How to have difficult conversations with employees

Discovering problems with employees is a bit like hearing an ominous noise from your car while driving. At first, it's easy to ignore. You think, maybe it'll go away on its own. But as the noise gets louder, you're forced to face it. And by the time you get to the mechanic, what could've been a quick fix has become a very expensive problem.

While putting off difficult conversations with employees can be similarly tempting, waiting only makes things worse. Performance problems escalate, team dynamics suffer, and trust begins to erode. Tackling issues early may be uncomfortable, but it prevents the situation from worsening and becoming a much bigger problem down the road.

Let's explore how to have difficult conversations with employees the right way - proactively, effectively, and with lasting impact.

Why are difficult conversations important?

Knowing how to have difficult conversations with employees is crucial because the cost of avoidance is steep.

Failing to have difficult conversations can lead to:

• Employees remaining unaware of their poor performance, causing delays, errors, and tension within their team.
• Managers dealing with high-performers who lose motivation due to a manager's perceived tolerance for mediocracy.
• Businesses experiencing reduced productivity, a toxic work culture, and increased turnover.
• HR and Talent teams spending more time cleaning up the aftermath than they would if the issues were addressed head-on.

However, when difficult conversations are handled with clarity, empathy, and skill, they can boost motivation, strengthen relationships, and foster a culture of accountability.

Simply put, these conversations are not optional.

Ensuring your managers know how to have difficult conversations with employees is critical for organisational success and long-term growth.

When should you have difficult conversations with employees?

Timing, as they say, is everything. In the context of how to have difficult conversations with employees, it can be the difference between a productive discussion and an emotional confrontation.

As a manager, if you see a problem brewing, address it as soon as possible. Delaying the conversation doesn't just give the issue room to grow - it also robs the employee of the chance to improve.

Imagine someone unknowingly making the same mistake for weeks or months, only to hear about it long after the fact. It's not only disorientating but also unfair.

How to prepare for difficult conversations with employees

The key factor in how to have a difficult conversation with employees is preparation. Being prepared ensures the discussion is as clear, productive, and pleasant for both parties as possible.

1. Outline the purpose and desired outcome

Before sending any diary invites, clarify why you're having the conversation and what you want to achieve. Vague feedback leads to vague results, so take the time to clearly define the ideal outcome for you, the other person, and the relationship.

2. Gather information

Go into the conversation armed with facts, not assumptions. Take the time to gather all the relevant information.

• Establish the facts: Understand exactly what has happened and when.
• Review documentation or data: Performance reviews, project outcomes, or even emails can provide helpful context.
• Ensure you have specific examples of the problem at hand: Making general claims isn't helpful for an employee to understand the issue or be able to find a solution.

However, it's also important not to be over-prepared. Managers who stick too rigidly to a script risk turning the conversation into a one-sided lecture, shutting down any chance for meaningful dialogue.

3. Set the right conditions

Even the best preparation can be derailed if the logistics of the conversation are off. Here's how to set the stage for success:

• Find a private, neutral location. This helps maintain confidentiality and minimises distractions.
• Time it right. Avoid scheduling the conversation right before a big meeting or deadline. If it's likely to be emotionally challenging, consider timing it for the end of the day so the employee has time to process.
• Don't rush. Block out enough time so you're not hurried. Employees should feel that this conversation is a priority, not a box tick.
• Give a heads up. If possible, let the employee know in advance that you'd like to speak to them so they're not blindsided. But ensure you're doing so in a way that doesn't exacerbate their anxiety.
• Share an agenda. If appropriate, outline key topics ahead of time to allow the employee to prepare.

When preparation is thoughtful and strategic, difficult conversations transform from dreaded obligations into opportunities for growth.

How to have difficult conversations with employees

You've done the prep work, taken a deep breath, and now it's go-time. This is where the rubber meets the road - or, more aptly, where you sit down and navigate a potentially tricky conversation.

It's important to get this right, as one seminal study found that 33% of feedback actually decreased employee performance.

But fear not: with the right tone, a clear framework, and a collaborative mindset, you can make even the toughest conversations productive.

Here's a step-by-step guide for how to have difficult conversations with employees:

1. Create a clear and confident opening

First impressions count - especially in difficult conversations. Your opening sets the tone for everything that follows. If you have nervous energy, overly rehearsed phrasing, or excessive sugarcoating, the employee will pick up on it immediately. The key is to strike a balanced tone: calm, professional, and approachable.

To start the conversation effectively, you need to share your side of the story. So make sure to hit these points early on:

• Name the issue
• Describe how you feel about it
• Explain the wider impact

For example, instead of saying, "Your performance isn't meeting expectations." try something like, "I've noticed you've missed three deadlines this month. This has been very frustrating for the team and has delayed project timelines, creating extra work for your colleagues."

Then, you can outline the objective of the meeting by saying "I'd like to use our time today to understand your perspective. Then, together, we can create a plan of action to ensure you are able to meet your deadlines going forward."

This sets a constructive tone, giving the employee a clear understanding of the problem while creating space to move toward a solution.

