15 Tips on Asking More Powerful and Relevant Questions

By Stephen Dupont, APR

So there you are, interviewing someone – for a job, an article, a podcast, or a research report.

Or maybe you bump into a leading influencer at a major conference, or the CEO of your company in the hallway at work.

Is it better to demonstrate that you know the answers, or is it more important to ask a particularly relevant question?

The Impact of a Great Question

We all know the power, emotion and the impact of a great question.

“Will you marry me?”

“We need a person like you. Would you join our company?”

“Will you be my partner and start a business with me?”

In my experience in conducting hundreds of interviews as well as discussions with clients, asking the one question that no one else has thought to ask, or has the courage to ask, is the key to obtaining the respect you seek and the insight you need to become more successful at whatever you are seeking to achieve.

Just as important: asking the wrong question, or an uninformed question – such as a question for which you should obviously already know the answer – could jeopardize the respect you seek, or the standing for which you have worked so hard to attain. For example, there are questions that may reflect your lack of planning (which, in turn, can waste the interviewee’s time).

So how do you ask effective, relevant questions?

There’s more to this than just coming up with a clever question or two. Asking the right question at the right moment can be critical to:

  • Defusing a tense situation
  • Building respect with your peers, senior leadership or a client by demonstrating your understanding of an issue
  • Obtaining important insights to make more effective decisions
  • Reducing the chance of a preventable mistake or miscalculation
  • Obtaining the cooperation or agreement of others
  • Persuading a group to see an issue from your perspective
  • Suspending judgment and being open to new perspective

Questions come in many forms. There are questions we ask when interviewing for a job, or when we interview someone else for a position. There are questions asked to obtain insight and information, such as interviewing a customer about their experience with your company’s products or services. And there are questions where we are asking someone to do something for us, such as persuading someone to write a story about your organization, to give to a charitable cause, or to buy a product or service from you.

The keys to developing more powerful and thought-provoking questions involve four factors, reflecting the ability to:

  1. Listen carefully (and deeply);
  2. Hold two or more perspectives in your mind as you seek clarity;
  3. Exercise your curiosity; or
  4. Gain a higher level of understanding.

Based on these elements, here are 15 tips on how to formulate powerful and effective interview questions:

1. What is the goal? Whether you’re in a one-on-one meeting with an important person, you’re interviewing someone, or you’re in a meeting to discuss an issue, make sure you clearly understand what the desired outcome is that you’re driving toward. If you don’t know, then the most important question may be, “What are we trying to achieve?” Guaranteed: If the goal is not defined, there will be others in the room who want to ask that question, but are too afraid to ask.

2. Brainstorm questions. To prepare for an important discussion, consider pulling together some of your friends or colleagues and brainstorming possible questions. Frame up the opportunity or challenge and invite the participants to write down questions that they would ask.

3. Cover your bases. When I do an interview, the most important question I ask is: “Tell me how to spell and pronounce your name?” Why? Because I absolutely do not want to spell a person’s name wrong in an article, a news release or any other type of content. When it happens (and it has), I die a thousand deaths! The point is: Make sure to ask questions to obtain the most basic details and understanding of a situation. A good rule of thumb is to ask the 5 W’s and H questions: Who, What, Why, When, Where and How.

4. Do a deep dive. To prepare for a meeting, an interview or an important conversation, it is to your advantage not only to research the topic that you’ll be discussing, but the person(s) whom you’ll be meeting with. In doing your research, you should:

  • Study what is being done about an issue
  • Conduct a Google Search (including Google Scholar) to obtain articles, videos and research papers about the topic
  • Interview others to gain insight about what you should ask of your interviewee

5. Conduct a pre-interview. Before a TV producer brings a guest onto a live radio or TV program, they often conduct a pre-interview with a guest (or a representative) to gain insights and information to formulate questions to ask the guest. You can use this technique to prepare for an important meeting or an interview. Sometimes, for example, I’ll send some questions to a person in advance of a conversation to let them know the line of thinking that I’m considering – and I’ll invite them to comment on these pre-questions so I can refine my questions for the actual sit-down.

