There are some tough conversations that all employees have with their bosses at some point in their career. This can be hard for both parties, as the employee may feel intimidated by the conversation, and the boss may feel fearful of how their employee will respond to what they are asking them to do.

To ensure an effective workforce management strategy, it is essential to understand what these thirty-one tough conversations are and how you can have these discussions with your employees effectively.

So with no delays, let’s get started with our workforce management guide.

1) Discussion Of Poor Performance

While it’s common to dread difficult conversations, that doesn’t mean you should avoid them. When an employee isn’t performing at his best, it’s hard to have tough conversations and address poor performance as a manager.

Some things you could say include: “I’m sorry to have to bring this up, but I’ve been noticing that your performance has been slipping lately,” or “I know you may not be happy with this, but I think it might be time for us to discuss an improvement plan.” You can include factors like:

  • Performance affected by over breaks
  • Performance affected by low productivity
  • Performance affected by procrastination

Even so, it’s what your job demands as a manager. It’s your responsibility to hold employees accountable for their actions. You may not enjoy having tough conversations with employees, but they are necessary in order for everyone involved to grow professionally. After all, if you don’t have these tough discussions when things aren’t going well, how will they ever improve?

2) Request An Overall Review

As a manager, you should be able to ask for an overall review of your employee’s performance. This will give you a good idea of where they are at the current moment and where they need to improve. It also allows them to ask for feedback on their performance and how they can improve. For example as a manager, you can have a discussion like:

I would like to review your overall performance. I feel like you have been working hard and meeting all of your goals, but I want to make sure you are on track. Let’s schedule a time to sit down and go over your progress?”

Points that discussion can include are

  • Overall productivity
  • Time spent per project
  • Total milestones achieved

If you have concerns about their performance, you can also use that time to discuss them. It can be a bit difficult to ask for a complete review from your employee, but it is essential to do so in order to keep track of their progress.

3) Dealing With Bad Attitude

A bad attitude is a tough situation to face. However, you have to have tough conversations with your employee in order to solve the issue. As a manager, you have to deal with your employees’ lousy attitudes and have conversations with them to bring them back on track.  For example, you can say:

I’ve noticed that you’ve been having a lot of attitude problems lately. Your attitude has been really causing problems in the office. We’ll have a meeting next week to talk more about this. Points you can include

  • continuously coming late
  • Rudeness
  • Not following their work responsibilities.

Communicate with your employees to know the reason behind their bad behavior. If they face any issues or problems, then try to solve them as soon as possible. Make sure whatever conversation you are having with your employee must be kept confidential. You should always keep these tough conversations positive and constructive so that you can benefit from them.

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4) Firing An Employee

You’ve already laid out your plan to provide needed support and encourage your employees to remain on board while transitioning into their new roles, but what happens if they quit?

If your employee quits in anger or because you’ve asked them to leave, it can be a significant blow to morale. Be prepared for situations like these to remain professional during a difficult conversation.

Here is an example of communicating this difficult news while maintaining a respectful and positive relationship with the employee.

“Hi Sam, I wanted to have a conversation with you about your job performance. Recently, your work has not been meeting our standards. Unfortunately, we’ve decided that it’s time for us to part ways. We will be terminating your employment effective immediately.

We want to thank you for your contributions during your time here, and we wish you good luck.

Handling these tough conversations with employees head-on will help ensure an effective workforce management strategy and keep your business running smoothly.

5) Termination Versus Resignation

Termination Versus Resignation

Sometimes a job isn’t working out, and there’s no quick fix in these cases. It might be time to consider letting someone go. It may not feel like your finest hour as a manager, but these difficult conversations can strengthen team dynamics over time if handled appropriately. Example of Termination Versus Resignation as a manager is mentioned below.

  • A resignation is when an employee provides notice to their employer that they will be leaving their job.
  • A termination, on the other hand, is when an employer dismisses an employee from their position.

