Writing difficult emails

Writing difficult emails is a skill worth developing.

Sometimes it can feel like writing difficult emails is a full-time job. Every week it seems like I have an opportunity to write a difficult email. At least once. As I talked about it with a colleague, we realized that we had each learned tricks from mentors over the years.

It seems like you don't just learn it from doing it. In fact, I'm pretty sure that if I hadn't gotten mentoring in this area, I would still be writing difficult emails as horribly as I did when I was 25 – 25 years ago.

Back then I wrote an angry email, to someone in a role two levels above mine, copying way too many people. I would have been fired, except for one thing – I had already given notice. Maybe I wrote that email that way because I knew I was stepping out. But it and I were wrong.

He didn't fire me, but on that day, even as I only had a week left there, he decided to invest some time in talking about how to write challenging emails that we never are excited to write.

Some Tips for Writing Difficult Emails

Over the years I've pulled together several tips that help me when I have to write a challenging email, or when I have to write something that won't challenge me, but will challenge someone else.

Don't write when you're upset

When you're upset, it's easy to let emotion seep into your writing. I've told you before, sometimes your emotion isn't serving you. More importantly, it's easy to throw in a few jabs (if someone else is at fault) or to build up a pretty tall wall (if you're at fault).

So the best thing you can do is calm down. Take a walk. Take some time. Breathe.

Some people say that you should write the email you want to write and then you can write the email you really are going to write.

I don't recommend that strategy if you aren't 100% clear that first email isn't going to go out.

I say this because years ago a coworker of mine had written one of those emails. They left it in their unsent email. But they had even put the person's email in the To field. They just hasn't mailed it.

You know where this is going, right?

A couple of weeks later, they had a problem with their email software and needed to reset it, etc. The result? You guessed it. That email that was sitting in an unsent folder ended up getting sent. Ouch!

So if you can, just don't write when you're upset.

Don't use a sandwich structure

Do you know when they told you that feedback should be sandwiched between compliments? They were lying. You hear it all the time, but the advice is there to help you more than to help the person you're writing to.

People want feedback. They want to hear the truth. And you don't have to waste time by trying to come up with silly statements before and after. It's pretty clear you're giving them feedback or frustrated with something. Your best bet is to skip the, “I hope this finds you well,” because it doesn't come across as authentic.

So skip the front sweets and the, “looking forward to…” at the end.

Whether you're providing the details for why you've not given someone a contract, decided not to hire someone, announced a reduction in force, or articulated the reason you failed at something—whatever it is, keep the main thing the main thing.

Don't ramble

That last suggestion for writing difficult emails needs to be reinforced with this suggestion. Don't ramble. Know why you're writing. And articulate it. State it. Sooner rather than later.

“I'm writing to let you know you didn't get the job.”

“I want to let you know that as of today we'll be closing/cancelling/discontinuing…”

“After 8 years working with an incredible team of people, I've decided it's time to take my talents….”

Some people put paragraphs of the story at the beginning of a difficult email because they're trying to create a larger narrative. And those emails just end up rambling. Don't do it.

Don't be harsh. Don't be mean. But be honest and direct. Waste no time getting to the point.

Don't use broad generalities

When we have to write difficult emails because we're giving people feedback they need to hear, writing in generalities not only makes it seem like you don't know (to a deeper degree) your main point, but it can often come across as an exaggeration that isn't helpful.

So if you're letting someone know that things aren't working out, make sure you're not slipping into “always” and “never” land.

Don't forget to give the benefit of the doubt

When my mentor sat me down years ago, his main point was that I never knew the whole story. And because I didn't know the whole story, I was going to end up telling myself some part of a story that I had made up for myself. And that would impact my reactions. I would react differently, not because of what really happened, but because of how I filled in the blanks.

Assume positive intent. That's the phrase I've learned. And even when it's hard, it's worth doing – especially when you have to write a challenging email or deliver tough news. Don't add to the challenge by making poor assumptions and reacting to them.

Don't forget you need data and a heart

It may not be the first rule, but it's clearly not the last. You can't ever forget that you need to bring more than just facts to a challenging situation.

