78 Important Questions Every Leader Should Askand Answer JSF Flying.machine@rotario.com “I would rather die standing up, than live life on my knees.”
From India, Bangalore
35From India, Bangalore
1 QUESTIONS LEADERS NEED TO ASK THEMSELVES . . . . . . . . . . .9
1. What does leadership mean? . . . . . . . . . . . . . . . . . . . . . 11
2. How do you feel about being a leader?. . . . . . . . . . . . . . 13
3. What do you want to be remembered for? . . . . . . . . . . . 15
4. Are you happy?. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 17
5. What are you afraid of? . . . . . . . . . . . . . . . . . . . . . . . . 19
6. Are you sure you want to ask questions?. . . . . . . . . . . . 21
WHAT DID YOU LEARN? . . . . . . . . . . . . . . . . . . . . . . . . . . . . 23
CHAPTER ONE WORKSHEET . . . . . . . . . . . . . . . . . . . . . . . . . 23
2 QUESTIONS LEADERS NEED TO ASK CUSTOMERS . . . . . . . . . . .27
7. Why do you do business with us?. . . . . . . . . . . . . . . . . 30
8. Why do you do business with our competition?. . . . . . 31
9. How and when have we made it hard for you to
do business with us? . . . . . . . . . . . . . . . . . . . . . . . . . . . 33
10. What will you need from us in the future? . . . . . . . . . . 35
11. If you were me, what’s one thing you’d change about
my organization? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 37
12. How can we effectively tell you that we’re grateful
for your business? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 39
WHAT DID YOU LEARN? . . . . . . . . . . . . . . . . . . . . . . . . . . . . 41
CHAPTER TWO WORKSHEET . . . . . . . . . . . . . . . . . . . . . . . . 42
3 QUESTIONS LEADERS NEED TO ASK EMPLOYEES
ABOUT THE BUSINESS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .45
13. How do we make money?. . . . . . . . . . . . . . . . . . . . . . . 48
14. How does your work contribute to our success?. . . . . . 50
15. How could we save money? . . . . . . . . . . . . . . . . . . . . . 52
16. How could you make your job more effective?. . . . . . . 54
17. What’s the most important thing you know about our
customers? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 55
18. What’s something we could offer to our customers?. . . 57
19. Who do you see as our competition, and what do you
know about them? . . . . . . . . . . . . . . . . . . . . . . . . . . . . 58
WHAT DID YOU LEARN? . . . . . . . . . . . . . . . . . . . . . . . . . . . . 60
CHAPTER THREE WORKSHEET . . . . . . . . . . . . . . . . . . . . . . . 61
4 DEEPER QUESTIONS LEADERS NEED TO ASK EMPLOYEES . . . . .63
20. What gets in the way of your doing your job? . . . . . . . 67
21. What does our leadership team do that gets in the
way of your doing your job? . . . . . . . . . . . . . . . . . . . . . 69
22. What’s a recent management decision you didn’t
understand? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 71
23. How could we communicate management decisions
more effectively?. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 73
24. If you could change one thing about our organization’s
collective behavior, what would it be?. . . . . . . . . . . . . . 75
25. What’s a potential benefit we could offer that would be
helpful to you? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 77
26. What is it like to work on a team in our organization?. 79
27. How do you feel at the start of your workweek?. . . . . . 81
28. How do you feel at the end of your workweek? . . . . . . 83
29. What volunteer work do you do? . . . . . . . . . . . . . . . . . 84
30. What makes you proud of working as a part of our
organization?. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 86
31. What’s something you’ve learned in the past week? . . . 88
32. What brings you joy in your work? . . . . . . . . . . . . . . . 90
33. What do you do just for the fun of it? . . . . . . . . . . . . . 92
34. What gives your life meaning? . . . . . . . . . . . . . . . . . . . 94
WHAT DID YOU LEARN? . . . . . . . . . . . . . . . . . . . . . . . . . . . . 95
CHAPTER FOUR WORKSHEET . . . . . . . . . . . . . . . . . . . . . . . . 96
