"Judge a man by his questions rather than his answers"



Our strategy has to answer the most important questions facing the business. We should ask our team, our advisors and our board/HQ for their input on these to ensure our strategy process includes the best thinking of all stakeholders. Our questions should include the most urgent challenges as well as the important long term choices.

These strategic questions should……..

….collectively cover the most important challenges facing the company

….have an uncertain answer (or don’t bother asking the question!)

….are specific to our company  (NOT “how can we grow share” or “how can we increase profits?”)

…..are goal-setting questions, not research/diagnostic questions (so “What markets should we enter?” not “What markets are most attractive”)

Prioritise to identify the 4-5 most important questions and ensure that alternative solutions are developed in the alternative development phase.

If we have a Boss/Board/Trusted advisors we should share these key strategic questions with them before moving in in order to check that we will address the challenges they think are most important to the business, and get their input on possible solutions.

Key Strategic Questions Example

  • Should Twitter be a social media or a broadcast media channel?

This is an existential question - what type of company do we want to be? Even if Twitter ultimately decides it’s strategy should remain pursuing both, it will gain insights from exploring these two focused alternatives separately.

  • How can Twitter deepen the engagement of its users?

This is a good example of a high leverage question. If Twitter can increase engagement (measured by hours per day using Twitter) it will both improve user retention and increase potential advertising revenues

  • Should Twitter make a “big bet” on data analytics?

This type of question could have been identified from the Trends Matrix. Of course Twitter will build its analytics capability, but “big bet” level of investment would be a bold move.

  • Which applications should Twitter build itself for its platform and which should it leave for its Third Party Developer ecosystem?

This question could emerge from the Industry Ecosystem Analysis. Is Twitter a two-sided platform like WeChat or Windows that encourages developers to innovate to build apps to enhance user experience or is it a stand-alone product providing services to users? Is there a line to clearly denote what should be part of the platform and what should be safe for Third Parties to build their businesses on?


At the start of the strategy development process


"First who, then what?" Before we get too deep into the content, we need to have the right leader of the strategic process. There are several options:

  • The CEO/General Manager. This has the advantage of ownership, there will be no disconnect between the strategy and the person responsible for executing it. However. does the boss have the time and process skills to do this properly?
  • A member of the Executive team. This is the best answer if someone on the team has the skills and the ability to pursue the right answer objectively.
  • Outside expertise. If the management team lacks the time, objectivity or experience, outside consultants can drive the process for you.

Regardless of who is going to lead the strategy development process, put some thought into the brief you give the leader. How broadly do you want to engage the organisation in developing the strategy?


  • Do want to let them focus on the day job, then reveal the final polished strategy in a powerpoint presentation in 3 months time?
  • Or do you want to fully engage your team, find out their ideas, be part of creating their future, harness their best thinking, build their strategic skills, inspire their imagination and win their full commitment behind the strategy? (Was that question loaded enough?)


Alternative Frameworks