9 Strategic Thinking Questions to Improv in New Situations

What strategic thinking questions work when you don’t know what’s coming in a conversation? Specifically, what can you ask to learn, explore, diagnose, and adapt recommendations, without knowing what opportunities and issues the other party will mention?

I was on a call like that recently. After a month-long gap in chatting, we talked with a client about current initiatives. The call featured new, important news in multiple areas.

During our talk, we identified multiple valuable ideas. While that didn’t surprise me, I ALWAYS appreciate having several solid ideas waiting in the wings. I can share them if no other ideas come to mind. Developing the ideas in advance depends on prior insight into topics or issues. Without that, it falls completely to asking the right strategic thinking questions to stimulate productive ideas.

9 Strategic Thinking Questions to Improv

What strategic thinking questions worked?

That was something I asked myself after the call to attempt to turn strategic improv into a more formal script for future calls. Here are the questions (I think) I asked myself during the call to generate ideas:

In a situation with a clear, positive outcome

• How was the positive outlier different?
• How or where can we recreate that difference?

When several things all performed well

• What was the comparable about the things performing similarly well?
• Who or where can we make more things like that?

Seeking to leverage already-developed capabilities

• Where might we have a recipe already completed that’s the same or close to the same for a new situation?
• Are there instances where we’re neglecting things we already know will work?

Seeking to expand the range of active participants

• Who else can we involve to help us?
• Who has a self-interested motive to help us now, in exchange for a future opportunity?

Expanding the impact

• What can we to do to make other parties successful?

This isn’t our first list of improv strategy questions. It probably won’t be our last.

Contact us and let us know what situations demand that YOU are better at strategic thinking question improv. – Mike Brown