How to coach a problem employee: The pessimist

Help habitual complainers find their happy place.
By Matthew Philpott

Pessimistic employees can seriously drag down a team's morale.

"Complainers are toxic to any team culture," said Michigan-based speaker and career coach Heather Hollick. "Negativity not only stifles creativity, but it stifles conversation. People tend to keep to themselves when around a complainer. Negativity is a downer."

Fortunately, there are ways managers can help turn complainers around. CPAs and career coaches suggest the following tips for working with a pessimistic employee:

Identify the complainers. Of all the negative behavior patterns common to employees, habitual pessimism may be the most self-evident. Pessimists tend to voice complaints at meetings, and when their coworkers suggest new ideas, they're quick to point out potential pitfalls.

Another way to identify them is to notice how their attitude trickles down to their teammates, particularly at the beginning of new projects.

"When you have someone against innovation, it can stifle co-workers from wanting to bring new ideas if they anticipate not getting support for them," said Jessica Iennarella, CPA, CFF, forensic accountant supervisor at HSNO in Scottsdale, Ariz. "It's a contagious behavior, and someone on the fence might be prone to being dragged into a negative mindset."

Help these employees develop a more productive attitude. One way to turn pessimists around is to get them to reframe their complaints as constructive criticism.

"This employee may feel like they aren't being heard. You may need to listen to their thoughts more often," said Atlanta-based career coach and author Hallie Crawford. "They may have some valid ideas for changing a process or a program, and it may be part of their strength that they bring to the table—to identify possible issues. If their ideas are valid, ask them to create a plan for implementing their idea."

Asking pessimistic employees to shift their perspective from "what is wrong?" to "what would you do?" can empower them. It can also clue them in to how their attitudes may be affecting those around them: They "realize they can either be part of the problem or part of the solution," said Iennarella, a 2016 graduate of the AICPA Leadership Academy.

Make their pessimism a force for good. While you might be able to persuade a complainer to see the bright side, chances are they're always going to be the first person to spot a problem on the horizon. The good news is that can be a valuable skill.

"What I've found is that complainers are very detail-oriented," said Matthew Morey, CPA, CGMA, senior staff regulatory analyst at Entergy in New Orleans and a 2016 graduate of the AICPA Leadership Academy. That means they can alert the team to small issues before they become large ones, troubleshooting before projects get too far underway.

The outcome? Putting a habitual complainer in a position to help rather than hurt can help your resident grouse find a new life as a canary in a coal mine.

Matthew Philpott is a freelance writer based in Durham, N.C. To comment on this article or to suggest an idea for another article, contact senior editor Courtney Vien at

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