Dealing with Difficult People Title Image. Shows venn diagram of personal, interpersonal, and organizational excellence. Strategeis to help you identify character and personality problems early, keep them from draining your energy and wasting your time, and discern whether to coach, reprimand or fire difficult employees.


High Achievers are problem-solvers. They think they should be able to problem-solve people as well.

High Achievers are tenacious and dislike admitting defeat. This tenacity makes them stay in toxic situations.

High Achievers try to use logical arguments on illogical people. (It doesn’t work).

High Achievers’ overdeveloped sense of personal responsibility makes them second-guess their judgment.

High Achievers are used to creating positive outcomes and have difficulty firing difficult people.

Cartoon that shows woman thinking her boss is fantastic one day and hating him the next.

The Fastest Way to Identify if Someone is a "Difficult" Person

Do I feel like every conversation will be a circular diatribe about how it’s someone else’s fault?

Do they have unrealistic expectations but make me feel like I am mean or selfish if I don’t accommodate them? 

Do I dread conversations because I’m left completely drained, with no positive outcome? 

Do I feel like this person is trying to “pull” something out of me or elicit some type of reaction?

Do I have notebooks of documentation but still feel like maybe I’m the one doing something wrong?

Fundamentals of Dealing with Difficult People

1.  The other person is unlikely to change.

2. Handling them the way you have in the past 50 conversations will not yield different results.

3. You CAN be assertive and kind at the same time.

4. Conversations to help them see your point of view is a waste of your time.

5. You will probably offend them.

6. Strategic actions are more effective than conversations.

Mistakes that High Achievers Make in Dealing with Difficult People

1.  High achievers can under-estimate the toxicity of difficult people, many of whom have personality disorders. People with personality disorders can be very intelligent and project as competent and as a team player. Because of this, many high achievers ignore the red flags and either believe that they are at fault for the negative interactions or continue to expect the person to change.

2.  High achievers value hard work and goal achievement over work-place “politics.” They may make the mistake of thinking that they can just “not play the game.” In work-place conflict, knowing and responding to the relationship and personality dynamics at hand is crucial to both protecting oneself and being able to manage the situation.

3.  Working harder will not solve the problem.

4.  High achievers who are nice and reasonable assume that this approach wins the game. It does with rational people. It makes you a target in toxic situations.

5.  High Achievers want to be fair, so they give grace too early for good behavior. The difficult person perceives “grace” as successful manipulation. Rewards or consequences need to be consistently applied. Consistency = 100% of the time. The research from behaviorism indicates that intermittent reinforcement maintains behavior the longest (i.e. gambling…a reward is coming if you keep trying). You don’t want to train a difficult person that the bad behavior will eventually get his/her desired result.

6. High Achievers are sometimes afraid of being mean. Usually, they are mean when they have “held it in” too long. Consistent firmness allows one to be kind.

Recommendations for High Achievers

1. Learn others’ motivation. What motivates the difficult person? Power? Attention? A need for drama? Try to figure out what is important to them so that you can build  a strategy based on their personality.

2. Develop specific strategies. Discuss the situation with trusted friends and advisors. Use their feedback and your knowledge of the work dynamics to develop a short-term action plan for daily coping and a long-term plan in case the situation does not improve.

3. Protect yourself. Be sure to surround yourself with positive social support, both at work and outside of work. Protect yourself professionally by documenting incidents. Protect yourself personally by maintaining a strong exercise, nutrition and self-care regimen.

4. Assess the system.  Is the system toxic? Do the leaders have the courage to fire toxic people? If they don’t, it is unlikely that the culture will change. Assessing the system is helpful in understanding your limitations and your next steps.

You cannot have a rational conversation with an irrational person.

Dealing with Difficult Employees

Defining "Soft-Skill" Expectations for Employees

Do you provide clear expectations about job tasks? I bet you do. Do you do the same for soft skills? Many leaders list specific task objectives that are measurable and can be updated at performance reviews. Often, leaders forget to similarly provide clear and measurable objectives on the “soft skills. ”

Examples of soft skills include: being a team player, arriving to work on time, accepting and giving appropriate feedback or communicating in a positive manner with others.

It takes creativity and effort to make soft skills measurable. The problem with not operationalizing and measuring the soft skill expectations is that it leaves no clear path for the reprimand and remediation (or firing) process.  Leaders resort to “I’ll have to talk to her again. ” Let’s face it. If the first 3 “talks” didn’t work, the next one will be equally ineffective.

Suggestions for Making Soft Skills Measurable

360 Feedback

Use a 360 mode of obtaining feedback from peers, subordinates, and supervisors. Likert scale ratings (0-5) provide the quantification that is necessary for tracking progress or lack thereof. The process can be presented as a tactic to maximize professional growth and to ensure a positive work atmosphere. People may be initially uncomfortable, so an honest but positive explanation will go a long way in creating buy-in.

Items that might be addressed on a 360 feedback include the degree to which a person unnecessarily interrupts others, if they make positive and supportive statements during team collaboration, how often they directly resolve concerns with relevant people instead of gossiping to others, and if they take initiative with new tasks. The surveys should be tailored specifically to what you want from the employees and leaders in your organization.



Set boundaries to flexibility. If you want to maintain a flexible work environment but find that some employees take advantage, reel them in instead of punishing everyone else with stricter expectations. For example, if you want people to have the flexibility to leave early for personal appointments, let them know the upper bounds of what is acceptable (i.e. 2 times each month). Put the expectation in writing and have people shoot out a quick email that they will be leaving early.

The dedicated workers who do not take advantage of perks will be really grateful to maintain the perks AND to see that their lazier colleagues are held accountable. This strategy can apply to flexibility in working hours, the policy on personal phone calls and breaks, unpaid leave requests, and any other area where you want to create a flexible but responsible atmosphere. Always remember the power of social pressure. In group settings, praise employees who handle the flexibility in a responsible manner. This strategy allows you to create the tone that responsibility is rewarded.


Track and Document

Set up a system for tracking problems and use it consistently. If you have a warning system for all of the hard skills, it is necessary to have one for the soft skills as well. It may be the same system or a different one. It is necessary to use it and follow-through in order for everyone to take it seriously.

DO NOT fall into the trap of making excuses for employees. Just build in enough flexibility and a system for extenuating circumstances, so that the genuine problems that are left are obviously outside of the expectations and are reprimanded accordingly. Remember, only 1 verbal reprimand and then you need a set of written reprimands and consequences to be in place.