5 QUESTIONS TO ASK IN SPECIAL SITUATIONS . . . . . . . . . . . . . .99
QUESTIONS FOR NEW EMPLOYEES . . . . . . . . . . . . . . . . . . . 102
35. Why did you decide to join our firm…really? . . . . 102
36. If you had to describe our organization in one word,
what would that word be? . . . . . . . . . . . . . . . . . . . 104
37. What’s a great question I could ask someone who’s
new to our organization? . . . . . . . . . . . . . . . . . . . . 106
38. What questions can I answer for you? . . . . . . . . . . 108
QUESTIONS FOR COACHING AND MENTORING SESSIONS . . . . 110
39. What are the strengths you bring to the workplace? . 110
40. What skills do you need to learn? . . . . . . . . . . . . . 112
41. What skills do you need to practice? . . . . . . . . . . . 113
42. Who in our organization do you need to know? . . 115
43. What work would you like to be doing in five years? 117
QUESTIONS FOR NEWLY PROMOTED LEADERS . . . . . . . . . . 118
44. Why do you think we made you a leader? . . . . . . . 118
45. What did the best leader you ever had do?. . . . . . . 120
46. What do you need to learn to be a great leader? . . 121
47. How can we support you as you grow into this
leadership position? . . . . . . . . . . . . . . . . . . . . . . . . 123
QUESTIONS DURING A CRISIS . . . . . . . . . . . . . . . . . . . . . . . 125
48. Are you all right? . . . . . . . . . . . . . . . . . . . . . . . . . . 125
49. What do you need to know? . . . . . . . . . . . . . . . . . 127
50. What do you need? . . . . . . . . . . . . . . . . . . . . . . . . 129
WHAT DID YOU LEARN? . . . . . . . . . . . . . . . . . . . . . . . . . . . 130
CHAPTER FIVE WORKSHEET . . . . . . . . . . . . . . . . . . . . . . . . 131
6 QUESTIONS LEADERS NEED TO ANSWER . . . . . . . . . . . . . . . .135
51. What do you see happening in our organization over
the next twelve months? . . . . . . . . . . . . . . . . . . . . . . . 138
52. What is the future of our industry? . . . . . . . . . . . . . . 140
53. What gets you excited about the future?. . . . . . . . . . . 142
54. How do you learn about our customers? . . . . . . . . . . 144
55. How do you know what I do in my job?. . . . . . . . . . . 146
56. How can I advance in our organization?. . . . . . . . . . . 148
57. How do you make decisions? . . . . . . . . . . . . . . . . . . . 150
58. How do you take time to think? . . . . . . . . . . . . . . . . . 152
59. What makes you angry in the workplace?. . . . . . . . . . 155
60. How do you measure success? . . . . . . . . . . . . . . . . . . 157
61. What are you learning? . . . . . . . . . . . . . . . . . . . . . . . 159
62. How do you stay positive? . . . . . . . . . . . . . . . . . . . . . 161
63. How do you re-ignite your enthusiasm for your job? 163
64. What do you love about your job? . . . . . . . . . . . . . . . 165
65. What do you do just for fun? . . . . . . . . . . . . . . . . . . . 167
66. What gives your life meaning? . . . . . . . . . . . . . . . . . . 169
WHAT DID YOU LEARN? . . . . . . . . . . . . . . . . . . . . . . . . . . . 171
CHAPTER SIX WORKSHEET . . . . . . . . . . . . . . . . . . . . . . . . . 172
7 ANSWERS FOR SPECIAL SITUATIONS . . . . . . . . . . . . . . . . . . .175
DURING A BUSINESS CRISIS. . . . . . . . . . . . . . . . . . . . . . . . . 177
67. What’s happening? . . . . . . . . . . . . . . . . . . . . . . . . . 177
68. What’s going to happen next? . . . . . . . . . . . . . . . . 178
69. What’s going to happen to me? . . . . . . . . . . . . . . . 179
70. Am I going to have a job next month? . . . . . . . . . . 180
71. What’s the long-term impact of this crisis? . . . . . . 181
DURING A MERGER OR ACQUISITION . . . . . . . . . . . . . . . . . 182
72–73. What’s going to change? What’s going to happen
to my job? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 182
74. Who will be my leader? . . . . . . . . . . . . . . . . . . . . . 184
75. Will our values last? . . . . . . . . . . . . . . . . . . . . . . . . 185
DURING THE PERSONAL CRISIS OF AN EMPLOYEE . . . . . . . . 186
76–78. What will the organization do to support me?
