Writing the Hard Messages: Feedback, Increments, and Goodbyes

A lot of what a founder writes never appears in a product launch or a press release. It is the quieter writing: a performance review for an engineer who is struggling, an increment letter that is smaller than someone hoped, a policy change the team will not like, or the message that ends someone’s time with the company.

I have written a lot of these over the years, for people across engineering, support and accounts. They are some of the hardest things I write, and I have not always got them right. This post is what I have learned about writing them better.

The core principle: clarity is kindness

When a message is uncomfortable, the instinct is to soften it. Add qualifiers. Lead with three paragraphs of praise. Use phrases like “we might want to think about” when you mean “this needs to change.”

I understand the instinct — it comes from not wanting to hurt someone. But in my experience, vague hard messages cause more hurt, not less. The person leaves the conversation unsure what you meant, fills the gap with their own worst guess, and is then surprised when consequences follow that they did not see coming.

The kindest version of a hard message is the clear one. Warm in tone, specific in content, and impossible to misread.

Performance feedback

Be specific about behaviour, not personality

“You are not proactive” is a judgement about a person. It is hard to act on and easy to resent. “In the last two releases, the bugs you found during testing were reported only at the standup, after the release was already planned” is a description of behaviour. The person can see it, discuss it and change it.

When I draft feedback now, I check every critical sentence: can I point to a specific example? If not, I either find one or remove the sentence.

Separate the message from the cushion

There is a well-known technique of sandwiching criticism between two compliments. I have mostly stopped using it. People learn the pattern, and then they discount the compliments because they know a “but” is coming.

Instead, I give positive feedback on its own, when it is earned, and critical feedback on its own, when it is needed. Both become more believable.

End with what happens next

Feedback without a next step is just commentary. Every serious piece of feedback should end with what success looks like, by when, and how we will check in. That turns a difficult conversation into a plan.

Increment and compensation letters

These are emotionally loaded in a way that is easy to underestimate. For many people, the number in that letter is the clearest signal they get of how the company values them.

Explain the system, not just the number

A number without context invites comparison and speculation. When people understand how compensation decisions are made — what levels exist, what is expected at each level, what moves someone between them — the number makes sense even when it disappoints.

This is one reason we introduced a clear level structure for our engineering teams, with defined expectations for each level. It does not make every conversation easy, but it moves the conversation from “why did I get this number?” to “what do I need to demonstrate to reach the next level?” — which is a far more useful discussion for both sides.

Do not hide bad news in good formatting

If an increment is lower than expected, say so plainly and explain why. Do not bury it in a long, cheerful letter and hope it goes unnoticed. It will be noticed, and the cheerful tone will feel dismissive.

Say what would change the outcome next time

The most useful sentence in a disappointing increment letter is the one that tells someone what would make next year different. That gives the person agency, and it gives the company a fair standard to hold itself to.

Policy announcements

When a policy changes — working hours, leave rules, process changes, compliance requirements — the announcement is often written as if the reader only needs to know what is changing. In practice, people care most about why and how it affects me.

A structure I use:

1. What is changing, in one or two sentences.
2. Why, honestly. If it is a legal requirement, say so. If it is a business decision, own it.
3. What it means for you — practical examples for the most common situations.
4. When it takes effect.
5. Who to ask if your situation is different.

Changes driven by new laws or regulations deserve particular care. People hear about legal changes from the news and from friends, often inaccurately. A clear internal explanation of what actually applies to them reduces anxiety and rumours.

Exits

This is the hardest category, and the one where the principle of clarity matters most.

Make the decision before you write

A termination message that sounds uncertain is cruel. It invites argument and false hope. By the time you write it, the decision should be made, reviewed and final. The message communicates a decision; it does not reopen one.

Keep it factual and brief

This is not the moment for a long account of everything that went wrong. The person will not absorb it, and it can feel like piling on. State the decision, the effective date, and the practical details.

Get the practical details exactly right

What the person needs most in that moment is certainty about practical things: last working day, final settlement, how and when it will be paid, notice pay, gratuity if applicable, how to return equipment, what happens to their access, who to contact with questions. Indian labour rules on these timelines have been changing, and getting them wrong adds stress to an already difficult moment and creates legal risk. Check them, and put them in writing.

Preserve dignity

How someone leaves is remembered — by them and by everyone who stays. Thank them for their contribution where it is genuine. Do not announce the departure in a way that embarrasses them. Offer a reference if it is deserved. The team is watching how you treat people on their way out, and they draw conclusions about how they will be treated.

A few habits that help across all of these

• Draft, then wait. Hard messages written in frustration are almost always worse. Sleep on it if you can.
• Read it as the recipient. Before sending, read the message as if you were the person receiving it, on a bad day. What would you misunderstand? What would hurt unnecessarily?
• Have one other person review sensitive messages. HR, a co-founder, a trusted manager. A second reader catches tone problems you cannot see.
• Write it, then say it. For the hardest messages, the written version should follow a conversation, not replace it. The writing is the record; the conversation is the respect.

What I believe now

Early on, I thought good leadership communication was mostly about inspiration — vision documents, all-hands speeches, big announcements. Those matter.

But I have come to believe that people judge leadership far more by the hard, private messages: whether feedback was fair and clear, whether compensation was explained honestly, whether exits were handled with dignity. Those are the moments when trust is built or lost, one message at a time.