A Leader’s Guide: How To Deal With Difficult People

The Six Personalities that Make Teamwork Difficult and How to Manage Them

Managing different personalities on your team is one of your greatest challenges as a leader. If you’re lucky, your team gets along splendidly and consistently performs at a high level. But for most of us, there’s always That One Person on your team who can be difficult to work with.

According to a study by the University of Phoenix, 70% of respondents admitted to being part of a dysfunctional team — having to work with difficult personalities seems to be the norm and not the exception. As a leader, it’s your job to handle the dynamics of your team and ensure they’re able to work effectively together.

Here are six common difficult personalities you can find on a team, and tips for dealing with them:

1. The Negative Ned

What is a Negative Ned? Someone who always complains. It rained during his commute to work? He’ll grumble about the traffic jam on the highway. The meeting got moved to another timeslot at the last minute? He’ll talk about how he had to spend 10 minutes shuffling his other appointments so he could fit it in. He wasn’t included in that new project team? He’ll badmouth the project leader and the other people on the team.

We all have bad days at work, and expressing frustration when things don’t go our way can be a healthy exercise. After all, it’s better to let out bad feelings than to let them fester. What makes a Negative Ned different is the frequency and consistency with which they speak negatively – that is to say, all the time. A Negative Ned is the pessimist who only sees the bad in every situation and constantly expresses those feelings.

Being around such negative energy all day, every day in the office can be draining for everyone involved. The morale of the team can be affected by one team member who always points out what’s negative in a situation.

How to deal with a Negative Ned: The first thing you can do is to assess if his complaints have any validity. Perhaps he grumbles about the system being down 80% of the time — and it’s true. If his complaint is legitimate, then it’s your responsibility as a leader to acknowledge and resolve the problem.

You could also have a private meeting to discuss his attitude. Sometimes, a Negative Ned doesn’t realize that he grumbles that much.  Let him know how his negativity affects team morale, and suggest that he reduce the complaining. Offer him another feedback channel where he can constructively make  suggestions for improvements.

Another way to deal with a Negative Ned is to counter his negativity with positivity. If you make the effort to cultivate a positive work climate, it’s more difficult for Negative Ned to continue his endless grumbling. If a Negative Ned complains about having to stay late for the fourth day in the row in order to complete the project, make sure you take the time to verbally thank your team for their hard work or even reward them in some way for the extra effort. When your team feels valued, there will be less negativity.

2. The Know-It-All Norman

What is a Know-It-All Norman?  Someone who has a superiority complex, and constantly puts others down. A Know-It-All Norman tends to dominate a team setting because he thinks he’s always right. If there is a problem, he has the solution. He shuts down ideas and opinions from others, or is quick to dismiss any input that doesn’t align with his own thoughts about an issue. He may also correct others in a condescending manner.

A team member who has a know-it-all attitude can stifle discussion and collaboration because of their closed attitude. Others on the team may become less willing to share their comments in fear of being publicly corrected or dismissed by the Know-It-All Norman.

This abrasive attitude not only alienates Know-It-All Norman’s colleagues, but could also negatively affect other business relationships or interactions with clients.

How to deal with a Know-It-All Norman: Behind the bluster of a Know-It-All Norman is often a desire to be valued for his knowledge and skills. His attitude could be rooted in personal insecurities, so it’s important to be empathetic when dealing with them.

As a leader, model the behaviors you’d like your team to exemplify. Be willing to say “I don’t know, but let’s find a solution that works.”  Sometimes just admitting that you don’t have all the answers will give the rest of your team (as well as Know-It-All Norman!) the permission and confidence to do the same when they’re faced with a challenging situation.

It is also possible that Know-It-All Norman is unaware of how his attitude comes across to others. Have a private chat with him and offer some constructive criticism. Acknowledge his good work and contribution to the team, but also mention how the team works better when everyone has the chance to share their input. Gently urge him to give others in the team the space and opportunity to do their part.

3. The Social Sarah

What is a Social Sarah? Every office has a social butterfly! A Social Sarah is the person who’s friends with everyone in the office, loves gossip and is always up-to-date on what’s going on. She’s always checking in with people, asking how they are, how the new project is doing. She’ll be the one who whispers to you that the business development and sales departments will be merged. She will organize the secret 50th birthday party for the CEO and make sure it goes off without a hitch.

A Social Sarah can be an asset; she is the one who livens up the workplace, volunteers to plan the office parties and is willing to lend a listening ear if you’re having a bad day. But she can also turn into a disruptive force in the office, if not kept in check.

For any introverts in the office, the seemingly endless orbiting of a Social Sarah can be tiring. Yes, some social chat at the water cooler can be relaxing but too much can be distracting! A Social Sarah, who isn’t aware of boundaries, may also disrupt others’ concentration and focus. Imagine trying to finish a monthly report but having a colleague who’s trying to engage you in conversation about the latest office gossip!

How to deal with a Social Sarah: It’s all about setting boundaries. A completely quiet and sterile workplace is hardly desirable, so it’s not ideal to eliminate all socializing. Most of us want a friendly and warm work climate! Let the Social Sarah know that you appreciate her friendliness and warmth, but that there’s a time for socializing and a time for work.

One thing to consider is whether Social Sarah’s behavior stems from a lack of meaningful work to do. Perhaps she does not feel engaged at the office and is looking for other ways to feel connected to the team. It may be helpful to check in with her and see if she’d like to be more involved in upcoming team projects. Getting Social Sarah to contribute in a more meaningful way could improve team dynamics and performance.

If a Social Sarah is spreading negative gossip, a firmer hand is needed. You should speak with her privately and explain how office gossip is hurtful and creates an environment of distrust. If the behavior continues, advise her you may need to take additional steps with your Human Resources department.

