The Promotion Conversation Most People Avoid

The topic of money is uncomfortable for most people.

We want more of it, but feel ashamed to ask.

When we earn it, we question if we deserve it.

When we don’t get what feels fair, we take it personally—even if no one ever promised otherwise.

If someone we perceive as less deserving earns more, we start to wonder if effort even matters.

If we get too much too soon, we self-sabotage because we’re not yet the person who knows what to do with it.

If we stay silent about our desire for a promotion, we assume someone will notice.

When they don’t, we carry quiet resentment no one even knows is there.

If something this universal causes this much grief, why don’t we talk about it more?

Well… because the first time we do, it feels like taking a crowbar to the windpipe.

So we avoid it.

This breakdown happens at every level.

Business owners don’t say what it takes to earn more because half the time, they aren’t clear themselves.

Or, they’re too busy trying to grow the business while managing fire drills to stop and think.

Leaders don’t clarify the path because no one ever taught them how.

So they have no idea how to measure performance, tie it to pay, or talk about advancement without fumbling the bag.

And employees?

Most are too scared to ask.

Worried they’ll look greedy or that it’ll be an automatic NO.

So all sides end up frustrated, blaming each other for a conversation that never happened.

Pay starts to feel personal. Resentment becomes policy.

The fix to this isn’t “complicated.” It’s just uncomfortable.

If you’re a business owner:

You need to define what growth looks like and how performance is connected to pay.

This means telling your people what you’re looking for before they ever have to ask.

If you’re a leader:

Ask the leadership above you what success looks like in every role.

Then learn how to evaluate performance and talk about advancement without tap-dancing around it.

And if you’re an employee:

Don’t wait to be picked.

Ask what “ready” looks like.

Ask what would make it a “yes.”

And if the answer isn’t clear, ask again until it is.

It doesn’t matter if you’re the owner, the leader, or the new hire—these are the conversations that moves things forward.

Without them everyone ends up confused, frustrated, and mad for reasons that could have been avoided.

Clarity is as much of an individual responsibility as it is a collective one.

The first time you bring it up, it’ll feel awkward.

The second will feel easier.

By the third... it’ll just feel necessary.