Changing the Way the World Thinks about Strategy
Strategic Planning Questions

Strategic Planning Questions

Ask strategic questions

Once a client was chatting with me and mentioned something about my strategic planning: I ask weird questions.  Not so weird, in my mind – but my favorite questions are always strategic. Furthermore, they always lead to excellent discussions about the sources of value in business and how you can create more.  This is the essence of competitive strategy (beating or avoiding competition).

As a result, I created a list of fun questions that I like to pose in the strategic planning process.  I don’t recommend tackling them all at once.  In Simplified Strategic Planning, however, there is a concrete, data-driven process that creates a framework for addressing these questions.  That being said, you might want to think about how to incorporate these key questions into your own strategic planning.  Otherwise, pick up a copy of Simplified Strategic Planning, and learn a structured approach.  This could save you time and give you better answers.

First strategic planning question – Why do our customers choose us?

I think of this as THE question for business strategy.  There are many, many possible answers.  In most markets, however, the decision seems to boil down to about 3-5 variables that dynamically drive customer preference.  For example, in the airline industry, low fares, convenient schedules, and extensive network explain a huge portion of ticket purchases.  Likewise, in banking, convenience, relationships and fee structure seem to be the top drivers.  You don’t have to be the best in all of the factors, but you do need one or two.  Those one or two must lock in a sustainable customer base for your business.

Second – How will technology change our industry even more?

Of course, most of us are currently riding some of the biggest waves in the market oceans already.  If you think those changes are big, you may be surprised at what the future has in store.  We are wearing computers.  We are tinkering with the chemical and genetic makeup of familiar products.  Our world is getting smaller and more segmented.  These factors – and dozens like them – will not stop changing to give us a breather.

We will continue to be buffeted by technological changes that can wipe out entire industries. In addition, they spawn entirely new ones.  When was the last time you used a pay phone? And your cell phone?  Just a second ago?  Again, in strategic planning, we don’t need to get these 100% right.  However, we need to ask this strategic planning question, so we can move to the front of our industry.  Better yet, we need to ask this question, so we can escape the next wave, if it’s heading for disaster.

Third – If customers could change ONE thing about our industry, what would it be?

I like this strategic planning question, because it forces us to look at the problems of our industry from the customer point of view.  Good market segmentation might lead us to very different answers for different customer groups. On the other hand, some of the best opportunities to grab new market share come from the customers’ frustrations.  Are there unmet needs or preferences?

If your industry is highly oriented towards operational efficiency, there may be opportunities in becoming more personalized and human.  If your industry offers a plethora of choices, a simplified product may be welcomed.  Whatever the frustrations are, it’s likely you (and your competitors) have great reasons for creating the frustration.  Also it’s likely someone will come up with a clever way to sidestep it, leaving the rest of the industry playing catch-up.  Therefore, be sure to ask this strategic planning question!

These are just three of the best strategic planning questions I like to use.

Naturally, if you’d like us to drill into your team with these and other penetrating questions that will improve your market share, contact me at Do you have any questions that you find useful in your strategic planning?  Please comment below and let us know!  Consider holding a one-day workshop on Simplified Strategic Planning.

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Robert Bradford is President & CEO of the Center for Simplified Strategic Planning, Inc.  He can be reached at

Dana Baldwin is Senior Strategist with the Center for Simplified Strategic Planning, Inc.  He can be reached by email at

Co-Author Robert Bradford

Co-Author Robert Bradford

Co-Author Dana Baldwin

Co-Author Dana Baldwin


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