We’ve all known students who apply to a huge number of colleges on the theory that some of them will say yes; or people who send out hundreds of resumes hoping to get a positive response. These are aspirational, sure, but too often they are based on false hopes and rarely lead to the desired result. Sadly, the same seems to be true for many people seeking headships. We see too many candidates who aren’t competitive because they’ve misjudged either their experience or their capability.

If a school is looking for a head who has significant experience with budget, finance, and fundraising, don’t try to fudge it—you’ve either done it or you haven’t. Same with enrollment management; many schools these days are seeking heads with admissions experience. Again, you’ve either done it or you haven’t.

A background as a classroom teacher is something nearly all search committees seek in a head but there almost always needs to be a heavy dose of administrative experience to complement it. It is as rare as proverbial hens’ teeth for someone to go straight from being a teacher or department chair to the head’s office.

Friends and colleagues are often a source of unhelpful encouragement: “You really ought to be a head” doesn’t necessarily mean tomorrow or next year. Too many candidates apply for headships early in their careers as administrators, don’t get the job they’re seeking, and figure if they apply more widely, they’re more likely to get a job. And then they get known for their indiscriminate searches. We’ve seen candidates who apply simultaneously to small market K-6 schools and large urban PK-12 schools, which makes no sense and leaves the candidate looking clueless.

To be successful, the candidate must have a deep understanding of the Self. There is no substitute for self-knowledge and people who fail to demonstrate it in their applications raise a question about their judgment in other areas as well. Such questions don’t lead to hires. So, know yourself: know what you’re good at, know what you need to learn, know what your weaknesses are and how you can strengthen yourself in those areas. Don’t sweep them under the rug.

The clearer you are about who you are and what a school needs and whether you fit those needs, the greater the likelihood you’ll do well in a search.