Most business writing has a clear goal: inform, request, confirm, close. But some messages don't fit any of those categories. They exist in a harder space, where what to say when words feel hard is the only question that matters. A colleague loses a parent. A client is going through something awful. You made a serious mistake. The blank page sits there and you type nothing.
The difficulty is real. But there's a structure underneath even the most personal messages, and learning it makes the blank page a little less frightening.
Why difficult messages feel so different
Normal business writing has clear inputs and outputs. You know what you want the reader to do after reading. Difficult messages don't work that way. There's no call to action. There's no outcome to optimize for. The only goal is for the reader to feel that someone genuinely noticed them.
That goal makes writers freeze. And when they freeze, they reach for formulas. "Please accept my condolences." "I am sorry for your loss." These phrases aren't wrong. They're just empty, in the way that form letters are empty. The reader can tell they could have been sent to anyone.
The fix isn't to write more. It's to write something specific.
The one rule that covers almost every hard message
Be concrete about the person. Not about your feelings. Not about the situation in general. About them.
Compare these two openings for a message to a colleague whose father died:
- "I was so sorry to hear about your father. Please let me know if there's anything I can do."
- "I was so sorry to hear about your father. I remember the story you told about him teaching you to drive on that gravel road. He clearly shaped you."
The second message takes four more seconds to write. It lands entirely differently.
If you don't have a specific memory, say something specific about the person you're writing to. "You've always handled hard things with so much grace. I hope you give yourself the same care right now." Specific to them. Not to the situation.
A structure for condolence messages
Condolence messages are the hardest category, and the most common. Here's a structure that works whether you're writing to a client who has suffered a bereavement or sending a message to a colleague you've known for years.
Acknowledge the loss directly. Don't circle around it. Say the person's name, or the pet's name, or the thing that happened. "I heard about your mum" is warmer and more direct than "I heard you've been going through a difficult time."
Say one true thing. One specific, true thing. A memory. An observation about the person. Something you genuinely know. This is the sentence that makes the difference.
Offer something small and real. "Let me know if there's anything I can do" is almost meaningless. "I'm going to send lunch to the office on Thursday, no response needed" is real. If you can't offer something specific, skip the offer entirely. An empty offer is worse than none.
Close warmly, briefly. "Thinking of you." "Take the time you need." Don't linger. Don't end with a pivot back to work.
For more on what to avoid in these messages, the guide on what to say (and not say) in a condolence email covers the specific phrases that undermine an otherwise sincere message.
Apologies in writing
A written apology is different from a spoken one. It sits on the page. The reader can reread it, share it, quote it. That permanence is why writers over-complicate apologies: they're trying to hedge against every possible interpretation at once.
Don't. A good written apology has three parts, and they're short.
First: say what happened. Not "if mistakes were made" or "to the extent that anyone was affected." Say the actual thing. "I sent the wrong figures to the client." "I forgot the meeting." "I copied in the wrong person."
Second: say what the impact was, from their perspective. Not how bad you feel. How it affected them. "That meant you had to present without the data you'd asked for." This sentence is uncomfortable to write. Write it anyway. It shows you understand what you actually did.
Third: say what you're doing differently. One specific, real thing. Not "I'll do better." "I've set a calendar reminder at the start of every client report cycle" is something. "I'll be more careful" is nothing.
Four sentences can make a genuine apology. Twelve sentences of explanation and justification usually don't.
Messages about personal hardship (not yours)
Sometimes a colleague tells you they're going through something. Illness. A divorce. A sick child. They didn't ask for advice. They probably didn't ask for anything. They just told you.
The instinct is to respond with information or encouragement. "Have you tried..." or "I'm sure it'll work out." These responses are about managing your own discomfort, not about them. The better response is almost always smaller.
"That sounds really hard. I'm glad you told me." Then stop.
In writing, you have an advantage over conversation: you don't have to fill silence. You can send a short message that does nothing except say you heard them. That's often exactly what the person needed.
When you don't know what happened
Sometimes you know something is wrong but not what. A colleague has been absent. A client canceled unexpectedly. Someone you work with closely is clearly struggling.
Don't pretend to know. And don't ask directly if the relationship doesn't warrant it. Write something that opens a door without pushing through it.
"I've noticed you've had a tough few weeks. No need to explain anything. I just wanted you to know I'm thinking of you and here if you need anything."
That message asks nothing and offers something real. The tone sits between professional and personal, which is usually exactly where it needs to be.
The words that get in the way
A few phrases consistently damage otherwise sincere messages. Avoid them.
"Everything happens for a reason" implies the loss was somehow deserved or useful. It isn't your place to say that. "At least..." almost always minimizes something real. "I know how you feel" rarely lands well unless you genuinely share the exact experience. "Stay strong" puts a burden on someone who's already carrying one.
If you're not sure whether a phrase helps, cut it. Shorter messages that say one true thing outperform longer messages every time. And if you're worried your message will sound too brief, read it aloud. If it sounds like a person talking, it's long enough.
Actually sending the message
Writers who struggle with difficult messages often spend twenty minutes drafting, then don't send. They second-guess the wording. They worry it'll come across wrong. They decide they'll send something later, when they have better words.
Send the imperfect message. A sincere message that arrives on the day someone is struggling does far more than a polished message that arrives a week later when they've already felt abandoned. Late is better than never. Now is better than late.
The words don't need to be perfect. They need to be real.