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78 Important Questions Every Leader Should Ask and Answer

Great leaders have many talents, but one critical skill -- often unrecognized -- is the ability to ask and answer questions.

This unique book offers 78 questions that leaders at all levels need to ask and answer both inside and outside the organization.

Leaders who master this question-response technique will gain much useful information about what is really going on in their businesses, as well as the admiration of employees, customers, and others with whom they interact.

The questions and answers cover a range of common and uncommon situations, including: the need to connect employees' efforts to company goals; layoffs, business downturns, and mergers; personal crises of employees; coaching and mentoring sessions; and customer retention.

The book even includes advice on answering questions when the answer is ""I don't know"" or ""I can't tell you."" With worksheets in each chapter, it prepares leaders to ask important questions of:

* Customers (""Why do you do business with our competition?"")

* Employees (""What's a recent management decision you didn't understand?"")

* And even themselves (""What do I want to be remembered for?"")

Book contents

  • 78 Important Questions Every Leader Should Ask and Answer
  • Contents
  • Preface
  • How to Use This Book
  • A Warning
  • Acknowledgments
  • Introduction: Answers, You Want Answers
  • The Power and Problem of Why
  • Chapter 1: Questions Leaders Need to Ask Themselves
    • 1. What does leadership mean?
    • 2. How do you feel about being a leader?
    • 3. What do you want to be remembered for?
    • 4. Are you happy?
    • 5. What are you afraid of?
    • 6. Are you sure you want to ask questions?
    • What Did You Learn?
    • Chapter One Worksheet
    • Other Notes
  • Chapter 2: Questions Leaders Need to Ask Customers
    • 7. Why do you do business with us?
    • 8. Why do you do business with our competition?
    • 9. How and when have we made it hard for you to do business with us?
    • 10. What will you need from us in the future?
    • 11. If you were me, what's one thing you'd change about my organization?
    • 12. How can we effectively tell you that we're grateful for your business?
    • What Did You Learn?
    • Chapter Two Worksheet
    • Other Notes
  • Chapter 3: Questions Leaders Need to Ask Employees About the Business
    • 13. How do we make money?
    • 14. How does your work contribute to our success?
    • 15. How could we save money?
    • 16. How could you make your job more effective?
    • 17. What's the most important thing you know about our customers?
    • 18. What's something we could offer to our customers?
    • 19. Who do you see as our competition, and what do you know about them?
    • What Did You Learn?
    • Chapter Three Worksheet
    • Other Notes
  • Chapter 4: Deeper Questions Leaders Need to Ask Employees
    • 20. What gets in the way of your doing your job?
    • 21. What does our leadership team do that gets in the way of your doing your job?
    • 22. What's a recent management decision you didn't understand?
    • 23. How could we communicate management decisions more effectively?
    • 24. If you could change one thing about our organization's collective behavior, what would it be?
    • 25. What's a potential benefit we could offer that would be helpful to you?
    • 26. What is it like to work on a team in our organization?
    • 27. How do you feel at the start of your work week?
    • 28. How do you feel at the end of your work week?
    • 29. What volunteer work do you do?
    • 30. What makes you proud of working as a part of our organization?
    • 31. What's something you've learned in the past week?
    • 32. What brings you joy in your work?
    • 33. What do you do just for the fun of it?
    • 34. What gives your life meaning?
    • What Did You Learn?
    • Chapter Four Worksheet
    • Other Notes
  • Chapter 5: Questions to Ask in Special Situations
    • Questions for New Employees
      • 35. Why did you decide to join our firm... really?
      • 36. If you had to describe our organization in one word, what would that word be?
      • 37. What's a great question I could ask someone who's new to our organization?
      • 38. What questions can I answer for you?
    • Questions for Coaching and Mentoring Sessions
      • 39. What are the strengths you bring to the workplace?
      • 40. What skills do you need to learn?
      • 41. What skills do you need to practice?
      • 42. Who in our organization do you need to know?
      • 43. What work would you like to be doing in five years?
    • Questions for Newly Promoted Leaders
      • 44. Why do you think we made you a leader?
      • 45. What did the best leader you ever had do?
      • 46. What do you need to learn to be a great leader?
      • 47. How can we support you as you grow into this leadership position?
    • Questions During a Crisis
      • 48. Are you all right?
      • 49. What do you need to know?
      • 50. What do you need?
    • What Did You Learn?
    • Chapter Five Worksheet
    • Other Notes
  • Chapter 6: Questions Leaders Need to Answer
    • 51. What do you see happening in our organization over the next twelve months?
    • 52. What is the future of our industry?
    • 53. What gets you excited about the future?
    • 54. How do you Learn about our customers?
    • 55. How do you know what I do in my job?
    • 56. How can I advance in our organization?
    • 57. How do you make decisions?
    • 58. How do you take time to think?