One time someone on my staff created a prototype of a software program with sample data from our actual customer database. This data appeared and was cached by Google, long after the prototype was cancelled. The last four digits of their SSN had been captured by Google and was being presented in that xxx-xx-1234 structure online when you searched for their name.

The facts included several data points that mitigated the fear of the person who discovered it. Very few records had been used. No records had presented any additional personal information (like addresses, age, gender, etc). And even though the data had been available for a year, none of the few records exposed had led to any consequences whatsoever. But that's just the facts.

When we had to write the apology email, we were really writing the first of several crisis communication emails. And that's when empathy is way more powerful than just the facts.

We had to connect with the audience in what might be a stressful day for them, and make sure they heard that we cared and were going to help them get thru it—all while explaining what happened and what we were doing about making sure it never happened again.

Empathy is a powerful tool. Use it.

Don't hesitate to use the phone

I know these are rules about writing difficult emails, but never forget that you have another tool at your disposal. You can always pick up the phone and make a call. And sometimes that's the best move.

I once said something that clearly touched a nerve. I felt bad because it was clearly not my intention, but I had hurt someone's feelings. I just knew it.

So I wrote an apology. Trying to make it clear I had no intention of hurting them, but also acknowledging that my intention was secondary to their actual feelings.

Then I did the thing they didn't expect. I called them.

“Hey, I just emailed you an apology. I realized that I must have hurt you by my words and that was the last thing I ever wanted to do. But I understand I still did it and I wanted to apologize.”

They were quick to explain that in reality, the issue had been on their side. They knew, the moment they'd reacted, that their response was out of line and not really about my words.

They loved the call and I'm pretty sure it built a stronger relationship because we talked about it, rather than just sending two emails back and forth.

How do you structure a difficult email?

There's a book that goes into one structure, called The Minto Pyramid Principle. It's a book on writing and logic and it's not an easy read. But the structure the author introduces is:

  • Situation: Explain what some may already know. But set the stage.
  • Complication: This is the change, the tension that is introduced.
  • Question: This is the “what do we do now?” It flows from the complication.
  • Answer: This is the proposed resolution. It's also the reason for the email.

There's another structure that I find is also helpful, and it uses the acronym, SCRAP.

  • Situation: What are the facts? What's the reality of this situation?
  • Complication: What introduced the challenge or tension?
  • Resolution: What are possible ways to resolve the issue?
  • Action: What specifically are you going to do? Or do you want to happen?
  • Politeness: End with goodwill.

Here's an example from the Doris and Bertie blog:

Dear Jim,

I attended the site of 21 Union Street today. (SITUATION)

I noticed parts of the roof are already showing damage because the correct insulation material has not been used. (COMPLICATION)

We need to replace the current materials with those we recommended in our original plans, which I’ve attached. (RESOLUTION)

In the meantime, please halt work on the building immediately until we can take steps to conduct the work properly. (ACTION)

If you have any questions, please do not hesitate to call me on 020 5678 910. (POLITENESS)

Best wishes, Dan

It gets better. It gets easier

Last month I wrote more than a couple of difficult emails. Each time, I waited until evening. I waited until I was sufficiently calm, had the data I needed, was able to articulate what I wanted to happen, and could write it from a position where I could be polite.

What I can tell you is that it does get better. It does get easier. But that comes with practice. And honestly, nothing ever gets better by ignoring it. So start writing those emails!

Sign up for free content. People still do that.

Thousands of folks (7000+) regularly get my posts in their inbox. For free.

We won't send you spam. Unsubscribe at any time. Powered by ConvertKit

This post may contain affiliate links. If you click on them and make a purchase, I'll get a commission, at no cost to you.

Default image
Chris Lema
Chris Lema has been working with WordPress since 2005. Over the years he's been a blogger, a speaker at WordCamps, a coach for WordPress product companies, and the founder of the conference for WordPress business owners, called CaboPress. Today he's the VP of Products at Liquid Web, where he manages the world's first managed platform for WooCommerce stores.

Have a specific question?

Over the last few years, through private consulting, coaching, and using the pay-by-the-minute Clarity service, I've helped hundreds of folks like you solve their business, strategy & WordPress problems.

Let's chat. Most calls last less than 20 minutes.

Chris Lema on a Video Call