Clarifying Questions That Clarify

CEO Briefing

Several years ago, I spoke to a CEO Forum in Minnesota, where we discussed the value of asking clarifying questions so that group members could better understand a challenge or opportunity that a CEO presented to his/her fellow members. I asked them how good they were at doing so. Their response was not born out of curiosity but impatience. As natural problem solvers, they felt that asking too many questions was a waste of time.

I pushed back, and they pushed back harder by saying, “We’re never going to shake our natural inclination toward offering solutions. It’s what we do every day.” In that moment, I decided to swim with the current, if you will, by suggesting, “Okay, for the sake of argument, stay in solution mode then, but let me challenge you to change what you are solving for. Rather than ask questions that inform a quick solution, ask questions to uncover whether the person is asking the right question. If you give someone the right answer to the wrong question, there’s no telling how much damage you could inflict.

The exchange gave these CEO members cause to rethink their position. Trying to offer their peers valuable feedback may not be as helpful as they think if their understanding of what’s happening is incomplete. Imagine a friend in crisis calling you, and after listening to them for just a few minutes, you begin to spew advice in their direction. Not a great idea. Even on the off chance you were lucky enough to land on something that provided value, it would likely fall on deaf ears because you were the one who lacked the patience to understand what was really going on. Leaning into our impatience rather than our curiosity will bite us every time. Ask questions that only scratch the surface, and you’ll likely never get to the root cause. As a result, you’ll address what you think is the problem only to wonder later why it failed. Spoiler alert: it failed because you jumped to conclusions, rushed to judgment, or made erroneous assumptions that kept you from having a prayer of addressing the root cause. As you think about 2025 and what opportunities and challenges await, consider holding open discussions with your CEO Forum members or executive leadership team that prize curiosity over impatience.

Leaning into our impatience rather than our curiosity will bite us every time. Ask questions that only scratch the surface, and you’ll likely never get to the root cause. As a result, you’ll address what you think is the problem only to wonder later why it failed. Spoiler alert: it failed because you jumped to conclusions, rushed to judgment, or made erroneous assumptions that kept you from having a prayer of addressing the root cause. As you think about 2025 and what opportunities and challenges await, consider holding open discussions with your CEO Forum members or executive leadership team that prize curiosity over impatience.

Food for Thought

Fast forward, I spoke to a wonderful CEO peer group in Canada last week, and out of curiosity, one of the CEOs asked, how can we do a better job of asking clarifying questions? While I offered an answer in the moment, I also felt that I could be more specific, so I committed to doing so. To that end, here are eleven suggestions about asking the right kind of clarifying questions. (If anyone has more, I would love to hear them).

1. Open-Ended Questions: Start with broad questions that encourage the leader to elaborate on the situation. For example, “Can you describe the challenge you’re facing in detail?”

2. Probe for Details: Ask specific questions. For instance, “What factors do you believe contribute to this issue?”

3. Focus on Objectives: Clarify the leader’s goals by asking, “What outcomes are you hoping to achieve?”

4. Explore Context: Inquire about the environment and the conditions surrounding the issue, such as, “How does this challenge affect other areas of the business?”

5. Understand Previous Efforts: Explore past solutions and outcomes with questions like, “What have you tried so far to address this issue?”

6. Examine Assumptions: Challenge the members with questions such as, “What assumptions are you making about the situation?”

7. Identify Constraints: Ask about limitations or barriers by questioning, “Are there any constraints we need to consider?”

8. Explore Alternatives: Encourage exploring different routes by asking, “What other possible solutions you’ve considered?”

9. Encourage Self-Reflection: Prompt introspection by asking, “What strengths and resources can you help overcome this challenge?”

10. Summarize and Validate: Summarize the discussion to validate understanding, saying, “So, what I hear is… Is that correct?”

11. Prompt for Action: Encourage taking actionable steps with questions like, “What is one small step you can take towards a solution today?”