Ask Probing Questions
You’re heading into a meeting. You’re focused on many things—the information for the deal or the initiative, the competing agendas in the room, the relationships you are trying to build. These aren’t all distinct issues. They are interrelated. How do you think about the information in a way that helps you manage the group dynamics and foster better relationships? How do you avoid making assumptions that misdirect you?
Think about information like a pyramid. At the top of the pyramid, the smallest amount of information available is the content that you know that you know. You have complete command over that content. The next part of the pyramid, somewhat larger, is the information that you think you know. You’ll ask some confirming questions to make sure you got it right, but you’re pretty sure of that content already. The next, much broader, part of the pyramid is the information that you know that you don’t know. You have all sorts of questions to ask the other person or group to find out that information because you need it and don’t have it yet. But the huge base of the pyramid, the greatest amount of information out there, is the stuff you don’t even know you don’t know. You don’t have any questions written down to ask your client or your colleague because you don’t even know that content is out there.
Your job in any business meeting is to dig down until you’re uncovering information you didn’t even know you didn’t know. Early in our careers, when we are young and insecure, we tend to stay at the top of the pyramid. We only talk about the stuff that we know for sure or are fairly confident that we understand. This keeps us safe. I won’t make any mistakes if I only talk about the stuff I know inside out. We quickly learn we need to ask questions to make sure we learn. It takes a brave soul, however, to not only ask intelligent questions, but to listen so carefully to the answers that he can ask a follow-up question that delves deeper into an issue than he anticipated was necessary.
Your job when meeting with others is to assume there’s lots of stuff you didn’t know you didn’t know and to drill down to where you are hearing that type of content. That’s when we grow and can be more helpful to others.
Ask Closed Questions or Open-Ended Questions, Depending on Your Goal
Different types of questions elicit different responses, both verbal responses and emotional responses. Most conversations require a combination of open and closed questions. However, we all tend to be more comfortable asking closed questions. This means that in order to create a reputation for ourselves as good listeners, we need to ask more open-ended questions.
Closed-ended questions usually begin with “Did you. . .,” “Can you. . . ,” “Have you. . .,” “Would you. . ..” They can often be answered with a “yes” or a “no.” You receive a very narrow, specific answer.
Open-ended questions, on the other hand, usually begin with, “What,” “Why,” or “How,” and they require the other person to give a more complete and substantive answer.
Closed-ended questions are great if you need to get a specific piece of information and if you want someone to feel the pressure to make a decision. Open-ended questions ask the person to reflect and respond more completely. See the chart for some examples.
| Closed | Open |
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“Did you finish the memo?” May put pressure to get it done. |
“Where are you with the memo?” Might open a dialogue and facilitate a discussion around challenges completing an assignment. |
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“Can you move the meeting to 3:00?” If that’s your only open slot, this is efficient. |
“What’s your schedule this afternoon?” Opens a discussion around options. |
|
“Have you tried Thai food before?” A “yes” or a “no” could be misinterpreted as “. . . and I’m open to having it again.” |
“How does Thai sound to you?” Gets more to the point and asks for opinion versus experience. |
Giving specific options in a closed-ended question is a closing technique employed in sales situations.
“Would you like to meet again on Tuesday or Wednesday?”
“Do you want the couch in red or blue?”
“When would you like us to start work on this?”
When you are encouraging someone to disclose more information, asking closed-ended questions simply isn’t as effective as asking open-ended questions.
Often when asked a closed-ended question, we will self-censor our answer.
You ask a client or colleague: “Any other challenges with this issue?”
The person responding thinks: “Well, there is that one little problem. . . .” But instead of raising the problem, he decides he’d rather move on and deal with it later or not at all, so he says, “No.” You’ve made it easy for him to dodge the question.
If instead, you ask, “What other challenges are you facing with this issue?” there’s almost a presumption that he is facing other problems, and he will feel compelled to share the challenge.
Asking open-ended questions helps you probe not just for content, but also for the feeling behind the issues. It also helps you avoid making assumptions.
“What are your concerns with this matter?”
“What are your priorities?”
You may think you know what their concerns are or should be because you have worked on similar issues on other deals or projects. But you don’t know what this particular client’s or colleague’s concerns actually are unless you ask.
“How has this issue affected you?”
“How did this problem begin?”
Both are better ways of delving into the issue than to ask:
- You:
- “Did this problem begin with X?”
- Other person:
- “No.”
- You:
- “Did it begin with Y?”
- Other person:
- “No.”
