One of the most common topics that my clients ask about is how to have a tough conversation with someone at work.

In most cases it’s with an employee or a boss, but it usually goes something  like this… 

“I’m really nervous about a conversation I need to have with Mary coming up this week and I was hoping you could help me to prepare for it.”

Difficult work conversations can feel like stepping into a minefield—but what if you could navigate these situations with calm confidence? 

(Hint: You totally can!)

In this article, we’re going to dive deep into how to approach those conversations with confidence and clarity.

 I’ll walk you through some of my favorite prep strategies, tools, and mindset shifts that will help you move from dread to “I’ve totally got this!” by the time the meeting rolls around. 

Whether you're worried about saying the wrong thing, coming across as too harsh, or just unsure how to kick things off, you’re in the right place!

By the end, you’ll have a simple step-by-step approach to handling any workplace conversation, no matter how awkward or tough it seems.

Ready to dig in? Let's do this! 

The 7 Steps to having difficult conversations with your employees:

1. Master your mindset to handle those tough conversations - Shift your thinking from tough to transformative. 

Alright, let’s talk about what’s really going on. You’re nervous which is totally normal. 

You might be thinking what if I say the wrong thing? What if they get mad? What if I look clueless? What if I just freeze up? 

Here's the thing: when you let your brain spiral into worst-case scenarios, you’re focusing on fear, not solutions. 

And by the way…. That fear is usually way worse in our heads than it ever is in real life. 

When you can start to see the conversation not as a confrontation, but as a chance for collaboration, growth, learning, or even connection—the fear begins to fade away.

So instead of bracing for a meltdown, you looked at the conversation as an opportunity for growth—for both you and the other person? 

This simple tweak in shifting your mindset helps you to shift your focus from thinking about all of the things that could go wrong during the difficult conversation with your employee  to what could go right and one that you can actually look forward to. 

Difficult conversations become transformative when you allow yourself to see the potential they hold. Everyone feels nervous before these moments, but you hold the power to rewrite how it unfolds.

And trust me, the other person will pick up on your energy—when you’re confident and clear, they’ll feel it too.

Here’s a practical tip: before the conversation, take a few minutes to go for a walk. Clear your mind. Play your favorite hype song. (And hey, if that happens to be Footloose, no judgment here—dance it out if you need to!) 

There’s something about moving your body and stepping away that just recharges your brain. Trust me, a little movement works wonders when it comes to shaking off those pre-conversation jitters.

2. Prep like a pro 📝

Now that your mindset’s on point, let’s talk prep. Because walking into a conversation with your head in the game is one thing—having a plan sets you up to have next-level confidence.

First things first! Before you hit the ‘let’s talk’ button, here are some super helpful tips you can use to make sure you’re ready to have a smooth, focused chat.

• Be sure to schedule more time for the meeting than you think you’re going to need! Trust me! There’s nothing worse than being in the middle of a difficult conversation with your employee and feeling the pressure of needing to rush the conversation along because you have another meeting to get to.  
• Don’t put it off! Unlike fine wine, tough news doesn’t get better with age

Prepare them in advance for what the conversation will be about.  No one likes to get that vague e-mail or message from your boss that says “I need to talk to you about something” 

A little transparency goes a long way and can put their mind at ease and come ready to collaborate. 

Try something like: I wanted to schedule some time to connect so that we can get on the same page and brainstorm ways to make things better.

Next, you want to select the best location 

• Where should I have this conversation?  Put yourself in their shoes. Depending on your office culture, you may want to have it in person, either at the office or potentially at a local coffee shop. Keep privacy paramount!
• If it’s a virtual meeting, be sure they are prepared to be in a quiet, private space where there won’t be any distractions. 

Schedule the necessary prep time for yourself that you need to feel confident to have the conversation. 

• Review any notes from previous meetings. 
• Prepare any talking points (keep it brief, bullet points only) you don’t want to sound like you’re reading from a script. 
• Gather examples of any previous guidance, directions, notes etc. that described expectations.
• It doesn’t have to be all doom and gloom! Provide examples of behaviors or work that you can recognize them for - be specific! 

By having a clear plan of the goal of what you want to achieve by having the conversation along with the specifics and details that you want to include, not only will you feel more comfortable and confident going into the conversation, it will help the conversation to be a lot more productive and go a lot more smoothly.

3. Be clear (yep, crystal clear!)

How to be direct (with a splash of kindness):

You might be tempted to sugar coat certain details in an attempt to spare their feelings, or to make yourself feel more comfortable, but beating around the bush without including specific details and examples can leave your employee wondering what exactly went wrong, and why, how to fix it and left feeling frustrated and confused instead of having clarity.

 So, ditch the dance-around and aim for the truth—kindly, but directly.

• Stick to the facts. The key here? Steer clear of personal feelings and judgments. For example, instead of saying “You’re always unprofessional,” try “I’ve noticed you’ve been late to the last three meetings.” See the difference? Facts, not feelings.
• Constructive, not crushing. Frame your feedback in a way that opens up solutions. Try: “How can we make sure this doesn’t happen again?” It’s all about collaboration, not condemnation.
• Real-life scenario: Let’s say you’re discussing missed deadlines. Instead of: “You never turn your work in on time,” (ouch) go with: “I noticed that the last two projects were submitted late. Can we brainstorm ways to streamline the workflow?” Now you’re guiding the conversation toward improvement and inviting them to contribute ideas.

