of the problem, or even their ambition:

  • "How did you arrive at that goal?"

  • "Do you think 10% is ambitious enough, give what your competitors are doing and investor expectations?"

  • "You've framed this as an efficiency problem. What other contributing factors have you looked at? For example, I've often found that collaboration between marketing and sales can be a major issue."

Strong: Questions that help you understand and align with the client's higher-level goals and aspirations:

  • "Why do you think this is happening?"

  • "What's driving the need to do this, now?"

  • "What is the overall business goal that you're responding to with this initiative?"

  • "Who is the executive sponsor of this effort, and why is it important to them?"

Weak: Questions that you could probably could have answered before you even showed up in the client's office:

"How many employees do you have?" Or, "How long has your boss been with the organization." (Better: "What are the particular challenges of providing training and development to employees who are dispersed in over 50 offices?")

Weak: Questions that have been used so much they now sound like utter cliches. Sometimes just a re-wording can help. For example:

  • "What keeps you up at night?" (Better: "As you think about these three initiatives, what are going to be the likely challenges or barriers to implementation?")

  • "What will success look like?" (Better: "If you are successful at doing this–a year from now, what will be different?" Or, "What measures will you use to gauge success?"

  • "If you could wave a magic wand and change one thing, what would it be?" (Uh, make you leave my office immediately?) (Better: What one thing, if you could change or improve it, would make the biggest difference to your business?")

Weak: Manipulative or "sly" questions. For example:

  • "What can we do to earn your business?"

  • "If I could show you how to save 20%, would you give us an order?"

  • "What question haven't I asked you?"

  • "What has surprised you?"

Remember: A successful sales process combines advocacy and inquiry. That is, you go back and forth between asking throughtful questions and adding value by sharing best practices, making observations about what your other clients are doing, and suggesting ideas to your client. And yes, if you can challenge and provoke them with some strong points of view, please do so. 

Strong questions engage. They create commitment. They help clients reframe their issues. They reveal the client's highest level goals. They access emotions not just logic. They create a great conversation. 



Andrew Sobel helps companies and individuals build clients for life. He is the most widely published author in the world on the topic of business relationships, and his bestselling books include Power Questions, All for One, Making Rain, and Clients for Life. His clients include many of the world's leading companies such as Citigroup, Hess, Ernst & Young, Booz Allen Hamilton, Cognizant, Deloitte, Experian, Lloyds Banking Group, Bain & Company, and many others. Andrew's articles and work have appeared in publications such as the New York Times, USA Today, strategy+business, and the Harvard Business Review. He spent 15 years at Gemini Consulting where he was a Senior Vice President and Country Chief Executive Officer, and for the last 15 years he has led his own consulting firm, Andrew Sobel Advisors.

He can be reached at

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