Asking Great Questions Fuels Positive Communication

Great Questions Fuel Positive Communication

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

Like many of you, event attendance is an enormous part of my personal and professional life. 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 a 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 the good, bad, and ugly of human behavior.

At one such event a couple months back, I found myself engaged in a conversation with a man who, during the entire span of the 10+ minute conversation, never asked me a single question. Not one. Not even asking what my name was (although, in his defense, I was introduced to him by another). 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 for some people asking great questions is simply too big a challenge (or a risk) to bother doing it. .

5 Qualities of Great Questions

Of course, genuine talkers are that way for a variety of reasons – some we must respect as being related to larger and more serious than bad judgment or being self-absorbed. But for many, the behavior is a result of never having proper training in the art of making conversation. Specifically, making conversation with strangers. For those of us who have been educated on this topic, however, we know that the foundation of positive communication hinges on our ability to ask great questions.

When it comes to positive communication, you may know that I tout the importance of questions. And not just any type of questions, but really, really, good questions. Questions so good that when you ask them, people open their eyes wide, take a big breath, and say, ‘Wow – that’s a good question.’ Bonus points if they struggle to respond right away.

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 an of itself. For the purposes of this article, however, let’s assume that everyone is coming into a dialogue with a modicum of self-awareness. Today, let’s focus exclusively on the Anatomy of Great Questions.

And before delving into the Anatomy of Great Questions, know this: excellent questioning is a matter of timing, relevance, appropriateness, intent, and finally construct. Five qualities which require more than a mouth or fingers to deliver. To construct and deploy great questions we need to open our eyes, ears, and minds along with our mouths. With all this said, let’s have an anatomy lesson:


Great questions are beautifully constructed. They are not easy-to-answer Yes/No questions which are conversation killers. They are questions which 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 a future opportunity? All important aspects of considering whether what you’re about to ask is relevant. If you are at a networking event, career or work-related questions are reasonable and fair. If you’re at a funeral, no. In an elevator, asking for someone’s availability to get questions answered is relevant – not asking the actual question itself and giving your responder 4 floors to respond. Look around, open your eyes, and 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…


Slightly different than intent, appropriateness is recognizing that there are certain questions and topics which are sensitive and require awareness. Especially when speaking to a stranger. I commonly refer to bad judgment on appropriateness as Showing Up/Throwing Up. 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 which are pleasant to respond to.

The other aspect of timing? 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.

And one more thing, time yourself when responding to a question. Be mindful of delivering a lecture versus responding in a way that leaves the other person wanting more.

To be fair, this is a topic I deliver up to half day presentations on for my clients – it’s a big and meaty topic which isn’t easily covered in a blog post. Being an excellent questioner is hard, even for the most seasoned and experienced professionals. Remember that it takes practice, research, trial and error, and continuing education to master the art of being a thoughtful questioner. I only ask that you consider pursuing the art of great questioning because doing so has wonderful outcomes.

Whether it’s long lasting and meaningful relationships which lead to new clients, a closer connection to your employees and clients, or your child spending 20 minutes telling you about their day instead of going to their room after getting off the bus, asking great questions is a meaningful and worthwhile skill with big payoffs.

Learn More: Read our previous blog post to learn more: Listen: Effective Communication Isn’t Easy.