Our partner David Clutterbuck suggests these Massively Difficult Questions for your coaching and mentoring conversations.

by David Clutterbuck

A bundle of MDQs 


1. What’s the biggest lie you have told yourself recently?

2. What’s the biggest lie you have told to someone else recently?

3. What don’t you know you don’t know?

4. What don’t you know you do know? (What will you realise in a year’s time you knew today?)

5. If you can’t, you’re not in control; if you don’t, you are. Which describes your situation and which do you want it to be?

6. What do you want to believe about this?

7. What are the risks of success?

8. How much worse does it have to get before you have to do something?

9. If you knew you couldn’t possibly fail, what would you do differently?

10. What will you start doing now to make that (goal) happen?

11. What’s stopping you doing that?

12. If you had made my day, what would you have done?

13. What’s the dialogue you really need to have but haven’t had so far?

14. Where do you get your energy from (in life and/or work)?

15. What would you want not to be afraid of?

16. If at the end of the day, you felt you had become a better person, what would have happened to you?

17. What would other people feel least comfortable about telling you?

18. What’s the question you would least like to be asked about your work?

19. What’s the question you would least like to be asked right now?

20. Who does your inner voice remind you of?

21. Are you ready to make and commit to a decision now?

22. When did you last feel content with yourself?

23. How could you find peace with your current situation?

24. Who are you trying to avoid being like?

25. Would you choose the status quo alternative if it wasn’t the status quo?

26. What questions would you least/ most like to be asked about your role? Your organisation?

27. What do you already know that you will only realise you knew in a year’s time?

28. What decisions did you avoid this week?

29. What would you like to believe about yourself?

30. Do you have the courage to tackle this issue / pursue this course of action?

31. What are you ready to commit to?

32. What questions should you ask yourself before our next meeting to make good use of our next coaching/ mentoring session?

33. What are the three things you have to be really good at in your role? Which are you least confident about?

34. What have you done today to help make a dream a reality?

35. How ready are you for change?

36. What is it about you that made you notice that behaviour in someone else?

37. What’s your best (most useful) mistake recently?

38. Looking back to now from a year ahead, what will you wish you’d have done now?

39. Who are you trying to please?

40. What assumptions or beliefs do you hold that limit you?

41. What has changed that might cause you to question long-held assumptions?

42. What have you not noticed, that is important?

43. What have you done recently that you should give yourself a pat on the back for?

44. What’s the most useful thing you’d could do right now? That others could do right now?

45. What are you doing that gets in the way of what you want to achieve?

46. What is your general sense of direction? Are you going towards what you want to achieve or being blown off course? If the latter, what by?

47. Who believes in you? Who do you want to believe in you and why?

48. What do you avoid admitting to yourself?

49. What insights would you like to bring to our next session?

50. What other goals do you have that might / will take higher priority than this one?

51. What other goals do you have that are conflicting/ supporting/ compatible with this one?

52. What baggage are you / we bringing to this conversation?

53. Why do you care?

54. What did you do today that helped your direct reports perform?

55. What did you do today that got in the way of their performance?

56. How important to you is it to like yourself?

57. Will this make you like yourself more or less?

58. What could you do today that would make you like yourself more?

59. How do you reward yourself?

60. How much [money, time, recognition, etc] do you need to be happy?

61. When would be the best time to procrastinate about this?

62. What is your personal unique selling point?

63. What are you addicted to?

64. How easily do you get bored?

65. What is your contract with yourself?

66. Will this make you feel better or worse about yourself?

67. Will it take you nearer to where you want to go?

68. What do you do that you can no longer afford to do in the same way?

69. What’s in the best interests of … the team, the customer, the future, our children?

70. Are there any emotions you are trying to avoid here?

71. By how much do you want to improve, by when?

72. Could you treat this as an experiment and see what happens between now and our next meeting?

73. Do you dread the conversation with X? What’s causing that feeling? How might that emotion affect whether you achieve the outcome you want?