6. Write and re-write your questions. If there is a lost art, it is this. We rely too much on our ability to think on our feet. When you do that, you can end up asking trivial questions, rather than penetrating questions that uncover greater truth. If a conversation is really important to you, spend time writing out, editing, and refining your questions.

7. Forward questions in advance. The questions you ask reflect your thinking about the topic at hand. When I forward my questions to the interviewee ahead of time, it helps that person prepare their thoughts, which generates better information and quotes. In forwarding my questions, I always invite the person I’m interviewing to review those questions and share with me their thoughts about additional questions I should consider asking them.

8. Invite engagement. When we ask “how” questions, we invite people to share solutions. “How would you fix that?” “How did you help others address this issue?” Most people like to offer their thoughts about how to solve a problem, and open-ended questions, such as a “how” question invite additional dialogue.

9. “Can you give me an example?” People love to share stories, especially of how they developed a solution or overcame a challenge. Asking “Can you give me an example of how you…” can bring more context and texture to a discussion, as well as clarify a larger thought.

10. Clarifying a position. In your preparation, you may come across an article or video showing the interviewee answering questions posed previously. Consider citing those interviews – and the responses – to obtain more clarity. For example: “In your interview with CNN, you were asked, ‘What key trends do you see in technology?” and you said….’” Do you still hold that view? Why?” In our fast-paced, tech-driven world, the person being interviewed may have adjusted their thoughts since that last interview.

11. Clarify facts and emotions. A hungry mind is always looking for its next meal. A speaker may throw out a fact or a generalization. Don’t take that statement for granted. Instead, ask: “How do we know that for sure?”

12. Prioritize your questions. In an interview, you’ll likely have only so much time with a person. To ensure that you obtain the information you that you absolutely need — prioritize your questions. For example, let’s say that you’re interviewing a customer to obtain a quote about how well they liked your company’s product or service. Don’t wait until the last minute to ask the customer! Get right to it – then use additional questions to obtain needed details to tell the customer’s story.

Interviews are often based on time. There’s a big difference if you’re only given 15 minutes versus 45 minutes. Look at your list of questions and boil them down to your top five, then prioritize again based on the time you have available.

13. “What questions should I ask?” When interviewing an expert, I always ask, “Because you’ve been in this field for many years, is there a question that you think I should be asking that I haven’t?” This shows deep respect for someone who has devoted a great deal of their life to a particular field, and it may open up a new line of thought that you had not considered.

14. “What would you tell your 15-year-old self?” One of the reasons we ask questions is to tap the wisdom that is often hidden within our fellow human beings. Wisdom that can help us solve problems faster, or help us accelerate our efforts to achieve a specific goal. I like to ask the question, “Knowing what you know now, after working in your field for so many years, what would you tell your 15-year-old self?” The beauty of this question is that you allow a person to share wisdom accumulated over a career or lifetime.

15. Prepare your follow-up questions. Even though you have meticulously planned your questions, you also need to be prepared with a follow-up question(s) to dig deeper into a conversation. For example, if you’re interviewing someone about their experience with your company’s product or service for a white paper. Be prepared with questions such as: “How did that make you feel?,” “Why did you take that course of action?” or “Can you tell me how you arrived at that decision?”

Powerful Questions Transform Experiences

When you think about it, developing powerful questions is not easy, especially if you’re not in the habit of asking questions on a daily basis. But learning how to develop better questions is critical if you want to transform your own thinking, as well as stretch the thinking of others. Powerful questions can ignite creativity.

Thoughtfully designed questions can educate, enlighten and open up new possibilities.

When that happens, we all benefit.

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Stephen Dupont, APR, is VP of Public Relations and Branded Content for Pocket Hercules (www.pockethercules.com), a brand marketing firm based in Minneapolis. Contact Stephen Dupont at stephen.dupont@pockethercules.com or visit my LinkedIn page at: www.linkedin.com/in/stephendupont.

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