Managing Difficult Employees: A Guide for New Managers

By Shelley Brown, CHRE, FHRPA

Senior HR Consultant

Stepping into a management role is a significant milestone. It also comes with a responsibility that new managers sometimes underestimate: managing people.

Working with a strong, engaged team can make management look easy. The real test often comes when an employee is consistently missing deadlines, creating conflict, resisting feedback or affecting the productivity of others.

In our two decades supporting Canadian businesses with talent management and recruitment, we have seen firsthand that effective managers are not defined by how they handle their best employees. They are often defined by how they address problems before they begin affecting the rest of the team.

The first step is recognizing that a “difficult employee” is not necessarily a bad employee. A behaviour change can sometimes be caused by unclear expectations, inadequate training, excessive workload, a management issue or circumstances outside of work. Before deciding how to respond, make sure you understand what is actually happening.

Recognizing 5 Common Difficult Employee Behaviours

Difficult behaviour can take several forms. The important thing is to focus on the behaviour itself rather than labelling the person.

1. The chronic complainer: This employee regularly identifies problems with projects, processes or coworkers but rarely offers potential solutions. Constructive feedback is valuable, but constant negativity can eventually affect team morale.

2. The disengaged employee: Their work may technically get done, but deadlines are missed, quality declines, participation drops, and they show little ownership of outcomes. A previously engaged employee who suddenly becomes withdrawn may require a different approach than someone who has always performed at a low level.

3. The passive-aggressive employee: They agree to tasks in meetings but fail to follow through, make sarcastic comments, resist decisions indirectly or have side conversations that undermine team discussions.

4. The abrasive high performer: Technical ability does not excuse behaviour that makes collaboration difficult. An employee may consistently deliver strong results while dismissing colleagues, refusing feedback or creating unnecessary conflict.

5. The employee who avoids accountability: When something goes wrong, the explanation is always someone else's responsibility. They blame processes, coworkers, resources or management without taking ownership of their part in the problem.

These behaviours should not automatically lead to disciplinary action. They should lead to a closer look at what is happening and a conversation with the employee.

Related: The Hidden Costs of Undertrained Managers

Start With the Behaviour, Not the Person

One of the biggest mistakes new managers make is making the conversation personal.

Telling someone, “You're difficult to work with,” doesn't give them much to work with. It also invites an argument about whether the characterization is fair. Instead, focus on something you can observe and explain.

For example:

“We've had three project deadlines missed in the past month without advance notice. This has affected the team's ability to meet its commitments. I want to understand what's happening and discuss what needs to change.”

The difference is important. You are addressing specific behaviour and its impact rather than making a judgment about the employee's personality.

Address problems early, but don't rush to conclusions. Take enough time to establish what happened, whether there is a pattern and whether there are factors you need to understand before deciding what action is appropriate.

How to Have a Difficult Conversation

A difficult conversation doesn't have to become a confrontation. In fact, the most effective approach is usually straightforward and calm.

Start by explaining what you have observed. Then explain why it matters.

Allow the employee to respond. There may be information you don't have. Perhaps expectations were unclear, the employee hasn't received adequate training, or a workload problem is contributing to missed deadlines.

Once you understand their perspective, make your expectations clear.

The goal isn't to “win” the conversation. It is to make sure the employee understands the issue, knows what is expected and has an opportunity to improve.

Leadership training resources: Mid-Year Course Correction: The Case for Ongoing Leadership Training

Document Important Conversations

Documentation is an important part of managing performance and employee behaviour.

Keep a factual record of significant conversations, including the date, the issue discussed, specific examples, expectations communicated and any agreed follow-up.

Avoid emotional or subjective statements. For example, “Employee has a bad attitude” isn't useful documentation. 

Documentation also helps managers identify patterns. One missed deadline may be an isolated incident. Six missed deadlines over several months is different.

It also gives HR a clearer picture if the situation eventually requires formal performance management or disciplinary action.

Know When to Involve HR

New managers sometimes wait too long before involving HR. They may worry that asking for help makes them look incapable of managing their team. The truth is it doesn't.

Managers are responsible for managing their employees, but HR can provide guidance when a situation becomes more complicated.

Involve your HR team or HR advisor when issues involve potential harassment or discrimination, accommodation, workplace safety, significant performance concerns, complaints involving other employees, or potential disciplinary action or termination.

Canadian employment requirements can also vary depending on the province, the employee's circumstances and the nature of the issue. Managers should not assume that the same approach applies to every situation.

Getting HR involved early can help ensure that the organization follows its own policies and handles the situation fairly and consistently.