What are my benefits? What will this mean
for my career? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 186
WHAT DID YOU LEARN? . . . . . . . . . . . . . . . . . . . . . . . . . . . 188
CHAPTER SEVEN WORKSHEET . . . . . . . . . . . . . . . . . . . . . . 189
8 DELIVERING TOUGH ANSWERS . . . . . . . . . . . . . . . . . . . . . . .191
Answering when the answer is I don’t know. . . . . . . . . . . . 193
Answering when the answer is No. . . . . . . . . . . . . . . . . . . 194
Answering when there isn’t an answer . . . . . . . . . . . . . . . 195
Answering when you can’t answer . . . . . . . . . . . . . . . . . . 196
Answering when no one wants to hear the answer . . . . . . 197
Answering a question that’s just too personal . . . . . . . . . . 198
WHAT DID YOU LEARN? . . . . . . . . . . . . . . . . . . . . . . . . . . . 199
CHAPTER EIGHT WORKSHEET . . . . . . . . . . . . . . . . . . . . . . 200
CONCLUSION: SOME FINAL QUESTIONS . . . . . . . . . . . . . . . .203
APPENDIX: GOOD QUESTIONS FROM OTHER LEADERS . . . . . .207
SUGGESTED READING LIST . . . . . . . . . . . . . . . . . . . . . . . . . .212
INDEX . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .215
From India, Bangalore
1. What does leadership mean? . . . . . . . . . . . . . . . . . . . . . 11
2. How do you feel about being a leader?. . . . . . . . . . . . . . 13
3. What do you want to be remembered for? . . . . . . . . . . . 15
4. Are you happy?. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 17
5. What are you afraid of? . . . . . . . . . . . . . . . . . . . . . . . . 19
6. Are you sure you want to ask questions?. . . . . . . . . . . . 21
WHAT DID YOU LEARN? . . . . . . . . . . . . . . . . . . . . . . . . . . . . 23
CHAPTER ONE WORKSHEET . . . . . . . . . . . . . . . . . . . . . . . . . 23
2 QUESTIONS LEADERS NEED TO ASK CUSTOMERS . . . . . . . . . . .27
7. Why do you do business with us?. . . . . . . . . . . . . . . . . 30
8. Why do you do business with our competition?. . . . . . 31
9. How and when have we made it hard for you to
do business with us? . . . . . . . . . . . . . . . . . . . . . . . . . . . 33
10. What will you need from us in the future? . . . . . . . . . . 35
11. If you were me, what’s one thing you’d change about
my organization? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 37
12. How can we effectively tell you that we’re grateful
for your business? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 39
WHAT DID YOU LEARN? . . . . . . . . . . . . . . . . . . . . . . . . . . . . 41
CHAPTER TWO WORKSHEET . . . . . . . . . . . . . . . . . . . . . . . . 42
3 QUESTIONS LEADERS NEED TO ASK EMPLOYEES
ABOUT THE BUSINESS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .45
13. How do we make money?. . . . . . . . . . . . . . . . . . . . . . . 48
14. How does your work contribute to our success?. . . . . . 50
15. How could we save money? . . . . . . . . . . . . . . . . . . . . . 52
16. How could you make your job more effective?. . . . . . . 54
17. What’s the most important thing you know about our
customers? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 55
18. What’s something we could offer to our customers?. . . 57
19. Who do you see as our competition, and what do you
know about them? . . . . . . . . . . . . . . . . . . . . . . . . . . . . 58
WHAT DID YOU LEARN? . . . . . . . . . . . . . . . . . . . . . . . . . . . . 60
CHAPTER THREE WORKSHEET . . . . . . . . . . . . . . . . . . . . . . . 61
