The ability to ask questions effectively is one of the most important skills in business as is the ability to actively listen. Yet as important as these two skills are they really don’t seem to ever be taught in school. I wonder if more college students ought to take a journalism course for a semester or do an internship at their school newspaper in investigative reporting. It’s the only place I could imagine these skills being taught today.

Over the years I’ve been in many meetings where a group of people that I was with wanted to extract information out of a group of people with whom we were meeting and failed to do so effectively. Witnessing this can be frustrating.

There are many different meeting types where asking different types of questions may be appropriate. If you’re:

raising money you might like to ask how the investor makes decision

developing a product you might like to survey prospective customers without biasing their answers

interviewing a candidate for a job you might like to ask about his / her performance at the last job

trying to determine one’s math capabilities you might like to ask a detailed analytical problem to solve

doing a reference call on a prospective employee

There are many different question types dependent on the scenario you’re in. But there is only one type that I want to focus on today because it’s one of the most important and most poorly executed question types I have seen.

The “Wide” (and uninterrupted) Question:

You ask a very broadly defined question and intentionally don’t try to offer specificity in what you mean by the question. It is designed to get the person you’re asking to reveal more than they would if your question directed them toward a more narrowly defined path. There are definitely times where a more narrowly defined question makes sense and where you want to guide the person you’re talking with to a narrow boundary to elicit a certain type of response. For extracting the maximum range of information in an interview nothing beats “wide” and nothing beats silence from your side.

Some quick stories

1. FUND RAISING: I was once in a fund raising meeting. There were a group of us and I wanted to know more about the individual with whom we were sitting across. I wanted to know what made him tick. I wanted to know what he liked and what he didn’t like. I wanted to understand how he had arrived at his previous investment decisions. We were not actually raising money yet, we were “pre marketing,” “relationship building” or whatever you want to call it. At this time I wasn’t the senior guy on our team in the meeting so I wasn’t leading the charge.

We started presenting our company and talking about our views of the industry. I noticed that the guy from our side doing all of the talking was a “crocodile” (you know, big mouth and no ears). We were selling and not listening. I chalked this up as both a sign of nervousness, a certain social awkwardness / lack of confidence and a basic lack of interviewing skills.

I tried to do a real-time intervention. I waited politely for a break in the conversation (about 20 minutes in) and then politely inserted, “I know I’m the least experienced in the room so I hope my question doesn’t come across as naive, but I really don’t know how you arrive at investment decisions. I’d love to learn more about this and what your views on our industry are?” This was a wide question and I could see a smirk from my colleague but the investor started talking.

It was golden. It was as wide as you could get. No real interpretation — just an invitation to talk. And this is wise because most people love to talk. In fact, in my experience the more they “inform” you the more they tend to have good feelings toward you. Dumb, I know. But I’ve found it to be true. But more than anything I just wanted the nuggets of information to help me better target this individual in the future. I wanted to learn.

Boom! He started opening up. He literally pulled out a list of all of his investments in the area and started walking us through why he had invested. I couldn’t believe it. I was madly scrawling notes on everything he said. I noticed my colleagues wrote nothing down. He then started to get a little bit negative on our industry. He was criticizing investments in our area that hadn’t performed relative to other areas and that some people were advising him to hold back on our area. This was the most valuable bit. I didn’t feel offended — I felt he was offering us a roadmap on how to avoid his “buying obstacles.” And at a minimum he was giving us some data points about what the industry thought of our sector.

My colleague felt uncomfortable. He couldn’t let those zingers about our industry go unanswered. So he shot back at why we were different than others in the industry and then started selling our positive points. He did it with a smile and with good data, but still: Crocodile, crocodile, crocodile. I was infuriated because the flow of our conversation never returned to letting the guy inform us how to better sell to him.

I would have had let him speak for an hour if he wanted to. A random walk down whatever path he wanted to take as I would have gotten to better know the man, his preferences, his biases, what excites him, etc. A “wide” question has the beauty of sometimes veering off into unexpected and wholly valuable information.

You obviously can’t just walk into the meeting and start with a “tell me what you think about life” type question. You need to establish some basic rapport first and I think this is always best done by doing (brief!) personal introductions and a quick overview of your firm. But whether you’re raising money, selling to customers, looking to make an investment or whatever — listening pays more dividends than talking. And a properly steered wide set of questions gives you facts you’d never expect.

