How to Click Send: Writing Difficult Emails

By - April 25, 2018

Everyone has those moments at work when they need to plan and write difficult emails that provide critical feedback, convey some unwelcome news or detail a tough client situation. We don’t look forward to it, but there are steps you can to write that email and write it well.

First, let’s review some quick planning tips:

  • Make a list of what you need to say
  • Identify what effect you want your email to have
  • Focus on what you need to do, not imagining how people will react

With those points in mind, take a look at four important tips for writing that email.

Tip 1: Don’t Write Angry

Let’s be honest, if you’re writing a difficult email, chances are something about the situation isn’t sitting well with you. You can seesaw between going through all the details of the conflict and assign blame, all while giving yourself whiplash thinking about what’s going to happen after this email is sent. Neither of those trains of thought are effective. All they’ll do is affect your tone and the way you choose to phrase things, which can obscure your message.

The best way to avoid writing angry is to understand three important things:

  1. Get some space (literally!). Find a quiet place to think about what you need to do, and develop a plan. Think it through. Take a few deep breaths.
  2. Get some perspective. When you’re detailing a tough situation, you need to consider all the angles. You want your representation of the situation to be fair, even-handed, tactful and results-oriented. That’s a tall order in the best of times, so give yourself a little time to think about all the different people and situations involved, and strive to understand the bigger picture. Remember, it’s important to be honest and forthright, but you should also remember that people make mistakes, including you sometimes.
  3. Get some feedback. Write an email draft, do the best you can, and then ask a trusted colleague, manager, or mentor to look it over. Tell them what you’re trying to convey, the tone you want, and why this is difficult for you. Once you get their feedback, take it seriously.

Tip 2: Don’t Put it Off

Don’t get yourself caught in the trap of avoiding difficult emails. Waiting doesn’t make them easier to write. Just give yourself the time necessary to do it right, including the time to write, review, proofread and get feedback.

Tip 3: Don’t Take It Lightly

Typically, difficult emails have the potential to open a can of worms. You have one chance to get that initial communication right, so plan it carefully and take the time to review it. Don’t go for the easy satisfaction of blaming or deflecting. Any day you have to write a difficult email is not likely to be your best day, but you should be able to look back on that email in six months without wincing or regretting it.

Tip 4: Share Responsibility

Bad situations don’t represent anyone’s best moments, and sometimes that means you’re highlighting your own share of the responsibility. If you bear responsibility for something that happened, make sure you say so. Doing so will display your maturity and your commitment to finding a resolution, not just identifying the problem.


By: Daniece Rainville


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