top of page

Coaching Clinic Lesson #7: A Good Question

The seventh in a monthly series of 11 posts.

With few exceptions, the leaders I work with understand the importance of listening and asking good questions. They’ve been through training programs that emphasize these habits, and they’ve heard the litany of reinforcing slogans:

“Better to remain silent and be thought a fool than to open your mouth and remove all doubt.”

“If you want obedience, tell. If you want deeper thinking, ask.”

“People learn more from questions than from answers.”

Yet despite their intellectual grasp of the importance of curiosity, most leaders fail miserably at asking the kinds of questions that promote greater confidence, responsibility and autonomy.

Seeing Blockages

The trick to asking a good question is awareness: the ability to see and remove the blockages that compromise meaningful questions at work and at home.

Blockages that come to mind include lack of faith in one’s own native curiosity, being too quick to shut down an uncomfortable question, and caring more about “fixing” than about learning something new.

I use the term “blockage” because, like fatty deposits in arteries, curiosity lapses strain the flow of open dialogue. Weak questions often lead to the relationship equivalent of a mild heart attack: superficial exchanges, misunderstanding and emotional distance.

Native Curiosity

Except in cases of brain-impairment, every human is endowed with native curiosity.

We want to know what makes others tick, what they’re up against, what kinds of situations they find most challenging and what they lose sleep over. We are naturally curious about where others come from, what they’re doing with their lives and what they’ve learned from their successes and failures.

This is not just a work thing. We want to know what our children, siblings and parents think about. We want to better understand our spouses and close friends.

We possess native curiosity about every important relationship in our lives, but how often do we express that hunger to know more? Questions percolate inside us, but we typically don’t ask.

Here’s an example:

I spoke with a father who founded the family business where two of his children hold leadership positions. The father sought my assistance to help with a succession process because he had decided he wanted his oldest son to take over the business.

I asked the father a series of basic questions:

“Does your son want to run this business?”

“Does he know you want him to do so?”

“What qualities reveal that your son can lead this business? Have you shared with him your view of his strengths and qualifications?”

“Do your two sons initiate discussions with you about the future of the business?”

“What degree of excitement, relief or reservation would your younger son have about reporting to his brother?”

The father told me that he thinks often about those questions. He sincerely wants to hear his sons’ responses to those questions. But he hasn’t asked. What explains this?

Discomfort Drives Avoidance

In large part, the limiting variable is emotional discomfort. We are not accustomed to genuine, person-to-person conversations with those whom we imagine we already know.

We tell ourselves: “This is my adult child, my spouse, my business partner, of course I know them well.” The narrative we spin about our close bonds doesn’t always reflect reality.

It’s always a bit of a jolt to discover how little we know the people around us. Some leaders connect the dots: “I can’t expect to know people better when I continue to avoid the personal and direct questions that lead to greater understanding.”

Because out-of-the-ordinary discussions trigger nervousness and self-doubt, we end up ducking important dialogues to preserve our comfort.

Too often, anxiety squelches our natural fascination about others.

A Good Question

One medicine for this dilemma is developing the maturity to befriend our discomfort and ask a good question.

What is a good question?

A good question is the question that’s most uncomfortable, most embarrassing and the one we are most interested in avoiding. It’s usually the most thought-provoking question that’s possible to ask.

It’s the question that no one else will ask, because they (like us) are terrified of discomfort.

It’s the question that’s obvious, but nerve-wracking and heart-thumping to consider.

It’s asking our business partner why she thinks she deserves a higher compensation than anyone else.

It’s asking a mother whether she wants to continue not speaking to her brother.

It’s asking an aging father if he learned anything from failing or falling short in life.

It’s asking a boss, “What are your plans for me in this business?”

It’s asking a spouse, “What do you need from me that you’re not getting?”

Asking a good question requires courage and risk. It also requires faith that the other can handle the question. In general, leaders spend too much energy shielding others from good, penetrating questions.

Skill and Will

To ask a good question, leaders need skill and will. Skill can be taught. For example, how to use appropriate language and tone in asking a question.

What cannot be taught is courage. For example, the will to learn about another. That emerges only from integrity and perspective.

Do you want to get good at asking questions? Here’s a worthy experiment:

Go back into your extended family, and into your nuclear family, and make a list of the people you think you know the best. For each, come up with one or two genuinely curious questions about that person that you’ve never asked or outright avoided.

Reflect on whether the questions are “clean” or “contaminated” (Contaminated questions spring from a motivation to lead, control, persuade or manipulate).

Think through how to ask the questions respectfully and clearly.

Go ask your questions.

Do the same with your direct reports, peers and boss at work.

Then notice what happens.

bottom of page