A digital transformation project falls flat. Your company doesn't reach this year's growth target. You're just not able to improve the profit margin despite your best efforts.


When your company encounters strategic failure, what are the questions people inside your organization ask themselves? What questions are followed by the question of "how can we do better next time?"

  • Do we need to get better at modeling our environment and planning our steps? Should we get better at understanding strengths, weaknesses, opportunities, and threats? Or is it that we have the understanding, but we don't know how to connect the dots?
  • Do we need to get better at analyzing economic facts? Did we misinterpret the data?
  • Do we lack critical resources and capabilities? Did we try to bite off more than we can chew?
  • Does our CEO lack vision? Was she not able to guide us?
  • Do we need to get better at learning? Instead of trying to plan our steps better, should we make smaller steps and perhaps plan fewer steps ahead?
  • Are we not democratic? Did we have too little debate and too few people involved?
  • Do we need to change our culture? Did our beliefs and values prevent us from reaching our goals?
  • Have we picked the wrong time to have a company in this industry? Did we do the best we can despite the lousy market?

These questions are not neutral. There are assumptions baked into them. When you ask if your CEO has vision or not, you also posit the idea that CEOs should be visionary leaders (instead of generous leaders, for example).

These questions also affect outcomes. Discussions that start with the question of "how can we get better at analyzing financial data?" are different from discussions that start with "how important is financial data for our business?"

It doesn't take long for people to jump from "should we get better at X?" to "how can we get better at X?" especially if the question is voiced out by a high status person.

Questions can be more revealing than answers and more influential than memos. Maybe you can fix your problems by fixing your questions.