Mastering Difficult Conversations at Work
Apr 14
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Language of Leadership
When people talk about difficult conversations at work, they’re usually lumping together a few different things. But if you want to actually get better at handling them, you need to get more specific.
There are really three types of difficult conversations:
- Accountability: Someone didn’t meet expectations for a task or objective.
- Difficult feedback: A pattern or theme of behavior that’s not tied to a single event.
- Conflict: Repeated or egregious violations of expectations, like crossing boundaries on communication after hours.
Each one of these conversations is distinct. If we treat them like one big, messy thing, the whole idea feels nebulous and harder to approach. Recognizing which type you're facing helps you have the right conversation in the right way.
The real discomfort usually isn’t about the content. It's about what you think the reaction will be. We project our own feelings — how we would react if someone said it to us — onto the other person. And that makes us anticipate pushback, resistance, or even full-on conflict before the conversation even happens.
If that's the root of the discomfort, then the real skill is lowering those defensive barriers before you even dive into the tough stuff. That’s where enrollment comes in: opening the conversation in a way that makes the other person more likely to actually hear you.
At the end of the day, difficult conversations aren’t about delivering hard truths. The real skill is getting people to hear you — and helping them want to change.
In this post, we’ll break down examples of difficult conversations at work, how to prepare for them, how to lead them effectively, and why building this skill is non-negotiable for any leader who wants to build a strong team.
Why Difficult Conversations at Work Are Essential
It might be tempting to dodge difficult conversations at work. In fact, studies show that 70% of employees actively avoid difficult discussions at work, even when those conversations are necessary. But the cost of this avoidance is steep.
When you don’t address issues head-on, a few predictable things happen:
- Mistakes multiply. If you let something slide once, it usually happens again.
- Silence sends the wrong message. People assume their behavior is acceptable because no one said otherwise.
- Awkwardness grows. The longer you wait, the harder it feels to bring it up.
There’s a real pattern here— a Delay Loop:
- Week 1: You notice the problem.
- Week 2: You don't say anything. Now it feels a little awkward.
- Week 3: Still nothing. Now it feels even more awkward because the event is further in the past.
And so the issue lingers. Standards slip. Trust erodes. Clarity disappears.
It’s not just about the immediate problem. It’s about the culture you’re building without realizing it.
Here’s why that matters: A and B players — your top performers — want to work alongside other A and B players. When failure, excuses, or low standards are tolerated, those top players start looking for the exit.
And once your best people leave, the whole organization feels it.
This is where leadership really shows up. If you avoid difficult conversations, you’re prioritizing your short-term comfort over your team’s long-term success. It might feel easier in the moment. But it erodes everything you’re trying to build.
Real leadership means leaning into the discomfort. Because clear, honest conversations protect your standards, your team, and your culture.
Real-World Examples of Difficult Conversations at Work
When people talk about "difficult conversations at work," they usually mean one of a few things. Each one matters — and each one needs to be handled differently.
Performance Issues: Missed deadlines. Showing up late. Producing low-quality work.
These aren't isolated slip-ups. When employee underperformance goes unaddressed, it quietly lowers the bar for everyone.
Behavior Concerns: Negative or toxic attitude (even if performance is strong).
One person being a dark cloud in the break room can drag down the whole team's morale if it’s not addressed quickly and clearly.
Perception Gaps: Employees who think they’re crushing it... when they’re barely scraping by.
This gap between self-perception and reality is dangerous. When leaders don’t address it, people start believing they're entitled to promotions or raises they haven’t earned — and they often validate that inflated view by seeking offers elsewhere.
Compensation or Promotions: Conversations about raises or promotions when performance doesn’t justify them.
These are difficult because emotions run high. If leaders haven't been clear all along about performance expectations, these conversations get even harder.
Real-World Example 1: The Jace Story
I once managed a salesperson named Jace. He was good, functional… but not great. He was young in his career and had potential, but he wasn’t yet a top performer.
At one point, Jace came to me with a job offer he had secured from another company. He asked if we could match it. The problem wasn’t the offer itself — the problem was that I had never had the difficult conversation with Jace about his actual performance.
Had I sat him down earlier and said, "You’re doing well, but you’re not where you could be yet — and here’s what it would take to get there," we would have been on a path toward developing him into a top performer. Instead, my silence had unintentionally led him to believe he was already great.
