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On Becoming a Leader book club questions

Here are 11 book club questions for On Becoming a Leader by Warren Bennis, ordered to open easily and end somewhere worth arguing about. Copy them, print them, or bring them up one at a time.

On Becoming a Leader
On Becoming a Leader

On Becoming a Leader is Warren Bennis's argument that leadership is not a set of techniques to be mastered but a continuous process of self-discovery — and that the most important leadership development work is inner rather than outer.

Warren Bennis · 1989 · 4h 15m

Full summary and key takeaways →

The 11 questions

  1. 1.

    Bennis says leadership emerges from self-knowledge. What do you know about yourself — your values, your purpose, your working style — that you didn't know five years ago? What taught you that?

  2. 2.

    Think about a leader you admired. Was it their vision, their passion, their integrity, or their consistency that you most respected? Did they have all four, or was one especially strong?

  3. 3.

    The managers-do-things-right, leaders-do-the-right-things distinction is clean but is it real? Have you worked for someone who was genuinely both? Can you be both?

  4. 4.

    Bennis argues that reflection on experience is the essential learning mechanism for leaders. Do you build deliberate reflection into your work? What does that look like in practice?

  5. 5.

    What's the most significant failure you've experienced in your career? What did you learn from it? How deliberately did you process it?

  6. 6.

    Where in your organization is the biggest gap between managing and leading? What's the cost of that gap?

  7. 7.

    Bennis says trust requires consistency. Where in your leadership are you least consistent, and what does that inconsistency cost you with your team?

  8. 8.

    The book was written in 1989. What's changed about the leadership context since then? What's the same?

  9. 9.

    Who in your current organization or career has the four qualities Bennis describes — vision, passion, integrity, trust — most fully? What makes them stand out?

  10. 10.

    What adversity in your professional life has shaped you most as a leader? Would you have grown without it?

  11. 11.

    If you were to articulate your guiding vision — for your team, your organization, or your career — what would it be? Can you say it in a single sentence?

How to run the discussion

  • Pick six to eight, not all of them. An hour of real discussion covers fewer questions than anyone expects, and racing the list is what makes a book club feel like homework.
  • Open with what people noticed, not what they concluded. Asking for a verdict first hardens opinions before anyone has heard each other.
  • Let the disagreement run. The questions below that split a room are the ones worth the time; the ones everyone answers the same way can be skipped.
  • Ask the quiet person a specific question. A direct, narrow question is far easier to answer than an open invitation to contribute.

Themes worth steering toward

If the conversation stalls, these are the threads that usually restart it.

Common questions

What are good book club questions for On Becoming a Leader?

Here are 11 book club questions for On Becoming a Leader by Warren Bennis, ordered to open easily and end somewhere worth arguing about. The strongest openers ask what each reader noticed rather than what they concluded, and the discussion usually turns on leadership, self-knowledge, character.

How long should a book club discussion of On Becoming a Leader last?

Most groups run 60 to 90 minutes of actual discussion. That is roughly six to eight questions, not all of them, so pick the ones that suit your group rather than working down the list in order.

What are the main themes in On Becoming a Leader?

Leadership, Self-knowledge, Character, Career growth, Authenticity. Those are the threads most likely to divide a room, which makes them the useful places to steer a discussion that has gone quiet.

Picking the next one? See books like On Becoming a Leader or questions for other book club picks.

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