The previous Brainzooming article was on listening for strategic insights in order to not waste strategic conversations. If you understand the types of information you need to develop a strategic plan, you can often get a jump start on completing it simply by listening closely to strategic conversations for valuable input.

This is the flip of that post. If you have the right people present, and they are in a chatty mood, how can you morph the gathering into a strategic conversation?

One way is by introducing strategic thinking questions that steer meandering conversations into strategic conversations.

9 Strategic Thinking Questions to Start Strategic Conversations


Here are nine strategic thinking questions to try and spontaneously generate strategic conversations:

  1. What do we want the result to be?
  2. What will we need to get started? (You can direct this strategic thinking question to consider resources, people, ideas, support, etc.)
  3. What would be the first steps to take?
  4. What has to happen after the steps we've identified to ________? (Fill in the blank with “maintain momentum,” “get ongoing support from the people who will need to support this,” and “be ready to implement it when we're done”)
  5. How will we know we're successful at each step along the way?
  6. How will the most important audiences for what we're doing judge if we're successful along the way?
  7. What things can stop us dead in our tracks at each step?
  8. How do we manage around those things that REALLY seem insurmountable?
  9. What absolutely has to be in place for us to be successful overall?

Along with introducing these questions to steer strategic conversations, apply the listening routine from the previous article to identify the right snippets you’ll need to turn strategic conversations into strategic plans. - Mike Brown

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