Because I hadn't reset his perception, he went into the market with an inflated view of his own ability, got an offer, and validated that belief. And we lost him — not because he was ready to leave, but because I hadn’t done my job early enough to show him there was still more to grow into.
At one point, Jace came to me with a job offer he had secured from another company. He asked if we could match it. The problem wasn’t the offer itself — the problem was that I had never had the difficult conversation with Jace about his actual performance.
Had I sat him down earlier and said, "You’re doing well, but you’re not where you could be yet — and here’s what it would take to get there," we would have been on a path toward developing him into a top performer. Instead, my silence had unintentionally led him to believe he was already great.
Because I hadn't reset his perception, he went into the market with an inflated view of his own ability, got an offer, and validated that belief. And we lost him — not because he was ready to leave, but because I hadn’t done my job early enough to show him there was still more to grow into.
Real-World Example 2: The Barbershop Walk-In Problem
I’ve worked with a surprising number of barbershop owners over the years. One thing that comes up all the time is attendance.
Here’s the pattern: Barbers don’t show up unless they have a scheduled appointment. If their first client isn’t booked until 10 a.m., they won’t come in at 9 a.m. — even though there could be walk-in customers looking for a haircut at that time.
What happens next? Those walk-ins get frustrated, leave, and take their money somewhere else.
The problem wasn’t laziness — it was leadership. The owners had never had the difficult conversation explaining why it mattered for barbers to be there early, even if they didn’t have a scheduled appointment. They hadn’t helped their people connect the dots between showing up, catching walk-ins, and growing the business.
And because of that, they kept losing revenue they didn’t even realize they were losing. All because they avoided a conversation that could have changed the culture and the results.
Bottom line: When we avoid difficult conversations, perception gaps widen, standards slip, and key business opportunities — and people — start slipping away too.
For more strategies on addressing challenging behaviors before they become bigger problems, check out our guide to managing the 7 most challenging employee types.
Here’s the pattern: Barbers don’t show up unless they have a scheduled appointment. If their first client isn’t booked until 10 a.m., they won’t come in at 9 a.m. — even though there could be walk-in customers looking for a haircut at that time.
What happens next? Those walk-ins get frustrated, leave, and take their money somewhere else.
The problem wasn’t laziness — it was leadership. The owners had never had the difficult conversation explaining why it mattered for barbers to be there early, even if they didn’t have a scheduled appointment. They hadn’t helped their people connect the dots between showing up, catching walk-ins, and growing the business.
And because of that, they kept losing revenue they didn’t even realize they were losing. All because they avoided a conversation that could have changed the culture and the results.
Bottom line: When we avoid difficult conversations, perception gaps widen, standards slip, and key business opportunities — and people — start slipping away too.
For more strategies on addressing challenging behaviors before they become bigger problems, check out our guide to managing the 7 most challenging employee types.
How to Prepare for Difficult Conversations at Work
Difficult conversations don’t start in the room — they start in the prep. If you haven’t thought through what you need to say and why it matters, you’re setting yourself up to stumble when it counts.
Preparation is critical. If you can’t say it clearly when you’re planning it, you’re not going to say it clearly in real life. And when a conversation already feels uncomfortable, the last thing you want is to fumble the delivery.
Here’s how to set yourself up to run the play right:
1. Get Clear on the Outcome
Before you even think about what you’re going to say, get clear on what you want to happen. If you don’t know the outcome you’re aiming for, the conversation will wander — and probably get harder.
What’s the shift you want to see? Start there.
What’s the shift you want to see? Start there.
2. Gather Real Facts — Not Feelings
Anchor yourself in specifics. Vague generalizations like "you're always late" don’t hold up — and the second someone hears an exaggeration, they stop listening.
Instead, be specific and factual: "You were 30 minutes late on Tuesday. Last Monday, you were an hour late."
When you stick to real examples, you eliminate the debate over whether the issue actually happened.
Instead, be specific and factual: "You were 30 minutes late on Tuesday. Last Monday, you were an hour late."
When you stick to real examples, you eliminate the debate over whether the issue actually happened.
3. Stay Out of Their Head
Don’t assume you know why they did what they did. It’s easy to slip into thinking things like:
"They don’t care.”
"They meant well."
But whether those assumptions are positive or negative, they weaken the message. Focus on the behavior, not the motive.
"They don’t care.”
"They meant well."
But whether those assumptions are positive or negative, they weaken the message. Focus on the behavior, not the motive.
