5 Tips for Writing a Difficult Email

Someone neglected to pay you for a service you performed. An event venue raised their fees right before the charity concert you’ve been planning for months. You have to wait for a co-worker to be able to proceed with a project, but she won’t respond to your emails.

I know I’m not the only one who deals with frustrating situations like these on a daily basis. I can’t count all of the times I’ve faced an awkward or difficult situation, and I don’t want it to get messy. Guess what? It doesn’t have to.

Of course, there are some situations that are more awkward than others, but I don’t believe correspondence ever has to get nasty. I also don’t think it’s effective at all when it does.

The tips I’m going to share mostly come from what I’ve learned from reading Crucial Conversations and How to Win Friends and Influence People. If you haven’t read these books, do it now! I read them both while working in professional leadership positions. I’m a decent communicator (unless I’m hungry, tired, or emotional), and it’s mostly because of these books.

I wouldn’t share these tips if they hadn’t worked for me, so what I’m about to share comes from personal experience, too.

 

1. Collect Your Thoughts

Don’t write your message when you’re hot-headed and hungry and determined to get your way. It may be tempting to spit out a nasty letter, and it might even make you feel powerful, but it’s not effective.

If you feel really emotional about the situation, try to calm down as much as possible. Take time. In Crucial Conversations, the author suggests asking yourself these questions:

  • What do I really want for myself
  • What do I really want for others?
  • What do I really want for the relationship?
  • How would I behave if I really wanted these results?

Chances are, you want something, but you also don’t want to burn bridges. Consider what you really want before sending an angry email laced with expletives or accusations.

 

2. State the Facts

This is my favorite tip. It has helped me in multiple professional and personal situations! Even if you feel emotional about the subject, state the facts first. I’ll share a personal example.

When I got married, I hired a friend of a friend to take pictures of my wedding (someone else had taken our engagement photos). I didn’t know her very well, but I loved her work. A month after our wedding day, I hadn’t heard anything about our pictures and had no clue what time frame to expect. She responded after a few days, telling me the pictures would be done in a week to 10 days.

The time came and went and there were no pictures. She then gave me another timeframe, which also came and went.

I can’t remember exactly what I said because I sent it in a text message, but I remember using this principle. I understood that it takes time to edit pictures, but I also was frustrated that she had given me a timeframe and then didn’t explain why she hadn’t been able to send me my pictures in that timeframe. If she wasn’t able to do the work, I would have understood, but I needed her to communicate what was going on.

Two months after our wedding, I decided it was time to get firm. I wrote to her and basically said: I asked you when I’d get my pictures, and you told me a week to 10 days. That didn’t happen. I asked you again, then you said something else. That didn’t happen. I have paid you for a product, and I really want that product. If you don’t have it, that’s okay, but I need my money back.

Obviously, it was an awkward situation, and I had a lot of emotion tied to it, but by stating the facts, she couldn’t argue with me. I didn’t say anything nasty about her services or question her character in any way. Instead of letting my emotions take control, I repeated exactly what she had told me, then expressed what I felt without going crazy.

I use this principle all the time now, and it always helps make a situation less awkward. Can you think of ways you could use this in a situation you’re facing?

 

3. Show Empathy

Before writing a potentially awkward email, I try to imagine what kind of situation the other person is in. Why haven’t they responded? How come they haven’t followed through on what they said they would do? What are they going through right now? Then I express that in the message. Probably 99% of the time, that starts with me saying, “I’m sure you’re very busy.” Everyone is busy! I know I appreciate it when people recognize that I have a lot going on and don’t always have the time or brain space to think of everything I need to do.

Another personal example was pretty recent. My husband and I had started a small wedding rental business but quickly learned that it wasn’t the right time for us to thrive. We were having a baby, didn’t have a vehicle to deliver items, and couldn’t afford the extensive advertising that our success would require. We decided to sell all of our inventory.

I posted the items for sale in a local Facebook yard sale page in November, and someone we knew quickly expressed interest in buying all of our items. She let us know that she couldn’t pay until January, but since we knew her, we decided to sign a contract and let her take the items (I know, you’re probably shaking your head).

When January rolled around, this friend let us know that she didn’t have the money to pay for the items. We decided we could wait until April, but then we would really need to be paid in full.

April came and our friend still couldn’t pay us. I reached out to her and started with sharing the facts:

  • I told you in January that we would for sure need to be paid by April.

Then I tried imagining how she was feeling. She’d had a vision for how things would go for her, but it wasn’t working out. I tried to express sympathy.

  • I know things probably haven’t worked out like you had hoped, which really sucks. I’m sorry it hasn’t happened like you had planned.

Hopefully, that made her realize that I wasn’t heartless and only thinking of myself. This also set me up for the next step…

 

4. Tell Your Story

This tip also comes from Crucial Conversations. After stating facts, expressing sympathy or empathy, then share your story. Express why you need something or how you feel about the situation, but try to keep this part brief and free of insults.

Going back to my personal example, after I expressed sympathy, I told her our story:

  • Unfortunately, we do need to get paid for the décor or pick it up. I wish we could be more lenient about the payment, but we’re not in the financial situation where we can really do that.

I think this step is so important, but many people skip it (especially in movies)! If you drag on and on about your story or situation, it’s no longer effective, but it’s important to at least touch on it. Chances are the person you are communicating with has a heart and your story will affect their reaction.

I could have asked my friend to pay us for the wedding décor and there would have been no problem with that, right? We had a deal, and she owed us money. But if I had not told my story, our interaction could have been cold and ended awkwardly. Instead, it was cordial and much less awkward than it could have been.

You don’t have to be as personal as I was—I’m kind of an open book. 😉 But at least share part of your story.

 

5. End with a Friendly Invitation

You don’t have to invite the person to your backyard barbecue, but end the email with an invitation for communication. For example, you could say, “I look forward to discussing how we can work together,” or “Let me know what I can do to help.”

Don’t take responsibility that shouldn’t be yours, but do let the recipient know you’re waiting for a response.

 

What are your thoughts? How do you handle awkward situations, either in your personal or professional life?

 

 

 



Leave a Reply

Your email address will not be published. Required fields are marked *