When terminating an employee, you need to follow strict legal guidelines and will also want to remain tactful. When it comes to discussing resignation, employers should always respect their employees by offering alternative options.

Read: Work Tracking: How To Introduce Time Tracking System To Your Team?

6) Handling Employee Absences

Every once in a while, your employees will have to take time off for personal reasons. It is something you have to consider when you manage a workforce. For instance, you can have a direct conversation with the employee as below.

“I noticed you were absent from work last week. Can you tell me what happened?”

Fortunately, it’s easy to handle employee absences effectively by planning ahead and being open to a constructive discussion with your employees. Communication can go a long way in managing employee absences, and if you don’t communicate properly, things could get messy quickly.

7) Discussing A Problem Payroll Issue

If your employee has a problem with their paycheck, it can be uncomfortable. Payroll is out of your control and very complicated. Difficult conversations can easily turn into heated discussions.

For example, if an employee has not received their correct pay or has had incorrect deductions made from their pay, you’ll need to discuss this with them.

Try to remain calm as you listen to their issue and make sure you understand exactly what’s wrong before proceeding forward. You don’t want your emotions taking over and turning a simple payroll problem into a massive fight between you and your employee.

As a manager, you have a responsibility to help resolve any problems that may arise in your department. Ensure they know that you’re there for them and that they should feel comfortable coming to you if there are any issues with their paychecks or other department-related problems.

8) Handling Co-Worker Complaints

The key to handling co-worker complaints as a manager is to, first and foremost, focus on your relationships. If you’re able to manage difficult conversations to keep your relationship intact, you’ll be able to resolve problems before they become major issues. For example, as a manager you can say

We are getting a complaint from your co-workers that you bother them. They feel like you always put them down and devalue their work. Can you explain the reason for such behavior?

By interacting with your employees honestly and respectfully, you can ensure that any complaint will be heard. This approach will provide better results for everyone involved and help build trust between you and your team.

9) Employees Coming Late And Leaving Early

Employees Coming Late And Leaving Early

When it comes to dealing with employees coming late and leaving early, your role as a manager is a delicate balancing act. You want to maintain your employee’s trust, but you also need to ensure that work gets done and on time.

First of all, try talking to them about their tardiness and poor attendance. Make sure they understand that their behavior is affecting others in their department. For example, you as a manager can say:

I’ve noticed that you’ve been coming in late and leaving early lately. Is everything okay?

The best way to handle an employee coming in late or leaving early is through clear communication. If you notice these issues continuing after a conversation, you may have to take serious action if things don’t improve quickly enough.

Learn: Productivity vs. Efficiency: Which One Matter More in the Workplace?

10) Being Dishonest

No matter how much people lie to themselves, every business has dishonest employees. If you manage a business with many employees, chances are some of them are going to be dishonest.

How you deal with dishonesty is one of the important things that managers need to look after.For instance you can say:

I’m really disappointed. This kind of behavior is inexcusable. It not only hurts the company, but it also hurts your fellow employees who are working hard and playing by the rules.

As a manager, it’s my job to ensure that everyone is doing their part, and when someone breaks the rules, it creates an unfair playing field.

A dishonest employee can’t be stopped from speaking or fired. In that case, you’ll have to work with them on areas where they aren’t being dishonest for things to keep moving forward, and it’s up to you as their manager to figure out what these problem areas are and address them appropriately.

11) Clarify Their Responsibilities

When there are problems, it’s good to start by clarifying employees’ roles and responsibilities. Sit down with your employees and describe their duties in detail. Example of such communication is:

Hi John, thank you for coming in today. I wanted to clarify the duties and responsibilities you will be having for the upcoming projects.

Talk about it openly, so everyone agrees. This can help prevent confusion if any issues arise and make sure expectations are clear from day one.