74. Do you need to control this situation? If so, why?

75. How committed are you to achieving this?

76. How could you find the courage to do what you think is right?

77. How could you have done this better?

78. How do you like to be managed?

79. How does this fit in with your personal values?

80. How genuinely committed are you to this goal?

81. How open to constructive criticism are you? What could you do to improve your openness to criticism?

82. How much could you have contributed to the problem?

83. How much do you respect your colleagues? Yourself?

84. How much is enough/ good enough?

85. How much of your work is challenging intellectually?

86. How much/ often is enough?

87. How pure are your intentions?

88. How will you feel about this decision when you look back at it in two years’ time?

89. How will you make it possible to hear those unwelcome messages?

90. How would [role model] handle this?

91. How would you explain this to your children/partner/family?

92. How/ what do you feel?

93. I don't know what to do about that, what do you think?

94. If all the obstacles disappeared, what would you do?

95. If our roles were reversed, what would you be asking me right now?

96. If this is really what you want to do, why haven’t you started?

97. If this issue were an animal/ car can you describe what would it be like?

98. If you did know the answer, what would it be?

99. If you get that outcome will that give you what you want?

100. If you had another 100 years to live, would this still be a priority for you?

101. If you had only six months to live, would this still be a priority for you?

102. If you were independently wealthy, would you still come to work? So what is it your work gives you over and above money? Cold you get that another way?

103. If you weren’t here for a month, what wouldn’t get done?

104. If your direct reports could really say what they think, without fear of offending, what might they tell you?

105. Is it more important to you to be: right rather than respected? liked rather than efficient? understood rather than understanding?

106. What are your beliefs around this issue? Which are helpful and which unhelpful?

107. What are your responsibilities here?

108. What could increase your commitment?

109. What could you do to obtain timelier, more constructive feedback?

110. What could you stop doing that would help your situation?

111. What do you care about?

112. What do you fear most?

113. What do you notice about your part in this? 

114. What do you resent most about….?

115. What do you think you might be doing that would cause other people to fear/ mistrust/ resent you?

116. What do you want people to say about you at your funeral?

117. What do you want the outcome to be?

118. What do you want to be remembered for?

119. What do you want to become?

120. What do you/ could you do to show that you care?

121. What does this mean for you? 122. What does this situation / experience tell you about yourself?

123. What does your gut instinct tell you?

124. What else could you do?

125. What else have you done?

126. What first steps could you take that would give you the confidence to make real progress?

127. What happens if you do nothing?

128. What have you not done?

129. What help do you want/ would you most value from me?

130. What is the quick fix solution? The permanent solution? What are the pluses and minuses of each?

131. What is your need from this situation? 

132. What is your purpose? (either general – what are you on earth for?; or specific, about this issue)

133. What kind of role model do you think you represent here? What kind do you want to present?

134. What makes you feel valued?

135. What makes you get out of bed in the morning? What makes you think you’d rather stay there?

136. What messages do you not want to hear?

137. What need are you addressing when you behave in this way?

138. What permission have you given [other person]? Yourself?

139. What stops you walking away?

140. What two or three things would make a difference to how you feel, if you focused on doing them and ignored everything else?

