10 Questions to Jumpstart Your Strategic Planning Process

Sometime in the next two weeks--and certainly by next month-- tens of thousands of businesses, large and small, will have begun their strategic planning process for next year. And for about 90 percent of those businesses, the entire process will turn out to be, for all practical purposes, entirely futile.

"Left on the shelf", "Never really 'took'", "Fizzled after a couple of months", "Proved impractical", "Overtaken by events"-- Starting around March, year in, year out, I hear these and a hundred other ways of avoiding saying, "We wasted our time" over and over again.

There are many reasons why a strategic plan can be dead on arrival, but having facilitated hundreds of executive teams in developing their strategic plans, I've come to recognize the one reason that recurs with much more frequency than all the others combined: the plan was never "strategic" to begin with.

Something happens when teams get together in the fall to plan for the next year. The team gets locked into granular minutiae, running mind-numbing autopsies on the events of this year, using anecdotes in place of data, and generally thinking tactically rather than strategically.

The result? A brittle, uncreative, uninspiring--and ultimately unimplementable--hodge-podge of "this year plus 10 percent" spreadsheets, unsupportable underlying assumptions, pet projects and whizzo (read: not a chance in hell of succeeding) ideas.

Your strategic plan, of course, doesn't need to be that way. And the first step in avoiding such an outcome is to make sure your team come to the strategic planning offsite withstrategic intent.

So here are 10 questions to to prompt you and your team to think strategically about next year. Use them individually, or as a group exercise ahead of your next strategic planning session:

1. What is the one thing your organization* was worst at this year? What single thing most needs to happen to fix it?

2. What is the one thing your organization did best this year? What do you need to do to turn that success into a repeatable process?

3. Which individual was most responsible for standing in the way of your organization's success this year? What are you going to do about it?

4. Which department, division, team or function was most responsible for standing in the way of your organization's success this year? What are you going to do about it?

5. Which individual was most responsible for your organization's success this year? What are you going to do about it?

6. Which department, division, team or function was most responsible for your organization's success this year? What are you going to do about it?

7. What is the single metric or measurement you least liked hearing about this year? What will you do to prevent the same thing happening next year?

8. What is the single metric you will measure your success by (not how anyone else will measure your success-- how you will measure your own success). What are you doing about it?

9. If you fired yourself today, and came back tomorrow as a new boss with a clean sheet, what would you do?**

10. If a perfect competitor opened up across the street from you tomorrow, what would they be like?***

* Your business, division, department, project, group or team.

** See Hymowitz, Carol. 2006. Fire Yourself, Then Come Back and Act Like a New Boss Would. Wall Street Journal. October 9, 2006.

*** See Seth Godin: Small is the New Big, Portfolio Publications, 2006