 12) Discussing Failures

When a failure does occur, managers need to be open with their employees. Discussing failures is always uncomfortable, but they are also important. As difficult as it is for you as a manager, discussing failures can help your team learn from mistakes and grow stronger. You can say:

I’m sorry sid, but I need to talk with you about your recent work performance. You’ve been missing deadlines, and your work hasn’t met our standards. I know you are capable of more and with a bit of hard work you can make it.

By encouraging an environment of openness and honesty between employees and management, you’ll build trust in your team that will only benefit them in the long run.

13) When An Employee Wants To Quit

As a manager, interacting with an employee who has decided to quit the job can be difficult. In most cases, managers would prefer their employees to stay on board.

The first step to dealing with this is listening and understanding why they want to leave. For example you can say:

Thank you for coming to me with this. Can you tell me more about why you’re thinking about quitting? Is there anything I or we can do to change your mind?

You should ask if there is anything you could have done differently or if there are any issues that need to be addressed before they leave. By doing so, you will ensure that your relationship remains positive and professional.


Also Read: Employee Monitoring & Data Confidentiality Practices


14) Discussion With Your New Hire

The first day of a new job is never easy for either party. You, as an employer, have a lot of responsibility to take on right off the bat. You’re tasked with teaching your new employee how things work around here and getting them up to speed in their respective role. here is an example of what you could say as a manager when meeting with a new employee:

“I’m glad to have you aboard. I’m excited to work with you and see your skills in action. So far, what are your thoughts on the job and how we can make the most of your time here?”

Make sure you don’t rush into it. Instead, taking your time will help you get to know your new hire better, but it will also make that first conversation easier and help the new employee feel more comfortable in their new position.

15) Negotiating Salaries

Negotiating Salaries

If you are an HR department manager, you have to negotiate salaries for new hires. This can be a difficult conversation, but as a manager, you should understand that it is your responsibility to ensure that both parties (employer and employee) are satisfied at the end of negotiations. Here is an example of such communication

“We’d like to offer you a salary of $X. We feel that this is a fair and competitive amount, given your skills and experience. Are you comfortable with this salary? Is there anything else you’d like to discuss?”

Having proper communication during these negotiations will ensure that both parties feel respected and heard. The most important thing to remember in salary negotiation is that it’s not about winning or losing. Instead, it’s about finding common ground on which both sides agree.

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16) Accountability Discussion

Accountability Discussion with employees as a manager can be difficult, but it needs to happen. Being a manager is all about making sure your team is on track and working towards goals. For example, as a manager you can say:

I noticed that you didn’t submit your project on time. Can you tell me why this happens so frequently?

One of those goals should ensure that each employee is accountable for their actions and decisions at work. It’s essential to have regular meetings with your employees to hold them accountable for their work and discuss any issues they may have that could affect their performance.

17) Career Changes Discussion

Your company might value loyalty and dedication, but your employees might need more from you. The career conversation is one of the difficult conversations a manager can have with their employees.

But it’s also an important one to have. It’s natural for people to want to grow professionally, and if they don’t feel like they are growing at their current job, they may seek opportunities elsewhere.

So how do you tell someone that their role at work will be changing? Here is an example:

Hello Kim, I wanted to touch base with you about your career goals. You mentioned wanting to transition into a different field and I just wanted to check in and see how that’s going. Are you still interested in making a change?

By interacting with your employees daily, you’ll likely get a sense of when they might look for career growth. If you notice ‌an employee is unhappy in their role, consider having a conversation about it and offer to help them explore other opportunities within your company or elsewhere.

18) Business Transfer Discussion

When a business transfer has been proposed, it is common for employees to feel nervous about their future in their company. This can lead to difficult conversations with managers and confusion over whether they will be kept on after a transfer or as part of a business sale.

In this scenario, you as a manager should discuss with your employee regarding their employment status, if any changes are expected in terms of structure or management, and how any changes may affect them personally. You can say:

We’d like to thank you for your time with the company, and we’re sad to see you go. However, we have decided to transfer you to another branch. We hope that this new opportunity will be a good fit for you.

