Difficult Conversations At Work: Scenarios, Skills, and Exercises For New Managers

As a new manager, you will start having difficult conversations at work. How do prepare? Gather skills, scenarios, and exercises.

Are you a new manager who’s dreading the thought of having the difficult conversations that come with the role? Rest assured, you’re not alone. In fact, 69% of managers are uncomfortable giving feedback. 

The cause of today's workplace discomfort stems from the rise of remote working, as organizations struggle to balance flexibility with company culture and adjust to the overall shift in workplace dynamics since the pandemic. 

But, there will always be discomfort of some kind.

Having difficult conversations with employees is something everyone wants to avoid. The truth is that difficult conversations will occur in every single team and across every single service vertical. 

You might be a sales manager leading a commercial team of confident and productive employees, but that doesn’t mean you won’t be subject to difficult conversations. 

These conversations can be a result of a myriad of things, such as: 

  1. Conflicts because of different personality types in your team
  2. Behaviors and actions that don’t align with the business’ vision of success 
  3. Gaps in performance, motivation, or skill

Learning how to navigate those conversations will be an important part of your management skills arsenal

Which, granted, may need some training. But where some people train skillset, at Krauthammer we train behavior


Because carrying out these difficult conversations is about having a mindset based on learning and optimism.  

With that, we’re first going to tackle the exercises you need to carry out a conversation. Then, we’ll play out some scenarios to help you prepare for the real world. 

For more robust and personalized training on difficult conversations, Krauthammer’s offers a management course. 

How to prepare for difficult conversations with employees

It’s completely natural to feel nervous before entering a difficult conversation with an employee. However, arming yourself with the right tools can be a great way to offset those nerves. 

The good news?

These kinds of tools are plentiful, and can be leveraged to prepare your behavior and mindset. Here are four of our favorites. 

4 of the best difficult conversation exercises 

1. Talk to yourself

Talking to yourself may sound silly, but having an internal conversation about the situation before facing your employee, gives you an opportunity to ask questions that not many managers ask: 

  • Why is the thought of the conversation making you uncomfortable? 
  • What exactly is it that’s worrying you? 
  • Are you afraid of ruining a relationship you’ve worked hard to build? 
  • Are you worried about driving conflict, rather than resolving it?
  • Are you afraid that you lack the skills to communicate effectively? 

It’s vital to understand your own feelings about a situation. Especially if you want to try and understand the feelings of others. 

By knowing what’s bothering you, it becomes easier to take measures to make yourself feel more comfortable, confident, and courageous

2. Talk to someone else

One of the very best pieces of advice that new managers can take onboard is that the conversation you have with the person involved should look a lot like the conversation you’d have with someone else ABOUT that person and about that situation. 

For example, imagine you’re going to have a conversation about the situation with your organization’s HR manager. You wouldn’t blame them for what’s happened; you’d be more likely to:

  • outline the situation, 
  • stick to the facts, 
  • discuss possible resolutions. 

This is what a real-life difficult conversation should look like. Facts and logic should override emotion and blame. 

Collaborating with HR can be hugely beneficial in helping you to separate the emotional side of the situation from the logical one. 

3. Word association

Have a quick think about what it is you want to say in the conversation, and note down some of the words that you’ve used. A word association game is a fantastic difficult conversation exercise that can help you keep things under control. 

Once you’ve written your list of words, jot down associated words and phrases. How do they make you feel? 

You may have planned to say that ‘Annika feels isolated’, but the word ‘isolated’ can have negative connotations… how might your employee react to this?

Instead, it may be more appropriate to say ‘Annika feels as though she is unable to participate or contribute’, which gets the message across without assigning blame. Specific words use may seem trivial, but it communicates more than you may realize. 

4. Roleplay

Many managers – and employees – break out in a cold sweat when they hear the words role play! 

But in this situation, role-playing doesn’t necessarily mean mapping out the entire conversation from start to finish. 

It’s more about being able to anticipate what could happen in a range of possible scenarios and picking out questions that your employee is most likely to ask. This gives you a chance to be prepared, and have the answers to these questions ready to offer. 

Write down possible scenarios and prepare responses to them. This links with the first part: Talk to yourself. 

Roleplay does play a big part in anticipating scenarios as questions can arise as a natural part of each scenario. 

Questions are not always easy to determine simply from thinking about the situation from an outside perspective – you need to be involved in it. 

Difficult conversations: Two roleplay scenarios

Having a difficult conversation won’t just make you a bystander in ‘bad news conversations’. You’ll actually lead these conversations yourself – yikes! Nobody wants to be the bearer of bad news. 

On top of it all, carrying out difficult conversations is a huge responsibility. The board will almost certainly be watching to see how you handle things. 

