The relationship between a head of school and the board chair is often referred to as a marriage, and the analogy has some validity. You spend a tremendous amount of time together. Working in concert to lead and manage a school community is not unlike dealing with a large family, complete with shared values, common purpose, division of labor, and even the occasional argument.

So it only seems natural then that the head search process should be a lot like dating. Much of the initial phase of connection and communication in a search is conducted online. There is a period of checking each other out from afar, followed by a tentative first date, then a longer date or two before, hopefully, the prospective head and the school fall in love, and a proposal appears.

In typical fashion, schools will be “dating” several candidates at once, trying to find that right match. The question is: how do you know which is the one?

As in a successful marriage,match is everything when it comes to headship. When the match is right, financial challenges, problem children, and crazy uncles (or in the case of schools, eccentric English teachers) are easier to deal with because the partnership is strong, enduring, mutually supportive, and energizing. It is perhaps not surprising that most of us are initially attracted to potential partners by physical characteristics. This is true for schools as well. Location, name brand, perceived prestige, financial strength, or a beautiful head’s house are among the characteristics one might find initially appealing about a school. While important, and certainly nice to have, those features are meaningless if there is a mismatch in other ways.

After a few dates (or interviews) a school’s personality should come into focus. Does the mission speak to you? What are the espoused values? Do they match with the lived values? How does the culture match your view of a great school community? Do the opportunities and challenges—both immediate and long-range—fit your experience, skill-set, and interest? A marriage without mission and values alignment is doomed to fail, no matter how nice the house.

Of course, at the same time the school is evaluating you as a life-partner. No doubt you are on your best behavior those first few “dates.” Your resume is finely tuned, your outfits fancy, your impeccable manners on display. But as the search progresses be aware of whether you and the school are truly opening up to each other. When appropriate, are you able to show more of your personality? This looks different for each individual, but it amounts to a gut check. You don’t want to be in “interview mode” to the point where the search committee is determining their match under false pretenses. Rarely does a school or a candidate lie about who they are, but in “dating mode” we don’t always tell the full truth. No one benefits from being sold a bill of goods. When the school makes the right choice for the right reasons, everyone wins.

Most sitting heads of school will tell you that it is an amazing job—an amazing life—best they’ve ever had in many cases. But they will also tell you it is hard work. There are long days, difficult decisions, fraught relationships, and challenges that seem insurmountable. Accordingly, success is infinitely more likely in a place that feeds your soul, where you love the children and faculty, where the values match your own, and where you are energized by the path forward.

So, as you conduct your search for the perfect match, be honest with yourself and the schools, look for deep connections to mission and values, commit to being your full self in the wooing stage, and don’t get distracted by window dressing. If you do it right, a strong partnership will follow and you will have found a home. And if you’re really lucky, it might even come with a house.