HBR On Leadership

Episode: The Types of Questions Every Leader Should Ask

Date: September 17, 2025
Host: Sarah Green Carmichael
Guests: Leslie John & Allison Wood Brooks, Harvard Business School Professors

Overview

This episode explores the transformative power of asking the right types of questions in leadership contexts. Host Sarah Green Carmichael is joined by Harvard Business School professors Leslie John and Allison Wood Brooks to discuss how leaders can use thoughtful questioning to exchange information, build trust, increase likability, and enhance persuasion. The conversation is grounded in their research, with actionable examples for both cooperative and competitive scenarios—plus advice on handling tough situations, group dynamics, and becoming more effective listeners.

Key Discussion Points & Insights

1. The Underestimated Power of Asking Questions

• Main Benefits

  • Enhances information exchange, builds interpersonal connection, and increases persuasion.
  • Many leaders do not ask enough questions or don’t realize their impact.
    • Quote:

      "Most people do not ask enough questions and they're missing out on many, many benefits... it's just not obvious."
      —Allison Wood Brooks [01:57]

• Why Leaders Underutilize Questions

  • People are aware of question frequency, but underestimate the positive effects on likability and information yield.
    • Quote:

      "People... don't intuit the link between question asking and liking, persuasion and information exchange."
      —Allison Wood Brooks [03:14]

2. Types of Questions and When to Use Them

• Open vs. Closed Questions

  • Open-ended questions are ideal for brainstorming or learning broad interests.
  • In competitive, high-stakes situations, direct (“pointed”) closed questions surface the truth more effectively.
    • Example:
      • Instead of “Tell me about this iPod's history,” try “Has it been damaged?” for more candor.
        —Allison Wood Brooks [06:39]

• Presupposed (Pessimistic) Questions for Truth-Telling

  • Structuring questions to assume the less desirable truth makes it easier for others to reveal it.
    • Quote:

      "You want to make it easy for them to tell you the thing that's hard for them to tell you... structure your questions so it helps them to disclose."
      —Leslie John [06:02]

• The Magic of Follow-Up Questions

  • Follow-ups show genuine listening, empathy, and lead to deeper information.
    • Quote:

      "Follow up questions are almost always good... it's like all of the good things wrapped up into one question asking strategy."
      —Allison Wood Brooks [07:34]

3. Navigating Mixed or Uncertain Relationship Contexts

• Most work interactions have both cooperative and competitive elements.
• Leaders often fear asking questions that might be seen as rude or incompetent, but research shows the risk is overrated.
  • Quote:

    "There are very few questions that people perceive as rude, incompetent, or inappropriate... especially follow up questions."
    —Allison Wood Brooks [09:58]

4. Timing and Tone: When & How to Ask Tough Questions

• Warm Up or Dive In?

  • If the goal is relationship-building, start easy and gradually deepen.
  • If the goal is pure information, starting with the toughest questions can yield more honest answers—but be mindful of the risk of alienation.
    • Quote:

      "If the goal is to foster a relationship... easing your way into things is conducive... If it's a competitive situation where the goal is information elicitation, starting with the sensitive questions can increase disclosure."
      —Leslie John [13:56]

• Tone Matters More Than You Think

  • Overly earnest or confidential tones can make disclosure feel riskier; casual, nonchalant inquiry makes people more comfortable.
    • Quote:

      "Sometimes the more assurances we give... the more worrisome it is for that person to disclose."
      —Leslie John [14:58]

5. Group vs. One-on-One Dynamics

• In groups, speaking up is often dominated by those most comfortable, not necessarily the most insightful.

  • Advice: Try breaking these norms by encouraging quiet participants to ask questions.
    • Quote:

      "Your comfort in speaking up in groups... is unrelated to whether you have good things to say... seek diverse perspectives."
      —Leslie John [16:25]

• Asking questions is a low-bar, high-value intervention for those who feel they need 'brilliant' statements to speak up.

  • Quote:

    "Turns out that it's really, really useful to just be the person who asks questions..."
    —Allison Wood Brooks [17:31]

6. Handling Difficult Moments: Being on the Receiving End

• Prepare for Tough Questions

  • Anticipate likely uncomfortable questions and practice answers or artful dodges in advance.

    • Quote:

      "For any question that you could possibly get, there is a way to answer it and there's a way to dodge it. So just not being surprised and caught off guard is a huge help."
      —Allison Wood Brooks [18:32]

  • If truly stuck, use deflective questioning ("Why do you ask?") or humor, and admit when you don’t know—sparingly, as a sign of humility.

    • Quote:

      "Deflection by question asking... is a good kind of back pocket go-to strategy."
      —Leslie John [19:57]

    • Quote:

      "Jokes are a really, really easy way to dodge things..."
      —Allison Wood Brooks [20:17]

• What Not to Do

  • Never conspicuously refuse to answer; it appears less trustworthy than candidly admitting an unflattering truth.
    • Quote:

      "It's actually better if you're faced with a question where if you answer it truthfully, it might reveal some unglamorous fact about yourself. We find that if you just come clean and answer it, you'll come off better."
      —Leslie John [21:02]

7. The Role of Listening

• Asking meaningful questions is impossible without active listening.
  • Quote:

    "Listening enables you... to both ask questions effectively and answer questions effectively."
    —Leslie John [22:12]

Notable Quotes & Memorable Moments

• On underappreciation of asking questions:

  "We don't understand the abundant benefits that await us." —Allison Wood Brooks [03:14]

• On follow-up questions:

  "All of the good things wrapped up into one question asking strategy." —Allison Wood Brooks [07:34]

• Classic job interview dodge:

  "If someone asks you a pointed question you don't want to answer... that strategy is actually worse than saying something really unflattering about yourself." —Leslie John [21:02]

• On group conversation risks:

  "You have this... worry in group context is that kind of a few dominating personalities end up doing all the talking..." —Leslie John [16:25]

• On listening:

  "A risk... is you're going to shut yourself off and maybe not listen. And then if you don't listen, you're not opening yourself up to learning more..." —Leslie John [22:12]

Important Timestamps

• [01:52] - Initial discussion on the benefits of question-asking
• [03:14] - Why people underestimate the value of questions
• [04:53] - Types of questions and context (truth-eliciting strategies)
• [06:39] - Open vs. closed questions; follow-ups
• [09:19] - Navigating mixed (friend/enemy) contexts
• [12:19] - When to ask tough questions: first or last?
• [14:58] - Tone: casual vs. serious in sensitive situations
• [15:51] - Group dynamics and question-asking
• [18:32] - How to prepare for and handle tough questions
• [21:02] - What not to do when asked something awkward
• [22:12] - The crucial role of listening

Closing Takeaways

• Asking more and better questions is a skill every leader can—and should—develop.
• Different contexts require different strategies, but follow-up questions and active listening are universally powerful.
• Don’t shy away from tough moments: preparation, humility, humor, and honesty will serve leaders best.

Further Reading:
The Surprising Power of Questions — HBR article by Leslie John and Allison Wood Brooks
(HBR.org)