The Power of Asking Pivotal Questions

In a rapidly changing business landscape, executives need the ability to quickly spot both new opportunities and hidden risks. Asking the right questions can help you broaden your perspective — and make smarter decisions.

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Good strategic thinking and decision making often require a shift in perspective — particularly in environments characterized by significant uncertainty and change. What worked in the past simply may not apply in the future. Asking “what if” questions about the future may create discomfort, since answers are often not obvious. But asking such questions also forces you to step back and challenge current assumptions that prevent you from seeing breakthrough solutions. This article builds on our new book, Winning the Long Game: How Strategic Leaders Shape the Future,1 by focusing on the art of asking pivotal questions to improve strategic decision making. (See “About the Research.”) By presenting six questions that challenge executives to incorporate broader perspectives, our aim is to stimulate out-of-the-box dialogues that help leaders make better choices and find innovative solutions sooner.

Are You Solving The Right Problem?

Back in the 1960s, IBM Corp. had the opportunity to buy or license Xerox Corp.’s new reprographic photo process. IBM hired the consulting firm Arthur D. Little to answer a key question: If a more reliable, cheaper and faster process for photocopying were available, how many more copies would people make in a given year? Since copies in those days could only be made from an original specimen, ADL set out to estimate the number. Both companies framed the problem too narrowly as “copies from originals,” ignoring a new segment of the market that turned out to be many times larger (namely, copies of copies of copies).2 This huge, overlooked opportunity could only have been foreseen if different questions had been posed. IBM might have owned this new revolutionary technology if the key question had been framed as “how might the new Xerox process change when and how people make copies, and what might this grow to in total number of copies made in future years?”



1. S. Krupp and P.J.H. Schoemaker, “Winning the Long Game: How Strategic Leaders Shape the Future” (New York: PublicAffairs, 2014).

2. V.P. Barabba, “Meeting of the Minds: Creating the Market-Based Enterprise” (Boston: Harvard Business Press, 1995).

3. E. Schmidt and J. Rosenberg, “How Google Works” (New York: Grand Central Publishing, 2014).

4. G.S. Day and P.J.H. Schoemaker, “Are You a ‘Vigilant Leader’?” MIT Sloan Management Review 49, no. 3 (spring 2008: 43-51).

5. Transcript of Fareed Zakaria Global Public Square, aired Jan. 5, 2014,

6. “Making a Mark With Rockets and Roadsters,” NPR, Aug. 9, 2007,

7. W. Hall, “‘Father of the Prius’ Declares Electric Cars ‘Not Viable,’” Feb. 4, 2013,

8. R. Lawler, “Tesla CEO Elon Musk Says He Got Into the Electric Car Business Because No One Else Would,” May 29, 2013,

9. E. Musk,

10. R. Kabacoff, “Develop Strategic Thinkers Throughout Your Organization,” Harvard Business Review, Feb. 7, 2014,

11. L. Huston and N. Sakkab, “Connect and Develop: Inside Procter & Gamble’s New Model for Innovation,” Harvard Business Review 84, no. 3 (March 2006): 58-66.

12. For scenario planning books, see K. van der Heijden, “Scenarios: The Art of Strategic Conversation” (New York: John Wiley, 1996); P.J.H. Schoemaker, “Profiting From Uncertainty: Strategies for Succeeding No Matter What the Future Brings” (New York: Free Press, 2002); and L. Fahey and R.M. Randall, eds., “Learning from the Future: Competitive Foresight Scenarios” (New York: John Wiley, 1998).

13. P.J.H. Schoemaker, “Scenario Planning: A Tool for Strategic Thinking,” Sloan Management Review 36, no. 2 (winter 1995): 25-40.

14. Testimony of Deven Sharma, president of Standard & Poor’s, before the Committee on Oversight and Government Reform, United States House of Representatives (Oct. 22, 2008),

15. P. Krugman, “That Hissing Sound,” The New York Times, Aug. 8, 2005.

16. J.E. Russo and P.J.H. Schoemaker, “Winning Decisions: Getting It Right the First Time” (New York: Doubleday, 2001).

17. C.J. Nemeth, B. Personnaz, M. Personnaz, and J.A. Goncalo, “The Liberating Role of Conflict in Group Creativity: A Study in Two Countries,” European Journal of Social Psychology 34, no. 4 (July/August 2004): 365-374.