Pro Tip: Focus on the fix, not the fault. Sure, something went wrong, but instead of pointing fingers, use it as an opportunity to find solutions on how you both can work together to make it right. 

4. Stay calm and composed: control your emotions 

Here’s the deal: In a tough conversation, emotions are inevitable. You’re human, and so is the person on the other side of the table. The trick isn’t to suppress your feelings—it’s to manage them.

Why this matters: The moment emotions take over, logic and clarity fly out the window. According to research by Daniel Goleman, author of Emotional Intelligence,  who manage their emotions well are more successful in tough situations. 

Here’s how to keep your cool:

• Name it to tame it. If you feel your heart racing or your face heating up, mentally acknowledge what you’re feeling. Just recognizing “I’m feeling anxious right now” can help calm those emotions.
• Use calming techniques. Ground yourself by focusing on a specific detail in the room—a picture on the wall, the texture of the table—anything to anchor yourself in the present moment.
• Take a break if needed. It’s okay to say, “I need a moment to gather my thoughts.” Taking a short pause can help you reset.

Breathe and take your time!   You might be tempted to rush through the conversation as fast as possible so that you can “get it over with.” 

By rushing through the conversation, you risk missing some key points from the purpose for the conversation and not giving your employee a chance to ask questions and share their own perspective. 

Pro Tip: If you feel overwhelmed mid-conversation, take a deep breath and silently count to three before responding. This gives your brain time to shift from emotional reactivity to rational thinking.

5. Be empathetic not sympathetic

Being the boss comes with a lot of responsibility and sometimes that means having to deliver less than favorable feedback. 

You DO want to be empathetic, not sympathetic and consider the perspective of your employee, listen with curiosity and be as objective as possible. 

You DON’T want to get caught up in the story and excuses. This is the fastest way to derail the conversation and to have a negative impact on future ones. 

Your role is to remain neutral, fact based and solution oriented. 

Here’s an example….

If they say they’re feeling overwhelmed you may want to use one of these statements.....

Empathetic Statement: "It sounds like you’re feeling overwhelmed with your current tasks. Let’s prioritize what needs to be done and see how we can lighten your load."

Sympathetic Statement: "I feel bad that you’re so stressed out. It must be tough to handle all of this."

By staying empathetic, you are showing compassion and understanding, but keeping the conversation and the focus on finding solutions instead of getting caught up in excuses. 

6. Check for understanding & identify support needed

This is one of the most important steps in the process and one that is often overlooked. 

During every interaction or conversation we have, we primarily think about one perspective, our own. 

When we don’t take the time to pause and check for understanding, we are leaving a lot of room for misunderstandings and assumptions that might not lead to the outcome we had intended. 

By taking the additional time to check for understanding and ask questions to get their perspective, you’ll avoid the potential disappointment of having to repeat the conversation and potentially learn something new about the situation that you hadn’t considered before. 

Ask what support they need. They may already know that they are missing the mark and may already be beating themselves up more than you ever could.

In most cases though they won’t ask for anything because they may be concerned that you think they don’t know what they’re doing.

Who knows? They may not even be aware of potential support or resources that may already exist that they can ask for. 

You can be the super hero boss by coming prepared to have some recommendations in your back pocket to offer up and be ready to share the reasons why and ask for their opinion too! 

By including them in the plan, it shows your employee that you care, you are invested in their growth and development and that you value their perspective.

From there it’s more about offering support and creating a clear and specific plan of action.

When wrapping up the conversation, be sure to summarize the main takeaways and agree on any action items. 

It’s also a good idea to go ahead and put any follow up meetings on the calendar before the end of the meeting.  This ensures that you’re both  on the same page and leaves no room for confusion. 

7. Learn from It: reflection for continuous improvement

Congratulations!! You did it, you’ve made it through the conversation! 

 Now what? Time for a little (not a LOT) self-reflection. Think of it like a post-game review in sports. You don’t just want to forget about the conversation and move on—you want to learn from it so you can feel even more confident for the next one that rolls around.  

How to reflect :

• Ask yourself what went well. Did you stay calm? Did you make your points clearly? Give yourself credit for what you did right.
• Identify areas for improvement. Was there a moment where you got flustered? Did you forget to mention something important? Make a quick mental note so you can adjust next time.Don’t spend too much time ruminating about it or you’ll go down a rabbit hole like Alice in Wonderland.

Reflection helps you build resilience for future conversations. The more you practice, the easier these tough talks will become.

Don’t Forget the Follow-Up: Keep the Conversation Going

Here’s something many people forget: difficult conversations don’t always end when the conversation does. The real growth often happens afterward. Whether you’re giving feedback, resolving a conflict, or setting new expectations, follow-up is crucial.

Why follow-up matters:

• It shows accountability. Following up reinforces that you’re serious about resolving the issue and committed to finding a solution.
• It keeps communication open. Following up allows you to address any lingering issues or clarify points that might have been misunderstood.

How to follow up like a pro:

• Send a quick email summarizing the key points discussed and any action items. This gives both of you something to refer back to.
• Check in after a few days or weeks to see how things are progressing. For example, “I wanted to check in on how you’re feeling about our conversation last week—has anything improved?”

If you could remove the fear and uncertainty from difficult conversations, how would that impact your leadership?

Ready to step into a more confident version of yourself and transform the way you lead?

Book a strategy session with me to get the ball rolling on creating a custom game plan to get you from fearful to fearless. The first one’s on the house!