Asking for more without making it weird

I have sat on the other side of this conversation several hundred times, and I can tell you the most useful thing about it: the awkwardness you are feeling is almost entirely on your side of the table. From where I sit, someone asking what they are worth is a completely ordinary thing to deal with. It is not a threat, it is not a complaint, and it is not a demand.

It is also the single most reliable route to being paid more, and very few people use it.

Why the good people get least

There is a reliably cruel pattern here. The people doing the most careful, most conscientious work are usually the ones least likely to ask, because they would rather be quietly excellent than visibly ambitious. Meanwhile someone who is genuinely worse at the job has already asked, and got a yes.

I have hired for both. I can tell you that in the interview I have almost never managed to work out who is better at the job from what they say about themselves. Askers did not ask because they were unreasonable. They asked because they had noticed the pattern and decided not to keep accepting it.

Have the number ready

The single biggest advantage you have is a number. Not a feeling, not a sense of what is fair — an actual figure, and ideally two.

• Your current salary
• The number you want
• The evidence for why it is not absurd

If you cannot say the number, the conversation becomes a mood, and moods do not get costed. “I’d like to discuss my compensation” is a fine opening line, but it needs to be followed by a number fairly promptly.

On the evidence: what has your role actually absorbed since you last had this conversation? Scope you inherited. Responsibilities you did not sign up for. A team that grew, a process you built, a market you kept warm. If you have been doing two jobs, that is not a raise request, it is a staffing error, and it is fine to say exactly that.

Timing

Not in a review. Reviews are about the past, and past performance is comfortable territory for everyone — which is why money rarely moves there. Better: a promotion, an offer you are weighing, a renewal conversation, a significant anniversary, or simply a moment when the work has visibly changed and nobody has mentioned it.

If nothing like that is on the horizon and it has been a while, it is entirely reasonable to raise it yourself. People overestimate how much this is unexpected.

If the answer is no

Ask what would need to be true. Not rhetorically — actually ask, and take notes. “What would need to change for this to be on the table in six months?” gets you a real answer far more often than a flat refusal does, and a flat refusal usually means the conversation never happened properly rather than that the door is locked.

If it genuinely is locked, that is information too. A company that will not pay the number you are worth is telling you something about how it will treat you in two years, and it is worth knowing now rather than later.

The bit I always say last

Your employer is not doing you a favour by paying you. They are getting your work, and they are competing with other places that could get it instead. Keeping the conversation in that frame — quietly, in your own head — is most of what makes it easy to walk into.

If you would like to rehearse it out loud with someone who will tell you honestly whether your number is sensible, the Interview Preparation sessions include exactly this, and the negotiation one runs as a Group Workshop if you would rather practise on a few other people at once.

Bring your real number. Not a smaller one. We can work on the delivery all day and it will not help if the figure underneath it is a quarter of what you are worth.