4. Connect the Dots on Impact
Once you’re clear on what happened, you need to be able to explain why it matters. People don’t change because you tell them to — they change because they understand the impact of their actions.
If they don’t see it naturally, that’s your job to help them connect the dots.
If they don’t see it naturally, that’s your job to help them connect the dots.
5. Ask Before You Tell
You can tell someone the impact. But it’s way more powerful to ask them to name it.
Try questions like:
"What do you think happens when walk-ins leave without getting service?"
"What impact do you think that has on revenue?"
"How do you think that affects bonuses or profit-sharing?"
When people figure it out for themselves, they own it more — and that’s what drives real change.
If you run into excuses instead of real reflection, here's how to respond effectively without losing momentum: How to respond to people who make excuses.
Try questions like:
"What do you think happens when walk-ins leave without getting service?"
"What impact do you think that has on revenue?"
"How do you think that affects bonuses or profit-sharing?"
When people figure it out for themselves, they own it more — and that’s what drives real change.
If you run into excuses instead of real reflection, here's how to respond effectively without losing momentum: How to respond to people who make excuses.
6. Bonus Tip: Use a Leadership Prep Form
One simple tool that makes this easier? Use a prep form, like the Weekly Leadership Prep Forms we use in the Language of Leadership course.
A structure like this forces you to organize the facts, avoid loaded assumptions, and make sure you’re ready to run the play the right way.
A structure like this forces you to organize the facts, avoid loaded assumptions, and make sure you’re ready to run the play the right way.
How to Have Difficult Conversations at Work
When you finally sit down to have the conversation, the goal isn’t to get everything off your chest. The goal is to lower defenses, get the real message across, and drive change. How you open and structure the conversation makes all the difference.
Here’s how to run it right:
1. Open with Clarity and Respect
Start by sharing your intentions clearly. Be transparent about why you’re having the conversation — not to criticize, but to help them improve or move forward.
Use enrollment from the start: Help them see what’s in it for them, then invite them to participate in how and when the conversation happens.
Giving people agency lowers defensive barriers right out of the gate.
Use enrollment from the start: Help them see what’s in it for them, then invite them to participate in how and when the conversation happens.
Giving people agency lowers defensive barriers right out of the gate.
2. Stick to Facts, Not Assumptions
Focus on specific observations. What actually happened. Avoid broad claims like "you're always late" or assumptions about why they did what they did.
When you guess at someone’s motives — even positive ones — you give them an easy way to push back and derail the conversation.
When you guess at someone’s motives — even positive ones — you give them an easy way to push back and derail the conversation.
3. Use “I” Statements
Talk about the impact their actions have on the business, team, or mission. Frame it around outcomes, not their character.
Example: "I notice that when you’re late, our customers end up waiting, and it reflects poorly on the shop."
Instead of: "You're unreliable."
Example: "I notice that when you’re late, our customers end up waiting, and it reflects poorly on the shop."
Instead of: "You're unreliable."
4. Stay Calm and Avoid Defensiveness
Expect a little resistance. It’s normal. Research shows that over a third of managers (37%) feel uncomfortable giving direct feedback if they think the employee might react negatively.
You're not the only one who finds these conversations tough — but your job is to stay calm, stay steady, and stay focused on why the conversation matters.
The minute you get defensive or emotional, you make it easier for them to shift the conversation away from accountability.
The minute you get defensive or emotional, you make it easier for them to shift the conversation away from accountability.
You're not the only one who finds these conversations tough — but your job is to stay calm, stay steady, and stay focused on why the conversation matters.
The minute you get defensive or emotional, you make it easier for them to shift the conversation away from accountability.
The minute you get defensive or emotional, you make it easier for them to shift the conversation away from accountability.
5. End with a Clear Commitment to Change
Don’t leave the conversation vague or open-ended. Make sure you define exactly what needs to change — who, what, when, where, and how.
Pro Tip: See our guide to setting clear expectations for a breakdown on how to close this loop the right way.
Pro Tip: See our guide to setting clear expectations for a breakdown on how to close this loop the right way.
Having Difficult Conversations with Employees
When the conversation is with an employee, you’re not asking for permission — but you still have to approach it in a way that builds trust, not resentment.
Here’s how to handle it effectively:
- Be direct but compassionate. Don’t sugarcoat or dance around the issue. Clear is kind.
- Focus on what happened, not who they are. Stay anchored on specific actions, not assumptions about their character.
