Woman raising her hand in meeting

Asking Good Questions

In Personal Strategies & Goal, Anecdotes by Steve Sliwa

Asking questions is an essential skill for leaders and managers because it increases understanding, shows interest, and creates bonding. Good questions are more valuable than good answers. Asking the right questions exposes good material and creates an exchange of information. I’ve noticed that if you ask a question and people have a good answer, all the feelings they have with their reply get mapped onto you. I have several examples demonstrating this.

Making an Impression

When I was starting my job as a university president, my 16-year-old daughter and I drove from California to Florida. On the way, we were scheduled to have dinner with the chancellor and his wife of Embry-Riddle Aeronautical University – Prescott, one of the campuses in Arizona that would be under my leadership. I mentioned to my daughter that I expected her to engage and not retreat during the dinner. She said that was unfair because it was difficult for her to relate to adults. I told her that it was actually pretty simple. To get through it and make a good impression, all you need to do is to ask a couple of good questions, and their answers will reflect back on you. “No, that can’t possibly be the case.”

Since we were driving and pulling a trailer, we had a long time to talk about it. I explained that she needed to ask three questions during dinner, two of them related. We spent our time planning the questions and rehearsing them. I emphasized asking them in a loud, clear voice, not being a shy mouse talker. To engage directly with an adult, look them in the eyes and be interested in their answer. If you do this, then they will be impressed with you. “No, that’s hard to imagine.” I asked her just to try it.

We arrived at the dinner, and she did what we rehearsed, making eye contact and speaking clearly. “What is the process for getting and conserving water in Arizona?” The chancellor and his wife both answered, spending about five to ten minutes explaining it. “When we were driving in from California, I noticed some of the reservoirs looked low. Is this the current situation?” The chancellor thought that was a good question and spent a fair amount of time answering. The dinner continued for a couple of hours.

In the parking lot, he told me how impressed he was with my daughter, especially for a 16-year-old. I smiled to myself, and she heard his compliment. As we drove to our overnight location, she commented, “Man, I can’t believe that!” It’s easier than you think to interact with people and build rapport.

Developing Rapport

Another example was when I was a new programmer at NASA headquarters. I was about 30 years old and asked to make a site visit to the MIT Lincoln Laboratory. They were receiving grant money from NASA for fault-tolerant computers. I went and asked a couple of questions during the briefing. With one in particular, I challenged them when they said that there are only three ways to do something. “Well, this isn’t my field of study, but it seems to me that this additional case isn’t covered by the three you mention.” They were slightly puzzled and tried to explain how they had my situation covered but said they would think about it more.

We took a break, and I know that they phoned my boss’ boss and said that they knew NASA had sent a ringer. They asked him why he did it and if he didn’t trust us. “No, we’re just trying to get a good sense, and you are an important program. We thought it would be good to get someone to really dig in and understand what you’re doing.” “Okay, thank you.” After that, I had excellent rapport with the people. In fact, I ran into many of them throughout my career, and we always had a good relationship. It all started with asking good questions.

Reframing Questions

As a university president, I learned how important questions are. I went to each department at least once each year, which meant I visited one or two departments every week. During those 30-60-minute sessions, they briefed me on their status. If I sat there simply listening, then that wouldn’t be considered interactive. I had a series of generic questions to ask, but I tuned them for that department to show interest. I created a dialogue that resulted in good interactions with each department.

One of the departments, however, asked me a couple of tough questions. I still remember one. “Can you name three people in our department?” I was taken aback. I’m okay with names and faces. I’m pretty good once I know more about someone in terms of background, where they went to school, their children or pets, but I’m really nervous about not getting it exactly correct. And so, I was on the defensive, but I ultimately answered, “Well, I’m pretty sure I could do that, but I’m slightly nervous that if I name three people I know, then it would create problems in the department. I’d rather not answer that, but I’ll tell you what I think would be more valuable. I know the names and faces of the key legislators in the state and in Congress and the key donors and power brokers in the community. I think that’s a better measure of a university president. I’m going to skip the question you proposed and let you know that I think I’m progressing on the other end.” Everyone smiled and laughed.

While this question seemed innocuous enough, it saved me from exposing the people I knew in the department. In one case, it was someone who was having some trouble, and I was aware that were considering separating that person from the university. In another, it was someone I knew from activities in the community. If I mentioned these people, I might have put them in an awkward position like brown-nosing. I wanted to avoid that.

Avoid Difficult Situations

One item I mention is that when asking questions, be careful because one can put someone in a difficult position. Provide room for them to answer. I notice that sometimes in my company, someone will say, “You’re pretty smart. What do you think about such and such?” Of course, the person feels that if they don’t have an answer, then they aren’t smart. If you ask a question without an obvious way out for them when they aren’t in sync with you, then I think you create more bad feelings than good.

Don’t be out of sync or challenge their understanding. Support them. Do it such that they have room to bring up other ways to think about the topic or some issue that might be bothering them. Give them space where they don’t have to have an answer or follow-up question. Link in a question in a way such that it isn’t embarrassing for people not to have an answer.

