Seven Questions That Can Transform Your Next Client Conversation

Just as some medicines, depending on the patient’s condition and health, can be either helpful or deadly, the power of any particular question will depend on the context in which it’s used.

So whenever people ask me, “You wrote a book on questions—okay, so can you give me an example of a great question?” I tighten up inside because I know they are expecting to be “wowed” by an amazing question. But without understanding the context, whatever I propose could sound underwhelming.

All that said, here are seven client scenarios with questions that can really help you transform the conversation.

1. Scenario one: You’re trying to get to know someone early on in the relationship.

In this scenario, you’re trying to learn more about who they are as a person and what their formative experiences have been. This question is especially effective with a seasoned, older executive. Question: “How did you get your start (…in business, in the arts, in whatever their field is)?” This question invites the other person to share their personal “story.” It connects you to them on both a rational and an emotional level. I’ve had truly wonderful conversations with clients after asking this question—and learned important information about them.

2. Scenario Two: You are meeting with a prospective client for the very first time, and they are aloof and defensive.

Let’s say you have a prospect who is leaning into the back of their chair, glancing at their smartphone, and refusing to say anything of consequence to you. They give short, vague answers to every question. They have the attitude “So, what do YOU really have to offer me?” In this situation, you need to create “reach.” Put on a very relaxed smile and ask this Question: “You know, I’m sure there was a good reason why you took this appointment. What interested you in speaking with me this morning?” (… or, “I’m sure there was a good reason why you took this appointment. Are there any particular issues you’d like to discuss?”) This question forces the other person to get to what’s really on their mind (which, possibly, is nothing that you can help them with…in which case you may just have to agree to stay in touch).

3. Scenario Three: You are trying to understand your client’s agenda of critical needs, priorities, or goals—but not getting enough clarity.   

You have a prospect or client who isn’t that forthcoming about what their priorities are. Maybe you just don’t know each other well enough. Question: “I’m curious, how will you be evaluated at the end of the year?” (You can add, “What are the performance objectives that your leadership has asked you to accomplish over the next 6-12 months?”) If they balk or question why you want to know (which is actually quite unlikely), you can say: “I ask all my clients this question. The more I understand about what’s important to you in driving your business forward, the more I can be of help to you.”

4. Scenario Four: You are asked, “So tell me about you and your firm.”

Don’t assume you know what the other person is really interested in hearing about. Chances are, you will go on and on and share a lot of information they don’t care about.  Instead, first ask this Question: “What particular aspect of our company would you like me to talk about?” (Or, if they are asking about you personally, “What particular aspect of my experiences and skills would you like me to talk about?”) A key goal of “Power Questions” is to better understand your client. This question enables you to tailor your response and be more effective.

5. Scenario Five: You have a meeting with an unspecified agenda—or, you’d like to expand the agenda to make sure it is truly relevant.

Sometimes a prospect wants to talk for half an hour, and there’s no fixed agenda. Often, I go to see a client, and we have a presumptive agenda—but I want to make sure we are focusing on what’s really important to them. Question: “From your perspective, what’s the most valuable way to use our time together this morning?”

Alternatively, sometimes I ask, “From your perspective, what’s the most important issue you want to make sure we discuss this morning?” These questions allow the client to tell you what’s really important for them right now and how they want to use the time with you. You’d be amazed at the valuable, and hitherto unknown, information this simple question can reveal.

6. Scenario Six: You want to engage on an emotional/personal level.

Some questions are rational/analytical. For example: “How are you planning to implement this strategy?” Others—and these are often the most interesting and powerful—are emotional or personal. Question: “As you think about the various initiatives you have underway, I’m curious—what are you personally most excited about?”

Other sample emotional/personal questions:
• “I understand you’ll retire in a year. What legacy would you like to leave in this organization?”
•  “How will this program impact you personally?”
• “What’s your greatest concern about how this initiative is going?”
• “What’s the most fulfilling part of your job? The least fulfilling?”

7. Scenario Seven: You want to understand higher-level goals, not just tactics.

Clients often come to you with either a “problem,” which is just a symptom of something larger, or a “solution,” which happens to be their particular idea for how to solve the problem. But always, you need to understand the higher-level goal—the higher-level agenda. Let’s say a client comes to me and says, “We’d like to do a one-day trusted advisor training event.” My first Question is: “Why do you want to do that?” Asking “why?” gets you up to the higher-level business driver or goal. That’s why Sakichi Toyoda told his engineers, in the early days of Toyota, to always ask “Why?” five times about any quality problem. If you do, he said, you’ll understand the root cause of the problem and, most likely, the right solution.

Remember: When you prepare for a client meeting, invest serious time in formulating the questions you’re going to ask. It requires hard work to develop the thoughtful questions that are just right for your particular meeting.