Email Excellently: Practical Coaching Tips to Consider Before Clicking Send

Effective email communication is hard — especially in a leadership role

Whether writing to your Board of Directors or to a colleague across the organization, how do you demonstrate leadership excellence over email? This is important — after all, most executives spend tons of time receiving, prioritizing, and reflecting on email messages, pounding out responses and hitting SEND, thereby multiplying email for all involved.

Based on my experience as an executive and coaching others, bad email habits are the norm rather than the exception. Just ask anyone whose email has ever come back to bite them, ruffled the wrong feathers, or even been made public. But fear not. With some simple guidance, and by breaking a few bad habits, you can use email as an instrument of greater influence and make it work for you, rather than make work for everyone.

12 ways to upgrade your email leadership presence over email

In the heat of the moment, you may have hit “send” on one or two emails — and thought better of it later. Or perhaps, “in the interest of time,” you may not have given enough thought to how you were communicating something — meaning, did you ask yourself, "Does this need to be an email or a conversation?"

In fact, when was the last time you did an audit of your email effectiveness? Do you look back to see what you can improve? The simple approach here: periodically re-read a sampling of your sent email, to assess its impact on your colleagues or team. This is an experiment that some of my clients have tried — and that works to bring new self-awareness to how you use email as a tool.

Carefully select a sample of, say, 20 of your sent emails. Make sure they represent both smooth and stressful times, as well as a spectrum of recipients. As you carefully reread your sample, start to reinforce the following tips in your mind:

1. Don’t blow off your subject line

If your subject line is "FYI" or "Follow up" or "Update," then your message simply won't be read by many of the busiest people you know and love. Take the time to write a subject line that gets the correct attention and priority. Your email lands on long lists and your most important recipients don’t have time to decipher your code or infer your meaning. Be creatively concise on the headline and, if appropriate, the time frame. “Project X Phase 2 Needs Your Approval by 5/15” works better than “Project X Follow Up.”

2. Don’t bury the lead

Your subject line has grabbed their attention. Now what? Why should your recipients care about this message? What do you want from them? If it takes more than a sentence or two to figure out why you’ve written the message and what’s most important, you’ve buried the lead — and your email's potential positive impact along with it. Put your most important message(s) right up front, in the first sentence or two.

3. Be brief — very brief

Nobody wants to read a long email, and even if you think they SHOULD, they WON'T. If you need to write more than a few paragraphs, and certainly more than one email on the same topic, then there’s a problem: you’re likely trying to avoid, spackle over, or substitute for a conversation that needs to happen. Keep your emails short and sweet. If you can’t, then start an IM, pick up the phone, or go face to face. If you have a lot of information to deliver, do them the courtesy of putting it in an attachment (and follow these tips on the cover email).]\

4. Don’t confuse an email chain with a conversation

A string of emails and replies shouldn’t be considered a substitute for a conversation, a brainstorming session, or a decision-making process. Email is a one-way transmission of thoughts, ideas, questions, offers, or requests that may or may not be read, and with varying lag times that often lead to unnecessary churn. Voice to voice (primarily) then text or IM are much better forums for important interactions.

5. Don’t use email to confront, vent, process, or punish in public

If you have a complaint, concern, or issue with Sally or her team, then the explanatory email that “tells it candidly” to Sally (or to Sally PLUS other colleagues–ouch!) is a bad, bad idea! It’s the last thing you want to send. Lasting damage to your own impact (and reputation) as an executive will follow a pattern of this approach to email. As a therapist might say, “Write the letter and don’t send it.” Email isn’t the place for processing an issue, venting, or confronting someone. Since email lacks interactivity and the nuance and body language needed for deeper understanding, it will make thorny issues thornier, and rarely if ever solves anything. Sending a “here’s what’s wrong” email to Sally, especially copying others, is a sure way to diminish or destroy trust.

6. Follow the “New York Times rule”

You’ve heard this one before — now believe it: Email is barely communication. It’s certainly not a forum for disclosure of anything sensitive. (And unlike a conversation, an email is part of your record, forever.) Don’t put anything in an email today you wouldn’t be OK reading in the New York Times tomorrow. All emails could be (and perhaps are being) read by others. They are also subject to discovery in case of future legal action. Putting sensitive information in emails is tempting fate, and frankly, simply a bit lazy.

7. Check your grammar and spelling, and avoid text-speak in emails

Communicating effectively as a leader is harder when it's a bit shabby. Check your spelling. Read your email out loud. Look for words spelled correctly but in the wrong place, such as “here” versus “hear,” “affect” versus “effect,” or “your” versus “you’re.” Using text-speak like “FWIW,” “ur,” “btw” and “LOL,” even when sending from your smartphone, degrades your impact. Double-check these before sending.

8. Reread the message you received carefully, before sending your reply

Are you responding or reacting? Responding: good, reacting: not so good. Too many people scan and reply in a rush, and miss the point. Before replying to a message, read it twice. Think. Prioritize. Then, BEFORE SENDING, read the original email and your reply together. If you don’t have time for that, wait until you do, or connect with the recipient by another method.

9. Don’t be lazy about forwarding emails

We’ve all done it: forwarded emails without double-checking what lurks below, earlier in the chain. Before sending, please scroll all the way down and read the full chain. Delete irrelevant, outdated, or recipient-inappropriate stuff. You’ll not only better serve your recipient with crisp, relevant communication, you might also spare yourself a world of trouble.

10. Check and double-check recipients

Avoid over-sharing! That means overusing cc: and bcc: to send the wrong thing to the wrong person, or to more people than needed. Before clicking SEND, check and double-check your recipients. This may seem obvious, but it’s a step too often overlooked. And like the unchecked forward, it can lead to all kinds of unnecessary headaches.

11. Be thoughtful about timing and response time

Don’t send emails in the middle of the night or on weekends–as a leader, that telegraphs an expectation of response in kind. Put them in your drafts folder--or use delayed send options--and send them later. Also, no one likes an e-stalker. When you send follow-up emails too soon after the original (e.g., “did you have a chance to review my email from earlier today?”), you’re degrading your impact. If you’re going to need a response that quickly, you probably shouldn’t use email in the first place; make a call.

12. Effective business communication is interactive

When in doubt (e.g., “Should I do this on email?,” “Why am I having so much trouble writing this?”) delete your draft, and pick up the phone, open a video session and have a conversation.

Stellar executive communication starts with self-awareness

As suggested above, audit a sample of your previously sent email from time to time. What do you need to change? Answer that, and you can transform email from a weakness into a vehicle to enhance your communication, strengthen your influence, and build your executive presence.

Related: Three Must-do Practices for Leading Change