How do I deal with a dissatisfied leader?

Question:
I have a great team and a stellar second-in-command (SIC). However, my SIC is often overwhelmed and dissatisfied with what she sees as the “chaos” around her. I have offered help, resources, and a listening ear but nothing makes her happy. I don’t want her to leave. What should I do? B.B., Palo Alto, CA

Answer:
No matter what situation you’re faced with, your first question should be “whose problem is this to solve?” Her happiness is not your responsibility.

Based on your question, it sounds like you question her judgment e.g. “with what she sees as the ‘chaos’…” If you haven’t already, have a conversation with her to manage her expectations about what is “normal” in your company. She may be comparing apples-to-oranges without realizing it.

Or it may be that she’s one of those people who is invested in being unhappy. If that’s the case evaluate whether her attitude is infecting the rest of the team. Any time you have someone with a strong pessimistic bent, especially if they’re in a senior-level position, you need to be vigilant to make sure the team culture doesn’t become toxic.

It sounds like you’ve done what you can to give her the tools to solve her problem. Now it’s up to her. The next time she complains, ask her what she’s done to resolve whatever it is. Keep pushing the responsibility back on her and see what happens. If she chooses not to solve issues, have a conversation with her regarding whether this is the right position for her.