2. THE ANALYSIS MEETING: I once was doing some due diligence work on an industry. I was interviewing the founder of a prominent company of which many of you would have heard. I was honored to be meeting him and I was deferential. My goal was to learn as much as I could to help inform my analysis. After building some rapport by discussing my background and listening to his, I started by asking really wide questions. I figured I could do more specific “deep dive” questions later in the meeting. We knew the specific details we wanted to get about the company we were researching but we had an hour so I didn’t want to rush there.

I asked him, “What makes consumers want to use your product?” It was totally vague. And intentionally so. I know that I could have asked him, “Why would they use your product when it actually seems to not be in their financial interest?” or “Your supplier (the company we were evaluating) is in an industry seen as a bit shady yet you give them a lot of business. Does the industry just have them pegged incorrectly?” Those would have been good questions and I certainly wanted to know. I had intended to go down that line of thinking later on in our conversation. If I would have asked questions this way he would have given very different responses. It would have been defensive and a rebuttal of the true value they provide.

So I kept my question wide. The CEO started talking and rattled off for about 5 minutes with awesome information when my colleague jumped in for clarification, “But our research shows that while the conversion rates on that type of campaign are 3–4x what we’ve seen elsewhere the offer is of such low quality that it leads to a high long-term churn rate. Is that your experience?” I was gutted. The guy had been serving up unsolicited information that was valuable to us. By my colleague having asked a “clarifying question” he ruined the flow and got the guy off track. If he had written his question down to return to it at a later time he could have still asked it without interrupting the meeting flow.

The only reason I could think that he asked the question that way was to try and establish personal rapport with the CEO by showing that he was knowledgeable on the topic — that he was smart. As in scenario 1 above I think it came from a lack of self confidence. I felt perfectly comfortable asking the “dumb” questions since the CEO is clearly more informed on his industry and letting him teach me a thing or two.

What both of the scenarios above (and countless more meetings) have taught me is that to effectively employ this strategy I either need to be alone in the meeting or I need to be the lead and have agreement from others not to interrupt answers or to take my cue when to join in on the questioning.

3. THE JOB INTERVIEW: Me: “What makes you tick?” Silence. No guidance. Just a smile. If asked a clarifying question like, “what do you mean?” I respond, “Interpret the question however you like. I just want to hear how you think.”

4. THE REFERENCE CALL: Reference calls are hard. The person you’re calling has been prepped by the candidate you’re considering hiring and in many cases the questions you ask will be passed back to that candidate after your call. This is why I hate referencing only from the people that the candidate has asked me to call. Here is an example of the need for both wide and narrow questions. I always start wide, “so tell me about the circumstances in which you worked with Bob Smith?” “Yeah, how’d it go?” “Was he a good employee?”

Sometimes you pick up more than you expect in these wide questions but in this type of call you usually don’t. So I begin to narrow more quickly than I might in other meetings, “I’m very fond of Bob. We’ve obviously had a great experience interviewing him or we wouldn’t be doing reference calls. But I do want to be sure I hear any potential downsides. One thing we picked up from another reference call was that Bob has at times fought with co-workers. When this happened at your firm, do you think it was at Bob’s instigation?”

That’s pretty narrow. And I’ve applied a “assumptive question” as in “we know there was conflict with Bob at your firm” even if I didn’t know whether it was true. In this case I’m looking for the reference to deny my statement or to provide evidence that Bob didn’t cause conflicts. I only point this out because as I said at the start there are many question types and “wide” is only one type.

Conclusion

As with the reference call question above, wide questions will never yield you all the information you need in a meeting. Wide questions are to be used early in a meeting to learn as many unexpected facts as you can. Answers to wide questions can give you lots of nuggets to drill down into later in the meeting. But resist the temptation to seek clarification for a nuggets at that exact time or the “random walk” answer gets taken off course.

Wide questions lead to narrower and narrower of questions later in the meeting. I’ll likely write about other question strategies at a later time. There are many types I employ including “assumptive” questions, the “awkward” question, etc. But think about how you can use “wide” and “uninterrupted listening” with your customers, employees, business development partners and investors. You might be surprised how much you learn.