There sure is an art to finding mutually beneficial arrangements, but there is sometimes also a point where you need to recognize no such arrangement exists. It seems equally likely to me that the manager may have realized right away that there was no (or not enough) flex in the situation and decided that instead of the team member leaving immediately they could perhaps be strung along and provide value to the company for a few more months.

Some of the situations where no real flex exists are:

- promotion wish where there is no place. For example, someone 1 level below the CTO wishing to be promoted to CTO will not be able to get their wish unless the current CTO leaves. If they don't, promotion to the desired rank will not be possible without changing companies.

- salary demands that can't be met from the budget. Most middle managers do not have significant say over how much budget for raises they are allotted for the year. If one persons raise demand is bigger than the total then not all of it can be met.

- As in the GP post, the things the employee wishes to work on do not fit in the wider strategy of the company and/or will not provide value commensurate with the salary received. In this case, depending on how insistent both sides are, sometimes no compromise is possible.

100% agree. I look back to several situations in my own career as a manager where I did have this case arise and went looking around the org for other opportunities that might give my employee what they wanted. Some of those worked out, but many did not. The ones that did not would be indistinguishable to the employee from a manager just "stringing along" the employee to get a few more months out of them. (There are other cases where I was able to be more upfront as there was an obvious mismatch analogous to your CTO's direct report case.)