Looking for some management advice, my role has shifted from execution to strategy in the past few years - I have gotten great feedback on leading cross functional teams and my strategic chops, but I’m struggling to develop my direct report. This individual is project management/ execution minded, what are some questions I can ask this this person to guide and grow them into this new expectation? I feel like I’m still learning and trying to figure out the ambiguity myself - help!

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Sorry, just to understand the question, you are looking to develop someone who is a direct report but you are unclear of what you need to do to develop them as you are unclear of their role or of yours?

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Do you work in advertising?

Gotcha. I think the way to start to train their brain to think strategically is to ask questions that force them to.

What is the key objective of x?
How does y fit into the broader ecosystem?
What are some alternative approaches you considered to z?

Etc etc

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