4 DEEPER QUESTIONS LEADERS NEED TO ASK EMPLOYEES . . . . .63
20. What gets in the way of your doing your job? . . . . . . . 67
21. What does our leadership team do that gets in the
way of your doing your job? . . . . . . . . . . . . . . . . . . . . . 69
22. What’s a recent management decision you didn’t
understand? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 71
23. How could we communicate management decisions
more effectively?. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 73
24. If you could change one thing about our organization’s
collective behavior, what would it be?. . . . . . . . . . . . . . 75
25. What’s a potential benefit we could offer that would be
helpful to you? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 77
26. What is it like to work on a team in our organization?. 79
27. How do you feel at the start of your workweek?. . . . . . 81
28. How do you feel at the end of your workweek? . . . . . . 83
29. What volunteer work do you do? . . . . . . . . . . . . . . . . . 84
30. What makes you proud of working as a part of our
organization?. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 86
31. What’s something you’ve learned in the past week? . . . 88
32. What brings you joy in your work? . . . . . . . . . . . . . . . 90
33. What do you do just for the fun of it? . . . . . . . . . . . . . 92
34. What gives your life meaning? . . . . . . . . . . . . . . . . . . . 94
WHAT DID YOU LEARN? . . . . . . . . . . . . . . . . . . . . . . . . . . . . 95
CHAPTER FOUR WORKSHEET . . . . . . . . . . . . . . . . . . . . . . . . 96
5 QUESTIONS TO ASK IN SPECIAL SITUATIONS . . . . . . . . . . . . . .99
QUESTIONS FOR NEW EMPLOYEES . . . . . . . . . . . . . . . . . . . 102
35. Why did you decide to join our firm…really? . . . . 102
36. If you had to describe our organization in one word,
what would that word be? . . . . . . . . . . . . . . . . . . . 104
37. What’s a great question I could ask someone who’s
new to our organization? . . . . . . . . . . . . . . . . . . . . 106
38. What questions can I answer for you? . . . . . . . . . . 108
QUESTIONS FOR COACHING AND MENTORING SESSIONS . . . . 110
39. What are the strengths you bring to the workplace? . 110
40. What skills do you need to learn? . . . . . . . . . . . . . 112
41. What skills do you need to practice? . . . . . . . . . . . 113
42. Who in our organization do you need to know? . . 115
43. What work would you like to be doing in five years? 117
QUESTIONS FOR NEWLY PROMOTED LEADERS . . . . . . . . . . 118
44. Why do you think we made you a leader? . . . . . . . 118
45. What did the best leader you ever had do?. . . . . . . 120
46. What do you need to learn to be a great leader? . . 121
47. How can we support you as you grow into this
leadership position? . . . . . . . . . . . . . . . . . . . . . . . . 123
QUESTIONS DURING A CRISIS . . . . . . . . . . . . . . . . . . . . . . . 125
48. Are you all right? . . . . . . . . . . . . . . . . . . . . . . . . . . 125
49. What do you need to know? . . . . . . . . . . . . . . . . . 127
50. What do you need? . . . . . . . . . . . . . . . . . . . . . . . . 129
WHAT DID YOU LEARN? . . . . . . . . . . . . . . . . . . . . . . . . . . . 130
CHAPTER FIVE WORKSHEET . . . . . . . . . . . . . . . . . . . . . . . . 131
6 QUESTIONS LEADERS NEED TO ANSWER . . . . . . . . . . . . . . . .135
51. What do you see happening in our organization over
the next twelve months? . . . . . . . . . . . . . . . . . . . . . . . 138