The problem began with Q. Q isn’t even on your radar screen. It’s the stuff at the bottom of the pyramid. You are never going to ask about Q because you don’t know it exists. It’s much more efficient to just ask, “How did the problem begin?”
“Why do you think this problem is happening?”
Many people ask a wonderful, wide-open question like this, and then ruin it at the end.
“Why do you think this problem is happening? Is it because of A or B?”
Well, if the real answer is C, but you didn’t give me that as an option, then I answer “B” because that option is closest to the truth. Now I have given you misinformation, because you specifically asked me to give you misinformation. Instead, ask, “Why do you think this problem is happening?”
Have you ever been two weeks or three months into a project when the client shares a fundamental piece of information with you? Most of us with any significant work tenure have had that happen. You bite your tongue, smile weakly, and say to the client: “Well that’s important, so thanks for sharing it.” In your head, however, you’re screaming, “Well, if you’d told me that two weeks ago, we would have saved a lot of time!” or “If you’d shared that three months ago, we would have done this whole thing differently!”
Chances are the client didn’t know what was important. From today forward, think about turning around the burden implicit in that statement. Instead of thinking: “It would have been nice if you shared that,” think: “It would have been nice if I had asked the right questions three months ago.” That burden is on us as good listeners.
Our job, regardless of our role or career, is to be helpful to other people. If what you do at work isn’t helpful to someone else, your role won’t exist for long. So how do we make sure we’re being truly helpful to others? We could ask.
Here are three helpful questions to keep in mind. Note that two are open-ended and one is closed-ended.
- How can I help?
- What would be most helpful to you?
- Would it be helpful to you if I . . .?
Let’s examine each.
How can I help? It’s the most basic question, and yet all too often we don’t ask it. We want to show how smart we are by assuming we know what another person wants. We don’t. We can’t. We’re better off asking. If you routinely start conversations with “How can I help?” and then do what the person instructs, you build a reputation for yourself as a good listener and someone focused on the needs of the other person.
What would be most helpful to you? “Most,” “helpful,” and “you,” all in the same sentence. You’ll be surprised how people react to this question. I taught a program for 60 in-house lawyers at a global chemical company two years ago. We engaged in several exercises on listening skills. Then I distributed to each person a small card with these three questions printed on one side and suggested they keep them by their phones to encourage better questioning. After we returned from a short break, I started to address the next topic, but I was interrupted by one of the participants. He said, “I just need to share something with the group.” Turning to his colleagues he said, “During the break, I had to call the head of the business unit I support. We have been battling back and forth on a key issue for weeks, without any progress. I had this card in my hand, so I just asked, ‘Jack, what would be most helpful to you?’ And would you believe it, he paused, relaxed, and said, ‘Well, since you asked,’ and then he told me what would work for him. I think we would have gotten there eventually, but it certainly saved us a lot of back and forth and some nasty conversations.”
Would it be helpful to you if I . . .? Sometimes we can tell from a person’s tone that they are wandering in the wilderness. They have no idea what to do with the situation they are in. In that case, “What would be most helpful to you?” will only frustrate them. They haven’t got a clue. Instead, offering an option based on your own experience allows you to be more helpful. However, it’s done not as a directive or because you like to pontificate. It’s done because you want to be helpful, which is why it’s important to start with, “Would it be helpful to you. . . .” You are making it clear that you only want to go down a certain path if it’s genuinely helpful to the other person.
I started using these questions years ago when my kids were much younger. I would walk in the house after work. My wife, Mary, would be standing at the stove making dinner. Two kids would be at the kitchen table doing homework. The other two would be off doing God-knows-what. I like to be helpful, so I would assess the situation, see a sink full of mixing bowls, measuring spoons, and spatulas, and start washing dishes. Within a few minutes Mary would say, “Honey, I really appreciate you doing that, but John has to get to Scouts, Sam needs help on his science project, Teresa needs to be in here doing her homework, and Maggie needs to be in the bathtub.”
I learned very quickly that I was much more helpful if, instead of making assumptions about what needed to be done, I just asked, “Honey, what would be most helpful to you?”
Even with excellent listening and probing skills, you can’t guarantee every conversation will help you gather useful information. Everyone with teenagers knows this all too well.
“How was school today?”
“Fine.”
“What did you do in class?”
“Nothing.”
“What did you learn?”
“I don’t know.”
“Who did you talk to?”
“No one.” Sigh. “Why do you ask me the same questions every day?”
“Because I care. What else are you doing this afternoon?”
“Nothing. Can I go now?”
“Sure.”
Sometimes we ask because just asking is the important part.