How to Handle Challenging Employees

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Runner

How do you know whether an employee is a “challenger”? Here are a few hints:

– The first word out of their mouth is usually “No.”

– They treat any and every daunting task as sport.

– They’re the furthest thing from a “yes man” in the room.

Challengers are employees who live to, well,challenge. They challenge people, tasks, themselves, and everything else they come into contact with. Those who embody this strong – sometimes too strong – trait can be blessings in disguise, if you know how to handle them the right way.

Does That Sound Hard?

According to CareerBuilder, the No. 1 soft skill companies look for is a strong work ethic.

Nothing excites a challenger more than an ambitious task. Difficult and demanding work is the only situation where they will feel engaged. A new software platform to learn, a new coding language, a troubling client to manage, a process that has never been attempted: throw the new things their way. They will have no problem tackling them head-on.

As an added benefit, it turns out that this thirst for challenges is good for an employee’s health.

“Challenges at work may indeed be a positive element, if they build up a person’s mental reserve in the long term,” says Francisca S. Then, Ph.D., a researcher with the University of Leipzig in Germany. 

Management Tip: Cater to the challenger’s motivations by playing up the difficulty of a certain task. Dare the challenger to tackle it and commend them when they hit it like a lineman.

The Devil’s Advocate

MountainThe challenger never accepts anything at face value. Instead, they filter all information through their own internal sensibilities and search for flaws or weak points. The result is either thoughtful acceptance or a contrasting opinion and a solution.

This is why we appreciate challenger employees. Differing viewpoints is the new definition of “diversity”:

“In addition to creating a workplace inclusive of race, gender, and sexual orientation (to name a few), many organizations are seeking value in something even simpler[:] diversity of thought. In some industries that are known for being insular – think law or high-tech companies – seeking out talent with different thinking and problem-solving backgrounds in critical.” – Selena Rezvani,ForbesContributor. 

Management Tip: Have you exhausted every possible benefit, but haven’t thought of the downside? It can be as simple as asking the challenger for an opinion.

You’re Not Alone

In the end, it is a challenge to manage a challenger – but these employees are still worthwhile additions to your team. They will cast critical eyes on your processes, procedures, workflows – and they’ll help you improve these things after they’ve identified their flaws.

A funny thing about challengers, though: They’re not always aware of how they come off to others. Sometimes, that can make them seem abrasive to their colleagues.

Management Tip: Don’t take what they say personally. They only mean to be giving constructive criticism – not nitpicking or belittling anyone.


Use the challenger’s natural aptitude for innovation to your company’s benefit. Facilitate their critical instincts; don’t fight them. Use the challenger’s feedback to help you improve upon yourself and your company.

A version of this article originally appeared on the Vitru blog.

Ryan Mead is the CEO of Vitru.

By Ryan Mead