You may want to consider having regular meetings with each employee that discuss progress on objectives, performance issues (if any), etc so that everyone is aware of where they stand within your team.

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19) Removing Staff Members From The Team

Removing staff members from the team can be a difficult conversation to have as a manager. It may be best not to personalize the discussion by focusing on the employee’s behavior. Instead you can say

Thank you for joining our team. We wanted to discuss the removal of some staff members due to some organizational reasons. We appreciate all your hard work until this point, and we wish you good luck in the future.

The best way to do that is to address it as an overall problem rather than just the person’s behavior, which can help ease tension and help build understanding among all parties involved.

20) Giving Feedback On Performance

Giving Feedback On Performance

Giving feedback on performance is not an easy task. If you’re a manager and you give feedback, it can be difficult to approach your employee for a conversation about performance, but if it’s necessary and done well, good things can come from it.

Example of such conversation can be:

Hi Jim, As per our conversation earlier, I wanted to follow-up and give you some feedback on your performance. I noticed that you were a little slower than usual this week and I wanted to ask if there was anything that was going on that we should be aware of?

When giving feedback on performance as a manager, it’s essential to have open communication with your employees to know where they stand and need to improve their work.

21) Staff Burnout Discussion

Burnout is something that all employees face at some point. It’s important to recognize and address burnout before it can impact your work or productivity. One easy way to do so is to ensure you’re having open and honest discussions about topics like staff burnout as a manager. As a manager you can say

Hello everyone, I wanted to take a moment to discuss staff burnout with you all. I’ve noticed that you have seemed more stressed out lately, and I wanted to know, is there anything I can do to help support you?

These difficult conversations are meaningful because they help your employees feel heard, valued, and trusted. These are crucial elements in increasing employee morale and well-being, ultimately leading to increased productivity and job satisfaction.

Read: Work from office vs. Work from home vs. Hybrid: What & Best for Your Workforce?

22) Reassignment Based On Performance

Reassignment can be a difficult conversation to have, but an organization needs to manage its talent and achieve success. You may need to reassign your employees based on performance. This is hard because you tell them that they are not meeting expectations or goals.

However, if you don’t do it, they will never improve, and you will have to let them go. This is a tough conversation because most people don’t like being told that they aren’t good enough or aren’t doing well at something. But as a manager you have to take a responsibility you can say

Hi, Adam, I wanted to let you know that we’ll be reassigning you to a new team/project soon. This decision is based purely on your performance during your last project. We believe that this will help you reach your potential and be more successful in the long run.

If you want your business to succeed, you should politely tell them what they need to work on and give them some time to improve. If they still haven’t improved after a certain amount of time, you will need to let them go.

23) Dealing With Unproductive Employees

As a manager, you may have to deal with unproductive employees, which can be a difficult conversation. In such situations, it’s essential to remain calm and approachable. Your communication as a manager can be

“I’ve noticed that you haven’t been meeting the production goals we set for you. Can you tell me why that is?” Can you share what’s been causing the difficulty?

Try reaching out to your employees in person or over email before calling a meeting and asking other managers for tips and ideas about managing unproductive employees effectively. It is always better to help your employees by identifying what could be causing their low productivity than dealing with them in anger.

24) Discussion On A Tough Project Assignment

Good managers like to challenge their employees. They know that when employees take on projects that seem too difficult, they grow more comfortable taking on more complex assignments down the road.

So when you assign a new task to an employee, it’s essential to be honest about how challenging it will be and why you feel they are suitable for the challenge.

This is one of the difficult conversations with your employees because it also requires you to give them specific feedback about what needs improvement and exactly how much effort it will take to accomplish your goals. Example for such communication can be:

Hi Everyone, I wanted to let you know that we have been assigned to a new project due to our knowledge and skills. However, this project will be a bit difficult, but with the support of each other, I am sure we can do it.

