Five Tips to Asking Your Employees the Right Questions

by Mark Brewer, Adjunct Faculty
April 2, 2019

Good questions (and good questioning) require practice. Fortunately, we’ve been practicing our whole lives and we’re surrounded by professional question-askers. Think of talk show hosts, television and radio journalists, or inquisitive children. Questions abound for us to study and learn from.

To practice better questions you must be deliberate, thoughtful, genuine, and clear in your own mind what outcome you seek, even if it’s just to see something that’s not visible to you yet.

As with all human communication we make mistakes that obstruct our best intentions. When it comes to unleashing the power of questions, remember these five simple tips:

Mark Brewer, Adjunct Faculty

5. Change it up. Asking questions initiates thinking. Asking the same question drives thinking down the same path, creating a rut. Know what outcome you want to achieve, then imagine all the different questions that could lead you there, like multiple paths to the same destination. “What are you most proud of this week?” can ignite the same conversation as “Tell me about the work that makes you feel the greatest satisfaction?” Become a student of questions: listen to others, experiment with variations.

4. One question at a time. We often follow a question with another slightly modified version, usually without realizing it. Perhaps we aren’t sure we’ve been clear, or we are impatient. Sometimes we are thinking aloud, and a better rendering of the question comes to us as soon as we’ve asked the first one. Sometimes we just want to hear ourselves and cannot yield the floor. RESIST. Back-to-back questions confuse the other and often distract rather than clarify. Allow for a response to the first question before judging that another (better) question is in order. If this is difficult, try formulating your question ahead of time or writing it down.

3. Use “Why” with caution. Often touted as a cornerstone of discovery, in a problem-solving capacity there’s no peer for “Why.” However, for conversation and opening doors “Why” can have a dark side. In English the logical response to “Why” begins with “Because,” the first step on a path of thought that can become a slippery slope, leading us to look elsewhere -- outside of ourselves -- and ultimately to fault and blame. This can be a subtle and even subconscious thought digression, even with the most positive intent. Avoid it simply by rephrasing: “Why did you choose this option?” can become “Tell me more about this option.”

Special Note: One of the most powerful questions isn’t technically a question at all: “Tell me more…”

2. Use open-ended questions. Does this seem pretty obvious? Yes. Is this concept self-explanatory? Yes. Should I provide more explanation? No. I guess we’re done here.

1. Listen. This is the single most difficult challenge to using questions well. It is also the sole reason for asking. It is the seed from which this entire discussion grew. Without listening, there’s no point in asking questions. Don’t ask if you can’t or won’t listen. REALLY listen. Actively listen. Intently listen. Recall the dual purpose that questions serve: to gain insight and to build trust. The information will not flow freely and the trust will be eroded if the listening is not evident...and genuine.

Remember, the power of the question is that it puts us in the Listener role, allowing us to discover more than we would have known otherwise. If you aren’t going to listen, don’t ask.

If you lead people you need to listen, so you need to ask.

Read more about the importance of employee conversations

Improve your ability to communicate with your employees and ask them the right questions when you need to be asking them with Mark Brewer’s course Transition to Manager: A One-Week Boot Camp.