Ten years

Below are 215 questions that we distilled from the business books that we have covered with our clients over the last ten years. They are random, and some might not be relevant. However, they will make you think.

They might give you a headache too. Here it goes:


1. How random are you?

2. How far are you looking ahead?

3. What are your scenarios?

4. What is happening in your sector from a technology perspective?

5. How fast are things changing in your sector?

6. Why do you exist?

7. What phenomena are your addressing?

8. What is your purpose?

9. Why do you care?

10. Why, who, what, how, where, when?

11. What do you want to do?

12. What do you think is possible?

13. What do you need to do to achieve our goals?

14. When should you react to new opportunities and adapt your plans?

15. What does success look like for your organisation?

16. What would it take to do it ten times better?

17. What is the most important (root) issue you are facing?

18. What would you do with no limitations?

19. How many of those limitations are real?

20. What are older, younger, richer, or poorer people doing?

21. How much time have you invested in thinking about strategy?

22. How many options have you considered before the plan was written?

23. How have you ensured that the thinking behind the plan is challenged?

24. How much time do you spend exploring trends, possibilities and cool stuff?

25. How much time is spent playing with ideas, hopes and dreams?

26. Are you creating white space?

27. Who are the Mavericks in your organisation?

28. Are you applying the three rules when you make the strategic decisions?

29. Is 3D printing going to impact on your business?

30. Where is your big bang disruption going to come from?

31. How is value created, delivered and captured?

32. What is your network of capabilities?

33. Do you treat your staff as idiots?

34. How eccentric are your activities at the margin?

35. How strong are your shared values and culture?

36. How decentralised are you?

37. How adaptable are you?

38. Do you make good profit or bad profit?

39. Is your organisational structure linear?

40. Are you antifragile?

41. How replaceable are you?

42. What are you not doing?

43. What is the system of action?

44. What are the metrics?

45. Are they the right metrics?

46. How connected is your staff to your purpose?

47. Why does your company matter?

48. How curious are you?

49. Do you sell or serve?

50. How smart is your organisation?

51. Have you mapped your ecosystem?

52. What is the vision?

53. What are your plans for this week?

54. What trends can be applied to your business?

55. What are you disaster plans?

56. Which mix of the 33 strategies of war have you picked for your business going forward?

57. What platforms can you access or create?

58. What is your BTP?

59. Are you a firm of endearment?

60. Will you be missed if the company did not exist?

61. Do you apply the strategic box?


62. What innovation is happening inside your boardroom?

63. What steps are being taken to ensure that the board adds real value to the enterprise?

64. How have you organises serendipity in your organisation?

65. How have you organised innovation in your business?

66. What is your innovation focussing on?

67. What are the innovation goals?

68. Are you dependent on IP?

69. What virtual development lines can you apply?

70. Where are the black swans in your business?

71. Is your business on the extinction of innovation timeline?

72. Does your ISO, six sigma, TQM system kill serendipity and creativity?

73. What is your ROI (Return On Innovation)

74. What is your ROD (Return On Destruction

75. Who is your CDO (Chief Destruction Officer)?

76. Are you poking your box and out of your mind?

77. Do you have a future mind?

78. What are your flash foresights telling you?

79. Do you benchmark against the past or the future?

80. How many ideas are in the pipeline?

81. Do you apply Lean?

82. Do you prototype?

83. Do you iterate?

84. What is your failure fund or budget?

85. What is your attitude to mistakes?

86. Do you have an issue log?

87. How transparent are you with your staff?

88. How messy are you?

89. Do you apply biomimicry?

90. How circular are you?


91. Can you prove that your branding is working?

92. Is your brand name working?

93. Why is your brand important?

94. Why would you invest in your brand (over other spending)?

95. To whom should you be directing your message?

96. Whose hearts and minds do you need to win over?

97. Who loves you?

98. What is the emotional sweet spot?

99. How immersed are you with your client?

100.Do you master selling?

101.Do you love what you are selling?

102.How good is your customer care?

103.What do you want to be known for?

104.Who are your clients and why?

105.Is it a mistake not to buy from you?

106.How unique are you?

107.Have you mapped out the customer journey?

108.How are they talking about you?

