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  • James Young

Seven ways to assess thriving in uncertainty


When interviewed, entrepreneurial managers will ask bold questions, take the initiative in the conversation, exhibit little anxiety about fitting in or providing the desired responses, and exude sheer, almost impatient, enthusiasm. Do candidates’ answers feel safe or rule-bound? Don’t miss any opportunity that allows candidates to demonstrate their willingness and capacity to explore the unknown.


The following questions will help you identify candidates who will thrive in uncertainty. But don’t look for the best answers; look for the extent to which the candidate champions the value of exploration, learning, new approaches, and willingness to take on risk to achieve an important outcome.

  1. Which do you fear most, anxiety or frustration?

  2. Are you willing to get into trouble in order to make something important happen?

  3. Which is more valuable: instinct or wisdom? Why?

  4. Which is more valuable: imagination or analysis? Why?

  5. A space explorer is looking for people to colonize Mars. Have a conversation between the part of you that would say yes to the mission and the part that would say no.

  6. We (or a competitor) decided to launch this product in this way. How could we have done it differently?

  7. Rapidly, choose from one option from each of the following word pairs (Do not try to score these responses, but look for a general pattern). a. Consistency or flexibility b. Proven or potential c. Careful or bold d. Explore or settle e. Predictable or possible f. Bonus or salary g. Safety or opportunity h. Medal or joy i. Puzzle or blank canvas j. Nimble or steady k. Change or constant l. Known or unknown m. Patience or excitement n. Frontier or home o. Set or open p. Wild or tame q. Variety or certainty r. Inherit or create


Source: Butler, Timothy. Hiring an entrepreneurial leader. Harvard Business Review, March-April 2017.

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