52. What is the future of our industry? . . . . . . . . . . . . . . 140
53. What gets you excited about the future?. . . . . . . . . . . 142
54. How do you learn about our customers? . . . . . . . . . . 144
55. How do you know what I do in my job?. . . . . . . . . . . 146
56. How can I advance in our organization?. . . . . . . . . . . 148
57. How do you make decisions? . . . . . . . . . . . . . . . . . . . 150
58. How do you take time to think? . . . . . . . . . . . . . . . . . 152
59. What makes you angry in the workplace?. . . . . . . . . . 155
60. How do you measure success? . . . . . . . . . . . . . . . . . . 157
61. What are you learning? . . . . . . . . . . . . . . . . . . . . . . . 159
62. How do you stay positive? . . . . . . . . . . . . . . . . . . . . . 161
63. How do you re-ignite your enthusiasm for your job? 163
64. What do you love about your job? . . . . . . . . . . . . . . . 165
65. What do you do just for fun? . . . . . . . . . . . . . . . . . . . 167
66. What gives your life meaning? . . . . . . . . . . . . . . . . . . 169
WHAT DID YOU LEARN? . . . . . . . . . . . . . . . . . . . . . . . . . . . 171
CHAPTER SIX WORKSHEET . . . . . . . . . . . . . . . . . . . . . . . . . 172
7 ANSWERS FOR SPECIAL SITUATIONS . . . . . . . . . . . . . . . . . . .175
DURING A BUSINESS CRISIS. . . . . . . . . . . . . . . . . . . . . . . . . 177
67. What’s happening? . . . . . . . . . . . . . . . . . . . . . . . . . 177
68. What’s going to happen next? . . . . . . . . . . . . . . . . 178
69. What’s going to happen to me? . . . . . . . . . . . . . . . 179
70. Am I going to have a job next month? . . . . . . . . . . 180
71. What’s the long-term impact of this crisis? . . . . . . 181
DURING A MERGER OR ACQUISITION . . . . . . . . . . . . . . . . . 182
72–73. What’s going to change? What’s going to happen
to my job? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 182
74. Who will be my leader? . . . . . . . . . . . . . . . . . . . . . 184
75. Will our values last? . . . . . . . . . . . . . . . . . . . . . . . . 185
DURING THE PERSONAL CRISIS OF AN EMPLOYEE . . . . . . . . 186
76–78. What will the organization do to support me?
What are my benefits? What will this mean
for my career? . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 186
WHAT DID YOU LEARN? . . . . . . . . . . . . . . . . . . . . . . . . . . . 188
CHAPTER SEVEN WORKSHEET . . . . . . . . . . . . . . . . . . . . . . 189
8 DELIVERING TOUGH ANSWERS . . . . . . . . . . . . . . . . . . . . . . .191
Answering when the answer is I don’t know. . . . . . . . . . . . 193
Answering when the answer is No. . . . . . . . . . . . . . . . . . . 194
Answering when there isn’t an answer . . . . . . . . . . . . . . . 195
Answering when you can’t answer . . . . . . . . . . . . . . . . . . 196
Answering when no one wants to hear the answer . . . . . . 197
Answering a question that’s just too personal . . . . . . . . . . 198
WHAT DID YOU LEARN? . . . . . . . . . . . . . . . . . . . . . . . . . . . 199
CHAPTER EIGHT WORKSHEET . . . . . . . . . . . . . . . . . . . . . . 200
CONCLUSION: SOME FINAL QUESTIONS . . . . . . . . . . . . . . . .203
APPENDIX: GOOD QUESTIONS FROM OTHER LEADERS . . . . . .207
SUGGESTED READING LIST . . . . . . . . . . . . . . . . . . . . . . . . . .212
INDEX . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .215
From India, Bangalore
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