109.Is your company designed to deliver customer delight?

110.Is that reflected in the handbook?

111.How close are you to your customers?

112.Are you creating customers?

113.How happy are your customers?

114.How delightful, frictionless and social media savvy is your customer service?

115.Does your company matter?

116.How loyal are you to your customers?

117.Could you twitter your mission statement?

118.How compelling are you?

119.Where is the feedback loop in your product or service?

120.Is your marketing nasty?

121.How passionate are your clients?

122.What does “the long tail”, “buyology” and “free” mean to your business?

123.Is your business concept inside or outside the pack?

124. Do you understand FMOT, SMOT and UMOT?

125.How much value are you adding to people’s lives?

126.How integrated and holistic is your marketing?

127.What are the BITS metrics?

128.What is your “not to copy” message?

129.How different are you?

130.How lovable are you?

131.Do you apply neuroscience to your sales process?


132.What is your view on generation Einstein?

133.Do you have a funky business?

134.Are you a maverick, Calimero, spider, starfish, heretic, purple cow, emotional capitalist or wombat?

135.How persuasive are you and your business model?

136.How many of your actions are based on the collective wisdom?

137.How sticky are your stories?

138.What can you learn from Google?

139.Are you running a happy organisation?

140.Are you smart or outsmart?

141.Are you a Shackleton or a Scott?

142.Are you running a good or great business?

143.As a business, are you killing giants or being killed as a giant?

144.Do you master your talent?

145.What are the unintended consequences of your business decisions?

146.How many MBAs do you employ? How many artists?

147. Which balance sheet do you use?

• Assets and liabilities?

• Talent, idea pipeline, engagement, community, passion, culture?

148.Have you embraced the “new normal”?

149.Is your staff hacking your workplace?

150.What can you learn from Zappos, Basecamp and Facebook?

151.Does your business story resonate?

152.Are you suffering from HIPPO syndrome?

153.Who is your Chief Culture Officer?

154.Where is your invisible gorilla?

155.Which experts do you use?

156.Is there a cultural element to your business that you could exploit?

157.How does the technetium impact on your business?

158.Do you trust your staff?

159.Where is the next innovation coming from?

160.Are you quick enough?

161.What is your internal clock speed?

162.What is your transformative purpose?

163.Do your staff believe that? Do you?

164.Is your heart at work?

165.As a leader, how coherent are you?

166.Could you apply your organisation’s culture as a competitive advantage?

167.How engaging are you with staff?

168.How do you spot talent?

169.Are you a true business 4.0?

170.Is the organisational structure fit for purpose?

171.How do you organise teams?

172.Who is hacking?

173.What is the future of work?

174.Are you applying OKRs?

175.Why are games more interesting than work?

176.Are you tackling climate change?

177.In percentages, which part of your company is solid, fluid, superfluid?

178.What are the decision making principles?

179.What is your flow score?

180.Who is essential in achieving your goals?


181.How obsessed are you with your business?

182.How different are you?

183.What is your internal operating system?

184.How happy are your staff?

185.Do you see staff as an asset or as a cost?

186.Are you going the extra mile?

187.How centred are you?

188.Are you with the right people

189.What emotional wake do you leave?

190.Do you apologise enough?

191.Are you treating your staff as adults?

192.How do you manage your information and your thinking?

193.What bad management practices do you apply?

194.What do you base your decisions on?

195.How do you organise collaboration in your company?

196.Who takes action when you ask?

197.How adaptable are you?

198.Are you me or we?

199.How authentic are you?

200.How self-aware are you (heart, gut, brain)

201.Do you use your intuition?

202.What matters to you?

203.What leadership programmes do you have in place?

204.How well do you look after your staff?

205.Are you loose enough?

206.How critical/cynical are you about your what you see, read, belief?

207.Are you in a filter bubble?

208.Do you meditate?

209.How engaged and involved is your staff?

210.Is your staff happy?

211.Are you following your talent?

212.What intelligences are your strongest?

213.What thinking techniques do you apply?

214.Are you left or right brained?

215.Do you apply extreme ownership?

If we missed any questions, I would be much obliged if you let me know and drop me an e-mail (ron@strategycrowd.com).  We will include in next edition.

Thanks in advance.