The art of asking a good question

Asking good questions as an interviewee is an art, not a game.


Jane Sidebottom AMK LLC, Louisville, Ky.

Recently, I interviewed a candidate for a newly created business development position within a client’s organization. The candidate had been prescreened by both the head hunter and the hiring manager, and the individual’s resume looked very strong. After the initial 20 to 25 minutes of asking about him, his experience, and his interests, I turned the conversation over to the candidate and offered to answer any questions he may have. Unfortunately, he didn’t have any questions, for me or any of the other interviewers. That ended his possible career with this firm—he didn’t receive an offer as his actions sent a negative message. Asking good questions is often associated with setting a good first impression.

A quick poll of my colleagues revealed that few were ever taught how to ask questions. Yet, it is a skill that is important, whether you are looking for a new job, trying to win new business for your firm, or attempting to make a positive impression on your business leaders or colleagues.

There are two key parts to developing a good question: formulating the question and listening closely to the response. Whether you are starting from scratch or just brushing up on your skills, these guidelines will serve you well.

Do your homework: Know your audience. Make sure you understand their position and level of influence. Use your contacts to learn as much as you can about their background, experience, and interests. As other Career Smart authors and I have encouraged in previous articles, effective networking and good research using LinkedIn and other social media sources can give you a starting point.  

Have a cheat sheet: During an interview or meeting, you may not have control over the time or schedule, so have some notes and questions prepared for each interviewer. Then, identify one or two must-ask questions that will help you present yourself well and allow you to glean as much information as possible. Consider adding these to your cheat sheet:

  1. If you were sitting in my seat, what do you think would be most important to understand about this company or role?
  2. How much will I be working with you in this role, and how would you measure success?
  3. What role do you have in the decision-making process?
  4. Do you have any concerns with how I have answered your questions? If so, how can I alleviate those concerns?
  5. Would you feel comfortable sharing with me your impressions of me? Would I be a good fit for this position?

Develop a context for your question; interviewers are busy people. They are often taking a few minutes out of their day to meet with you and sometimes their brains are focused on other priorities. So use an old media trick to focus the questioning. For example: “I have a couple of questions that focus on the culture of the company and how it impacts the team with whom I will be working.” Or: “You mentioned earlier that you are looking for stronger communications from the team. Could you give me some specific examples of where it has failed in the past?” These types of questions not only show that you are listening but can provide relevant, focused answers.


Speaking of listening, listen to understand, not just to respond. Take a few brief notes based on the interviewer’s reply and then take a moment to make sure you understand what his or her answer means. Don’t be so busy preparing your response that you miss the point of the answer. And, don’t be afraid to give yourself a moment to think. Showing that you are thinking about your next question can be powerful and demonstrates understanding of the opportunity.

Asking good questions is an art, not a game. Focusing on the quality and not the quantity will showcase your interest, give you the opportunity to confidently share your knowledge and expertise, and make a positive impression. Don’t wait until you have been passed over for a new job, promotion, or other opportunity to strengthen your questioning skills.

Sidebottom is the owner of AMK LLC, a management and marketing consulting firm that provides market development and growth expertise to small- and medium-size firms. She has 20 years of management and leadership experience in both consulting engineering and Fortune 100 organizations. Sidebottom is a graduate of the University of Maryland.

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