Back on Track: 7 Tips for Managers Dealing With Difficult Employees

illustration of one employee lagging behind the rest representing dealing with difficult employees

Everyone has had experiences with a boss they don’t get along with. It could have been their management style, how they ran meetings or how they spoke to those under their authority, but something just didn’t click. After a less-than-great experience as the subordinate, it is easy to make promises like, “If I’m ever in charge, I’m going to do things differently!”—but you also need to figure out effective ways to do that.

Unhappy, underperforming or otherwise challenging employees are a fact of life, and figuring out how to fix the situation is an age-old problem that both supervisors and those they manage deal with on a daily basis.

Whether you’re now an established manager or doing a little career daydreaming to match your future ambitions, it never hurts to think through what you can do to get a difficult or underperforming employee back on the right track. We’ve rounded up advice from experienced managers with specific tips for how they’ve dealt with difficult employees in difficult situations.

7 Expert tips on dealing with difficult employees

Not every employee–employer relationship can be salvaged, but there’s still a lot you should consider before throwing in the towel.

1. Take the time to build a relationship

This is the foundational building block for all the other tips to follow. Everyone has their own life, struggles and motivations. A manager who makes assumptions about who an employee is and what drives their actions without taking the time to get to know them is a manager sure to have difficulties with personalities different from their own.

“The most effective teams are formed when a manager appreciates each employee’s strengths and flaws, knows how to exploit each member’s unique skills and motivates everyone to work together,” says David Reid, sales director at VEM Tooling. Reid describes having this relational understanding of each employee as being key to helping difficult employees develop. “Good managers aim to understand what is going on in their direct reports’ lives to understand better what motivates them, what keeps them awake at night and what they aspire to accomplish.”

2. Have an adaptable management style

The best coaches always find ways to maximize a player’s strengths while minimizing or improving weaknesses. In this vein, managers can make the mistake of letting their ego get in the way by refusing to adapt any aspect of their management style.

“If you want to be a good manager, you need to be ready to put yourself in several different pairs of shoes,” says James-Lloyd Townsend, CEO at Frank Recruitment Group®. His experience has taught him that personalizing how he communicates and addresses conflict on an individual basis is key to being a successful manager long-term. “Your ability to manage a team will depend largely on how well you adapt your management style to suit different personalities on your team.”

3. Use direct, in-person communication

Email and texting can cause a host of miscommunication. A face-to-face encounter will help eliminate any unnecessary misconstrued meanings. Setting up a meeting where you calmly address the issue and invite open communication will pay dividends in the end.

“Sit down with the employee and have a one-to-one, off-the-record conversation about what they think might be holding them back,” says Kyle Risley, CEO of LiftVault. For Risley, it is important that this conversation is ego-free, as it can be a struggle for managers not to take any form of insubordination personally. “Asking the employee to be honest and talking about what you both can do to improve that person’s performance can be a great way to clear the air.”

4. Better educate yourself on neurodiversity

One important element of building a thriving team is understanding that you may have some employees who are neurodivergent. It is estimated that thirty to forty percent of the population is considered to be neurodiverse and could have ADHD, dyslexia, dyspraxia or other neurodiverse conditions.

“Someone who may appear to certain people as a ‘difficult’ personality may in fact be presenting traits of neurodiversity,” says Renee Rosales, founder and CEO of Theara®. Rosales points out that it is common for those in management to misunderstand certain struggles that may present as rude or lazy to neurotypical people. “With the right education and resources, it’s possible to integrate a diverse range of personalities into a team where everyone can benefit from each other’s unique perspectives.”

5. Have the employee help create an action plan

Once you’ve taken the time to speak directly to an employee and have a better understanding of where they are coming from, the issue becomes what to do next. Many managers make the mistake of trying to complete this process on an island rather than involving the struggling employee in the process.

You may have a good idea of the steps an employee needs to take to get back on track, but their point of view is valuable as you plan what comes next. An improvement plan assigned from on high may feel punitive and cause the employee to withdraw even further. Working closely with them to set goals and expectations can help avoid this problem and result in greater buy-in.

6. Increase employee feedback

Encouraging staff members and reminding them of their value can go a long way in making a sullen, struggling employee change their ways. As with many things in life, it can be helpful to see a bigger picture of why an employee is doing what they are doing. “Be clear about goals and expectations, and help employees see how their work contributes to the success of the entire company,” says Dominique Jones, chief people officer at BusPatrol. “Give employees meaningful feedback on a regular basis. This means daily, or at the very least, weekly feedback.”

While off-the-cuff feedback is often a good thing, it may be helpful to find in your schedule more regular and official feedback times.

7. Know the right time for termination

It is impossible to have a conversation about difficult employees without understanding that letting someone go is an option that needs to be on the table. So how do you know when it’s time to move on?

While certain issues are grounds for immediate termination, more often than not, it can be a gray area. For Townsend, he asks three basic questions and weighs the answers. How is this employee affecting the rest of the team? Are their actions connected to something temporary they are going through, or is this something that is irreconcilable in the longer term? And perhaps most importantly, have you tried everything in your power to make this collaboration work?

If you have gone through these questions and find yourself still at an impasse, remember that firing a difficult employee can ultimately be the best decision for all parties. “Resorting to termination is never an easy decision,” says Townsend. “However—as with any other relationship—sometimes the people involved in it can only thrive by being apart.”

Do you feel equipped?

Hopefully, this series of tips has given you some ideas for how to help your employees and your business thrive. Working as a manager can be an extremely rewarding and exciting job, but these unique challenges of dealing with different personalities mean that the best managers need the right combination of heart and skill.

If you are looking for other ways to improve yourself as a manager, whether through formal education or additional advice, you’re in the right place. For more on what it takes to succeed as a manager, check out our article “What Makes a Great Manager? 7 Qualities Needed to Lead.”

Frank Recruitment is a registered trademark of Frank Recruitment Group Services LTD.
Theara is a registered trademark of Renee Rosales.

About the author

Patrick Flavin

Patrick is a freelance content writer at Collegis Education. As a former educator, Patrick is passionate about helping students find the professions that fit their skills, talents and interests.

Patrick Flavin

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