Looking for a starting point for stimulating new thinking as your executive team looks ahead to future plans and initiatives? The best way to stimulate future-looking conversations is through robust strategic planning questions.

How you use strategic planning questions with an executive team will vary based on your organization's strengths. If your executive team is strong at engaging in productive group discussions, bring a few to a meeting and introduce them. Alternatively, you can have individuals provide private responses via online surveys or interviews, then share and discuss the overall themes as a team.

20 New Strategic Planning Questions

Strategic Thinking Questions

These twenty strategic planning questions cover five of areas where most companies focus strategy discussions.

Brand and Customer Experience

Each of these strategic planning question can push your team to rethink what it currently believes about your brand and the expectations both you AND customers hold near and dear.

  1. What does the customer experience our brand delivers look like if we re-imagine it as totally bold, innovative, and customer-immersive?
  2. How can we produce more on-the-spot products, services, and experiences for our marketplace?
  3. If we couldn't add anyone – we could only vary how people and resources are deployed - what would we do to address the most pressing customer needs?
  4. What would we do if our goal were to maximize magical moments for our customers?


Use these questions to create bolder thinking about taking risks and exploring unconventional perspectives for innovation.

  1. How can we repackage the riskiest opportunity our organization has so it's a natural to start right away?
  2. How can we provide the environment to incubate a new segment of customers for our main offering? Or for new offerings that we can market and sell?
  3. How can what we did / enjoyed doing as children turn into a new product idea?
  4. How much time do we spend daily making an attempt to find the edge of what our audience won't let us do?

Competitive Dynamics

These strategic planning questions provide an intriguing contrast on dealing with your competitive situation: kill them with business aggression or kill them with kindness by sharing your secrets. The contrast should stimulate a diverse conversation!

  1. What is the enemy - human or otherwise - that our organization is focused on obliterating?
  2. Where are we willing to invest time and resources to win over people opposed to our brand's cause?
  3. What has our company figured out that we should reveal to other companies so that they can copy it and create better opportunities for the entire industry?

Internal Operations

Any of these strategic planning questions will underscore the importance of your internal capabilities and performance as part of routinely delivering incredible customer value.

  1. Where can we dramatically decelerate the crazymaking in our operations?
  2. What are the two biggest challenges in our organization? How can we address BOTH by rapidly prototyping solutions?
  3. What can we do to keep our organization's creative engine always running?
  4. Which do we do more of - work well or work long? How should we change that?
  5. Who are all the people who own responsibility for eliminating bad outcomes in our operational footprint? How can we equip them to do more of it, faster?
  6. If we have small data (not BIG data), what steps will let us collect dramatically more data to get to medium data ASAP?


Use these questions to call attention to all the audiences that depend on, serve, regulate, observe, or play any other role relative to your organization.

  1. Where can we identify opportunities to improve conditions for those in our ecosystem?
  2. What's the most beneficial offer of help we could tweet to our audiences to change more lives for the better?
  3. How can we bring the smartest, most future-looking people in our ecosystem together to innovate?

When does next year’s strategic planning start for you?

We suggest starting to use these questions earlier than later so you have plenty of time to imagine many possibilities, narrow them to an actionable number, and shape your next plan.

If you’d like an even bigger variety and number of questions, download our eBook with 600 strategic planning questions across many areas. It’s a one-stop for setting the stage for productive strategic conversations! – Mike Brown

How will you stay up on all the ideas for developing innovation strategies if you don’t join us and subscribe to the Brainzooming newsletter? We have a ton of ideas already out here, and more are coming all the time. Sign up to gain your strategic advantage!

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