The Power of Three Questions

When I first met my wife, Nancy, we were both recent graduates working at NASA. She was in a different department, Artificial Intelligence and Robotics, but our paths crossed from time to time. Once I remember attending a lecture by an MIT professor that was sponsored by her department. I was standing in the back of the room because it was packed. I couldn’t believe what I heard. The professor was extremely arrogant, saying something to the effect of, “I wish I didn’t have to spend my time briefing you because I’m doing really important things. I’m not even sure this audience can understand what I’m doing.”

He gave his lecture and continued with his haughty tone, “I know the content was probably over most of your heads, but if there’s anything I can answer, I’ll try to do it.” After about 30 seconds with no one responding, I saw Nancy, whom I had only recently met, raise her hand. I don’t remember the topic, but I clearly remember the tone. The professor answered her slightly defensively. “If no one has anything, then I have a follow-up question.” She asked her second question in a kind tone. He struggled to answer it and talked about some experiments he was working on. Then, she asked her third question. At this point, the professor completely broke and said he didn’t consider it academic fraud. He was trying as hard as he could, and people simply didn’t know how much pressure he was under. I chuckled thinking that Perry Mason couldn’t have done a better job! That taught me the value of three questions.

I had my own experience with Nancy and the three questions for the first time when we were getting ready to date. I met her for lunch and proposed a trip. She said that she needed three questions answered. Remembering the MIT professor, I thought “uh-oh” to myself. Luckily, the first question was for her boss. She had another trip planned and needed to confirm that she could take back-to-back trips. 

The second question was, “Are you sure there isn’t someone else you want to invite on this trip?” I shook my head no. “I don’t want anyone to get the idea that we are dating, so I assume that is OK with you?” I answered yes. “Now, do you want to reconsider your answer to question number two?” I said no. Somehow, I survived the three questions, but they were tough! For the record, we married about a year and a half later.


At Embry-Riddle, I taught an MBA course on leadership and entrepreneurship. For each session, I brought in a speaker who was either a leader or entrepreneur. They spent half a class with us, about an hour and a half, and talked about their observations.

What the lecturer didn’t know was that a large portion of students’ grades came from the quality of the questions they asked during the interactions with the speaker after their presentation. Students broke into groups of four to six people and remained with them throughout the semester. I knew which group people belonged to, and when someone asked a good question, their group received a checkmark. For an outstanding question, the group received a plus. I planned to give out two plusses each lecture along with checkmarks as appropriate. If a team didn’t receive anything, I was disappointed and gave that group a minus. I added these up over the course of the year, and that was a significant part of their grade.

Before each class, students were expected to research the upcoming presenter and their field or industry in preparation for asking questions. After the guest finished speaking and asked for questions, hands flew up across the room. Sometimes, students coordinated, and only one person spoke. They chose three questions with the expectation of receiving three checkmarks, hoping for a plus. They frequently conducted extensive background research on the people and industry and were well-prepared so that they could ask integrated questions.

One speaker, John Wing, told me that he had lectured at Harvard the previous week and couldn’t believe the quality of Embry-Riddle’s students’ questions, interest, and energy level. Many speakers bonded with the students. They went on to become involved on boards and advisory councils afterward. Others became donors. This put the university in a good light and demonstrated to the students the importance of asking good questions.

We had a guest lecturer who was pretty arrogant and over the top regarding his self-importance, which put the students in a poor frame of mind. When it came time to ask questions, they went for it. “With all the hard work you do, how do you feel about the balance in your life? I know you recently divorced.” He was shocked and said that maybe he didn’t do as good a job with his family and had some regrets. 

“What advice would you give us to avoid the failure you had?” I was slightly nervous about how he would react to the aggressiveness but found it somewhat cathartic that he admitted in public to total strangers, probably for the first time, that he made some mistakes and would change things. I’m quite sure that when he started his lecture, he didn’t plan on admitting that he had ever made mistakes. I was proud that the group did a nice job of turning this around. This was a very valuable lesson for the students.

Answering Questions

When a response to a question is another question, that creates dialogue, which is what you want in all interactions. Use the following three tips to create engaging conversations.

  1. Timing
    When you answer a question, don’t respond with too long of a reply. If someone asks a 20-second question and your response is five minutes long, then no one will ask you any more questions. The impression is that you don’t want dialogue. My ideal response time is three times as long as the question.If their question is about a sentence long, then answer with three sentences. If it’s two to three, then respond with a paragraph. For a paragraph, reply with two or three paragraphs. It certainly shouldn’t be five times as long. At that point, alarms should go off, and you should be embarrassed if it becomes that lengthy.

    I see lots of people weave their answers, trying to perfect and perfect and perfect them. The reality is that you’ve already lost your audience. It would be better to provide a quick reply and have them ask a follow-up question, which allows you to perfect your response as opposed to continuing to talk until it’s perfected. The goal is to create a dialogue to get the best interaction. If you provide a quick answer, you are more likely to receive more questions.
  2. Smile and Use Humor
    I think it’s important to smile and be happy about questions. Be expressive and add some humor.
  3. Anecotes
    Always have a collection of anecdotes that you can use as a bridge. Share some story from your past, about yourself or someone else. It can even be a little self-deprecating or a lesson you learned. Keeping those stories clear can create memories and good feelings. I find this approach useful.


In my post Flourishing in Interviews, I talk about using the strategy of asking good questions. Apply this technique when interviewing for a new job to stand out from the crowd and make an impression. 







Print Friendly, PDF & Email

Share this Post