Quality Questions: The Power of the Right Question at the Right Time

June 17, 2026
A weathered signpost stands at a fork in a misty forest, indicating multiple winding paths, symbolizing choices and directions.

As a coach, I know the power the right question can have on a conversation. As a leader, I wish I had learned it earlier. Leadership is full of difficult conversations and intense meetings. Changing the way you start a question can make a significant difference.

Imagine you have an employee that is late… again. The knee-jerk reaction may be to ask them why. Before you do, ask yourself what you really want to know. Are you looking for an explanation, or are you wanting to make sure they are okay and help them change their behavior moving forward?

Take these two paths to the situation above:

Why are you late?Is everything okay?
Sorry, it’s been a rough morning. My cat puked, I stepped in it and had to change my socks, and traffic was horrible.Yeah/no, it’s been a rough morning. My cat puked, I stepped in it and had to change my socks, and traffic was horrible.

Think about the tone of the conversation in each of these examples and where it would lead. Not only does the question affect the recipient, but it also affects the asker. “Why are you late?” can be said empathetically, but it needs a really solid relationship to start with and a lot of other cues. Depending on the asker’s mood, the responses may land differently too. If I am frustrated and ask why, I may hear excuses rather than reasons because what I really want is for the behavior to change.

On the other hand, if I start with “Is everything okay?” I can hear where they are in the moment and I am leading with empathy. That sets me up to be able to respond to the moment rather than my agenda. If they say yes, then we can move forward. If it is no, I am not okay, then this is not a productive time to continue the conversation. I have the opportunity to show empathy now and bring in accountability later when it will be received more readily.

Now we know they are okay; we want to know how to fix the problem of repeated tardiness.

This is becoming a problem, why can’t you seem to get here on time?Sounds like things have been challenging. What steps can you take to be here on time more consistently?
I can! I am here most of the time on time. The times I am late things just happen. Don’t you see all the good things I do?Well, I am here most of the time on time. It’s the days I oversleep that turn into days like today. I can move my alarm clock so I can’t just shut it off.

The why is focused on the past and doesn’t lend itself readily to problem solving. The “what” question immediately focuses the conversation forward and invites solutions. This could be developed further. How is another great question. How can I support you? How can you prepare better for challenging days like today? Again, these are solution-focused and future-facing.

This can also be helpful in meetings, especially those that are emotionally charged. What and how are great tools to move the conversation out of a reactive state and into problem solving. In the scenario below, why is the question of choice on the left and what and how on the right. Notice how quickly the conversation on the right moves into problem solving and strategy.

Why aren’t we meeting the metric?What obstacles are we facing in meeting this metric?
There just isn’t enough time, they aren’t doing the work.We have a lot on our plates; we don’t have enough staff for the workload.
Why isn’t there enough time? Why aren’t they doing the work?How can we solve the amount of work? What options do we have?

There is definitely a place for why. The Five Whys is a popular tool in root cause analysis and definitely has its usefulness. It is especially useful to drill down on one root cause. Why can be very helpful when there is a trusting relationship to dig deeper into a problem. And we all know, thanks to Simon Sinek, that knowing your why is especially important.

This is not a piece to discredit why, but rather encouragement to choose your questions strategically. What do you really want to know? Different questions lead to different destinations. Before asking a question, take a moment to consider what you are really trying to learn. The right question at the right time can turn a difficult conversation into an opportunity for understanding, problem solving, and progress.

Share: