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Difficult Emails - 4 Questions To Ask Before Sending

It's 2019. Emails are a part of life. We speed through them with the seemingly unreachable goal of getting that inbox to zero - or maybe you've completely given up on that goal. Yet all this practice probably has you feeling pretty good about your email writing skills. Well, that's what I say about myself, anyway. Although, every once in awhile, I open an email that takes me right to the jaw clenching! A simple click...and BOOM - a juggernaut of words and punctuation! And before I have the courage to begin reading, I'm already thinking, What do they want? Are they angry? Did I forget something important? Is my passport still up-to-date?

Once I get over the initial shock of this incendiary email, and am able to draft a reply, I turn to an old friend. Before clicking send, I ask myself *4 questions to help ease my mind, particularly if I'm fearful or uncertain of how the email will be received.

If I can truthfully answer, Yes, to all 4 of these questions I can click SEND with confidence (or at least more of it.) If I answer, No, to any of them, I try to explore why and make adjustments. If time allows, I save the email draft, and come back to it later that day or the next morning with fresh eyes and a fresh mind.

To apply mindful communication to your email writing, ask yourself...

Is what I'm writing necessary?

I like to ask this question particularly as I'm proofreading, and really go sentence by sentence. What "fat" can I trim off of this email? If I take out this sentence, are all my points still coming across? Do I really need to apologize 3 times? I'm a big advocate for "less is more." (See?)

Is it timely?

Often times, a sooner-the-better approach to email sending is proper etiquette. However, if you can afford a little more time, think about the best time of day for YOU to reply. Does it makes sense to squeeze it into your lunch break? Maybe you can afford to wait until after work when your mind is more calm and you're not feeling the weight of time restraints. Not feeling rushed to send an email allows space for more mental clarity, but it also shows respect to the email recipient that we are really taking the time to reply thoughtfully.

Is it true?

This feels pretty straight forward, but it can take some internal navigation. For example, avoid writing, "I'm so happy you brought this to my attention." if you're NOT happy about it. What would be more accurate? "I appreciate you bringing this to my attention." Refrain from saying things that "sound nice" (or sounds like something they'd want to hear) to leave room for more skillful honesty.

Is it kind?

Text is tricky since tone of voice, facial expression, and body language are lost. We can only hope they read it how we intend it to be read, and likewise, hope we read their text the way they've intended. Typically a safe(r) approach is to speak from your own experience and how you feel instead of using too much "YOU" language or "should-ing." Asking a friend or co-worker to proofread your email draft can be very helpful in picking out anything that might be inadvertently unkind.

2 More Tips (if all else fails)

1. Know that you have resources. Who do trust at work to proofread an email for you? I have definitely relied on co-workers and friends when I felt unsure of an email. Drafting one together with a trustworthy co-worker can be very reassuring as well.

2. If you are really having a difficult time drafting the email perhaps because you have so much to write or you feel it will be misinterpreted, you may consider scheduling a phone call or an in-person meeting instead. Some emails need to be replied to in-person.

There you have it! A little tried-and-true framework to practice mindful communication. Though I put it in the context of emails, this framework can be applied to any context where communication could be particularly difficult. Whether you're finally ready to speak to your cousin about his issues with addiction, or you're thinking about calling your ex, or you're preparing a big speech, (oh, and don't forget about those "head-scratching" text messages), these 4 questions will support you in the process. Necessary? Timely? True? Kind? Try these out to foster more mindful communication. You might not get your inbox down to zero, but...well, we gave up on that a long time ago, didn't we?

*These 4 questions are taken from different wisdom traditions, including Buddhism and Sufism, in which they are typically referred to as the "The 4 Gates of Speech."

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