A key part of the head's job on any day is to be the most-adult adult in the room, to lead by example and by calling others to their better angels. This role is even more important in moments of crisis, and although the end of the school year is no crisis, it's a predictably wiggy time of the year for which heads can and should prepare.
It's important to name some of the problematic behaviors and conflicts inspired by the end of the school year:
under the wire: School people are an assiduous bunch but not above procrastinating. This combination is particularly toxic when well-meaning school folk unearth a dormant project and insist that it be completed in the last month of school.
brinksmanship: Deadlines have always been tools for leverage (cf. Bay of Pigs). Feinting around the finish-line-in-the-sand on employment contracts, re-enrollment contracts, teaching and committee assignments, etc., generates unproductive energy.
culture clash: Not everyone at school lives by the academic calendar. The end of the school year can escalate latent resentment among year-round employees who watch their more celebrated teaching colleagues stroll into summer leisure (bearing boxes of parent gifts) even as they begin their busiest time of the year with the audit, the facilities shakedown, summer camp, etc.
dramatic finish: Some adults just can't resist the dramatic postures available in the final scene: the mortally wounded protagonist crawling heroically toward the goal, the last word-haver, the person who grants himself liberty to go unfiltered.
As with virtually everything in headship, preparation for the school year's end is equal parts art and science. Here's my rubric for identifying opportunities to install a little grace in the school year's end:
As you build next year's calendar in January and February, consider what you can unpack from the last month of the school year. What events can become simpler? Has the barrage of year-end celebrations become a kind of velvet (cupcake) tyranny (and socio-economic bias) for the parents at your school?
If your board does not meet over the summer (and it really shouldn't), how can you help committee chairs build work plans that don't leave unrealistic, enervating expectations for summer activity?
Adhere to and repeat year after year important mid-year deadlines so that they don't become end of the year deadlines.
When granting extensions on employment or enrollment contracts, what is the date of diminishing returns? At what date does the empathy you extend to an employee or family put the school's program and finances in jeopardy?
What is the legacy effect of these special considerations in your school culture?
Describe what you want, model it, say it again and again.
What vehicles do you use to communicate with faculty/staff, parents and the Board? How and on what timeline can you use those vehicles to communicate (without becoming a scold or a didact) your expectations for adults in the final weeks of the year?
What opportunities do you have to coach your admin team on their year-end communication and planning?
How can you help the Director of Business, the Director of Facilities, the Summer Programs Director, the Librarian, etc., communicate what they need from faculty before they depart for the summer?
How can you define limits for adult conduct by directly addressing end of school year situations or by simply saying no?
Chances are you're the host and emcee for at least 75% of the celebrations and facilitator for most of the wrap-up meetings at the end of the year. What kind of exercise, rest, meditation, planning do you need to do to be at your best in these moments?
Every school has many adults who naturally hit a second wind each May. How can you recruit these people to help you? In what productive roles can they be cast?