Strategy Questions Every Leader Should Be Asking

Strategic planning involves asking a series of important questions, collecting the right data needed to answer them and making tough choices among good alternatives. This paper addresses the questions typically asked over the course of strategic planning. The list is not exhaustive. Every company has a number of questions unique to it as an organization and especially important to where it is in the corporate life cycle. The questions below are listed merely to stimulate your own thinking about the business questions relevant for your company.

Note that for a number of questions we added a secondary question: “How do we know that?” The challenge in answering the strategic questions for any company is to get past the tendency of “I think.” “I think the answer is this” is a weak substitute for a data-based conclusion coming out of a bit of consumer or market research. “How do we know that?” ought to be the follow-up question for every question on the list below.


  • Can we clearly define our target customer or market where we will concentrate our attention and resources?
  • What do our customers value/need? How do we know that?
  • Do we provide that value? How do we know that?
  • What are our customer’s buying criteria? How do we know that?
  • Are there unmet customer needs that we could meet?
  • Are we clear about who our target customer is not so that we avoid trying to be all things to all people?

Product/Service – Customer Value Proposition

  • What makes our product/ service distinct/ different from competitors? How do we know that?
  • To what extent does our “total” value proposition meet customer buying criteria? How do we know that?
  • What makes our product/ service distinct/ different from competitors?
  • To what extent does our “total” value proposition meet customer buying criteria?
  • What capabilities/competencies do we need to deliver this distinct customer value proposition?
  • To what extent are these capabilities developed in our organization?


  • How big is our market(s)?
  • How is it defined (slices/segments)?
  • What is our share for each market in which we compete?
  • Are we losing, gaining, or holding share?
  • Where are the opportunities for growth (in our core business or adjacencies)?


  • Can we clearly articulate the unique benefits that we seek to provide to our target customers, the price/cost we expect them to bear, and how this entire value proposition is unique (our competitive advantage)?
  • How well are we communicating our value proposition to the market?
  • Do we have a clear idea about where our organization can be distinctively competent?


  • What is the short list of critical initiatives that the organization must successfully pursue in order to deliver the value proposition it is targeting, and accomplish its overall vision? Is the organization effective in distinguishing strategy issues from execution issues?
  • Do we “stay the course” when necessary, and shift strategies when appropriate, avoiding day-to-day reactions and programs of the month?


  • What is the competitive landscape?
  • Is it concentrated or fragmented?
  • Who are our competitors?
  • What is their share of market?
  • What are their distinctives/competitive advantages compared to us?
  • What are our competitor’s economic models relative to ours? Do they have significant cost advantages?


  • How do we measure success? What are the key metrics that the leadership team should regularly monitor in order to assure that the organization is on track and making progress toward achieving its goals?
  • Are these metrics purely financial, or has the leadership team determined the root causes and contributing factors that will lead to solid financial results?
  • What must the organization maximize in order to create superior value for customers, returns for shareholders and opportunities for employees?
  • Does the organization hold its leaders appropriately accountable for delivering targeted results?


  • What are the emerging trends that have the potential to change the way we do business? Do we fully understand key opportunities and potential threats influencing our customers? Competitors? Technology? Regulatory environment? Suppliers?
  • What’s propelling these trends?
  • How fast are they emerging?
  • What are the implications for our strategies and structure?

Going Forward

  • Have we clearly defined who we are as an organization (mission, vision, values)?
  • What are our strategic ambitions for this next period of time (3 to 10 years)?
  • What external opportunities and threats can help or hinder the achievement of these ambitions?
  • What internal strengths and weaknesses can help or hinder the achievement of these ambitions?
  • What strategic objectives need to be achieved to realize these ambitions?
  • What supporting tactics must be implemented to achieve these objectives?
  • What must be done to achieve alignment and commitment of key stakeholders to this strategy?
  • What metrics must we monitor to measure progress and success for this strategy?
  • Does everyone in our organization understand what we’re trying to accomplish overall – an aggressive, worthwhile stretch goal or vision significant enough to generate a shared passion and broad alignment across the entire organization?
  • Does everyone in the organization know how his or her job/role contributes to accomplishing this vision?

Again, the above questions are designed to merely to stimulate your own thinking regarding the specific questions confronting your own organization. Feel free to adapt, edit to the extent that they help you address your most pressing business issue. The strategy consultants at Triaxia stand ready to assist you in any way.