All You Need to Know About Having Difficult Conversations With Employees

Despite a seemingly booming job market (where there are two job openings for every unemployed person), more than 41,000 tech employees have been laid off this year in the US -- and that's just one industry, in one country. Little over two years ago, millions went home on lockdowns -- some to never return to their jobs ever again. Difficult conversations with employees are nothing new -- and they are definitely not limited to layoffs or the tech industry. Yet, these days, it seems that having those kinds of talks at work is just waiting to happen.

How to handle this situation, and what are some of the essential things you need to know about having difficult conversations with employees?

Read on and find out more.

What Are Difficult Conversations at Work?

As a general rule, difficult conversations at work can be defined as any situation where you need to have a conversation with an employee that could potentially result in them feeling upset, defensive, or even leaving the company.

This can include conversations about:

  • Performance issues
  • Behavioral problems
  • Job role changes
  • Disciplinary action
  • Redundancies/layoffs

For instance, you may need to have a difficult conversation with an employee about their job performance if they are consistently not meeting expectations or, in some cases, when you, as their manager, are not meeting their expectations (which, by the way, is a perfectly valid option too.)

Alternatively, you might need to speak to them about their behavior if it's having a negative impact on the team or company culture. For example, if they are regularly coming into work late or taking extended lunches without permission.

There are also conversations at work that are difficult because they involve change -- like telling an employee that their role is being made redundant or that they need to take on a different job within the company.

Last but not least, you may also need to have a difficult conversation with an employee if they have broken company rules and you need to issue them with a formal warning.

Whatever the reason for the conversation, it's important to remember that these are not easy conversations to have. They can be emotional, heated, and sometimes even downright aggressive. For some, they can be so difficult that they would rather avoid them altogether.

However, difficult conversations at work are a necessary part of management and, as such, need to be handled in a way that is respectful, professional, and fair.

exhausted woman after having a difficult conversation

Reasons for Having Difficult Conversations at Work

Nobody likes doing very hard work, and even more so when it's way out of their comfort zone. In fact, research shows that one in four people has been postponing a difficult conversation over the last six months.  Difficult conversations at work tend to be like that: they are hard, emotional, and very uncomfortable for most people -- so don't feel bad if you're not looking forward to having one.

The thing is, difficult conversations at work are an essential part of management. Why? 

Because they help:

  • Maintain standards
  • Build trust
  • Resolve conflict
  • Improve performance
  • Increase engagement
  • Foster a positive culture
  • ... and so on.

Without these difficult conversations, things can quickly start to unravel. For instance, if you don't address poor performance, then it sets a precedent for other employees and can lead to a decline in standards across the board.

Similarly, if you don't have difficult conversations about behavioral problems, then it can foster a culture of disrespect and entitlement, which will have a negative impact on employee morale and, as a result, performance.

And if you don't address conflict head-on, then it will fester and grow until it becomes unmanageable. The bottom line is that difficult conversations at work are an essential part of management and should not be avoided.

What's more, when these conversations are handled in the right way, they can actually have a positive impact on the workplace. For instance, they can help to improve performance, build trust, and increase employee engagement.

Why Does It Matter How You Handle Difficult Conversations with Employees?

The way you handle difficult conversations with employees will have a direct impact on the outcome of the conversation and, in turn, on the workplace as a whole.

For instance, if you go into a difficult conversation with an employee with the sole purpose of "winning" or being right, then it's likely that the conversation will quickly escalate into a confrontation. This will not only make the situation more difficult to resolve, but it will also damage your relationship with the employee and potentially have a negative impact on morale and engagement.

Alternatively, if you go into a difficult conversation with an employee with the intention of truly understanding their point of view and finding a resolution that works for both of you, then it's more likely that the conversation will be productive and positive. This will not only help to resolve the issue at hand, but it will also build trust and improve your relationship with the employee.

The bottom line is that how you handle difficult conversations with employees matters. It's important to remember that these are not easy conversations to have, but they are essential for maintaining a healthy workplace.

"I start by asking myself, What is the purpose of this conversation? If it's to improve performance or resolve a conflict, I need to be clear about what I want to achieve. What are my goals? What are my needs? What am I trying to communicate?

Once I know my purpose, I can begin to prepare for the conversation. This means getting clear on what I want to say and how I want to say it. I also need to think about what the other person is likely to say and how they might react."

-- Jamie Knight, CEO of Data Source Hub

two women colleagues having conversation

Examples of Difficult Conversations at Work

As briefly mentioned and exemplified above, there are many types of difficult conversations you can have at work. Here are some of the more common ones, as well as why having them is so important:


When it comes to layoffs, the key is to be as transparent as possible. This means being honest about the situation and explaining why the layoff is happening. It's also important to answer any questions that employees may have and to provide support during this difficult time. Last, but definitely not least, whenever possible, offering them financial support, as well as learning materials can help them bounce back quicker -- and perhaps have less resentful feelings about their experience with you.

