12 Time-Tested Strategic Planning Questions to Help You Plan Better

It’s that time of year when ambitious entrepreneurs and startup leaders plan for the next year of their quests.

Now it’s time to assess how you did this year and determine what needs to happen next year.

Great execution requires serious planning, especially as your team grows. Making clear strategic decisions and aligning everyone to the same goals are powerful force multipliers for your business.

Strategy is just the bigger decisions that make your execution better.

Here are 12 simple, time-tested strategic planning questions that are widely used in goal-setting, prioritization, and improvement:

  1. Strategic Planning – What’s the current situation? What are we trying to accomplish? What do we need to do to get there from here in the next quarter, year, or 3 years?
  2. SWOT Analysis – What are our internal Strengths and Weaknesses? What are our external Opportunities and Threats?
  3. Continuous Improvement – What is working? What’s not working and needs to be improved? What lessons have we learned?
  4. People & Organization – Do we have the right people in the right roles? Are all the major functions and priorities of the business “owned” by responsible leaders?
  5. Serving Stakeholders – How well did we serve our stakeholders–employees, customers, partners, owners/investors, and our community?
  6. Purpose and Values – Did we live up to (or fall short of) our stated Values? Are we hiring and firing to our Purpose and Values?
  7. The Dan Sullivan Question – “If we were having this discussion 3 years from today, what has to have happened for us to feel happy with our progress?” (Dan Sullivan of Strategic Coach)
  8. Hedgehog Concept – Three questions: 1) What are we deeply passionate about? 2) What can we be the best at? 3) What drives our economic or resource engine? Where do these three intersect? (from “Good to Great,” by Jim Collins)
  9. New Possibilities – What would we do if we could not fail? What would we do if we had no fear and no excuses?
  10. Stop Doing List – What types of customers and employees should we stop pursuing/hiring? Which initiatives should be stopped so we can use the resources more productively?
  11. Fire Your Old Self – If you fired yourself and hired the best candidate in the world to replace you, what would they do differently to get better results? How can you start doing that immediately?
  12. The One Thing – What’s the ONE Thing we can do right now, and by doing it everything else will be easier or unnecessary? (Gary Keller’s “The One Thing”)

Even disciplined entrepreneurs who take planning seriously face unexpected internal challenges, external forces they can’t control, and massive “learning opportunities.”

No problem, just keep moving and start again.

The growth game is won by teams who keep their eyes on the big goals and continually adjust to make progress.

Keep moving forward.

What other strategy questions do you find useful?


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