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STACK THE F*CK UP

How Do I Ask for a Raise Without Making It Awkward?

By Joshua S. Brogley · August 27, 2026

The awkwardness comes from treating a raise ask as a confrontation instead of a prepared conversation. Book the meeting rather than ambushing someone in a hallway, arrive with a short written record of what you have delivered, name a specific number rather than hinting, and stop talking once you have said it. Most people lose the ask by never clearly making it.

Schedule it, do not ambush it

Asking someone in passing invites a reflexive no, because they have no information ready and no authority prepared. Requesting a short meeting about compensation signals that you are serious and gives them time to check what is possible. It is also much less awkward for both of you.

Bring the record, not the feeling

The case is what you have delivered, ideally with numbers, ideally covering the last six to twelve months. Not how long you have been there, not what you need personally, and not what a colleague earns. If you have not been keeping this record, start now and ask later; a few months of documented output is worth more than an eloquent argument.

Name an actual number

This is where most asks quietly fail. People signal that they would like more, wait to be offered something, and accept whatever arrives. Say the figure. A specific number anchors the conversation and forces a real answer rather than a vague acknowledgment that you raised the topic.

Then stop talking

The silence after your number is uncomfortable and it is not yours to fill. Most people negotiate against themselves in that pause, walking the figure down before anyone has responded. Say it, then wait. If the answer is no, ask what would need to be true for it to be yes, and get a date. Related: the boring fixes on the spending side.

Stack The F*ck Up

365 daily money moves, written in pen. Know your three numbers, build the buffer, kill the debt, and sign every dollar you spend.

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How do I ask for a raise for the first time?

Request a short meeting about compensation, bring a written record of what you have delivered, state a specific number, and then stop talking. Preparation removes most of the discomfort.

What if they say no to a raise?

Ask what would need to change for the answer to be yes, and agree a date to revisit it. A no with clear conditions and a timeline is a useful outcome. A no with neither is information about the job.

written by the author, at the kitchen table, after work.