The Sense of Entitlement Among High Achievers… and What to Do About It

Written by: Brooks
entitlement high achiever

Ahh…the joys of top performers: They consistently crush their numbers. They come in with big wins when you need them most. They inspire your team. They’re hands-off.

If only they could all be like that. And much of the time, they are. Unfortunately, there are a few top producers who, despite their peak performance, also have another side: an unwelcome sense of entitlement.

They’re the folks who believe they’re owed something simply by virtue of who they are and ignore their impact on others in getting what they want. They’re sometimes even “uncoachable.”

They say things like, “Who cares about the rules, I’m bringing in the big money. I can do whatever I want.” They exhibit flippant behavior and ignore your expectations. They do what they want, when they want, and don’t care about their impact on your team or others inside the organization.

In short, they’re “counter-cultural.” Put it another way, in spite of their great results, they’re not really “top performers.”

Have you encountered one of these people?

Maybe you said they were a “cowboy” or a “non-conformist” or even a “renegade.” They have their own norms. They step on others and couldn’t care less about doing so.

Why are they like this? Well, not to put too fine a point on it: They behave this way because you allow it.

We don’t want to mess with Dave because whatever he’s doing is working!

In his book, What You Accept is What You Teach, Michael Henry Cohen didn’t need to go beyond his title to get my attention. As leaders, we tell our teams more about what’s okay when we’re silent than when we speak.

So, when you don’t confront Dave for failing to do what you ask him to, it becomes another “exception” that excuses the same behaviors on the part of the rest of your team.

And that’s trouble.

So, what can you do about these serial offenders? These members of your team who consistently defy you and enjoy great success. Here are a few ideas.

1. Shift Your Mindset

Some leaders we speak with are afraid of upsetting someone who’s delivering results  — regardless of how those results are achieved. Therefore, they leave these cowboys alone to do as they wish. A salesperson who’s behaving this way does more harm to your team than you might think. They serve as an excuse for weaker performers to ignore your expectations, too. Ask yourself: What would happen to the performance of the rest of the team if this top performer no longer acting this way?

2. Direct Conversation

First things, first: If you haven’t addressed the behavior, do so! By accepting that Sally won’t, for example, work productively with others in your organization “because she’s just being Sally,” you’re tacitly acknowledging that it’s okay to mistreat others. Have the conversation. Ask yourself: What’s holding me back from addressing this behavior? (As an aside, if you’ve already had the conversation before with no results, check out points 5 and 6).

3. Get Them to Teach

Asking a renegade to highlight a failure as a way to teach his or her peers can be an effective mechanism to show that all of us (even the best of the best) tend to learn more from our mistakes than our successes. Use time in sales meetings for loss analyses and be sure to include these cowboys. This kind of peer coaching can emphasize their humanity and the fact that they are not perfect. Ask yourself: What mistakes has this person made that would help peers learn?

4. Challenge Them

Look for opportunities to reward compliance. For example, include a bonus for forecast accuracy if you’ve got an entitled salesperson who refuses to forecast. Often, entitlement results when a person consistently gets what he or she wants regardless of reasons they shouldn’t. By rewarding the behavior you want – or disincentivizing the behaviors you don’t want – you can begin to put a stop to the cycle. Ask yourself: What can I do to get this entitled top performer’s attention?

5. Upgrade the Team

Stop accepting underperformance. Some organizations can’t afford to sacrifice a top performer – even if he or she is behaving in an entitled manner – because of the weakness in the rest of the team. In other words, the results of top performers may cover for weak players. If that’s the case, start replacing weaker players and, as the team gets better, it will become easier to stand up to an entitled top performer.  Ask yourself: What’s stopping me from elevating the level of capacity on this team?

6. Turn Them Over

Last, but not least, if you’ve got a top producer who’s so counter-cultural that it’s distracting from your ability to perform, it might be time to show them out. I’m consistently surprised to hear how many businesses mark as a turning point – for the better – the moment when they finally had enough of the entitled behavior of their “renegade” and released him or her. Suddenly – truly overnight – the rest of the team picked up the slack and all was well. Ask yourself: Why do I continue to accept this kind of behavior?

It may be difficult to acknowledge in the moment, but entitled salespeople hurt more than help.

What other strategies have you used to deal with entitlement among top performers?


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Written By


Brooks is Chief Barketing Officer at The Brooks Group. Brooks combines his 2+ years of experience in people-pleasing and chasing down deals (or tennis balls) with his infectious excitement to delight both customers and colleagues with every interaction.
Written By


Brooks is Chief Barketing Officer at The Brooks Group. Brooks combines his 2+ years of experience in people-pleasing and chasing down deals (or tennis balls) with his infectious excitement to delight both customers and colleagues with every interaction.

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