Big Strategic Questions That Will Eat Your Lunch and You With Them If You Fail to Act


Strategy: the word chills the spine, ignites excitement, or induces malaise like no other word I've observed people use.  When avoided, it can be quite costly but when articulated, integrated, and deployed effectively, can be extremely valuable for you and your organizations.  Strategy is simply "connecting ends with means", "connecting aspirations with capabilities", or as described in The Non-Profit Strategy Revolution "an organized pattern of behavior toward an end".  I think of Strategy like I do metabolism, I may not know everything there is to know about it but I know it's there, whether you think or act on it or NOT!  Strategies can be coherent or incoherent, articulated or unarticulated, designed or ad hoc, no matter what though, they're present in some way or another.  For most people and organizations though, if they're struggling, strategies are either unarticulated or ill-designed, and in many organizations or individuals, it's a product of a strong leader or innate characteristics of your personality or your organizations culture that contributes to your success.  The problem is, as many experience, that these ill-designed and unarticulated strategies do not stand the test of time, change of leadership, or significant change of circumstances.  Good strategies, well articulated, integrated, and deployed, can withstand all these changes but also result in vastly superior performance and bottom line results.  Sounds pretty good to me!

In my article "Going Where the Wind Blows You: The Ills of Having an Unclear Strategy", I described symptoms of poor or unarticulated strategies.  As in that article, I aim here to make strategy relevant and valuable for individuals and organizations in their transitions. This article is about recognizing when you're facing  a "Big Strategic Question", common types, and ways to think about these questions.

What is a Big Strategic Question?

These questions involve a change in circumstances that could have significant impact (both positive or negative) on your income/revenue, operational effectiveness/efficiency, regulatory or tax status, or more essentially on your ability to function well in your life or organization.  They can be a result of big changes  in market/customer base, competitive/industry dynamics, regulatory/tax changes (as we've seen recently), internal operational circumstances (change in leadership, legal or ethical lapses, etc.), or business model evolution (technology, industry available productivity improvements, etc.), and more.  Often, the answers to these questions are not immediately actionable but require architecting a coordinated set of behaviors, activities, resources, and more to fully achieve the outcomes sought in response to the Big Question.

Below are a few examples.  Use them to spurn your thinking about what your current Big Strategic Questions are and then spend some time designing a comprehensive response.  Contact Me for help if you should need it!

Market Changes

What if your customer base suddenly (or unrecognized over a longer period) shifts preferences and the way you currently provide value (products or services) no longer fits?

What if market wide shifts like higher/lower income levels, cultural considerations, or new substitute choices drive your revenues down?

Potential Market Strategic Questions:

  • How will this shift affect us? In what ways, for how long, is it temporary or here to stay?
  • What should our response be? Find a new customer segment? Shift our marketing efforts? Redesign or products/services to fit the new preferences?
  • Does this shift require improving our productivity to lower the price for the customer or does it require deeper changes like to essential components of our organizational model?
  • Our income and revenue has increased (for known reasons like inheritance, failure of a competitor and thus increased market share, etc.), how will we respond and build in a new, sustainable, lifestyle and market position with this new windfall?

Industry Changes

What should you do if your job is getting automated or your skills no longer fit the job?

What happens if your customers think they can do your companies work better than you can?

What if your competitors start competing more on price?

Potential Industry Strategic Questions

  • Should we compete on price? Do we have another advantage we can leverage?
  • Can we learn a new capability or skillset and out maneuver the competition?
  • Should we buy a competitor to gain further economies of scale and thus raise the barriers to entry?

Operational Changes

What if key operational characteristics or resources change?

What happens if the threat of natural disaster increases (as we see in Hawaii!)

What if critical elements of cost suddenly increase, like raw materials or skilled labor?

Potential Operational Strategic Questions

  • Should we improve our succession planning in the event key leadership changes?
  • Should we decentralize our operations to non-related regions so the threat of natural disaster won't have as high of an impact?
  • How should (or can) we incentivize employees in ways other than straight compensation?


As you can see, changing circumstances in your life and organizations environments require certain types of strategic questions to be asked.  The examples I include here are in no way comprehensive but are used to illustrate the point.  There is immense power in framing the question accurately and appropriately so that your response truly aligns with your values and outcomes you seek.  Good questions get much better answers, mediocre questions get diluted and mediocre responses.  Spend time crafting your strategic questions well in your life & business transitions and don't hesitate to Contact Me for help!