Boards often hire someone new to the presidency both to benefit from fresh thinking and to avoid tapping someone who has done the same thing in the same way at multiple institutions. And yet, the decision to take a chance on a rookie chief executive creates one of the riskiest situations in higher education. One reason it is fraught with risk is that the search and hiring process nearly always forces some unvoiced hopes into play. The board of trustees and the new president will have entered into collusion by tacitly agreeing to leave some of their mutual expectations unstated. And together, they have created a sure recipe for disaster. In this article, the authors explain how the practice of hiring a presidential mentor or an executive coach--with the president's blessing--can moderate or eliminate the negative force of these unvoiced expectations and produce a longer, healthier, and more productive presidency for an institution.