If done correctly, these difficult conversations can make all parties better in the long run.

Learn: Strategic Human Resource Management: What is it and how can it benefit your organization?

25) Ask For More Responsibility

Asking employees to take on more responsibilities can be difficult. But, if you’re a manager and want your team to grow and succeed, you must ask for more commitment from them.

This conversation can be a bit tough, but it will get easier once you initiate the conversation. You can initiate your conversation like:

Hey, I’ve noticed that you’re doing a great job with your current tasks. Would you be interested in taking on more responsibility? I think you would be ideally suited for it.

You may even find that your employee is excited about taking on new challenges and feel confident in their ability to handle them with support from you.

26) Career Growth Plans

An employee asking for continuous career growth can be a difficult conversation to have. If you’re an employer, it’s your job to help your employees grow and develop professionally by having a fine discussion about their professional goals and helping them plan out how they will achieve those goals. You can say

As per our discussion about your career growth, I have put in a good word for you and see if we can get you started on the next steps. Thanks for being so proactive about your career development.

This is good for your employee, and your business as employee engagement is linked to increased productivity, reduced turnover rates, improved customer service, and higher profits.

Learn: On-Premise or SaaS: Which is Better for Your Business?

27) Asking Employees To Wear Appropriate Work Attire At The Office

All workplaces have their formal attire code, and as a manager, it is your responsibility to ask employees to wear proper work attire at the office. If you are not doing that, and if you wish to change it now, then make sure you handle it professionally. You can say:

“Hello everyone, We would like for all staff to dress in formal attire while at work. This includes collared shirts/blouses, dress pants/skirts/ dresses, and closed-toe shoes, etc. If you have any questions or concerns, please let me know. Thank you.”

Have a formal discussion with the employees. Explain why you want them to wear formal attire at the office, and then make sure they understand how their dressing impacts others around them.

28) Lack Of Teamwork

If you notice a lack of teamwork, it might be because your employees think they don’t have any say in what happens around them. Sit down and talk to them about how they feel. Ask open-ended questions to get a better idea of what is going on. A good way to start might be

I noticed that we worked really well together as a team when we were able to delegate tasks evenly, and everyone was on the same page. I think it’s important for us to continue working that way because we have been slightly less productive since last week.

As a bonus, if your employees know that you care about them personally, they will be more apt to care about their work and help you succeed.

You may also evaluate how you’re delegating tasks and setting goals to ensure your workers are on board with your strategy for growth and success.

29) Handling Diversity Issues

In today’s workforce, it is essential to maintain an open line of communication among employees of all backgrounds. Part of an effective workforce management strategy includes diverse team building, meetings, and overall employee engagement.

When one employee feels their voice isn’t being heard or that they are not valued on a team due to diversity, problems can occur. However, a good example of communication of diversity issue might begin like this:

I want to talk with you about something that’s been bothering me lately. It seems like we’ve been having some problems with communication and respect for each other’s culture in the office. I think it would be really helpful if we could talk about what’s been going on and see if we can do anything to improve things.

With proper communication skills, you as a manager can address these issues before they grow into something bigger.


Also Read: How To Measure Productivity Of Employees


30) Employees Having No Passion For The Job

If you’re having a hard time connecting with your employees or feel like they’re not showing any motivation to do their best work, try to have a conversation with them about their lack of passion.  Here’s an example of how the manager can begin communication with an employee who lacks passion for the job.

Hello Jane. I noticed that you didn’t seem as engaged as usual during today’s meeting and tasks. Is there anything going on that you’d like to talk about?

Explain that it’s essential for everyone in the office to be passionate about what they do, as it will lead to better results for everyone involved. Ask them why they don’t seem interested in what they do every day and see if there are any ways you can help improve their situation or increase their passion for working at your company.

