How to Ask Powerful and Relevant Questions

February 1, 2018


We all know the power, emotion and impact of a great question such as “Will you marry me?”, “Would you join our company?” or “Will you be my partner and start a business with me?”

In my experience of conducting hundreds of interviews, 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 trying to achieve.

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:

  • Diffusing a tense situation
  • Building respect with your peers, senior leadership or clients by demonstrating your understanding of an issue
  • Obtaining important insights to make more effective decisions or persuasive arguments
  • Reducing the chance of a preventable mistake or miscalculation
  • Obtaining the cooperation or agreement of others

Questions come in many forms. There are questions we ask when interviewing for a job. There are questions we ask to obtain insight and information, such as interviewing a customer about their experience with our company’s products or services. And there are questions we ask that involve trying to convince someone to do something for us — whether it’s writing a story, giving to a charitable cause or buying a product or service.

The keys to developing questions that are more powerful and thought-provoking hinge on a person’s ability to listen carefully (and deeply), hold two or more perspectives in their mind as they seek clarity, exercise their curiosity and gain a higher level of understanding.

Based on these elements, here are 13 tips on how to formulate powerful and effective interview questions:

  1. Understand your goal. Regardless of the situation, 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?” Clearly understanding the goal will help you formulate more thoughtful questions.
  2. Brainstorm questions. To prepare for an important discussion, consider pulling together some of your friends or colleagues to brainstorm possible questions. You can simulate the discussion itself or even invite your participants to write down the questions they would want to ask.
  3. Cover the basics. When I interview someone, the most important question I ask is: “How do you spell and pronounce your name?” I absolutely do not want to spell a person’s name wrong in an article, news release or any other type of content. The point is: Don’t forget to cover the basics. A good rule of thumb is to ask the five W and H questions: Who, What, Where, When, Why and How.
  4. Do a deep dive. To prepare for a meeting, interview or important conversation, it’s helpful to not only research the topic of discussion, but also the person you’ll be talking with.
  5. Conduct a pre-interview. Before a 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 formulate questions for the on-air talent to ask the guest. Use this technique to prepare for an important meeting or an interview. Write down your questions and invite the interviewee to comment on them so you can refine them for the actual sit-down or phone conversation.
  6. Write and rewrite your questions. Planning is a lost art. We rely too much on our ability to think on our feet, and when we do that, we end up asking trivial questions rather than penetrating ones that uncover greater truths. If a conversation is important to you, then spend time refining your questions.
  7. Invite engagement. When we ask “how” questions — “How would you fix that?” or “How did you help others address this issue?” — we invite people to share solutions. Most people like to offer their thoughts about how to solve a problem, and open-ended inquiries, such as “how” questions, invite additional dialogue.
  8. Seek specific examples. People love to share stories, especially of how they developed a solution or overcame a challenge. Ask for specific examples to bring added context and texture to a discussion.
  9. Clarify their position. Cite previous interviews or articles to obtain more clarity about an interviewee’s position on a key issue. Say something like, “In your interview with CNN, you were asked, ‘What key trends do you see in technology?’ Does your answer to that question still stand? Why?” In our fast-paced, tech-driven world, the person being interviewed may have adjusted their thoughts since that last interview.
  10. Challenge their generalizations. A speaker may try and pass off a generalization as fact. Don’t take that statement for granted and ask them, “How do we know that for sure?”
  11. Prioritize your questions. In an interview, you’ll likely have only so much time with a person. To ensure that you obtain the information that you absolutely need, consider prioritizing your questions. If you’re interviewing a customer for a case history article, then don’t wait until the last minute to ask the customer for the “money quote” (“I love the product or service because…”). Get right to it and then use additional questions to obtain necessary details to tell the customer’s story.
  12. Ask them for advice. 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 profession, and it may open up a new line of thought that you had not considered.
  13. Prepare your follow-up questions. Even though you may have meticulously planned your questions for an interview, you also need to be prepared to ask follow-up ones 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: “Can you tell me how you arrived at that decision?”

Developing powerful questions is not easy, especially if you aren’t in the habit of conducting interviews 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. Strong questions can ignite creativity and uncover hidden truths. When you ask them, we all benefit. 

Stephen Dupont, APR

Stephen Dupont, APR, is vice president of public relations and branded content for Pocket Hercules (, a brand-marketing firm based in Minneapolis. He blogs at Contact him at


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