How to Have Difficult Conversations with Your Employees (with Examples)

How to Have Difficult Conversations with Your Employees

Have you ever been in a situation at work where you knew a difficult conversation was due? Maybe you’ve found yourself even avoiding one (or many). Does just the thought of needing to have a difficult conversation with a colleague, a manager, or an employee make you break out in cold sweats? Well, if this is you, you’re definitely not alone.

Avoiding conflict or simply avoiding saying the tough stuff in the workplace can be the natural tendency for most people. But when we shy away from difficult conversations, things don’t improve, teams start to feel disconnected, and when things go wrong, people start blaming and finger-pointing.

So how about we try and turn this mindset on its head and consider difficult conversations not as something that needs to be avoided at all costs, but as a preventative measure instead?

‘Preventative measure’ for what, I hear you ask? Simply, to prevent further problems. Because difficult conversations (the types people fear or tend to avoid) can be essential to preventing issues down the line. And when handled well, they can be a greatly positive experience for everyone.

In fact, knowing how to navigate difficult conversations ethically and effectively is hugely beneficial for building a business that champions an open honest and communicative culture.

So let’s look at some difficult conversation examples.

Examples of Difficult Conversations

Two men in office looking at document

Giving negative performance feedback

According to this article, giving feedback on poor performance features in the top three of the hardest conversation types you may ever need to have in the workplace. And if you’re curious, it’s up there with discussing pay or a colleague’s inappropriate behaviour. You know, the proper crunchy, nausea-inducing stuff.

But if you’re a manager or leader of people, I’m sure you’ve been there. Whether you’re sitting in a formal quarterly or end-of-year performance review with your employee or you’ve received negative comments from others in the company (a colleague or a stakeholder), giving someone in your team less-than-stellar feedback can be daunting. And knowing how to have difficult performance conversations doesn’t come naturally to everyone.

Yet, providing constructive criticism is absolutely necessary to build a strong performing team who can deliver on their individual and company objectives. When done ‘in the right way’ with as much truth and clarity as there is kindness and empathy, giving negative feedback can show your team that you’re an honest and supportive leader with their best interests at heart. And that’s not so bad, right?

Addressing personal hygiene or dress code issues

This can be a tricky one – the more personal the topic is, the harder it can be to know how to best approach it. Giving someone feedback about their body odour or poor hygiene can feel awkward, but the key here is to stay factual (how does it affect the business or the people around you?) and certainly to avoid any shaming or judgement.

Talking about adherence to the dress code can be easier, especially if you can quote the policy. But always be mindful of bringing an empathetic ear to the conversation. After all, you don’t know what personal circumstances someone might be going through, and you want to do your best to help them feel comfortable enough to tell you their side of their story. Can you meet them with genuine positive regard and curiosity as you share what you need to tell them about the dress code? And can you work with them to understand what they feel they might need in order to feel comfortable dressing as the company requests? Maybe then, you can even offer some help or suggestions.

Handling conflicts within teams

Another example of a difficult conversation that might arise in the workplace is handling conflict within a team or between separate teams or departments. Sometimes people’s personalities, attitudes, or points of view clash. Other times it’s about diverging company requirements or objectives. Whatever the reason for the conflict, leaving it unaddressed can only make matters worse in the long run.

Instead, by focusing on the positives, such as the different perspectives and knowledge that different team members or groups bring to the table, you can help improve problem-solving skills and overall performance. So while having difficult conversations with employees can seem like a negative activity on your to-do list for the day, it can be an incredible opportunity for improvement.

Discussing salary and compensation

As per this survey I quoted earlier, “When asked about what they found it hardest to talk about, 33% said talking about pay at work made it onto their list”. As an employee, if you’ve ever had to ask your boss for a pay rise or negotiate a larger bonus when starting a new job, you’ll know how uncomfortable it can be to even bring the topic up.

Talking about money always feels awkward, and if you believe you’re being paid unfairly, it can be hard to know where to start ‘building your case’ with your manager. Equally, if you’re a leader who needs to refuse someone a pay rise, for example, you’ll know that the topic can bring up strong feelings and emotions.

But in reality, all these conversations are only ‘difficult’ because leaders or employees don’t have the knowledge or support to deal with them in the best way. So can we learn how to have a difficult conversation with an employee?

Absolutely! Here are a few key steps for preparing and starting the conversation, navigating it, and even concluding it.

An example from my own experience with a client who had to have a difficult conversation

I recently supported a client who needed help communicating with a fairly toxic and bullying manager. Now I realise this blog post is about how to have difficult conversations with employees, but difficult conversations are not just reserved for managers.

Almost everyone in an organisation, no matter what their position, will have to have a difficult conversation – whether that’s with their manager, employee or a colleague. There’s no avoiding tough topics, just as in any relationship whether it’s family, or partner – tricky convos (?!) have to happen!

I helped coach this particular client with setting boundaries with her manager about the way I which she wanted to be spoken to. We…

  • Broke down why my client was feeling the way she was using psychological frameworks to help her understand the power dynamics at play
  • Dug down into her confidence and sense of self to clarify what her own needs were in this working relationship in order that she feel supported, respected and able to thrive
  • Prepped and planned an approach that allowed her to see a way to raise these needs and set clear boundaries with her manager in a way that was kind, human, in-alignment with my client’s values, but clear and non-negotiable at the same time. (Yes it’s totally possible!) And we practiced until she was ready 🙂

It was an amazing outcome. This person’s relationship with their manager improved beyond recognition. So instead of this fantastic employee jumping ship, our work together allowed her to set boundaries, cultivate a healthier dynamic that allowed her needs to be met, creating more professional, effective and less stressful environment! Win win win.

