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The Way of the Shepherd book club questions

Here are 11 book club questions for The Way of the Shepherd by Kevin Leman and William Pentak, ordered to open easily and end somewhere worth arguing about. Copy them, print them, or bring them up one at a time.

The Way of the Shepherd
The Way of the Shepherd

The Way of the Shepherd is a short leadership parable by Kevin Leman and William Pentak that uses the metaphor of shepherding to articulate seven principles of people leadership.

Kevin Leman and William Pentak · 2004 · 2h 0m

Full summary and key takeaways →

The 11 questions

  1. 1.

    The first principle is knowing the condition of your flock. For each person on your team, could you describe their current state — professionally and personally — with enough specificity to be useful?

  2. 2.

    The shepherd metaphor implies a power imbalance: the shepherd leads, the sheep follow. Is that an accurate model for how you think about your relationship with your team?

  3. 3.

    Leman and Pentak's principles are drawn from Psalm 23. Does the religious framing add or detract from the leadership argument for you?

  4. 4.

    The principle of discovering the shape of your sheep is about individual strengths and vulnerabilities. How does your current management practice make room for that individual understanding?

  5. 5.

    The staff and the rod represent guidance and correction. Are you more comfortable with one than the other? What effect does that preference have on your team?

  6. 6.

    The book argues that accountability is a form of care. Think of a time when honest, timely correction helped someone on your team. What made it useful rather than damaging?

  7. 7.

    Leading to green pastures means connecting work to purpose. How explicitly do you articulate why the work your team does matters? How do you know whether it lands?

  8. 8.

    Short parables like this one make leadership look simple. What's missing from the shepherd metaphor that matters in your actual work context?

  9. 9.

    If you asked your team to rate you on each of the seven principles, where would the biggest gap between your self-perception and their rating be?

  10. 10.

    The book argues the leader's character is the foundation of everything else. What aspects of your own character do you think most directly shape your team's experience of working for you?

  11. 11.

    Many people have experienced both a manager who knew them as individuals and one who treated them as interchangeable. What was the difference in your performance and engagement under each?

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 The Way of the Shepherd?

Here are 11 book club questions for The Way of the Shepherd by Kevin Leman and William Pentak, 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, servant leadership, people management.

How long should a book club discussion of The Way of the Shepherd 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 The Way of the Shepherd?

Leadership, Servant leadership, People management, Trust. 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 The Way of the Shepherd or questions for other book club picks.

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