It is always best, as the expression goes, to leave them laughing. One should want to walk through the door, not be shown it. So, knowing when it is time to leave the party (the college or university one is running) is crucial.
Periodically, then, one needs to talk to one's board chair about how things are going. As for board members, they need to talk honestly to their president. The obvious time is during the annual review. Some presidents dread those reviews; I relished them because I always wanted to improve my performance.
Yet, performance should not only be measured from the top down. One should have one's staff do reviews, too -- of you, And one should make sure that those reviews are anonymous, and leave comment or suggestion boxes around campus for others to comment on one's performance.
In the minds of most on campus, presidents are to be feared. Since knowing what others think of how one is doing is important, eliminate the fear element by having those on campus provide you with unsigned comments. One may not like what is said, but one will learn from those comments.
In my view, there are only two good presidential models. Five to 10-year presidencies have the virtue of allowing a president to plant some seeds and begin to see them sprout, while the institution benefits periodically from fresh energy and ideas. Longer presidencies, assuming the incumbent can be regularly reinvigorated or reinvented, provide the benefit of continuity -- particularly in fundraising.
I had the pleasure of experiencing both models, and I enjoyed both. Which one is right for you and for the institution is up to you and the board. Performance reviews will help both parties determine when it is time for one to leave.
Here the board plays a crucial role because the board's most important function is to hire and fire the president. If a president doesn't know when the time to leave has come, board members should not be fearful that too many changes in leadership can harm the college. Failing to make a change when change is needed is far more harmful.
The key, though, for both the president and the board is openness and honesty. To avoid bitterness over a decision to leave or to stay, both parties should be in regular communication.
I have known presidents who left for another (competitor) college, with the resultant anger and sense of betrayal by the board and the entire college community. I have also known presidents who were forced out when they and the board were in apparent agreement about the state of the presidency, with a resulting sense of anger and betrayal on the president's part. (In a dramatic example of what not to do, a board chairman called a president I knew who was on sabbatical -- a practice, sabbaticals for administrators, I don't understand and never personally engaged in -- and told him not to return.) Avoiding those feelings requires nothing more than honesty and openness.
One needs to ask one's board chair regularly how things are going; one's board chair needs to answer questions straightforwardly and ask you for your impressions. Neither you nor your board chair should hold back the truth. After all, much is at stake--for the institution and for you.