June 14, 2026, Issue #46
There are certain emails that make even the most organized, capable person pause.
You open a blank message, type one sentence, delete it, retype it slightly differently, then wonder if you should just “think about it a bit more” and come back later (which we all know sometimes means never).
It is not that the email is complicated. It is that we are trying to get it just right. Polite, but not weak. Clear, but not harsh. Professional, but still human.
And somehow, that combination feels harder than it should be.
Two types of emails tend to cause the most hesitation: the follow-up email and the “delivering the message nobody wants to hear” email.
Let’s start with follow-ups.
We have all written the “just checking in” email and immediately felt like we were being mildly annoying. But the truth is, most follow-ups are not annoying at all. They are necessary.
People are busy. Emails get buried. Calendars fill up. Things move faster than we expect.
A good follow-up does not need to be long or apologetic. It just needs to be clear and polite.
Something as simple as:
“Hi there, I am just following up on my message below regarding [topic]. When you have a moment, I would appreciate an update. If now is not a good time, no problem at all.”
That’s it. No overexplaining. No long backstory. Just a gentle nudge with space for the other person to respond.
Now for the slightly tougher one: delivering messages that nobody is excited to write or receive.
These are the emails where something is not moving forward, a request cannot be approved, or plans have changed.
The instinct is usually to soften it so much that the message becomes unclear. We add extra sentences, extra context, extra apologies, and by the end, the main point is hiding somewhere in the middle like it is in witness protection.
But clarity is actually the kindest approach.
A simple structure helps:
- State the message clearly and early
- Give a brief reason if needed (not a full essay)
- Offer an alternative if there is one
- End politely and move on
For example:
“Thanks for your request. Unfortunately, we will not be able to move forward with this at this time. If things change in the future, we would be happy to revisit it. Thanks for understanding.”
Short. Respectful. Clear.
Most people do not mind a firm answer nearly as much as they mind a confusing one they have to decode.
And maybe that is the real takeaway here. Whether you are following up or delivering news nobody loves, the goal is not to write the perfect email.
It is to write a clear one, send it, and let it do its job.
Quote
“Someone is sitting in the shade today because someone planted a tree a long time ago.”
Warren Buffet