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Smart Business Tips > Blog > Leadership > Asking the right questions – SmartBrief
Leadership

Asking the right questions – SmartBrief

Admin45
Last updated: October 2, 2025 5:24 pm
By
Admin45
6 Min Read
Asking the right questions – SmartBrief
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Contents
Clarifying factsFocusing prioritiesAligning with missionUse these tips when asking questionsEvaluate your progressWhat success looks like

In a meeting where a significant project is delayed and over budget, what single question could instantly cut through defensiveness and clarify the path forward?

Of course, blurting out, ‘Whose fault is this?’ usually is not the kind of powerful question we are talking about here.

The right question cuts through complexity and focuses attention on what truly matters. It clarifies priorities, identifies root causes and uncovers missed opportunities.

Strong leaders guide the conversation by asking questions that get to the heart of the issue. 

Clarifying facts

When Doug Conant took over as CEO of Campbell’s in 2001, employee morale was at an all-time low. Instead of relying only on reports, he engaged in hundreds of small, informal conversations with employees. He asked simple, direct questions such as:

  • “What’s getting in the way of you doing your best work?”
  • “If you were CEO for a day, what would you change?”

Conant used those conversations to help turn the company around by listening carefully and acting on what he heard.

Focusing priorities

When Steve Jobs returned to Apple in 1997, the company struggled with a bloated product line. During a leadership meeting, as the team presented dozens of ongoing projects, Jobs interrupted them and asked, “Which ones do we really believe in?”

It was not a demand; it was a clarifying question. Silence followed, and the team began narrowing down the list one by one. Jobs reportedly crossed out 70% of the products on the whiteboard.

The right question at the right time compels people to distinguish between what is essential and what is noise.

Aligning with mission

The management team considered customer surveys and cost analyses when discussing the possibility of adding a chicken Caesar salad to the airline’s in-flight menu. Herb Kelleher, the CEO at the time, cut through it all by asking: “Will adding this salad help us be the low-fare airline?”

The answer was no. Decision made. A simple, values-aligned question can instantly clarify priorities and help a company stay focused on its mission.

Good questions not only help you acquire the necessary information and engage people, but they also open the door to new ideas. One of my favorite questions is: What can we do that has never been done before?   

Use these tips when asking questions

  1. Be clear about your purpose. Identify what you want to learn or achieve. What is your goal? 
  2. Prepare in advance. Before meetings, write down your questions to guide the conversation. The quality of your questions shapes the quality of the discussion. Also, consider potential follow-up questions to solicit more details, examples and reasoning. 
  3. Ask one question at a time. Avoid asking multiple questions simultaneously and steer clear of rhetorical questions. Concentrate on gathering the necessary information. 
  4. Challenge assumptions. Great questions help people uncover and analyze beliefs they may not even be aware of. What do we assume our customers care about most? 
  5. Connect ideas. Strong questions help people make new connections between various factors, revealing new insights. How does our current strategy align with what our latest customers value?”  
  6. Be comfortable with silence. Give people space to think and respond thoughtfully. Oftentimes, the most informative response follows a period of silence. 
  7. Encourage broad participation. In a group setting, ensure all voices are heard. Invite input from quieter participants and manage the contributions of those who tend to dominate the discussion. Also, resist the urge to answer your own questions. 
  8. Capture notes promptly. Record key points during and immediately after discussions while details are fresh in your mind. 

Which of these tips are you best at? Which tip would you like to improve?  

I am working on Tip 6. When there is silence, I try to wait up to 30 seconds before responding.   

Evaluate your progress

Here are some ways to measure your effectiveness:

  • Monitor how frequently your question contributes to the group’s progress toward its goal.  
  • Monitor how frequently your questions uncover hidden assumptions, beliefs and facts.
  • Monitor how frequently your questions spark creativity. 

Additionally, consider asking a trusted colleague or team member for feedback on how effective your questions are.   

What success looks like

You ask one well-timed, well-framed question — and the meeting changes. Defensiveness decreases, clarity increases, hidden insights come to light and the team leaves with a shared plan instead of more confusion.

The worst thing you can do is stay silent and refrain from asking questions that could assist the group. 

Opinions expressed by SmartBrief contributors are their own.

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