4. The Anti-Social Aaron

What is an Anti-Social Aaron? On the other end of the spectrum from Social Sarah is Anti-Social Aaron, a person who is strictly 100% focused on work, getting their tasks done, and making minimal or zero effort to socialize with anyone else in the office.

Celebratory drinks to commemorate the successful end of a project? Year-end party? A team building day? Anti-Social Aaron is not interested in any of that; if attendance is not mandatory, he’ll find an excuse not to go. And if he has to be there, he will participate as little as possible.

A lone wolf approach isn’t acceptable in today’s office where work is becoming increasingly collaborative. While you may appreciate Anti-Social Aaron’s efficiency, his distance from the rest of the team can create an us-versus-him divide and ultimately fracture the cohesiveness of the group in the long-run.

How to deal with an Anti-Social Aaron: Understand that not everyone wants or needs to be friends with their coworkers, so forcing an Anti-Social Aaron to attend social events is not the answer!

Make the effort to get to know him. Perhaps he’s very shy and doesn’t know how to connect with his colleagues. Maybe he is going through a family situation and is focused on completing his work so he can be home with his loved ones. Find out why he behaves the way he does, and then you can find a way to address the issue.

There’s also a chance that Anti-Social Aaron is part of the 70% of U.S. workers who are not engaged at work. It is important to let him know that you appreciate his opinions and input; find out what dissatisfies him and, if possible, address those problems so he can be more engaged in the office.

Explain to Anti-Social Aaron that, at the very least, a cordial working relationship is necessary for the team to achieve their goals, and that his attitude is affecting the team dynamics. Discuss company expectations and agree on reasonable next steps. Perhaps he can agree to come for drinks after work on Friday at least once a month, or try to participate more in meetings

5. The Workaholic Wendy

What is a Workaholic Wendy? Workaholic Wendy wants all of the work. She’s the first to raise her hand for the new assignment. She offers to take on the workload of a team member who’s going on maternity leave. She emails you on a Saturday night with an idea for that client pitch.

Now to be fair, Workaholic Wendy can be an excellent person to have on your team. She’s eager to show how capable and hard-working she is. She is always willing to take on new tasks or projects, has no compunctions about putting in the hours needed, and she tends to get the job done well.

However, in the long-run, running your Workaholic Wendy ragged will lead to burnout and her departure from the company. It’s unsustainable for anyone to work at 150% at all times. Her long hours and overestimation of her abilities may also cause resentment within the team as the bar for quantity of work is raised. This can lead to less creativity, less innovation, and more stress for the team if everyone feels compelled to keep up with Workaholic Wendy.

How to deal with a Workaholic Wendy: Shine the light on Workaholic Wendy’s addiction to work; most workaholics are not aware of how “married” they are to their work and their office identity. There is often an underlying reason for her unwavering focus on her career, but it’s not necessary for you to probe. Instead, simply offer a listening ear if she is willing to share.

If a Workaholic Wendy shares with you that they are working hard to prove themselves and earn a promotion, then it can be useful to discuss their career goals and how her current approach to their workload may be inadvertently hindering her progress.

It’s important to highlight to a Workaholic Wendy that the number of hours spent on work is secondary to the quality of the work. Compliment her on her work ethic, but also advise that balance is necessary for a well-rounded life. It may also be helpful to set boundaries on appropriate times for communication (e.g. that email update at 2.00am is not necessary).

6. The Tactless Tara

What is a Tactless Tara? A person with no filter; someone who doesn’t think before speaking. A Tactless Tara is often brutally honest and doesn’t take into account the feelings of others when voicing her opinions or thoughts. Brash, rude, offensive — these are some adjectives usually associated with a Tactless Tara.

You can always count on a Tactless Tara to tell you exactly what she thinks about the new brand strategy or which supplier has provided the department with the best service this quarter. However, her unfiltered opinions can ruffle feathers due to their bluntness. A carelessly spoken word can damage business relationships or negatively impact your organization’s reputation.

Honesty from a team member is certainly valuable, but if it is always delivered in a thoughtless manner, then it is a problem. Tactlessness in a team member can lead to strained relationships, hurt feelings and lack of collaboration. A team environment should be safe for all; blunt and insensitive comments are a threat to the psychological safety that is key for high-performing teams.

How to deal with a Tactless Tara: As a leader, diplomacy is probably in your arsenal of skills. But with a Tactless Tara, leave diplomacy at home and be straightforward. She appreciates directness so it’s imperative that you are frank with her.

Highlight how her blunt manner has inadvertently offended or hurt others on the team. It may be helpful to have some specific examples on hand as a Tactless Tara may not be aware of how her offhand comments are received by others.

Encourage her to think before speaking, especially when it comes to off-the-cuff comments. Advise her to view everyone as super sensitive to negative comments and urge her to err on the side of caution. This ability to step into the shoes of the other person can minimize harmful words and behavior.


An important component of managing people is being able to communicate effectively and this skill becomes especially important when it comes to managing difficult team members. As a leader, learn the skill of providing constructive feedback without criticizing as it will help you coach your team and get them to perform at their best.

Ideally, you should regularly receive and get feedback from your team on how they’re doing, what can be improved upon, and whether their performance is up to par. While some of these meetings can and should be informal, these regular check-ins should also be documented so it is clear that everyone is aware of and has agreed to any corrective action that is needed.

And remember to always have your team’s best interests at heart; if you’re not able to resolve the issues with a difficult team member after repeated attempts, be willing to make the tough decision to let them go.


Like this post? Pin it to save and share with your friends!

How To Deal With Difficult People

Scroll to Top