18. J. Lehrer, “Imagine: How Creativity Works” (Boston: Houghton Mifflin Harcourt, 2012).

19. R. King, “Malcolm Gladwell: Disruptive Innovators Are Usually Disagreeable,” CIO Journal, Sept. 17, 2013,

20. J. Dewey, “Human Nature and Conduct: An Introduction to Social Psychology” (New York: Henry Holt, 1922).

21. D. Baer, “5 Brilliant Strategies Jeff Bezos Used to Build the Amazon Empire,” March 17, 2014,

22. Quoted in P.F. Drucker, “The Effective Executive“(New York: Harper & Row, 1967), 148.

23. R. Charan. “DuPont’s Swift Response to the Financial Crisis,” Bloomberg BusinessWeek, Jan. 7, 2009,

24. A. Hill, “Snapshot of a Humbled Giant,” Financial Times, Apr. 2, 2012. Also see G. Gavetti, “Kodak: Interview with Dr. George Fisher,” Oct. 1, 2005, DVD (Boston: Harvard Business School Publishing, 2006),

25. E.R. Tufte, “Visual and Statistical Thinking: Displays of Evidence for Making Decisions” (Cheshire, Connecticut: Graphics Press, 1997).

26. See H.J. Einhorn and R.M. Hogarth, “Decision Making Under Ambiguity,” The Journal of Business 59, no. 4, pt. 2 (October 1986): S225-S250, or the original study by Daniel Ellsberg, which became a classic in the field: D. Ellsberg, “Risk, Ambiguity, and the Savage Axioms,” Quarterly Journal of Economics 75, no. 4 (November 1961): 643-669.

27. R. Mundle, “Fatal Storm: The Inside Story of the Tragic Sydney-Hobart Race” (Camden, Maine: International Marine/McGraw-Hill, 1999).

28. P.J.H. Schoemaker and R.E. Gunther, “The Wisdom of Deliberate Mistakes,” Harvard Business Review 84, no. 6 (June 2006): 108-115.

29. D. Ogilvy, “Confessions of an Advertising Man” (London: Southbank Publishing, 2004). First published 1963 by Holiday House.

30. R.S. Root-Bernstein, “How Scientists Really Think,” Perspectives in Biology and Medicine 32, no. 4 (summer 1989): 472-488.

31. W.H. Hughes, “Alexander Fleming and Penicillin” (London: Priory, 1974).

32. R. Frank, “Billionaire Sara Blakely Says Secret to Success Is Failure,” October 16, 2013,

33. S. Kirsner, “Campbell Soup CEO Denise Morrison Talks Corporate Innovation in Boston,” Boston Globe, May 8, 2013.

34. C. Martin, “Wearing Your Failures On Your Sleeve,” The New York Times, Nov. 8, 2014,

35. M.E.P. Seligman, “Authentic Happiness: Using the New Positive Psychology to Realize Your Potential for Lasting Fulfillment” (New York: Free Press, 2002).

36. After-Action Review:

37. D. Senor and S. Singer, “Start-Up Nation: The Story of Israel’s Economic Miracle” (New York: Twelve, 2009).

38. The power of critical inquiry is highlighted in P. Thiel, “Zero to One: Notes on Startups, or How to Build the Future” (New York: Crown Publishing Group, 2014).

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Comments (5)
Omowunmi Elebute
Very informative. I will definitely put it into practice.
Spot On! Thanks for reaffirming that today the art of un-assuming, of being vulnerable and adaptable is supported by the courage to ask a primer for intense listening.  In both the long and short term leading.
Michelle Grey
Superb article Paul, There really is ever so much to learn every step of the way, I like the one about "What mistake have you made this week?" that in itself gives raise to thoughts that help the learning curve.
As for Pete's comment above, I think it would help if someone else asked the questions ~ then you'd be forced to reply and get it right, however quite a bit of this is a bit private and so maybe make a list for yourself and ask yourself the questions.
Thanks for posting this here and sharing
vishal cholkar
Asking Pivotal Questions will provide the insights on all the activities in each phase with Risks involved, so based on the Risk intensity it will improve our decision makings and gives energy to be more productive.
What a great article! The questions you ask should be part of every strategic planning process and discussion. I'm curious if you think executives can ask these questions of themselves, or whether they need someone from outside to ask these questions and to challenge them to answer them.