Has this ever happened to you?
Your organization has some team leaders who have been with you for a long time. Maybe they were instrumental to the firm’s success. Maybe they came in later and pushed it to another level. Maybe they single-handedly keep operations afloat. The point is, they’ve been irreplaceable to you.
But suddenly, you notice that they’re acting a little too entitled as a result of it. They walk around like they’re the greatest thing since sliced bread, and it’s not only affecting your perception of them, but the rest of the team’s morale as well.
They need to be humbled.
You don’t want people not to know how great they’re doing, to downplay their impact to keep them humble. That would be unfair, invalidating, and potentially creating an even bigger issue. So how do you solve (and prevent) this issue then?
Simple: by giving them a challenge.
The chances are, the people who act too self-important around the office do so because it’s been a long time since they’ve felt challenged by their work. Too long since they had to face a problem they didn’t know how to solve. Too long since a project dumbfounded them. Too long since they’ve encountered a puzzle that’s kept them past their 9-5 searching for a solution.
Give them that puzzle.
People don’t need to think they’re untalented or incapable in order to remain humble. They just need to remember that there’s no CV big enough to avoid struggling altogether. They need to remember that there will always be things and people big enough to faze even them.
When setting up this team member with a new challenge, you can even start by hyping them up first. Call them to your office and tell them that they’ve been doing so well, that you feel like they’re the only person for this particular job. Then, hit them with that difficult case, a firm-wide new initiative, whatever it may be that’s appropriate in scale.
They’ll likely approach it with initial smugness, but soon their confident smile will be replaced with a furrowed brow.
By putting some of your showboat leaders in a challenging and uncomfortable position, you will first force them to face their existing weaknesses — which they will have most definitely forgotten about — and then push them to develop new skills and gain new perspectives. That will not only return them to a much more humble way of operating, but also help them come out the other side as an even stronger professional.
You may feel a bit strange doing this, but remember, you’re not doing it to punish them. You’re doing it for their — and your firm’s — benefit.
I do this all the time, not just for my team but also for myself. That’s why I get into cold plunges: to be uncomfortable and as a result always keep myself on my toes, to never forget that I have to be war-ready.
That’s how we stay humble while devouring competition: by always seeking out new challenges.
So don’t be afraid to push back against entitled leaders in your organization, and don’t be scared to keep up the challenges even after the entitlement in them fades. Prevention is the best treatment, and the best way to prevent entitlement from ever setting in is by letting challenges sharpen your knives before they ever dull.
