Direct Report Keeps Pressuring You for More Money? Ask Madeleine

January 3, 2026 Madeleine Homan Blanchard

Two professionals engaged in a serious discussion in an office setting, with one person appearing frustrated and the other holding a tablet.

Dear Madeleine,

I manage a large global team of developers. I have one newer employee who is very good at his job, gets his work done on time, and gets along well with the clients. I made it clear when I hired him that his salary was fixed, with regular annual raises (per company policy) and that there would be no room for negotiation once he took the job.

My issue is that every time we have a one-on-one, he asks for more money. It is extremely frustrating. I have reminded him several times of our initial agreement, but he seems to forget from meeting to meeting. It is almost as if he thinks I will also forget and that he may catch me in a moment of weakness or something.

I have explained that in the coming year if he wants more than his annual raise, he could apply for extra overtime projects for which he could receive a bonus—but he doesn’t seem interested in that. He just insists that since he is doing such a good job, he should be making more.

I feel pressured and manipulated. What can I say to shut this down? I don’t want to lose him, but honestly I could replace him with very little disruption to our business.

Pressured

_____________________________________________________________________________________

Dear Pressured,

It can be so frustrating to have the same conversation over and over again. You certainly seem to be stuck. To change the dynamic, you might consider practicing the two skills of Conversational Capacity: candor and curiosity.

For the candor piece, you will first state your position:

    • State where you currently stand on the issue.
    • Be direct and to the point.
    • Use one or two sentences.

Then explain your thinking:

    • Show how you arrived at your position.
    • Share the evidence you are using and how you’re interpreting the evidence.

For the curiosity piece, you will test your own view:

    • Treat your own perspective like a hypothesis.
    • Open the door to contrasting perspectives.
    • Encourage disagreement.

Then inquire about the views of your employee:

    • Invite him to share his perspective.
    • Be genuinely curious.
    • Ask multiple questions, such as:
        • We keep having the same conversation. What do you hope to achieve by continuing to bring up this topic?
        • What makes you think you are going to get a different answer?
        • We made a deal. What has changed in your mind?
        • What are you seeing that I am not seeing here?

You may learn something!

One of two things is happening here: either your employee genuinely thinks that badgering you will wear you down over time and lead to the desired result, or he really doesn’t understand that the deal you made when you hired him is final.

Either way, it is up to you to be crystal clear. If you want the dynamic to stop, you will probably have to make an ultimatum that can’t be misinterpreted; something like: “This is the last time I am going to engage in conversation on this topic. If you bring it up again, it will result in instant dismissal.”

Harsh? Maybe. But sometimes lack of clarity and willingness to draw a line results in—well, exactly the situation you are in. Once your employee understands that there is no chance you will change your mind, and that if he keeps up the relentless pestering he will lose his job, he will probably cut it out.

Be kind, be curious—and, in the end, be clear and courageous.

Love, Madeleine

About Madeleine

A professional headshot of a woman with short blonde hair, smiling, wearing earrings against a blurred neutral background.

Madeleine Homan Blanchard is a master certified coach, author, speaker, and cofounder of Blanchard Coaching Services as well as a key facilitator of Blanchard’s Leadership Coach Certification courseMadeleine’s Advice for the Well Intentioned Manager is a regular Saturday feature for a very select group: well intentioned managers. Leadership is hard—and the more you care, the harder it gets. Join us here each week for insight, resources, and conversation.

Got a question for Madeleine? Email Madeleine and look for your response soon. Please be advised that although she will do her best, Madeleine cannot respond to each letter personally. Letters will be edited for clarity and length.

About the Author

Madeleine Homan Blanchard

Madeleine Homan Blanchard is a Master Certified Coach and cofounder of Blanchard Coaching Services. She is coauthor of Blanchard’s Coaching Essentials training program, and several books including Leverage Your Best, Ditch the Rest, Coaching in Organizations, and Coaching for Leadership.

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