2. Be specific and focus on the issue at hand

Generalisations are the enemy of clarity. Saying things like, "You're not reliable" or "You always miss deadlines" can come across as vague, unfair, or even accusatory. Instead, focus on specifics:

• Present concrete examples of the behaviour or issue and give the employee the opportunity to address each one.
• Avoid personal criticism. Keep the conversation anchored in how the issue affects work outcomes - not the employee's personality or character.

When done correctly, this approach keeps the conversation objective and professional, making it easier for the employee to understand what needs to change. If the conversation requires you to deliver negative feedback, ensuring that it is accurate and descriptive has the potential to actually boost employee performance by 39%.

3. Be present and listen

While you might've spent days preparing, the employee likely hasn't. Be mindful that they may need a moment to process or gather their thoughts. Then, invite them to share their side of the story by asking:

• What do they think is going on?
• How do they feel about it?
• What do they think the wider impact is?

Ask clarifying questions to ensure you fully understand their perspective. This shows you're genuinely listening and also gives you a better understanding of their point of view.

While listening, pay attention to their tone, body language, and facial expressions. If they seem overwhelmed or emotional, offer to take a break. A quick pause can help keep the conversation on track.

Don't forget to stay open-minded. It's natural for our perceptions to be shaped by personal assumptions or biases. When what we hear is channelled through filters, we only hear what confirms our suspicions or strengthens our arguments. However, the issue at hand may have contributing factors that you're unaware of, so it's very important to listen carefully.

Also, empathy goes a long way here. Acknowledge their challenges and validate their feelings, but don't lose focus of the conversation. If they bring up an unrelated issue, say something like, "I hear you, and I'd be happy to set up another time to discuss that. For now, let's focus on resolving this issue."

4. Collaborate on a solution

It's time to shift from understanding the problem to solving it. And the keyword here is collaborate. This is because, by working together you integrate one of the six conditions for high-performance: choice.

Simply prescribing a solution can feel like a command, which may breed resentment or disengagement. Instead, aim to co-create a plan. To do this, you could:

• Ask the employee for their ideas: Make them feel like their input is valued. Ask questions like, "What do you think would help improve this?" or "What support do you need from me to make this work?"
• Bring prepared suggestions: Bring a few ideas to the table. If the employee is struggling to come up with ideas, use them as a jumping-off point to develop a solution together.
• Outline specifics: The final plan should clearly define what the employee will do differently and how you, as their manager, will support them.

Collaborative solutions create buy-in, making it far more likely that the employee will follow through.

What to do after a difficult conversation with employees

So, you just made it through the hard part - the conversation. That's great! But the work isn't over just yet.

What happens next can determine whether the employee grows from the experience or slips further off track. Post-conversation actions are your chance to turn a tough talk into a turning point.

Let's dive into the steps to take after the conversation to keep that momentum going.

1. Commit to an action plan and stay on track

Think of the action plan as your post-conversation GPS. Without it, you're both just wandering aimlessly, hoping for the best. During the meeting, you should have outlined:

• Specific steps for the employee to take: Make these actionable and crystal clear.
• How you'll support them: Whether it's extra training, regular check-ins, or simply being available, show them you're in their corner.
• A timeline for progress: Set realistic deadlines for follow-ups and evaluation.

When they start hitting their targets, don't forget to celebrate! A quick "Great job turning this around" can mean a lot and reinforces that their efforts matter.

2. Prioritise inclusion efforts

A tough conversation can feel isolating for an employee, especially if it touches on team dynamics or performance. Your job now is to ensure they don't feel like they've been banished to some professional no-man's land.

• Highlight their contributions in team settings to rebuild confidence
• Actively involve them in projects, meetings, or decisions to show they're a valued part of the group.

Why does this matter? Because feeling excluded breeds disengagement, causing productivity to plummet and resentment to rise. By proactively fostering inclusion, you're helping the employee reengage, which benefits them and the team as a whole.

3. Implement frequent check-ins for all employees

One of the best ways to make future tough conversations easier is to build trust through consistent, meaningful communication.

Regular check-ins aren't just a nice-to-have, they're a proven tactic to prevent misunderstandings, disengagement, and other problems from festering.

• Schedule regular one-on-one meetings where employees can openly share their challenges, concerns, and wins.
• Establish a culture of continuous feedback where giving and receiving input is just part of the routine.

When employees feel heard and supported, they're more likely to flag small issues before they snowball into big ones. Plus, regular check-ins mean you're not starting difficult conversations from scratch - you're building on an existing foundation of trust and mutual understanding.

Key learnings: how to have difficult conversations with employees

Having difficult conversations with employees doesn't have to be a dreaded task. When handled with clarity, empathy, and the right strategies, these discussions become opportunities for growth, alignment, and stronger workplace relationships.

If you're looking to level up the conversation skills in your organisation, MindGym's Manager Conversation Solution is for you. With five essential learning sessions (called Workouts), your managers will master the art of conversations and drive their employees' performance.

After learning how to have difficult conversations with employees, managers can also activate their learning with Lio, our AI conversation coach. Lio enables managers to navigate difficult conversations with simulations and real-time guidance, backed by behavioural science.