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What is a “Difficult” Employee and Who Decides?

5/26/2026

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Have you been labeled as a difficult employee? Sometimes the label is attached to someone who is misunderstood, poorly managed, or reacting to a breakdown in communication. Too often, we have moved away from taking time to speak with people, understand their situation and try to respond with constructive suggestions.  

As a clinician, I have become interested in why some people are labeled “difficult” and what the label may overlook. Is the employee truly the problem or is the label a reflection of dysfunction in a workplace? The word can be assigned quickly without any thought. 
 
**Kathy is a 55-year-old labor manager, who has worked for her organization for 8 years. I have been working with her to examine how she is perceived at work. She reached out for help after some upsetting incidents at her job when she was called a derogatory name in a staff meeting. A couple of weeks later, she was screamed at by an employee. 
 
Kathy describes herself as friendly with staff and believes one of them misunderstood her actions. She noticed that this behavior often occurs close to major holidays-when stress can increase at work. We processed the incidents and made a plan for her to meet with her boss to address the issue. She wondered if it would do any good as he favors certain employees. 
 
Kathy met with her boss about the culture and her concerns. Instead of assisting, his response was, “I think some staff find you difficult.” She was taken back as she has been told she is “too nice” and could be “more assertive.” She decided that her boss seemed uninterested in helping with work issues. 
 
So, how should leaders and managers address workplace challenges under these circumstances?
 
Some Suggestions:
 
Meet with the staff person to find out specifics about their concerns and behavior of others.
 
Listen without defensiveness and offer to meet for a follow-up after you’ve considered the person’s concerns. 
 
Examine if there are frustrations due to disruptions at work, problems with direct communication and refusal to accept unprofessional behavior. 
 
Consider whether the employee was only labeled “difficult” after raising concerns.
 
Begin the meeting by acknowledging the person’s strengths, contributions and value to the organization.  

Sometimes an employee may genuinely not be the right fit for a particular role, and there may not be another position available. In those situations, honest communication, support, and a respectful transition are recommended. 

When both parties are willing to engage honestly, even difficult situations can move from a no-win dynamic to a more productive outcome.
If you have thoughts about this issue or the label “difficult employee,” feel free to comment below.


Kay Gimmestad, LCSW-C is a business coach and clinician in New York City with 20 years of experience working in the profit and not for profit sectors of Human Resources, Health and Human Services. She has built a reputation for being highly skilled in facilitating behavior change while working with employees, both individually and in groups, on matters relating to performance management, substance abuse, crisis intervention, and stress/wellness. ​​​​​​
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    If You Have a Problem Employee or an Employee with a Problem...

    Author Kay Gimmestad is a Business Coach and Clinician with 20 years of experience working in the profit and not for profit sectors of Human Resources, Health and Human Services. In this blog, she shares case studies and other observations from her decades in the field. 

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