Hi! I’m about to have a “skip level lunch” with one of my executive leader (e.g CFO, CIO, etc). What would be productive to talk about? I’ve been with the company for 1.5 years, and this is my first lunch with her although we’ve had weekly group meeting as well..

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When I meet with execs I like to break the ice initially with something trivial, not too personal but not necessarily work related to humanize my experience.

I think it’s good to share fresh perspectives and genuine opinions. You can offer a more “boots on the ground” perspective that an executive will never have.

Share a recent win for your team, and what that means for the organization as a whole.

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First things first, ask them if there’s anything you need to prepare for or have available for the lunch. This shows initiative.

Sometimes execs have these type of meetings to gauge your commitment to the company, gauge your willingness to learn and grow within. If that’s something you want, make that known.

Since you have weekly meetings with them I presume they may be familiar with you and your work style. Ask them if they have suggestions for improvements.

Above all, be yourself and be confident.

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Be prepared to give honest feedback about your leader, team, the organization that etc.

Some skip levels are very formal and structured but, in some organizations it’s a way for senior leadership to keep a finger on the pulse of the business in a relaxed/no pressure way.

Remember, yes they are your boss’s boss, but they are still people with blind spots.

Practice how to give constructive feedback if it’s something you aren’t already comfortable with.

I can tell you from experience, SLT members tend to remember the people that told them the truth about leadership/process/performance development opportunities and offered solutions.
If you present a problem that they didn’t even know was a problem AND a solution, you’ll put yourself on their radar which will do wonders for upward mobility.

Now remember it can’t be “hot gossip” about your boss, and don’t blind side your leader about anything that’ll go back to them.

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