5 Difficult Conversations Managers Hate To Have

No employee wants to hear “you’re fired” or “you’re not getting a raise,” but it’s no picnic for the manager either.

5 Difficult Conversations Managers Hate To Have
[Colorful speech bubbles: Mark Heider via Shutterstock]

From delivering poor performance reviews to telling someone that their coworkers have been complaining about them, no one likes to be the bearer of bad news, but as a manager, it’s likely that you’ll face at least a few instances where you’re required to confront an employee.


Fears that employees will become angry or even cry can be paralyzing. Donna Flagg, founder of The Krysalis Group, a New York-based consulting group and author of Surviving Dreaded Conversations, says delivering bad news is something many of us are not socialized to do. Here, she offers some tips on dealing with some of the most common difficult conversations.

1. “Your performance is lacking”

Wouldn’t it be wonderful if all employees performed exactly to the standard that we would like them to? The reality is, most managers will at some point in their careers have to deliver a poor performance review. While giving negative feedback can make anyone nervous, Flagg says the best way to deliver this news is to think about the message as being beneficial to the individual’s growth and development.

“In my career, I’ve always appreciated when people tell me what I’m doing wrong so I can do it right,” she says. Reframing the criticism as something valuable that will help the employee grow and develop, rather than a negative critique will not only help you deliver the message, but help the employee to absorb it.

2. “You’re fired”

Whether letting go of an employee due to poor performance or company restructuring, terminations are never easy. “It’s an emotional conversation,” says Flagg. “You’re changing someone’s life. You’re changing their sense of security.” While saying “you’re fired” Donald Trump style may seem like the best way to rip off the Band-Aid, Flagg says the best way to deliver this news is to go into the conversation sensitive to the effect that your words will have on the individual being let go.

“You don’t want to come off robotic or cold,” says Flagg. “I’ve seen people who are so uncomfortable with firing an employee that they exacerbate the problem because they go in looking unfeeling.” The most important thing to do during a termination, says Flagg, is to allow for processing time. Offer your emotional support–whether that means staying and talking it out or leaving the room if they would like some time and space to digest the news.

3. “You didn’t get the promotion (or raise) you applied for”

Denying an employee an increase in salary or position can be difficult, especially if you really want that employee to stay in the company. Managers often fear this conversation because they worry the employee will immediately want to jump ship.


Flagg says providing an accurate picture of the context is essential here so the employee understands why they weren’t offered the promotion or raise, so start a dialogue about how you can help them to work toward their goals.

4. “Other employees aren’t getting along with you”

First of all, says Flagg, never identify who has complained about a fellow employee. “The first thing they’re going to say is ‘Who told you that?’ and the answer is ‘It’s not important’,” she says.

Instead, Flagg says, the best thing to say is that you’ve been getting some feedback about the employee’s behavior and you want to make them aware. If the issue involves sexual harassment or bullying, though, Flagg says it’s best to first involve HR and the company’s legal team before confronting the individual.

5. “You haven’t been acting like yourself lately”

Sudden changes in behavior–such as coming into work late, or falling asleep at the desk-–can raise red flags around the office. Is this employee struggling with a mental health issue? Is there a problem at home that’s affecting their work performance? Tackling this issue is a lot easier, Flagg says, if managers have established relationships with employees. “If you don’t have a relationship, it might feel intrusive [to ask about one’s personal life],” she says.

A company culture that appreciates that people’s personal and work lives are interconnected is also important. These conversations are much more difficult to do in a company where the old-school mentality of “leave your problems at the office door” still resounds.



About the author

Lisa Evans is a freelance writer from Toronto who covers topics related to mental and physical health. She strives to help readers make small changes to their daily habits that have a profound and lasting impact on their productivity and overall job satisfaction.