Asking for a raise or promotion feels uncomfortable.

You don’t want to come off the wrong way.
You don’t want to seem entitled.
You don’t want to get shut down.

So most people wait.

They keep doing good work.
They assume it’ll be noticed.
They hope it’ll happen naturally.

It usually doesn’t.

This came up in my conversation on Episode 35 of Guyset with former Barstool Sports CEO Erika Ayers Badan, and her perspective on this is direct:

“You have to ask… but you also have to earn it.”

That’s the balance most people miss.

Doing Good Work Isn’t the Same as Being Recognized

A lot of people think:

If I work hard, it’ll happen.

But your manager isn’t tracking everything you do.

They’re seeing outcomes.

Impact.
Results.
Progress.

If you’re not making that visible, it’s easy to get overlooked.

Insights from Harvard Business Review show that employees who actively communicate their contributions are more likely to be considered for raises and promotions.

Ask Yourself First: Do I Actually Deserve It?

This is the part people skip.

Before you ask, be honest.

Have you:

Taken on more responsibility?
Improved your performance?
Created measurable impact?

Or are you asking based on time?

Time alone isn’t enough.

Growth is.

Know Exactly What You’re Asking For

Don’t go into the conversation vague.

“I was hoping we could talk about my role” isn’t clear.

Be specific.

A raise.
A promotion.
A title change.

And ideally, have a sense of what that looks like.

That makes the conversation real.

Build Your Case Before You Ask

This is where you separate yourself.

Don’t rely on your manager to connect the dots.

Do it for them.

Show:

What you’ve done
How you’ve improved
What results you’ve created

Think of it less like asking for something…

And more like presenting why it makes sense.

If you’re unsure how to build that kind of visibility, it connects directly to What Actually Matters at Your First Job?, because the same principle applies: you have to make your value obvious.

Timing Matters More Than You Think

Don’t bring it up randomly.

Pick the right moment.

After a strong performance
During a review cycle
After delivering something meaningful

That’s when your work is most visible.

And your ask has context.

Make It a Conversation, Not a Demand

This is important.

You’re not saying:

“I deserve this”

You’re saying:

“I want to understand what it takes to get there”

That shifts everything.

Now your manager can respond with:

What’s working
What needs improvement
What the path looks like

That’s how you turn it into progress.

Be Ready for a “Not Yet”

This is where most people get discouraged.

They ask.

And they don’t get an immediate yes.

That doesn’t mean it’s over.

It means you need clarity.

What’s missing?
What needs to change?
What would make this a yes?

Research from Psychology Today shows that people who seek specific feedback after rejection are more likely to improve outcomes over time.

Follow Through on What You Hear

If your manager gives you direction, use it.

This is where most people fall off.

They ask.
They get feedback.
They don’t change anything.

And then they ask again.

That doesn’t work.

Progress is what moves the conversation forward.

Don’t Wait Forever

There’s a difference between being patient and being passive.

If you’re consistently performing, improving, and delivering…

And nothing changes…

That’s information.

At a certain point, you have to ask:

Is this the right place for me to grow?

If you’re thinking about that, it connects directly to How Do I Know When to Leave My Job?, because that’s often the next step.

Confidence Comes From Preparation

The ask feels uncomfortable when you’re unsure.

When you’ve done the work, it feels different.

You’re not hoping.

You’re showing.

That’s what makes it land.

If asking still feels difficult, it often connects to a bigger pattern around risk. That’s exactly what Do You Have To Stay At Your First Job For 2 Years? helps you work through.

Know the Market Before You Ask

This is something people overlook.

You need context.

What are people in similar roles making?
What does the market look like?

Without that, you’re guessing.

Research from the American Psychological Association shows that preparation and information reduce anxiety in high-stakes conversations.

That applies here.

And Here’s The Thing

You don’t get a raise or promotion just for doing your job.

You get it for growing beyond it.

And for making that growth visible.

Because the people who move forward aren’t just working hard.

They’re communicating it.

FAQ

When should I ask for a raise or promotion?
After you’ve shown consistent performance and created measurable impact.

How do I ask without sounding entitled?
Focus on your contributions and frame it as a conversation, not a demand.

What if my boss says no?
Ask what needs to change and use that feedback to improve.

Should I bring up a specific number?
Yes, if you’ve done your research. It shows preparation.

How do I know if I deserve a promotion?
If you’re consistently performing at the next level, not just your current one.