Crucial Skills®

A Blog by Crucial Learning

Crucial Conversations for Mastering Dialogue

Q&A: Above and Beyond? How to Deal with a Strong-willed Employee

Dear Crucial Skills,

I manage a small technical team. One particular member of my team is a seasoned high performer who is very strong-willed. This person enjoys being the “hero” in the customer’s eyes by sometimes intentionally making commitments that lead to unnecessary and excessive overtime. Because of exempt status, this person is not eligible for overtime compensation and the company has no comp time policy. The employee has expressed an opinion of entitlement to compensation for this overtime, especially since the work brings in significant revenue directly to the company. This has put me, as his manager, in an uncomfortable and awkward position when I have had to address the issue. Despite repeated requests to stop this behavior, the employee persists in making commitments “for the good of the customer” even though we have told the employee we cannot provide compensation for overtime work. How should I deal with this?



Dear Manager,

What we have here is an archetypal crucial conversation! Clearly the stakes are high, you and your seasoned high performer see it differently, and the emotions have kicked in. As I have read and reread your question, my mind has been flooded with options. I have tried to sort through the flood to find a few bits of advice that I think are most cogent, noting that because I don’t know the context or history, some of this advice may be less cogent than I would hope. Nonetheless, here is some advice in chronological order.

Consider your options. All people facing crucial conversations have at least three options. You can remain silent, turn to violence, or hold a crucial conversation. If you choose silence, you are essentially giving the employee your permission to continue acting this way. However, most people don’t really remain silent—they gossip. And that generally unravels and hurts the relationship. Or you can choose violence—you can bottle up your emotions until you explode with accusations, sarcasm, or worse. Neither of these first two options, which are very common, will help. So the first bit of advice concerning how to deal with this is to speak up with candor and courtesy.

Get your head and your heart ready before you open your mouth. Give the other person the benefit of the doubt. Ask yourself: “Why would a reasonable, rational, and decent person act this way?” Do you really understand the reasons this seasoned, high-performing employee is acting this way? Have you asked him? Does this employee feel like you care and that you are trying to understand? Are his reasons limited to serving customers and compensation? Could the employee be identifying a big problem that you, as a supervisor, need to help solve? What is your purpose? What is his purpose? What is the Mutual Purpose? When we have an issue with someone, we are often too quick to generate conclusions that oversimplify. So make sure you have done your best to understand.

It’s likely you’ve noticed that the first two bits of advice deal with you and not the other person. Each of us needs to make sure we work on us first. We don’t want to charge into a conversation with incomplete and clever stories, with our faces showing that we have held court in our heads and found the other person guilty. Once you have carefully engaged in the first two pieces of advice, you can then proceed.

Talk about the real issue. Over the years we’ve talked and written about determining what conversation to hold using CPR—Content, Pattern, and Relationship. The problem that many of us suffer from is that we talk ourselves blue in the face about the wrong issue. We choose simple over complex, easy over hard, and incident over pattern. I’m not sure what the real issue is with your employee. Maybe the issue is a pattern of making inappropriate commitments to customers. Maybe the issue is a sense of entitlement about the lack of overtime pay or perhaps compensation in general. Maybe the issue is that you have made repeated requests and he has not made a firm commitment. These are things to think about. I will say that clearly you must address a pattern and probably a relationship issue. Again, without knowing the context, let me suggest a couple of approaches for when you open your mouth.

Speak up about what really matters. Of course, you want to make it safe to talk. Safety would include privacy (not having spectators), timing (choosing a time when you won’t be rushed or stressed), and purpose (clarify up front what you are trying to accomplish and ask if now is a good time for the two of you to talk).

You might begin by saying, “We’ve chatted at least three times about making commitments to customers that require overtime and your feeling that it’s not fair that you not be compensated for this. I’ve asked you numerous times not to make these commitments and you know the compensation policy. I’d like to understand and I would also like to talk about this so that we don’t have this issue recur. Is my purpose clear?”

What you have done here is clarify an outcome. You are not merely trying to solve the problem of his making commitments to customers; you are trying to eliminate a pattern and to build a relationship so that you can trust him when he makes a commitment. What the solution is, I’m not sure. Maybe it’s a motivation problem and when you share the consequences of the employee’s actions, he or she may understand them and comply. Maybe it’s an ability problem, and when the two of you identify how your employee can say no to customers, you’ll have a solution. Maybe you’ll learn something that will cause you to support a salary increase for the employee or a change in a process or policy. When you start the conversation, the outcome is not predetermined; but when you finish the conversation, the next steps and commitments should be very clear—as in Who Does What by When, and Follow up.

There is no magic solution to challenges like the one you are facing. There are some tested principles and I’ve based my advice on them. All of these tactics and principles stem from the Law of Crucial Conversations: If you’re stuck in some aspect of your life, at work or at home, there is a crucial conversation you’re not holding or not holding well. Get better at crucial conversations and get better at everything.

I wish you well in stepping up to this conversation,


Develop Your Crucial Skills

Image for

What's Your Style Under Stress?

Discover your dialogue strengths and weaknesses with this short assessment.

Take Assessment

Image for

Subscribe Now

Subscribe to the newsletter and get our best insights and tips every Wednesday.


Image for

Ask a Question

From stubborn habits to difficult people to monumental changes, we can help.

Ask a Question

5 thoughts on “Q&A: Above and Beyond? How to Deal with a Strong-willed Employee”

  1. Steven

    To me, the employee sounds like a racehorse in a draft horse stable. Nothing wrong with being either one, but the two don’t always work together well. Eventually, the racehorse gets branded as a loose cannon and becomes impatient with the slower pace of others. Reining in a racehorse wastes its best talents, which is a shame. A person who can work effectively at a fast pace is often viewed as a threat by other employees. If they can perform the work independently, why not let them run? If they bring in significantly more revenue each year, let a bonus be the reward. If they burn out…maybe it’s time for the pasture.

  2. Patrick Walsh

    The comment “…sometimes intentionally making commitments that lead to unnecessary and excessive overtime…” jumps out at me. If the “hero” is intentionally making such commitments, and he actually understands the company policy, then there’s something going on in his mind that Mr. Pickle could explore.
    Taking a page from the Vital Smarts books, he might ask “help me understand your thinking, or why you think this action is more important than sticking with company policy”. It may be that Mr. Pickle is being too narrow-minded about strict conforming behavior, and risking the loss of a customer relationship opportunity. How does Mr. Pickle know that the overtime commitment is “unnecessary” or “excessive” without asking for more information?
    Once Mr. Pickle takes the opening purpose and safety steps, he might get a different perspective from the “hero” and he might be motivated to defend the exception to policy to his superiors.
    Steven has a valid point that the significant revenue generated by this non-conforming, and high-performing person may be cause to examine the policies, and the work environment rather than slowing him down.

  3. Dale Force

    The thing that stood out to me is that the work “brings in substantial revenue to the company”. Strange that the manager doesn’t like that.

  4. Good Advice

    I am sure he likes the revenue, however my impression was that he felt it was possible to do without the need for the overtime situation.

  5. Zoe

    Why would an employee commit himself to “unnecessary and excessive overtime” if he doesn’t get paid for it?? Surely he feels that the activities performed in the overtime are essential to keeping the client/customer happy. Sounds like the problem is with the manager and not the employee.

Leave a Reply

Get your copies
The ideas and insights expressed on Crucial Skills hail from five New York Times bestsellers.


Take advantage of our free, award-winning newsletter—delivered straight to your inbox