Preparing for a difficult conversation with your employee

Woman in office preparing for difficult conversation

As with most things, preparation is key! Before you even sit down to talk to your employee, identify the issue and the desired outcome. What would you like to change? Why are you even having this conversation? Rather than thinking about this on your drive to work in the morning, dedicate some time to writing this down and ask yourself whether the proposed change you have in mind is realistic and achievable.

Now that your intentions going into the conversation are clear, make sure you choose an appropriate time and place to have a chat with your employee. Ideally, you want it to be somewhere comfortable and private. Think about accommodating your employee so that they feel at ease.

Then, rehearse what you’re going to say. This may sound silly and redundant, but trust me when I say you want to practise what you’ll say to your employee before you go and do it. Why? Because you might catch yourself using less-than-ideal language or articulating your points in a way that sounds unclear or convoluted. You don’t want any of that to happen in front of your employee.

And finally, as you prepare, spend some time acknowledging and managing your emotions. How do you personally feel about this issue? Are you angry or disappointed? Fearful and concerned, maybe? Your feelings are 100% valid, but it’s important you don’t bring them into the conversation. In fact, you want to make sure you accept them and address them before you even get in front of your employee. A conversation that’s charged with unresolved feelings may end up in a place where you didn’t intend it to go.

Starting the Difficult Conversation

Woman in office discussing something with her employee

Now that you’ve done your due diligence and preparation, as you start this conversation, make sure you set a positive tone and clearly communicate its purpose. What are you here to talk about? What is the problem and why do you need to discuss it?

Bearing in mind that your employee will have feelings of their own, be empathetic and gentle. They may be embarrassed, shocked, or even angry. Remember that you’ve had time to prepare and deal with your own emotions first, but they might have not. Depending on whether they had any notice in advance, they may now feel ambushed, taken aback, or ‘on the back foot’. Take all that into account.

Also, don’t jump straight into the solution. As a leader or manager, you may know (or think you know) what the best outcome of this conversation is. But once you’ve outlined the problem, let your employee speak.

For example, if you’re talking to someone because they’re consistently late to work, you’ll want them to feel comfortable enough to share anything that might be going on at home or in their personal life that’s making this happen. And even if this isn’t the case, there may be different avenues to “I expect you to be here at 9 am with no exceptions from tomorrow”. In a nutshell, the key here is to actively listen to your employee, empathise with them, and prioritise connection with them over proving you’re ‘right’.

Navigating the Conversation

Two men in office talking while standing

So how exactly will you handle the conversation while keeping an open mind, actively listening, and not jumping to conclusions or solutions?

First thing first, make sure you ask open-ended questions based on what they tell you. Actively try to understand why this problem is happening. And from your side, share specific feedback and examples. It’s important you stay factual and bring evidence to back up what you’re saying, so be as specific as you can be.

Also, during the conversation state expectations and set goals. If at all possible, try to do this together so you can come up with an action plan about how things can change. For instance, using the example above, you could agree that for two weeks the employee who’s consistently coming in 20 minutes late can stay a little late in the evening to make up the time. It could just be that this will allow them to solve a particular problem they’re having at home so they can be punctual in the long run.

Of course, don’t forget to ask and address any concerns and questions your employee might have.

Closing the Conversation

Two women in office shaking hands

So you had the conversation. Was it as bad as you were expecting? Hopefully not!

Before you leave, ensure you summarise the conversation and agreement. By the end of this, you and your employee want to be on the same page regarding what needs to happen next. If necessary, offer support and resources. Do they need assistance going forward? Is there any information you said you’d provide? Do you need to put them in touch with someone else, such as the HR department, for example? If you committed to any next steps, make sure you keep your end of the bargain.

Equally, set clear expectations on when you’re going to follow up on progress. If relevant, set a date on when you’re going to check in again. Do you need another meeting? Will the employee need to send you anything (such as a proposal to be reviewed and approved, for example) by a certain date?

And finally, don’t leave that conversation without thanking the employee for their time and understanding. This is important, especially if the conversation is something they found uncomfortable or difficult to deal with in any way.

Do you want some help facing difficult conversations at work?

As you can see, with the right training and support, conversations don’t need to be ‘difficult’. Rather than seeing tricky topics as something to be avoided and never talked about, we can switch our mindset to seeing them as essential and healthy steps towards a culture that’s both human AND performing well.

If you or your organisation would like any training or are looking for support on how to have difficult conversations at work, check out my services or drop me a line to have a chat about how I can help you.

Giving advice is one thing, but when it comes to having difficult conversations, there’s no one-size-fits-all solution.

That’s why I work with organisations to help their leaders and managers have tough talks with their staff in a way that’s customised to the situation. Good communication means understanding everyone’s needs, personalities, and viewpoints.

By working together, I introduce leaders and managers to the skills and strategies they need to have successful difficult conversations, even in tricky or emotional situations. With my help, they can approach these conversations with confidence and professionalism, knowing they’ve got the tools and knowledge to handle anything that comes up.

Difficult conversation coach

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