Managing the Challenging Employee

Creating a positive relationship with someone that challenges you can be a very difficult, but also rewarding, experience. There are ways to do this that reduces stress for everyone.

Managing a challenging employee can be difficult

Managers need to work with a variety of different personality styles. In this video I want to talk about how to work best with the individuals who are more challenging. These employees may be obstinate, or may be doing the things that you think they shouldn’t be doing. There are effective ways to do this that will reduce the stress on both sides.

This topic was generated from a question that came in from a member of the Learning Resource Center. She posed a situation where one of her managers continues to make decisions outside of the realm of her responsibilities. Unfortunately, these decisions are really based on the needs of an individual employee versus looking at the company perspective in terms of the decision. She has had conversations with this manager about the decision-making process. She thinks that they are on the same page and then, bam, it happens again in another way or another different situation. She is confused about whether she’s not giving enough clear direction, or if she should be waiting longer to see changes happen. Both of those could be the case.

And then, in a related question that came in to me, someone said how do you deal with an insubordinate employee. I feel like these are similar situations, because in both cases the employee is not doing what the manager wants to do and, in fact, is going around them in ways that are frustrating and are ineffective for everybody.

Is this behavior in the employee’s nature?

My first take on these situations is to understand whether the individual is the type of person who always wants to challenge the status quo. We can do that in a number of ways, by looking at trends and patterns that we’ve seen with them over working with them over time. Of course you know that I use the assessment tool to have a very, really clear, objective way to look at that, particularly through the manageability scale. If for instance, it’s just who that person is, we have some context for how we can handle them knowing that it’s just their natural way to deal with change or situations. If it’s not, if the person is much more easy-going and willing to go along with the flow, we get a sense that this issue that they’re bucking or resisting is really important to them for some reason.

Understand the employee’s perspective

This gets us to the second point. In order to understand where they’re coming from we really need to understand that this person is doing this behavior for a reason that suits them. They’re trying to get a point across in a way that may not be the most effective way, but it’s the way that they know how to do it. So really try to get out of them where’s this frustration coming from. What’s the root cause? What are the issues? What do they need? By having more of that dialog it’s going to give them the comfort that you understand, that you’re willing to work with them, and that you want to address their issue, even though you may be coming to a different approach in how to do that.

Set clear expectations

Next, make sure you’re very clear about the expectations you have for acceptable behavior. In the example of the manager who continues to make decisions that are based on the needs of an employee versus the whole company, you might have a conversation with the individual about what kinds of decisions they can make on their own, what kind of decisions they would make with your involvement, or what kinds of decisions are not up to them at all.

When the individual goes outside of those boundaries, come back with an explanation about where that decision fell in your mind and why it didn’t meet the criteria that was set. Involve them in that discussion about what it was that was not acceptable so they can learn from that situation. So that’s the fourth and last step that I would recommend. That is that you ensure that you have ongoing communication and feedback with the individual to let them know when they’ve gone outside the parameters that you’ve established. What does being obstinate or challenging mean to you? It might mean something different to them.

Create and maintain healthy work relationships

To recap the steps, the first is to really understand who this person is. Do they naturally challenge everything? That’s going to give you greater context to how to work through these kinds of situations. The second it is to understand the root cause of the frustration. Learn what the message is that they’re trying to share, and that will help you work through it more constructively. The third is to set clear expectations about what behaviors are acceptable and what’s not. And the fourth is to give them ongoing, constant feedback when they go outside of those parameters, as well as when they’re meeting your expectations. When you do that you’ll have a much calmer and more effective relationship.

Check out other videos at the Learning Resource Center, available to you as a member. Here’s to your graceful leadership.


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