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We are restructuring our organization and have a team member who is unwilling to switch managers - they have been reporting to me as the CEO for 5 years now, and in the new team structure would be reporting to someone 2 levels down from me in the organization. They've shared that they are unwilling to make that shift, and acknowledged that this is an ego/pride thing for them.
I don't really want this team member to leave, and he has shared that he doesn't want to leave either. But allowing him to continue to report to me when everyone else in his position is reporting to a new manager does not feel like the right call, either (even if it was only for a temporary basis while he wrapped up his work on the team).
We have been using Patrick Lencioni's Hungry-Humble-Smart model as one of the ways we assess team members, and to me, this is a clear example of a team member who lacks humility and is not willing to do "lower level" work for the good of the team, since nothing about his roles or responsibilities or title would be changng, and we are a very small company so he could still send me any ideas / recommendations he has for the company through Slack and/or set up a meeting with me anytime he wants - the ony difference is the reporting structure and that he would be having his O3 meetings with the new Director of Coaching instead of directly with me and he feels like this is a "demotion".
I'm wondering if there is any way I could give this team member feedback, and/or to work with him on developing more humility? Or if this is a trait that you either have or you don't, and I need to just make the tough call to let him go because he's not a culture fit for our team moving forward?
Difference between the work and where one lives in the org
If it's the same work, it's not "lesser work" to be reporting to a manager versus the CEO. The org needs to be a different shape around him, is all. This falls within your role-power to speak as the organization as it continues to change to fulfill its future.
Not sure I can suggest anything to help with him realizing this. Is it enough to tell him (or do you want to say only) "I've had to delegate a piece of my previous work down to the Director of Coaching, and the org needs your [team member] work to live there."?
Hard call. He's no longer your direct, though, so feedback about this "should" go through that Director of Coaching he now reports to. If they can figure it out, he'll stays on; if not, he'll eventually find someplace [else] where his overriding need for "status" doesn't interfere with his ability to contribute value.
Welcome to CEO life. I hope that, should you find _yourself_ needing to be replaced by a necessary organization shift, you can handle it with more grace.