5 Tips to Help Leaders Get Control of Their Email

Seth remembers, in the early 1990s, sitting for his first lesson on a new technology called “email.” The district IT coordinator reassured everyone: “This will save you time”... famous last words! A decade later, in our respective jobs as a principal and a superintendent, our inboxes were jammed with hundreds of new emails every day.

We all know the benefits of email—leaders are more accessible to students, staff, and parents, information can be conveyed efficiently to broad audiences, and there’s a capacity to transmit a wide variety of information.

At the same time, managing the torrent of email is also overwhelming. To keep up, administrators are confronted with a lose-lose option: confine yourself to the office during the school day when you should be a presence in the building, or sacrifice free time on evenings and weekends. We have all probably fallen into another trap: the temptation to shoot off an email when a telephone call or face-to-face conversation would be a better choice for expressing emotion and engaging in dialogue. Email, in short, is simultaneously useful and grievously overused.

5 Email Management Tricks

1. Sort your inbox. Some administrators assign a capable secretary to continuously screen email throughout the day, asking them to delete undesirable mail the spam blocker may have missed. Other administrators maintain that assigning screeners violates the sender’s expectation of privacy.

The subject of involving assistants raises the matter of artificial intelligence. AI bots are able to sort incoming email into subfolders; flag high-priority messages requiring immediate attention; generate accurate, contextual responses in the administrator’s voice; instantaneously manage a large volume; and sync appointments proposed in email with the user’s calendar. Concerns include the possibility of an AI assistant misinterpreting human communication, sending a response that lacks circumstantial awareness or sounds phony and impersonal. Bots certainly need to be monitored.

Email is just one channel of communication in a growing relationship between the leader and a member of the school community. While bots can handle certain repetitive tasks and autoreply to some questions, they can’t build connections, the mutual feeling that you’re genuinely getting to know each other. For building partnerships, AI is no substitute.

2. Evaluate the email. We suggest scanning all email the day it arrives, checking for urgent problems that can’t wait, such as a parent alerting the school that their child is being bullied. Non-crisis email should also receive a same-day answer unless the message arrives in the late afternoon. If it is not possible to send an appropriate quick response, send a template acknowledgment to the effect of, “Thanks for your correspondence. I plan to give the matter more thought and respond shortly.” Acknowledgments build trust by conveying to the sender that their concern is deserving of the recipient’s considered attention.

3. Craft your response. The first principle of time management on the job is “touch it once,” referring to completing a task on the first go-round. Deferring an email for future handling increases time spent on one task. On most occasions, leaving an email unresolved only exacerbates the inbox management problem, as the dreaded number on the counter inexorably rises.

There are exceptions to every rule: Sometimes an email requires consultation with others or more thorough contemplation. Email from a parent, for instance, often calls for checking with the teacher or other staff member. In any event, consider whether more time spent answering an email is worth the opportunity cost of putting off mission-critical instructional leadership tasks before choosing to delay.

The aphorism “less is more” frequently applies to writing emails. Given the deficiencies of email correspondence discussed above, a simple reply, in contrast to a wordy and dense treatise, may be preferred. However, short emails are sometimes excessively pointed. One more sentence may helpfully contribute positive emotion and connection. For example, instead of leaving it as, “Let’s meet at 9:00 tomorrow,” think about tacking on another sentence—perhaps, “I’m looking forward to hearing your views.” An extra sentence in an otherwise terse “just the facts” email often gets to the heart of the matter in every sense of the phrase.

Emails that arouse strong feelings are best addressed by waiting until the emotional temperature decreases. We’re all guilty of violating this common sense counsel and know the result: You immediately regret a snarky reply and begin checking whether your email platform has a recall feature. Write it if you must, but move it to the drafts folder. (This practice is a wise exception to the principle of “touch it once.”)

4. “Just eat the frog.” This maxim concerns thorny situations that people would rather avoid. “I’m uncomfortable answering the email, so I’ll wait another day or week.” When attending a dinner party, learning the host has prepared frog legs, and you’re no fan, what do you do? The longer you hem and haw and hesitate, the harder the situation becomes. Grandma’s sage advice? “Just eat the frog!” Whether you write or call in response to a sensitive email, the stress will no longer weigh on you, and if you delay, the other party will have more reason to be upset and angry.

5. Consider a phone call. Regarding email, Dan Fisher wisely recommends, “Good or neutral news via email, bad or sad news in person.” Consider this rule of thumb: If you find yourself debating whether to call or email, you should probably call. Err on the side of enhanced communication.

One regularly neglected time-saver is picking up the phone and talking. When receiving email, it’s easy to misunderstand; and when sending, it’s easy to be misunderstood. Communication between two people is a complex exchange: Words convey different connotations to different people; tone of voice (e.g., anxiety, pique, tentativeness) is a pivotally meaningful cue that is hard to distinguish in emails. The following are occasions when telephone talk is preferable:

• When building relationships while trust is paramount.
• When issues are complex and likely to prompt follow-up questions and discussion.
• When the matter is sensitive and laden with emotion.
• When you’re worried about someone.
• When conflict might arise or needs resolution. 

When calling, starting a discussion with “Thanks for your thoughtful email. Can we talk?” may ultimately consume less time. And there’s the additional benefit of authentic conversation.

A final piece of advice comes from Jessica Cabeen: She advises educators to set boundaries by scheduling email time, practice mindfulness exercises to manage anxiety, and take a break—a digital detox—now and then. The goal for school leaders facing the onslaught of queries and comments from students, staff, parents, and the public is to ensure that technology serves human beings, not the other way around, and to use email to enrich, not obstruct, relationships in the school community.