Middle Management Training: Dealing With Difficult Employees

Middle Management Training Dealing With Difficult Employees

**Human Resources Disclaimer: Through this exploration of dealing with difficult employees during middle management training, Hallett Leadership is sharing an individual perspective on managing collaboration in high performance teams. When dealing with a problem employee, always include your Human Resources representative in the process.**

On the quest to create an organizational culture with high performance leadership at every level, we begin with alignment around a common vision. A vision that will inspire your people, align them around a common cause, and serve as a point of reference when things inevitably become busy and people need to recalibrate and, again, point all boats in the same direction.

It is also a reality that when people align around a common vision after participating in its creation, there typically are still some people who resist change, or otherwise continue behaving in ways that don’t align with the new vision and direction of the company. These people, who for whatever reason, continue to behave in ways that are not aligned with the common vision, are who we are characterizing in this article as “problem employees.”

Let’s say for the purposes of discussion that you are the manager of a team that has rallied around a new and inspiring common vision… but there is one person from the company’s older days who is behaving in ways that don’t align with the new vision, and whose energy is steadily deflating the team’s newborn enthusiasm.

One solution may be to have a conversation with this person. Here are a few guidelines for how to approach such a conversation:

Invite Them To A One-on-One Meeting


The first step is to invite this person to a one-on-one meeting. When you are both seated and have exchanged pleasantries or salutary greetings, bring up the topic of the desired culture that the team has aligned around, and remind them of what exactly that is.


Solicit Input


Solicit their input on their perspective around the new vision, and their role in it. Perhaps their behavior is a blind spot. Or, perhaps the person in question truly doesn’t like the new collaborative culture, and the values that underpin it.

It is important for you to listen well to the person’s responses to understand where the disconnect is between the desired culture and their willingness to participate.

Pay special attention to determining whether the employee believes bad behavior is being rewarded and therefore reinforced.


Provide Feedback


Indicate through feedback how this person’s behavior is out of alignment with the desired culture.


Together, Determine Appropriate Steps Toward Alignment


Assess what this person needs to come into alignment.  Work with the employee to determine appropriate steps, which might include:  alignment goals, a mentor, a coach, etc.  It may even include incentives – perhaps this individual is being incentivized solely based on his or her own area’s results, and not the contribution to the overall company goals.


Establish a timetable


Retaining employees that are out of alignment can zap the energy of the entire team and hinder the realization of the desired company culture. It is important to balance regard for this individual with the well-being of the entire team. Therefore, once you determine what is necessary to bring this person into alignment, establish a timetable.


Create An Opportunity


In the event that your employee is truly willing to shift and demonstrates substantive progress in the time period set forward in the timetable, consider placing them on a task force or team where they can demonstrate their commitment to collaboration.




Dealing with an employee who resists participating in your group’s desired company culture is never easy. Yet through communication, feedback, listening, and good-faith collaboration, the person who demonstrates a willingness to change and embrace the desired company culture may yet turn out to be the poster-person for the new way forward.  We can only know in hindsight. At the moment you are in the arena, facing the challenge, we encourage you to do what must be done, with your sights steadily fixed on your team’s shared vision, and upon bringing out the best in each and every person.

If you are considering getting some support in this area, we invite you to reach out.

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