"Letting go of team members is never an easy conversation. Emotions will always be high and sometimes words aimed to hurt are said. This is why when this happens it is best to stick to facts and figures while being empathetic. It sounds like a contradiction but the aim is to stick to what needs to be said but deliver them conscientiously.”

-- Jake Marmulstein, CEO of Groundbreaker

Getting Emotional at Work

We are all wonderfully human, and that's perfectly fine. Unfortunately, however, sometimes our emotions can get the best of us and we can find ourselves getting emotional at work.

If this happens, it's important to take a step back and understand why you're feeling this way. Once you know the root cause of your emotions, it will be easier to deal with them in a productive way. For instance, if you're feeling overwhelmed, it may be helpful to take a break or delegate some of your work. If you're feeling angry, it may be helpful to take some deep breaths or to talk to a trusted friend or colleague.

Likewise, if you are a manager handling an overly emotive employee, it's important to be understanding and to give them the space they need to calm down. Once they're feeling better, you can have a productive conversation about what happened and how to prevent it from happening again in the future.

"Prepare, but don't follow a script. Preparing for a discussion by writing down notes and bullet points may assist. However, it is pointless to spend time writing a script. Your opponent probably doesn't know his/her lines, so when he/she goes off script, you'll be stuck with a dead end and the conversation will become weirdly artificial. Because of this, it's important to have a flexible strategy that includes a repertoire of possible responses, in case things don't go as planned. Aim for simple, straightforward, direct, and unbiased language."

-- Patrick Johnson, Owner of C&H Essentials


If you have an employee who is underperforming, it's important to have a conversation with them about it. After all, if the problem is not addressed, it will likely only get worse.

When having this conversation, it's important to be clear about your expectations and to give specific examples of what the employee isn't doing in accordance with your expectations. It's also important to ask them how they feel about their performance and to give them the opportunity to explain their side of the story. Finally, it's important to come up with a plan of action for how the employee can improve their performance.

"Remember to think about the team as a whole. In performance dialogues, I recommend putting the team's success above any individual's ego. Conduct yourself in a methodical manner; have a first chat that is fact-based, kind, and upbeat. Don't just talk; listen, offer explanations for your reasoning, and solicit feedback. Achieve long-term viability by emphasizing cooperation over dictatorship. Permit the worker to participate in the development of a constructive strategy to enhance their performance."

-- Andrew Priobrazhenskyi, CEO of DiscountReactor

exhausted man working on computer

Why You Should Not Avoid Having Difficult Conversations at Work?

While avoiding difficult conversations at work may be tempting, it's important to remember that doing so will not make the problem disappear. In fact, it will likely only make things worse.

Not only will avoiding difficult conversations prevent you from addressing the root of the problem, but it will also damage your relationships with your employees. After all, if you're not willing to talk about difficult topics, your employees will likely see you as someone who is not open to feedback or to constructive criticism.

Additionally, avoiding difficult conversations will make it more difficult to resolve conflicts and to move forward. So, while it may be tempting to shy away from these types of conversations, it's important to remember that they are an essential part of being a good leader.

Difficult conversations are not just part of the job, but a step towards health -- yours, your team's, and your business'. The more open you can be with your team members, the more you will foster an organizational culture of feedback and respect.

"Trust and respect must be established before challenging conversations may take place. Employees are less inclined to be honest with you if they believe that doing so could put them in jeopardy professionally, financially, socially, physically, or emotionally. Knowing they can openly (but politely) express their opinions without fear of retaliation encourages open dialogue. Maintain an atmosphere where people feel comfortable sharing personal thoughts and feelings. It's unreasonable to expect employees to open up in the future if they've seen bosses stifle their voices or retaliate against them when they've been honest."

-- Michael Dadashi, CEO of Infinite Recovery

Regardless of whether you're a manager, an entrepreneur, or simply a workmate, having talks like these at work can be very distressing. The essential is to keep your cool, go in with a plan, and really aim for genuine, good, open communication. 

Nobody knows how to tackle these situations from the get-go. But empathy and honesty do go a long way in ensuring both you and your interlocutor will come out of the discussion better, more productive, and more keen on making great things happen. 

Topics: Employee well-being

Still using makeshift workplace
management tools?

Join the thousands of forward-thinking companies that use YAROOMS
to manage their workplaces.

Still using makeshift workplace management tools?
Join the thousands of forward-thinking companies that use YAROOMS to manage their workplaces.
Schedule a demo Platform Tour