How to Get Answers to Powerful Coaching Questions

Powerful questions are commonly used by leaders and coaches to draw attention to key problems and blind spots in someone’s thinking. They’re usually open-ended questions that start with key words like “what,” “how,” and “why”:

“What’s standing in the way?”

“How do you think it should go?”

“So what?”

“Why not?”

As the questions become more open-ended and direct, they get harder to answer because of the discomfort they can cause. Why, the one that gives the most space to answer, can be tricky to ask. Delivering “why” in a manner that shows recipients that they’re safe to answer honestly is a skill that has to be honed. I wrote a short guide to asking “why” here.

In this follow-up guide, I give attention to setting up a powerful question that you expect to be hard to answer. Giving a little effort to create the right conditions before asking sets any question up for success, even with people who feel touchy or sensitive.

It’s not your job to tiptoe around sensitive people all the time, but everyone benefits from little things that make meetings less stressful…especially review meetings like AARs, Agile retrospectives, and project postmortems. After all, why waste time holding a meeting where no real information is learned?

Here are two simple methods for setting up a powerful question before you ask it.

Tell them how you feel

Imagine that you’re sitting across the table from an auditor as they review your project. They might be an accountant in your company, or they might be the director of your division. You quietly wait for them to flip through slides and spreadsheets. They’re studying the close details of your expenditures and progress. After what seems like an eternity, they flatly pose a question to you:

“Why did you approve this purchase?”

What do you think they’re looking for? What are they trying to accomplish with the question? If they’re looking at a purchase for a disallowed expense, or if it was larger than the allowed limit, you might hear it as an accusation. It might come across as “How could you approve this, you buffoon?!”

Your blood pressure might rise. You might feel your heart beat harder. You might suddenly start to concoct an apology or excuse instead of answering them directly. It wouldn’t be your fault per se; the human brain tends to see disapproval by a superior as a threat to survival.

When I want to make it easy for someone to answer “why” honestly and directly, there’s a simple trick I use. I tell them how I feel about asking. If I’m just curious about the answer, I say:

“I’m curious, why did you approve this purchase?”

See how that works? It’s like waving a white flag overhead before approaching the opposing faction. I’ve shown them a glimpse of my thoughts instead of letting them guess and fear what I’m thinking.

Here are some other non-confrontational motives that can be signaled verbally:

“I wonder…”

“I’m excited to know…”

“I’m afraid of the answer, but I have to ask…”

In all these examples, I’m displaying not only thoughts but emotions. Emotions are an important part of the human experience. Among other things, they signal safety and danger to the brain. (In the extreme case, consider the fight-or-flight response.) Letting the other person know how I feel cues them into my mental state, and that gives them a hint of my intention for asking questions.

To help someone feel safer answering a powerful question, tell them how you feel about asking so they can interpret you as non-threatening.

Of course, if I’m feeling something dangerous to the other person — like angry, frustrated, or alarmed — they’ll correctly interpret the danger. In those situations, I fall back from stating my feelings to just stating my thoughts.

“I can’t figure out why…”

“I keep coming back to the question of why…”

“What I don’t seem to understand is why…”

Phrases like these might not put someone at greater ease, but they display my thought process. Sometime that gives them enough insight into where my thinking is stuck, and their answer could help me get unstuck. It creates an opportunity for collaboration.

Get consent

Which do you like more, a Slack message asking if you’re free for an ad-hoc meeting, or a manager appearing outside your cube to say, “I need your attention on this report I just got. Come with me.”? In either case, you’re probably going to set aside whatever you were doing and join a meeting you didn’t know was coming. In the first case, you’re probably a lot less surly about its happening.

People like autonomy, the feeling that they’re in control of their lives and get to make choices about what they do. Taking autonomy from someone is a surefire way to make them feel anxious or upset. When asking “why” in a context where you have higher status — you are their direct manager or product owner, or you’re running a review meeting — the easiest way to help someone retain their sense of autonomy is to get their consent.

Getting consent is simple. Before you do something that will involve the other person — for example, asking an invasive question — ask them to sanction it. That conversation stem might sound something like this:

“I wonder if you’d be willing to tell me why…”

“Would you help me understand why…”

Does the other person really have a say over whether you’ll ask your question? Probably not. But creating space for them to voice their consent or dissent gives them the feeling of autonomy and puts them at ease.

When I use this tool, sometimes the other person declines to answer. That’s great! They almost always give a reason, and I can use that reason to talk about their involvement in the process of the meeting. If they don’t give a reason, it’s simple enough to ask for one.

Getting consent to ask a powerful question is especially useful when talking to a superior. Imagine asking a hard question of a senior manager or executive. Asking directly, such as “Why did you publicly tweet about our sales forecasts?”, could be taken as an attempt to inflate yourself or take them down a notch. You probably won’t get the answer you want. By getting their consent first, you let them retain their status.

Practice, practice, practice

Uncovering answers is a complex skill. There are excellent methods for reviewing, investigating, and analyzing information to find deep truths. Similarly, working and communicating with people is a complex skill. When seeking a truth held in someone else’s head, these skills have to be used together.

Analytical skill is improved through practice. So is conversational skill. Take these methods and play with them. See what works in various situations. Try combining methods into a single question or sequencing them in a line of questioning. Pay attention to the result each time, and you’ll learn quickly. Before long, you’ll find yourself uncovering valuable information more quickly, and everyone involved in the process of investigation will feel better.