- Give them space to respond. Difficult conversations shouldn’t feel like one-way lectures. Let them share their side.
- Clarify expectations moving forward. Define exactly what needs to change — and how you’ll measure success.
- Follow up. Circle back after the conversation to reinforce accountability and support their growth.
How to Have Difficult Conversations with Your Boss
When the difficult conversation goes up the chain, the approach changes. You’re not leading the conversation — you’re influencing it.
Here’s how to navigate the power dynamic:
- Recognize you don’t have positional authority. You’ll need to be even more thoughtful about how you frame the conversation.
- Use stronger enrollment upfront. Clearly state your positive intentions. Show how the conversation serves the boss, the team, or the bigger goals — not your personal agenda.
- Pick the right time and setting. Avoid emotional or public situations. Choose a calm, private moment where they can actually hear you.
- Be specific, not vague. Stick to facts and observations. General complaints shut people down fast.
- Anchor everything to shared goals. Frame it as a conversation about improvement, collaboration, or performance — not personal critique.
The Importance of Practicing Difficult Conversations
Most leaders know they should have difficult conversations. What trips them up is the lack of practice. These conversations aren't just uncomfortable — they’re unfamiliar. And when you don't have a clear playbook or enough reps under your belt, hesitation takes over.
Practicing difficult conversations isn’t about scripting every word. It’s about building comfort with the process: prepping the facts, enrolling the other person, keeping your emotional balance, and moving the conversation toward action. The more you practice those steps, the less intimidating it feels when the real moment arrives.
If you want to speed up the learning curve, tools like AI roleplay can help you simulate difficult conversations safely. They give you a chance to test your phrasing, gauge your reactions, and refine your approach without the real-world pressure.
Practicing difficult conversations isn’t about scripting every word. It’s about building comfort with the process: prepping the facts, enrolling the other person, keeping your emotional balance, and moving the conversation toward action. The more you practice those steps, the less intimidating it feels when the real moment arrives.
Reflection is part of the practice, too. After each real-world conversation, take a moment to look back. What worked? What didn’t? Where did you hold steady, and where did you get knocked off balance? That kind of honest post-game review is how good leaders become great communicators over time.
If you want to speed up the learning curve, tools like AI roleplay can help you simulate difficult conversations safely. They give you a chance to test your phrasing, gauge your reactions, and refine your approach without the real-world pressure.
Bottom line: Practicing isn’t just preparation. It’s leadership development in real time. Every rep builds skill, lowers fear, and raises your ability to lead the hard moments that shape team performance and culture.
Difficult Conversations Training for Leaders
Difficult conversations aren’t something you master by reading advice. They’re a skill you build through real practice and feedback — and that’s where training makes the difference.
When teams go through difficult conversations training together, it doesn’t just improve individual skills. It raises the standard for communication across the board. Clear expectations become the norm, not the exception.
At Language of Leadership, we focus heavily on roleplay because that’s where growth happens. You have to practice the conversations you want to lead. Training isn’t about knowing the right answer — it’s about building the muscle memory to stay calm and focused when it matters most.
The more you practice, the more natural it becomes. And the more confident you are when it counts.
Formal leadership training provides frameworks and tactical language you can actually use. Instead of guessing your way through a tough conversation, you learn proven methods to open the dialogue, lower defenses, and guide it toward real change.
When teams go through difficult conversations training together, it doesn’t just improve individual skills. It raises the standard for communication across the board. Clear expectations become the norm, not the exception.
At Language of Leadership, we focus heavily on roleplay because that’s where growth happens. You have to practice the conversations you want to lead. Training isn’t about knowing the right answer — it’s about building the muscle memory to stay calm and focused when it matters most.
The more you practice, the more natural it becomes. And the more confident you are when it counts.
Knowing How to Handle Difficult Conversations at Work is a Leadership Must
Difficult conversations aren’t a side skill for leaders — they’re core to the job. If you can’t address issues clearly and directly, you can’t build trust, set standards, or grow a strong team.
When you master this, everything changes:
When you master this, everything changes:
- Trust goes up.
- Accountability strengthens.
- Performance improves.
- Top performers stick around because they know the bar is high.
The best leaders don’t avoid conflict. They lean into it — and they do it skillfully enough to turn tension into growth.
Leadership isn’t about having hard conversations. It’s about getting people to hear you — and want to change.
Ready to step it up? Check out the free sneak peek of our training course for leaders or get in touch to see how we can help you and your team lead stronger.
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