141. What unintended messages might you be sending in this situation?

142. What was your part in that?

143. What were the differences between the best and worst (career) decisions you have made?

144. What will/ could you lose by winning?

145. What would a fly on the wall say was going on?

146. What would be the impact of doing exactly the opposite of what is planned?

147. What would put you back in control?

148. What would the other party see you doing?

149. What would you ask yourself if you were me? 

150. What would you have liked the other person to say? Why didn’t they?

151. What would you like to have said? What stopped you?

152. What would your best self say or do here?

153. What’s stopping you facing up to this? (Less confrontive than ‘Why don’t you?’)

154. What’s the consequence of not doing that?

155. What’s the danger here?

156. What’s your greatest ambition?

157. What’s your greatest fear?

158. When your future self looks back at this, what should you have learned from it?

159. Where’s the enjoyment in what you do?

160. Who are you? Who do you want to be?

161. Who could/ should you ask for help? What’s stopping you doing so?

162. Who do you compare yourself with? Who would you like to compare yourself with? Why?

163. Who do you need to give you permission to do this? What’s stopping you giving yourself permission?

164. Who do you want to be?

165. Who else exerts control on your decisions?

166. Who else has call upon your time, your mental energy, your attention?

167. Who else shares ownership of this issue with you?

168. Who else’s job are you doing as well as your own?

169. Who is in control of this situation?

170. Who knows? Who can? Who will?

171. Who owns your time?

172. Whose opinion do you value?

173. Why do you think people say/ think that about you?

174. Why does this matter?

175. Why might that not be the right way forward?

176. What are you like at your best?

177. How would X describe you at your best?

178. When do you get the best out of others?

179. What really matters for you?

180. What’s the real issue for you in all this?

181. What would have to change for you to rule in solutions you’ve ruled out?

182. What does the gap between success and failure look like?

183. If you are stuck, where precisely are you stuck and how?

184. What happens just before you get stuck?

185. To what extent do you think your perceptions and expectations of X may be contributing to the problems in your relationship with them?

186. Choose a point between now and, say 12 months hence. What are your options at that specific point?

187. In what ways do you want to be different?

188. What could you do that was neither X nor Y?

189. How sure are you that the other person knows your intentions?

190. Who do you know who handles this differently? What do they do?

191. What would you expect your hero to do in this situation?

192. What would help you generate the right question for this situation?

193. If the worst happened, what would the silver lining be?

194. What are you not noticing / choosing not to notice?

195. What do you notice now that you weren’t aware of before?

196. What are you growing out of? 

197. What do you think you should be growing out of?

198. If you looked in the mirror now, what would you observe about yourself?

199. What do you say to yourself silently, that you could say out loud now?

200. What would help you become more aware?

201. What would help you become fully receptive to uncomfortable feedback?

202. How does your work help you fulfil your life purpose? Where are they in conflict?

203. If you were coaching yourself right now, what would you focus on?

204. Why is this topic important to you right now?

205. You know what you need to do, but what do you choose to do?

206. Where are the walls of your box? Do you want to move them? If so, how could you do so?

207. What do you know about yourself? What do you not know about yourself?

208. How do you give yourself acknowledgement?

209. Who is your harshest critic?

210. What are you valued for?

211. What do you value yourself for?

212. How do you reward yourself?

213. Who are you in danger of growing into? (What is the person you want to avoid becoming [like]?) What can you do now to prevent that happening?

214. What are you assuming that stops you doing what you need to?

215. If you were to seek advice from someone else on this, who would that be?

216. What do you think you might be doing that might reinforce other people’s negative impression of you?

217. What could you do without permission that would show what you are capable of?

218. What habit do you have, which you would like to get rid of? What habit could you develop, which would support your goals? How could you substitute one for the other?

219. What has to shift in your thinking about this?

220. What would be a clearer way of saying that?

221. What inspires you (about this)?

222. If you look 5 years into the future, how did your leadership change the way things work here?

223. What captures the essence of you?

224. How would you summarise this into something truly memorable?

225. What happens if you turn up the volume on that statement about yourself --- how does it sound?

226. How does what you do differ from what your job description says you do?

227. What will you do today that will help take you where you want to be?

228. What did you do today that helped take you where you want to be?

229. What will you think about on the journey to work? On the journey home?

230. What would positively stretch you now?

231. What’s the most outrageous solution to this?

232. What is it that you really desire?

233. Is there anything other (key) people don’t understand about you?

234. What would your worst enemy say about you? Who would / could they be saying this to?

235. To what extent does this job help you achieve your career?

236. What’s the best possible job anyone could offer you right now? In two years’ time?

237. Who in this organisation thinks like a customer? Why isn’t it you?

238. When is this a problem for you? Today or tomorrow?

239. Which of your values is driving your frustration with this?

240. Do you choose to be hurt by this issue?

241. What’s the boldest thing you could do?

242. How does the normal you differ from you under stress?

243. What’s the right amount of risk to take at this point in your career/ relationship/ project etc?

244. What question would your future self ask you that would be really useful now?

245. What are you drawn to in this situation?

246. What is happening for you now, at this moment?

247. Where are you now in relation to where we started this conversation?

248. What’s missing in the logic of this story (or metaphor)?

249. How do I need to change to achieve the change that's needed here in the session today?

250. What risks have you taken in the past month/ year? What risks did you need to take? What risks do you need to take now / this month/ this year?   

Bu makaleyi paylaş;