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What’s your Questioning Strategy?

Asking to be a strategic advisor to your client usually never happens. But, having the right questioning strategy can build the credibility required to become one.

The questions that you ask and the way that you ask them can define how you operate and how you are perceived by clients.

Do you ask the questions that get you paid? These questions are your bread and butter; they’re part of your comfort zone. These questions allow you to position your solution and the need for your product or service. These are what we call “current situation questions” — questions that probe how the client is currently operating, his/her level of satisfaction with the operations, and facts about how he/she does business.

All good questions, but they’re the wrong places to start.

The best first questions are strategic ones that explore the client’s main objectives. What is he/she trying to accomplish? What are his/her key priorities and objectives? Why did he/she decide to change from X strategy to Y?

Why should we ask these questions first? Because we don’t want to focus on our agenda; we want to focus on the client’s. At this point, we want the client to talk about what is most important to him/her. We want the client to take the conversation — and us — where he/she wants it to go, not where we want it to go.

Some people think that asking too many questions makes you look unprepared. Others think there are no stupid questions. The best strategy when selling to C-level executives is to leverage your preparation and ask questions that demonstrate an understanding of the client’s business. Don’t waste clients’ time with a generic, “What are your main objectives?” Instead, show that you’ve done your homework. You might say, “In speaking with Tom in Western Region sales, he mentioned the key areas of focus for the company are X, Y, and Z. I would like to get your take to find out how you feel these are working.”

Asking open-ended, strategic questions allows you to go deeper into the iceberg. We don’t want to just uncover the obvious, observable things (the tip of the iceberg) or what we know about similar companies. We want to see beneath the waterline, to uncover the bigger issues that we might not be aware of.

The first questions should uncover short-term business objectives, strategic goals, and key needs. Then, switch the focus to the present. What is most important to the client NOW (the client’s current situation, his/her process, operations, etc.)? Is the client satisfied with the current situation? Is it going well? What changes would the client make?

From there, move to future needs (long-term plans and goals), personal needs (what is at stake for the individual?), the client’s nonbusiness interests, preliminary thinking about possible solutions, and the client’s feelings about you as a sales professional and your company. Any implementation questions should come last (budget, decision making, and time frames).

To avoid sounding like a prosecuting attorney, it’s important to make questioning a conversation and not an interrogation. It helps to remember these three basic skills:

  • Prefacing to introduce the question with a rationale that makes you sound more credible and the client more comfortable answering the question
  • Trading information based on your knowledge of the market, industry, or similar clients to add value to the discussion and encourage the client to share new information
  • Acknowledging what the client is saying to show that you are listening

The types of questions that you ask will determine whether you are perceived as a vendor or as a partner. It will become difficult to differentiate yourself from the competition, and you may end up selling a solution that isn’t a customized fit for the client. The more generic your questions, the more generic the sale. You will also lose the ability to use the client’s own words when positioning solutions or to uncover additional opportunities. Most importantly, you will have a harder time accessing and connecting to C-level executives and company decision makers.

To make sure this doesn’t happen, prepare your questioning strategy and questions in advance. Let your questions show your preparation and understanding of the client’s needs, and leverage your industry knowledge.

Most of all, make it conversational and focus on the client’s agenda, not yours.

About the Author

Karen Klein is a Senior Training Consultant and Executive Coach with Richardson. She has worked with global clients in the US, South America, Europe and Asia, spanning different industries. Prior to working with Richardson, she was an Account Manager and then District Sales Manager for a telecommunications company, where she was in charge, among other things, of improving the employee job performance. As a consultant, Karen has worked in conjunction with the Puerto Rico State Department, researching and conceiving innovative market strategies and cost-effective measures for improving its economic activities with sister states. She collaborated with Microsoft Mexico to help increase the effectiveness and efficiency of the company’s call center; and she analyzed and assessed the effectiveness of General Motor's operations in Hungary, and developed a case study that was distributed to international executives attending business school at Georgetown University. She is bilingual in Spanish and English and fluent in French and has lived in Europe and the US.

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