12 Valuable Pointers on How to Write That Difficult Email

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It was still a few weeks before my training session on Preparing for Difficult Conversations for a large organization. It would be my first in-person training in a few years since COVID. The planning team had been emailing, as we arranged the details for the larger event, when we hit a snag. A conflict, really. I shouldn’t have been surprised. I was speaking on difficult conversations; of course, we’d have some conflict beforehand!

So now it was time to write a difficult email. Things like this are ideally done in person, but on some occasions, writing is all you can do. One advantage of writing is that it slows things down and gives you time to think and prepare well. Nothing says we have to respond in the moment. In fact, it’s often unwise to respond too quickly.

Our Top 12 Suggestions for Writing a Difficult Email:

1. Start with attitude. If your attitude isn’t aligned with a humble posture that wants something good for the recipient, not just for yourself, you might want to consider waiting until it is. Your attitude, whatever it is, will leak out. Yes, you can still use these skills even if your attitude isn’t healthy, but it will eventually show that you are using the skills to get your desired outcome. People will see that for the manipulation it is. 

2. Start and end positively. This is often known as “the sandwich method”. Some people have been negative about this method. I would, too, if it’s just a method you are rotely using to deliver the news you want to deliver. But if you can do it from a genuine attitude of humility and the ability to try and understand their perspective, it actually helps set up a space for humble learning for all parties. It gives the message, “I value our relationship. I’m in this to learn and grow. This is not a setup for a fight, but for a meaningful dialogue.”

3. Consider the recipient’s experience. Take some time to consider what the experience so far has been like for the other person. If you are responding to something they wrote or said, consider how it might have felt like for them to say or initiate that. Then, acknowledge what they did with a genuine, yet, tentative attempt to show you’ve considered their side. For example, “I imagine that was a hard thing to share,” or “Maybe that felt disrespectful when I shared my comment in front of others.”

4. Show Appreciation. Validate any, even small, effort they made. Affirm the difficulty or emotional impact the situation may have had on them. And don’t just do this once, write about it several times. Why? Because like you, they are concerned about themselves—they want to be heard and understood. Most of us have rather fragile identities, and hearing your repeated affirmation has the potential to guard the relationship even while you are sharing something difficult. 

5. Define the objective. If your objective is to win, get your way, or change them, you might want to take a longer pause before you write. If you can sift through your mixed motives and grab hold of the part of yourself that wants to have an interaction of learning, growth, and respect, then you’ve found an objective that can really help both you and the other person. That kind of objective will be your guide as you write and will lay the foundation for an email or letter that has the potential for more helpful outcomes. 

6. Think through the “Three Conversations”. Read about the three conversations here and share at least “The What” and “The Feelings” conversations. Sharing “The Identity” conversation may also be helpful. Do not neglect to share your feelings. They are probably the driving factor; otherwise, you wouldn’t consider this a “difficult” email. Simply state your emotions (using actual feeling words that you are experiencing, like those found here), rather than thoughts or interpretations.   

This: I felt frustrated when I didn’t receive the information on time. 

Not this: You didn’t care enough to get it to me on time. 

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7. Share observations. Having used an Other-Centered Listening attitude, share your observations of what you think the other person's point, feelings, desires, and experience may have been, so they feel that you are, at the very least, trying to understand their perspective. They can correct you if you don’t get it right.  

When addressing the issue, share observations by using statements of fact, not opinions or judgments.   

This: Your text said, “I probably won’t get to this until Monday.”

Not this: You delayed the process again.  

8. Explain your “Why”. Our minds desperately want to understand the “Why” behind things. When we aren’t given a “Why,” we often make one up. If you don’t want the other person to make up your “Why,” be sure to share it with them clearly and often. One way to do this is to briefly explain your process and how you got to your current thinking. 

9. Acknowledge impact and intentions. When thinking about ourselves, we consider our intentions. But, when thinking about what others did, we consider the impact. So, when they read your comments, they are likely to consider their intentions. You can help the recipient by specifically sharing the impact their actions had. It may be helpful to also acknowledge that they may have had good intentions.

10. Share assumptions and contributions. This means you have to take time to consider what assumptions you’ve made. That’s not easy, but it helps put you in a learning stance and will better set up your discussion for them to also take that posture. 

Similarly, share the ways you contributed to the problem. If you can’t think of any, don’t send the email yet. In 99.9% of situations, you also contributed. This could be assumptions you made, not asking for clarification, putting off addressing the issue, etc. 

11. Share specific suggestions for moving forward. You can communicate helpful next steps clearly and succinctly, even firmly, without setting an ultimatum. You can do this mostly through taking responsibility, sharing your affirmations, and inviting further communication.  

12. Communicate openness to other ideas. Invite the recipient’s thoughts and responses. Doing so signals that, while you may have stated your suggestion, you can continue your humble learning posture and be open to other ideas. 

Do these ideas work? You’ll need to try them out and decide for yourself. 

I consider myself someone learning to handle conflict more productively. So when the recipient of my difficult email responded by saying how much she appreciated how I wrote it, I asked her, “What specifically did you appreciate?” So, these suggestions are actually from her! I trust they’ll help you as you write that next difficult letter.

Much of what applies to writing is true in preparing to speak to someone as well. You might want to take a look at “Our Top Strategies to Get Ready for That Sticky Conversation” before reading on.