While no one enjoys this aspect of the job, it is part and parcel of being a manager and can make or break your efforts to build a good team culture: How you handle the bad news will shape how your team thinks, feels, and behaves overall. 

Let’s take a look at two real-play scenarios by, 

  1. analyzing the original behavior,
  2. exploring how to do better through observation and training. 

Difficult conversations scenarios

Scenario #1: An employee is speaking to and about another employee (Rob) in a disrespectful way 

What you would normally say: I don’t like the way you’re speaking to Rob in that tone. Please stop. That’s not the way you talk to someone. I won’t allow it in the future. You should apologize to him. 

Your goal in this context is to realign your employees’ behavior, right? But this kind of interaction is likely to make the employee feel:

  • Defensive
  • Unappreciated
  • Misunderstood

That’s why the most important question you can ask yourself before trying to align someone’s behavior is, “what is my mindset?” 

The more conscious you are of your mindset and how it causes you to behave, the clearer your goals become – and the closer you get to achieving them.

In fact, we’ve written an entire ebook around this. Reading Manage Your Mindset will help you even further when it comes to getting clarity on how this works in practice. 

Let’s rewind our first scenario. Here’s what it should look like. 

What you should say instead: Hi, do you have a second to talk about what happened with Rob? I wanted to let you know that I appreciate how hard you’ve been working on meeting your sales quota this quarter, and it hasn’t gone unnoticed. 

I know you snapped at Rob because you really want the rest of the team to meet these targets. But maybe in the future, you could approach Rob with more empathy – he’s also under immense pressure to close his sales so that the whole team can meet their targets. How do you feel about apologizing to him so he feels heard?

Something like this will make your employee feel valued. You can empathize with your employee’s situation and show him how to empathize with Rob too. Plus, you’re asking him to apologize – an end resolution that is a request, and will prime a response on your employees part. 

Having a culture built on empathy and understanding is always better than having one built on giving a ‘good telling off’.  

Scenario #2: An employee is continuing to work remotely when company policy dictates a 50%-only remote work 

What you would normally say: Our company policy dictates a 50%-only remote work. You’ve been abroad for longer, so please stop doing this. Next time you want to work abroad, let your manager know.

Again, this situation seems, on the surface, to lead to results. In other words, your employee really has no choice and will stop working abroad.

But it will also breed discontent and mistrust. It may also lead to questions about why they can’t work abroad which may make them feel they are not trusted to complete their work. 

What you should say instead: I understand that with previous COVID uncertainty, our remote work policy wasn’t clear. Now that we understand the trajectory, we feel it’s important for the company culture that we see each other at least 50% of the working week in person. This, of course, should be done in a healthy and safe way to ensure you are comfortable working alongside others. If there is something that’s making you feel uncomfortable, please let us know. Otherwise, would you be willing to let us know in the future what your working abroad schedule looks like? Maybe we can find a way to manage everyone's time better. 

In this second scenario, you’re actually pinpointing why your colleague/employee isn’t adhering to the company policy. In a real-life setting, of course, you would ask them the right questions to determine this why. This scenario would look more like a conversation. 

Because the more you can understand where a person is coming from, the more you can help them overcome their challenge.

After all, whatever your challenge is, it’s likely your employee is facing a similar challenge that needs coaching by you – as their mentor or manager – to tackle.   

Difficult conversations at work might just be the thing you need 

At Krauthammer, we advise trainees to assess the ABCs:

  1. Exploring your behavior
  2. Changing your attitude
  3. Becoming capable 

If you’re afraid of these difficult conversations, why do you think that’s the case? If you react in a certain type of way to an employee, why?

Asking why to determine your behavior is the first step. This requires a lot of rational thinking to get to the crux of your self-reflection. 

When you can assess your own behavior, you’ll stop getting in your own way. 

Common behaviors we’ve seen managers exhibit are:

  • Lack of confidence 
  • Need for harmony
  • Fear of risking relationships 
  • Anxiety around making things concrete

Need help spotting these behaviors? Reenacting difficult conversation scenarios will help. That’s what we start with at Krauthammer, to give you enough training to take this out into the real world. 

It’s all about you

You may think that difficult conversations are about your team. They’re not. They’re about you. 

If you lack the courage and confidence to engage in difficult conversations, it’s possible that difficult situations may not be resolved, or may not be resolved in the way that you were hoping.  

Which can significantly affect the culture and performance of your team. 

Handling a challenging situation poorly can be more detrimental than the situation itself in terms of keeping your team happy and achieving your goals. 

Start today by working on your own skills so you can communicate with effectiveness and help nurture the performance of your team.

Future of Sales