    • 59. What makes you angry in the workplace?
    • 60. How do you measure success?
    • 61. What are you learning?
    • 62. How do you stay positive?
    • 63. How do you re-ignite your enthusiasm for your job?
    • 64. What do you love about your job?
    • 65. What do you do just for fun?
    • 66. What gives your life meaning?
    • What Did You Learn?
    • Chapter Six Worksheet
    • Other Notes
  • Chapter 7: Answers for Special Situations
    • During a Business Crisis
      • 67. What's happening?
      • 68. What's going to happen next?
      • 69. What's going to happen to me?
      • 70. Am I going to have a job next month?
      • 71. What's the long-term impact of this crisis?
    • During a Merger or Acquisition
      • 72-73. What's going to change? What's going to happen to my job?
      • 74. Who will be my leader?
      • 75. Will our values last?
    • During the Personal Crisis of an Employee
      • 76-78. What will the organization do to support me? What are my benefits? What will this mean …
    • What Did You Learn?
    • Chapter Seven Worksheet
    • Other Notes
  • Chapter 8: Delivering Tough Answers
    • Answering when the answer is I don't know
    • Answering when the answer is No
    • Answering when there isn't an answer
    • Answering when you can't answer
    • Answering when no one wants to hear the answer
    • Answering a question that's just too personal
    • What Did You Learn?
    • Chapter Eight Worksheet
    • Other Notes
  • Conclusion: Some Final Questions
    • What will you take away from this journey we've made together?
    • Do you find yourself with a broader view of leadership?
    • Are you one who takes big steps or baby steps?
    • Have you given yourself goals and a deadline?
    • Do you need to ponder more?
    • Are you feeling confident or anxious?
    • What support system can you count on?
    • Is leadership worth being passionate about?
    • Do these questions never end?
    • Are we done now?
    • What would I do if I knew I could not fail?
  • Appendix: Good Questions From Other Leaders
    • What's the risk of doing nothing?
    • Does what you are doing make you and the organization grow?
    • What ideas do you have?
    • What if none of this works? What next?
    • How do we WOW this customer?
    • What difference will you make for the organization today?
    • How do you face disappointment with grace?
    • How will we know when it is enough?
    • How can you ensure that this plan will be effective?
    • How can we make a change for the better of the business?
    • If you owned the company, would you do it the way you are proposing?
    • What do you think?
    • Do you honestly have the time to put this new task on your calendar?
    • What should I do to make sure you've got no worries on this project?
    • What support do you need from me to make that happen?
    • Do you think the culture of an organization can be changed by one individual? Why or why not?
    • How are you doing today?
    • What is it that we want to accomplish in the long run?
    • I know it can be done … but should it be done?
    • What's the new learning here?
    • Suppose you owned the situation, what steps would you take?
    • How did you get into this profession?
    • Why have we always done it this way?
    • How can I be part of the solution, not part of the problem?
    • What can I do to make myself more valuable to the company?
    • Can you give me specific feedback on how I can be a better leader for our organization?
    • If you could make one decision that would put this organization on a more positive course
    • What is your true passion?
    • What are the greatest needs and challenges facing your customers?
    • What are you taking time to do these days?
    • Is there a better way to do this?
    • How can I make a difference to the team?
    • What have you done today to develop your leadership skills?
    • Does this meet the highest standards of quality?
    • Do we all have the same sense of purpose and understanding of the desired outcomes?
    • What about your job inspires you to help a customer?
    • What went wrong?
    • What questions should we be asking our customers?
    • Why?
    • Use these questions to start your list
    • If you'd like to add some questions to our list
  • Suggested Reading


“The greatest danger in times of turbulence is not turbulence; it is to act with yesterday’s logic”. — Peter Drucker

The shift from manual workers who do as they are being told — either by the task or by the boss — to knowledge workers who have to manage themselves ↓ profoundly challenges social structure

Managing Oneself is a REVOLUTION in human affairs.” … “It also requires an almost 180-degree change in the knowledge workers’ thoughts and actions from what most of us—even of the younger generation—still take for granted as the way to think and the way to act.” …

… “Managing Oneself is based on the very opposite realities: Workers are likely to outlive organizations (and therefore, employers can’t be depended on for designing your life), and the knowledge worker has mobility.” ← in a context




These pages are attention directing tools for navigating a world moving toward unimagined futures.

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working something out in time (1915, 1940, 1970 … 2040 … the outer limit of your concern)nobody is going to do it for you.

It may be a step forward to actively reject something (rather than just passively ignoring) and then figure out a coping plan for what you’ve rejected.

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