How To Deal With A “Difficult” Employee

The other day someone asked me how to deal with a “difficult” employee as a new supervisor with a new employer.

After getting some background information, the new supervisor advised that the employee was engaging in what could be construed as insubordinate behavior, however; that was a bit of a stretch.

Having dealt with my own fair share of difficult employees, my first piece of advice was: “don’t be afraid to manage.”


When you move into a new supervisory position whether for your current employer or a new one, setting aside some time to set expectations with your employees will be a good first step in the process.  Be sure to ask questions or gain feedback to ensure that your employee understood your message clearly and correctly.

Making the employee aware of what the expectations are and the process for achieving those expectations will set the foundation you need to hold some accountable.


As managers, we have the responsibility to hold our subordinates and team members accountable for their actions, if we’re not doing so, then we are failing in our own duties and responsibilities.

As a new manager or supervisor you need to be able to establish your authority, setting expectations and ensuring that goals are being met to your standard is a part of that. If goals are not being met then there has to be accountability, whether that is through coaching for improvement or taking disciplinary action for more serious issues, this is next step in the process.

At this stage, you need to gage where the disconnect lies: is it a skill vs. will issue? Did your employee understand the initial instruction given to him? If it was, you may have an employee beginning to engage in insubordinate behavior.

Keep in mind that if the issue in meeting goals is performance related but there is a sincere effort to achieve goals from your employee, then you will want to continue coaching for improvement and encouraging the positive behaviors that your employee displays.

Employee’s beginning to engage in negative behaviors may be having difficulty in adjusting to the change in their environment, especially if you are a new supervisor.

Personally, I’m an advocate of showing a person the door if their not happy with their work environment. Why should you department’s productivity have to suffer because of an employee’s negative behavior, but not everyone thinks like me.

If you happen to identify the underlying issue is a difficult employee and your HR department won’t terminate them, well; needless to say you have a difficult road ahead of you.

Being in that position previously, I can understand how difficult employees can be draining both mentally and emotionally. Don’t get discouraged though, make sure that you continue to communicate with the employee (in a professional manner of course) and continue to identify the negative behaviors and advise them that those behaviors are unacceptable. Whether that’s done formally or informally you will want to ensure that you are documenting your process.


If your company has a formal documentation process then go ahead and use that so that there is a written record that both you and your employee can refer back to. If your company doesn’t have a formal documentation process then feel free to use Word to highlight keep points discussed during your meeting or conversation with your employee (be sure that your employee receives a copy also), or you could use Outlook, create a calendar invite with the date and time of your meeting with your employee and notate the items discussed there and send the invite to your employee so that have it on their calendar also. Note: if your Outlook calendar is shared, I would discourage this practice as it can make sensitive employee information available to others. Continue to escalate the disciplinary process if you do not see any improvement.

It’s important to remember that throughout this process you need to continue being a manager/supervisor and continue to set new expectations as they arise and coach accordingly.

If after all the above steps have been taken and you continue to see no improvement in your employee’s behavior, well it may just be time to count your losses and end the employment relationship.

Does anyone have any other suggestions or best practices for dealing with difficult employees? Let us know in the comments section!

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