100 Questions Every Manager Should Ask
A Reflection Companion to The Real Work of Management
A practical reflection companion designed to help managers pause, think, and apply management lessons to their own situations.
The book teaches the lesson. The questions help managers practise the lesson.
Each question is designed to help managers think more clearly about the choices they make, the people they lead, the conversations they need to have, and the kind of manager they are becoming.
A practical tool for management reflection
Managers do not always need more information. Often, they need a better question.
A good question helps a manager slow down, see the situation more clearly, and move from reaction to judgement.
100 Questions Every Manager Should Ask is designed for managers who want to reflect on real management situations before deciding what to do next.
It can be used individually, in a coaching conversation, in a mentoring discussion, in a team setting, or as part of a leadership learning program.
This should feel like a working companion — something a manager can return to when they need to think more clearly.
How it connects to The Real Work of Management
The Real Work of Management introduces the stories, frameworks, and lessons.
100 Questions Every Manager Should Ask helps managers apply those lessons to their own work.
The companion is not intended to repeat the book. It is designed to help readers move from understanding to practice — from reading about management to reflecting on how they manage.
The book explains the lesson. The questions help managers practise the lesson.
Who this companion is for
This companion is designed for people who want to become more thoughtful, effective managers.
It is especially relevant for:
• New and emerging managers
• Professionals preparing for people leadership
• Managers promoted from technical specialist roles
• Team leaders and project leaders
• MBA and executive education learners
• Coaches, mentors, and facilitators supporting manager development
• Managers who want to develop better judgement through reflection
If you are working through real management situations and want better questions to guide your thinking, this companion is designed for you.
What the questions help managers practise
Clarify the situation
Questions that help managers step back from activity, pressure, and noise to understand what is really happening.
Make better choices
Questions that help managers examine priorities, trade-offs, focus, and the decisions they may be avoiding.
Turn intent into action
Questions that help managers think through execution, operating rhythm, accountability, metrics, and follow-through.
Lead through others
Questions that help managers reflect on trust, feedback, development, team dynamics, coaching, and people leadership.
Develop themselves
Questions that help managers examine their values, habits, triggers, assumptions, and leadership growth.
How to use it
The companion can be used in different ways depending on the situation.
Use it when you want to:
• Reflect before a difficult management conversation
• Prepare for a one-on-one
• Think through a team issue
• Clarify a decision or trade-off
• Review a project or execution challenge
• Support a coaching or mentoring discussion
• Work through a leadership development exercise
• Pause and reflect on your own management practice
You do not need to answer all 100 questions at once. Choose the question that fits the situation. Sit with it. Write your response. Discuss it with someone you trust. Apply one practical action. Then return to the question after experience has taught you more.
Be notified when 100 Questions is ready
100 Questions Every Manager Should Ask is currently in preparation as part of the Riverstone Coaching Cafe resource library.
Join the Riverstone mailing list for release updates, article reflections, and early news about the book, Companion App, course, and future coaching availability.
