What is/has been your most challenging hire? If you're a Head of School, was it your lieutenant? By that I mean, was it your administrative assistant? That position requires someone with a great deal of tact, an ability to handle volumes of confidential information, the perspicacity to share things with you at the right time -- even to pre-empt certain things by letting you know in the knick of time. Yes, detail-oriented, excellent communcator, and so on. What else?
If you're a division head or department chair, what has been your most challenging hire? Has it been someone whom you could groom (theoretically) to take over your position, should you either move on or something befall you? Was it intentionally hiring someone whose perspective diverges (perhaps greatly) from your own? Was it a moment of discomfort, of joy, or some odd combination of the two?
Please reply in the "comments" section of this post in order to share your most challenging hire. I will publish the comments, so that others can read. I'd love to hear what you have to say!