The anatomy of great questions

Just as eyes are considered the window to the soul, questions are the window to positive communication

Whether they are to celebrate, educate, build networks or something else, most events tend to have a networking or mingling component built into the agenda. These opportunities to meet and connect with others are, for lack of a better word, fascinating for someone in my field. Why? In one brief, 30-60-90-minute networking window, one can sit back and observe human behavior. 

At one event a couple of months back, I found myself engaged in a conversation with a man who, during the entire span of the 10-plus minute conversation, never asked me a single question. Not one.

I’m sure you’ve each encountered a situation like this yourselves. How did you feel afterward? Exhausted? Frustrated? Annoyed? This type of “non-exchange” happens all the time. Whether in meetings, events or even family dinners, it seems like some people find asking great questions is simply too big a challenge (or risk) to bother. 

Of course, genuine talkers are that way for a variety of reasons. But for many, the behavior is a result of never having proper training in the art of making conversation — specifically, making conversation with strangers. Those of us who have been educated on this topic know that the foundation of positive communication hinges on our ability to ask great questions. 

Great questions, however, are not effective on their own. Along with the art of questioning comes the art of self-management, internal timekeeping and observational skills. The latter — those self-management skills required to be a stellar communicator — is an entire topic in itself. But for now let’s assume that everyone is coming into a dialogue with a modicum of self-awareness. Let’s focus exclusively on the anatomy of great questions.


Great questions are not easy-to-answer, yes/no questions that conversation-killers are. They require the responder to explain, tell a story or emote. For example: 

 • What was it like to…?

 • When did you decide that…? 

 • Help me understand why you chose…?

 • Tell me the story of how you…?

 • How did you feel when…?


Where are you? What is the nature of the questioning opportunity? Is this your only chance to ask a question or will there be future opportunity? These are important aspects of considering your question’s relevancy. If you are at a networking event, career or work-related questions are reasonable and fair. If you’re at a funeral, no. Think about whether asking your question will feel relevant and appropriate to your responder. 


What is it that you’re looking to accomplish with your questions? Building rapport or getting instructions? Sharing appreciation or sharing criticism? Whatever your desired outcome, know it in advance and think about creative approaches to realizing your goals. Blurting things out mindlessly is not intentional questioning. Whatever your intent is, state it before proceeding. 

For example: 

 • It would be wonderful to discuss how we can help each other’s companies. How do you feel about scheduling a meeting or coffee? 

 • I need your help…

 • I do not know anyone at this party and would love to learn more about you…


There are certain sensitive questions and topics that require awareness, especially when speaking to a stranger. Can you build up to a personal question to a stranger in a single conversation? Absolutely. Do you lead with a personal question? Absolutely not. 


Timing really is, as they say, everything. Ask too many, too quickly, and you’re performing an interrogation. Ask too few, with too much time in between, and it looks like you’re uninterested (or unprepared). Always have a few questions ready to go that can be applied in any situation at any time, neutral questions to which people respond favorably. 

The other aspect of timing is timing yourself. When asking a question, stop talking after where a question mark would appear on a page. Resist the urge to ask a question and then provide extraneous detail about the question. 

Also, be mindful of delivering a lecture versus responding in a way that leaves the other person wanting more.

Being an excellent questioner is hard, even for the most seasoned and experienced professionals. It takes practice, research, trial and error, and continuing education to master the art of questioning. But pursuing the art of great questioning has wonderful outcomes.  

Pubali Chakravorty-Campbell, vice president of organizational strategy for Human Resource Partners, can be reached through or by calling 603-749-8989.

Categories: Business Advice