31) Demoting An Employee

One of the most challenging conversations you will have as a manager is telling employees that their performance isn’t up to par and needs to be demoted. Before making such a bold move, make sure you have documented all previous warnings, reprimands, and attempts at coaching your employee on how to improve. This interaction can begin like:

I’m sorry Alex, but I’m going to have to demote you. Your performance has been slipping, and I need to make some changes to improve the team’s overall productivity. I know this is a tough pill to swallow, but I hope you’ll be able to pull yourself together and continue to contribute positively.

Sit down for a formal meeting where you can explain why they are being demoted and make sure it’s clear why they deserve another chance to improve before being let go.

Workstatus- The Best Employee Time Tracking And Productivity Tracking Software


Workstatus is the best employee time tracking software that helps managers to have difficult conversations with their employees with strong facts. Workstatus offers a simple way to track and manage your team’s productivity, and You can easily see how much time they spend on different tasks, get detailed reports and know what they are working on at any given moment.

With the Workstatus workforce management system, you can understand the overall workforce performance and status. You can measure work performance, track employee time online and offline, calculate the revenue generated by employees, and create detailed reports on activity in real-time.

Overall, Workstatus productivity tracking software is an excellent tool for tracking employee time and performance. The best thing about it is that it will save you a lot of time because you won’t have to do anything manually. Its productivity monitoring feature gives you an overall view of your team’s performance and allows you to manage them more effectively.

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As an entrepreneur or manager, making tough decisions and having difficult conversations is a fact of life. These unpleasant but necessary aspects of business won’t go away, and if you don’t learn how to deal with them effectively, they can become more stressful and anxiety-inducing than they should be.

So it’s important to know what you need to do to have these difficult conversations as professionally as possible. While there’s no way to guarantee that every difficult conversation will end happily ever after, knowing strategies for keeping things professional can help minimize stress and make sure everyone comes out on top.

By understanding your role as a leader and being prepared to handle difficult situations head-on, you can keep your team productive and happy while still accomplishing your goals.


Q1 – What is a tough conversation?

In a business setting, tough conversations typically refer to firing or laying off employees. Other tough situations might include performance reviews or disciplinary action. If you’re a manager, supervisor, or HR, part of your job is to perform these unpleasant but necessary conversations when required.

When you know how to handle them effectively and avoid making them worse, you can get through them and move on without damaging anyone’s morale or causing additional problems for yourself and your company.

Know more: How Workstatus Can Help You In Flextime Management?

Q2 – What are some difficult conversation topics?

Here are ten tough conversations that every manager should be prepared for:

1) Performance Review

2) Disciplinary Action

3) Termination

4) Layoffs

5) Raises

6) Career Advancement

7) Poor Behavior

8) Conflict Resolution

9) Reassignment

10) Retirement

These conversations can be difficult, but they are necessary for an effective workforce management strategy. If you’re a manager, it’s your job to have these conversations and manage these issues respectfully for all parties involved.

Q3 – What are the 5 Tips for Handling Difficult Conversations at Work?

Here are five tips for handling difficult conversations at work:

  1. Preparation is key. Before heading into a difficult conversation, think about what you want to say and how you want to say it.
  1. Be direct and honest. Don’t beat around the bush or avoid addressing an issue that needs to be discussed. Be direct and straight to the point.
  1. Listen and be empathetic. It’s easy to get caught up in your thoughts during a difficult conversation, but don’t forget to listen to what your employee has to say. And, if possible, try to put yourself in their shoes and be empathetic.
  2. Don’t be afraid to apologize. If you’ve made a mistake, don’t be afraid to apologize. It shows your employee that you value their opinion and are willing to own up to your mistakes.
  1. Have facts-based conversations. When you’re having a difficult conversation, it’s important to have facts to back up your statements and opinions. It will help ensure that any decisions made are based on facts rather than emotions.

Many difficult conversations can arise in a workplace, but these five tips will help you handle them effectively. You’ll be able to approach these conversations head-on and provide constructive feedback to your employees, ultimately leading to a better working environment for everyone.