5 Difficult Personalities and How to Deal with Them

Written by lewsauder

September 18, 2020

Difficult Personalities

I have always felt like I could get along and work with just about anyone. Some people are easier to work with than others. And some seem to do their best at being as challenging as possible. It has been my experience that some people focus their aggressions on consultants because they get into less trouble than taking them out on their own people.

In any case, I have identified some key difficult personalities that I have dealt with and how I learned to deal with them.

Laid-back Larry

Personality Profile: Larry has been known to wear sandals and a Hawaiian shirt to a client meeting. His normal posture is slouching in his chair. He generally procrastinates his work until the last minute. As a result, there is never time to do an internal review of his work before meeting with the client.

Tips for dealing with Larry: It is important to stay on top of Larry. No matter how good his work product is, Larry needs to be a team player. I schedule regular check-ins with him and the team to review the work. I also distribute the work so that there are dependencies he needs to complete his work.

I have never been a big fan of escalating issues to a team member’s superior, because it can sour a relationship for the long-term. But if I am unable to get someone to be a team player or to be professional, I am willing to have a conversation with that person’s boss to suggest a conversation about their behavior. I make sure to do it in a diplomatic manner. I also make sure to highlight the positive aspects of the team member. I want to make sure that I am not completely unhappy with them. I just need some adjustments to be made.

Obstinate Olivia

Personality Profile: Olivia has been with the company for about twenty-five years. She holds a lot of tribal knowledge that may or may not be documented – somewhere. If you are lucky enough to get a response from her to your email, it is rarely a friendly response. She will happily berate you in front of others in a meeting. She may also deny a request from you for missing an unimportant piece of information. Because she holds so much knowledge, her boss is afraid to fire her.

Tips for dealing with Olivia: Olivia wants to be respected and does not want people to waste her time. Because her own boss is afraid of her, there is rarely an upside to escalating her behavior to the boss. Escalation would only put you on her naughty list.

I have found that the best way to deal with her is to do your best to respect her and her time. Get on her good side by always overdoing your homework when dealing with her. If you need her in a meeting, let her know that you need her expertise. If you submit a request to her, make sure they are succinct and correct. Know your facts every time you deal with her.

You may not enjoy kissing up to someone this nasty. But the ultimate goal is to get output from her. Like the famous line in The Godfather, “It’s not personal. It’s business.” You will need to leave your pride at the door to get the job done. If Olivia bothers you that much, I have always found it helpful to smile and think about what I will say at her funeral.

Explosive Emma

Personality Profile: Emma is a nice person to have a beer with. But she had a bad experience at her previous company. They overworked her, promised impossible things to the client, and expected her to do whatever it took to get it done. Her boss successfully destroyed her self-confidence enough to make her think she could never find a job somewhere else. On a whim, she applied to your company and was hired away.

Emma’s behavior is similar to a pet that has been abused by a former owner. Any time you ask her to do anything or ask for status, she gets angry. Her anger boarders on abuse at times, with salty language and name calling. Just saying something wrong can set her off into an angry tirade.

Tips for dealing with Emma: Emma needs help. This is not normal behavior. She cannot be trusted to be in front of a client if there is a fear that she will explode in front of them.

If Emma is not senior to you, you may need to have a confrontation with her. Explain that her behavior is not professional, and you will not allow her to speak to you that way. Be prepared for this not to go well. It may provoke another outburst. But she may be crying out for help.

On the other hand, it may be the start of a beautiful friendship. You may end up being a mentor to her and help her to change her behavior.

Assuming the rosy mentoring scenario does not come to fruition, it is time to escalate. As I mentioned, I am not a big fan of escalation, but this is a situation that calls for it. I recommend talking to the person first because escalation should only take place if you have tried to confront the situation first and failed.

Before escalation, you should also document specific situations detailing her behavior and how she has spoken to people. Then, speak to Emma’s superior – or to HR – and tell the story. Share the documentation. Explain the conversation that you had with her. It is very likely that you are not the first person to raise this issue.

Political Paul

Personality Profile: Paul is a firm believer that knowledge is power. He holds on to information and shares it only if there is an advantage to him. His favorite ploy is to set someone up in a meeting with their boss present. He will keep some information from them and then ask them a question in the meeting. When the victim provides the wrong answer, Paul pounces. He will point out that that his colleague is wrong and provide the information to prove it. Paul’s career advancement is his only motivation, even to the detriment of the organization.

Tips for dealing with Paul: The biggest tip with Paul is to watch your back. He will bring you down if it advances his career. Beyond that, if you are dealing with a politician, it is important to play the political game with him – within limits.

Become Paul’s ally. Provide him with information that might be helpful to him. But step softly. Making Paul a friend can make other enemies. Do your best to “play both sides” to maintain as many alliances as possible. Do not provide him information that could be used as dirt on other people. That is sure to create an enemy if it ever gets back to you.

Some political people will require loyalty to them. Avoid this. Do as much as you can to get on his good side without damaging any other relationships.

Escalation is rarely an option with Paul. Chances are that Paul is politically aligned with his boss. It is also likely that if you try to go to his boss, Paul has a file on you that he can – and will – use against you.

Negative Nate

Personality Profile: Nate is someone who advocates for change but tends to come up with every reason not to change. He shoots down every idea in a meeting for one reason or another. Every sentence from Nate seems to start with, “That will never work because…”

In addition to being resistant to change, Nate can be cynical. He does not believe people and always thinks in the worst-case scenario. He can be so effective, that many people do not even bother to suggest things in his presence.

Tips for dealing with Nate: Nate’s biggest fear is change. As much as he condemns the status quo, he is stubbornly stuck in it for fear of any change being worse than it is today. The best way I have found to deal with Nates is to sell the advantages of a change. Describe the benefits to him in such an advantageous way that he will have trouble criticizing it. Be careful though. He is very experienced at selling the negative benefits. Be ready for any counterarguments Nate could present. Be prepared with facts also. If you can prove the benefits with facts, figures, and even some charts or graphs, you may remove any objections Nate can come up with.

Also, if you plan to present a discussion, prepare by lobbying some peers to be on your side. Nate may speak louder than others, but you may be successful if you have strength in numbers.


There are many types of difficult personalities that you deal with on a daily basis. Some are not as extreme as discussed here. Some are a combination of a multiple of these personalities.

It is important to maintain professionalism when dealing with any difficult personalities that you encounter. As difficult as it may seem, try to develop an alliance with them. Try to identify what motivates them and focus on that. If you find their weakness, you may be able to fill a void for them and make them a little less difficult to deal with.

What types of difficult people have you had to deal with?

As always, I welcome your comments and criticisms. 

If you would like to learn more about working in consulting, get Lew’s book Consulting 101: 101 Tips for Success in Consulting at Amazon.com 

Image courtesy of imagerymajestic at FreeDigitalPhotos.net

Lew’s Books at Amazon:

Project Management 101
Consulting 101
The Reluctant Mentor

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