A Grinchy Reflection on Holiday Email or Confessions of a Recovering Email-holic

‘Tis the season, and this year. when the Grinch hitches up Max and loads his sled full of all the Whoville presents, I wish he’d also collect all non-emergency vacation school emails and whisk them to the top of Mt. Crumpit until school begins again in January.

Perhaps Covid was the culprit. It may have then that school emails escaped the bounds of the conventional workday.  Of course, there were always the occasional unhinged late night emails from disgruntled individuals that I instructed my faculty to ignore—no good ever came from an email sent after midnight—but, in general, people mostly knew how to behave in the before-times. However, in those first panicked days/weeks/months of the pandemic, email etiquette and so much of what “we had always done” was jettisoned. My school leader pals and I worked 24/7 to navigate a world that required more pivoting and do-si-do-ing than a square dance. We were thinking about how to bring kids and teachers back to school; about how to reconfigure classrooms, serve food, develop protocols. Our priority was keeping our communities as healthy as we could. We zoomed with colleagues at 7 a.m. and held leadership meetings after dinner. We sent messages at any hour of the day or night. School life and home life boundaries blurred, and bad email etiquette has lingered like a cough that never leaves.

We need the Grinch to free us—at least temporarily—a sort of reversal of his meanness. If he were to pack up all the unnecessary emails we are all guilty of sending, we could all have a guilt-free rest!

When an email or a text arrives after hours or during a vacation from a faculty member’s boss—department head, division director, head of school--it can make the recipient feel anxious—just as heads may feel a frisson of worry when the board chair texts with the words, “Got a minute?”  Is the summons urgent or mundane? Should we interrupt Love Actually to respond? Could it wait until morning? In the face of uncertainty, most of us, hard-wired as dutiful, respond.

A coaching client recently shared that throughout the Thanksgiving vacation, she was determined not to answer emails that arrived about non-urgent school business.

“How did you know the emails were pouring in?” I asked. 

“I checked,” she confessed. “I didn’t want to, but I looked—at least once a day.”

She is good at her job; of course she checked her email daily. But she also shared that she grew tense considering the mountain of unanswered emails she knew would confront her on Monday morning. We talked about the reality that the energy she expended feeling resentful might have been better spent responding, but, for her, it was the principle of the thing.

“Why,” she asked, “do people send so many emails over vacations?”

And that is a million-dollar question.

I began my headship proud of how fast I responded to emails; while my inbox was never clear—far from it—I was good at managing anything important, seizing on five minutes afer a meeting or late at night to answer what I could. I rarely missed anything critical. Subsequently, though, I remembered two old adages: “No good deed goes unpunished,” and “Begin as you mean to go,” My misplaced self-satisfaction at my at my email prowess meant folks began to expect that I would always respond fast—and there were times when that was not possible. Along the way. I also learned that it is often wise to let a lengthy email steep a bit. Speed doesn’t always help.  A few hours for the writer to reflect on tone and content can sometimes be instructive.

As a recovering email-holic, who, in these first month of re-wirement, marvels at how few meaningful emails I now receive (beyond the many One Time Only sale announcements that cascade into my inbox) I think, sheepishly, about the fact that, early in my headship, I sent emails at every hour of the day and night. I was not thinking about the impact such a habit had on those with whom I worked. “There,” I’d think with satisfaction as I pressed SEND, “I’ve taken care of that.” In fact, all I’d done was take something off my plate and dump it onto someone else’s plate, someone who, likely, worked for me. I was trying to show how hard I was working, how, as a leader, I was always dreaming up new ideas and possibilities. But everything in moderation is another good adage. We ultimately decided Ann would have no new ideas on Fridays or during the month of May, and when I traveled to a conference and was inspired by all sorts of books or speakers or workshops, I would wait until I got back to school and sit down to share my ideas instead of barraging those around me with countless emails. Frankly, I suspect my team was exhausted by my Energizer Bunny persona and my never-ending stream of messages. Eventually, that beautiful feature, Schedule Send, helped me learn I could write what I was thinking without foisting it on anyone else.  Unless there is blood, most things can wait until morning, or, if it’s a weekend, until Monday!

Megan Weiskopf, the brilliant Director of Teaching and Learning at Laurel School and my beloved colleague, tried to tame the email beast some years back by creating email etiquette guidelines for our school.  Her kind reminders helped us re-establish better habits.

Email, she explained, and I reiterated—several times over the next few years, (in email, ironically), is for sharing information, nothing more.  It is not for having nuanced discussions. It’s difficult to discern tone in email, so don’t use it for complicated topics. Pick up the phone or use email to schedule a time. Don’t avoid a hard conversation by having in via email; talk to one another. Receive a tome from an unhappy parent? Write back and ask to schedule time to meet—in person is always best, but if Zoom is the only option, it’s still better than email. Use your school’s existing systems and structures to share deadlines, important dates, etc. Don’t clog everyone’s inboxes by sending information they already have. Refrain from putting 17 people on an email unless you are explicit about why you are doing so and which single person needs to respond. Including the Head on an email can be perceived as passive-aggressive tattling, so be judicious about making that choice. And beware of BCC; I have sometimes seen someone who was BCC’d respond to the whole group when the others didn’t know that person had been BCC’d.

Rules to live by for holiday email:

·      Is it necessary?

·      Is it kind?

·      Could it wait until January?

·      If you must write it, could you schedule send it?

What if you stepped away from your laptop or phone, found some stationery and a pen and wrote to an old friend, a former colleague, or someone you appreciate? 

Many of us in schools have a sense that we are always waiting for “the other shoe to drop.” We check our email compulsively—out of a sense of duty or FOMO or low-grade constant worry about the world and about the people we care about in our schools. But if it’s urgent, someone will likely text you. And you can model for your students what it means to take a real break from screens.

Use your holiday to re-charge, to fill your cup, to be with people you love. Give the email a rest. It will be waiting for you in January.

I hope Max is strong enough for the journey!