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Facilitation tool · 24 prompts

Leadership conversation prompts

Choose one group that matches the situation. Ask fewer questions, stay with the evidence and resist turning the conversation into a list of initiatives.

01

Direction

Use these when activity is high but priorities still feel disconnected.

  1. Which outcome are we trying to influence - and what makes it important now?
  2. What have we explicitly chosen not to optimize?
  3. Where do leaders tell different stories about the same strategy?
  4. Which current priority would we stop if we had to make the strategy credible?
  5. What context do teams need that they are not currently receiving?
  6. Which technology choice can no longer be explained by our strategic intent?
02

Decisions

Use these when progress slows around escalation, ownership or repeated debate.

  1. What decision is waiting, and what is it actually waiting for?
  2. Who should own the decision after listening to the right perspectives?
  3. Which decisions need alignment, and which only need visibility?
  4. What assumption would change our choice if it proved false?
  5. Where are we using consensus to avoid accountability?
  6. What evidence should trigger us to revisit this decision?
03

Operating conditions

Use these when the same problem returns under different project names.

  1. What does the organization say it wants while the current system rewards the opposite?
  2. Which dependency do we repeatedly coordinate instead of removing?
  3. Where does work wait longer than it moves?
  4. Which governance activity produces information but no useful decision?
  5. What must a team navigate informally to get ordinary work done?
  6. What are leaders doing that makes local optimization rational?
04

Learning and capability

Use these when change depends on a small number of experts or external support.

  1. What must the organization learn to do repeatedly, not only once?
  2. Where are we treating an operating constraint as a skills problem?
  3. Which important lesson is trapped inside one team?
  4. What would capability transfer look like in the work itself?
  5. What signal tells us that people are making better independent decisions?
  6. Where has new evidence changed the transformation plan?