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How to have difficult conversations at work: 5 key steps

June 4, 2021 - 14 min read


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What you need to know about having difficult conversations

Preparing for the conversation

5 steps to help you navigate through difficult conversations

What to do after a difficult conversation

Learn how to have difficult conversations

Most people do their best to avoid conflict. Even when a situation is uncomfortable, it may seem like the path of least resistance is to wait out the discomfort.

However, avoiding difficult conversations doesn’t make them go away, and having them can substantially improve our work and home lives. 

Many people don’t engage with difficult conversations because they don't know how to have them.

Many of us fear that having difficult conversations will damage our relationships or negatively impact our work environment. 

In reality, avoiding these conversations can lead to resentment and create even bigger rifts between people.

Here’s a complete guide on how to have difficult conversations at work, including five steps to help you navigate them successfully.

What you need to know about having difficult conversations

Contrary to popular belief, conflict isn’t inherently bad. 

Difficult conversations are a necessary part of working well with others. Reaching an understanding is often the first step toward creating a better work environment.

Meanwhile, avoiding conflict can cause big rifts in the workplace. These ignored conversations lead to lower employee engagement and productivity.

When employees don’t feel safe talking about work-related issues, it can create a toxic culture that impacts business success. 

Still, 40% of people think their managers won’t have honest conversations about work topics. That can make having difficult conversations seem even more intimidating. 


Managers need to learn how to have difficult conversations with employees and handle conflict at work productively.

As a leader, it’s important to demonstrate conflict resolution as soon as you identify a problem.

But, not every conversation will lead to a solution. Solutions are only one type of resolution for difficult situations. You may come up with a plan to find a solution or reach a mutual understanding instead.

Aim for understanding first. Understanding is the foundation of many solutions, so both people in the conversation must be on the same page. 

Preparing ahead of time can help you focus on having a productive conversation instead of searching for a solution.

Preparing for the conversation

Often, we go into tough conversations with our desired outcome in mind. When an issue weighs on you, it's normal to imagine a solution without consideration for the other people involved.

It’s crucial to remember that these types of conversations should be a dialogue, not a monologue. Self-reflection and empathy play key roles in having an open discussion.

Without properly preparing for the conversation, it’s possible that a tough talk could end in hurt feelings. Examine how you are feeling about the situation before you have the conversation, so your emotions don’t surprise you.


Reflecting on your role in the dilemma can help you see what’s at the core of the issue. For example, a manager can reflect on how they could better support an employee with poor performance before confronting them.

Then, exploring the other person’s point of view can offer a new perspective. Imagining the other person’s perspective helps you garner empathy before the conversation. 

72% of employees think empathy drives motivation, so empathy is a must for managers. Plus, 84% of employers say empathy leads to better business outcomes. Empathy in tough conversations can make everything run more smoothly. 

If you’re worried about how to have a difficult conversation with your boss, you’re not alone. 20% of Americans are uncomfortable talking to their managers. But, preparing for the conversation can make the process a bit more manageable.

Take a deep breath and relax. You will get through this!

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5 steps to help you navigate through difficult conversations

Most of us know from experience that the earlier you have difficult conversations, the better. 

But, starting a tough conversation can feel daunting. That makes it easy to put it off and hope that the issue disappears on its own. In fact, 40% of people report that they have put off a conversation for six months or more. 

Unfortunately, that usually doesn’t work. Avoiding conflict often makes the problem bigger. Learning to navigate a challenging conversation well is much more effective. 

Here are five steps you can take to make having difficult conversations easier.


1. Consider the situation from their perspective

Often, a conversation feels difficult because we’re hung up on our own perspective. When we have a fix in mind, we may not be open to hearing other solutions or points of view. 

Set your view of the situation aside and look from the other person’s perspective. Imagine how they feel about having this difficult conversation with you. 

You may not fully understand their perspective right now. Get yourself to a place where you’re interested in discovering what’s happening with them.

This can help you have feelings of empathy throughout the conversation.

2. Have a goal in mind, but be flexible

Having an agenda can make tough conversations feel one-sided.

It’s important to go into the conversation knowing your ideal outcome. However, be ready to compromise once you have a deeper understanding of the other person’s experience.

The objective of the conversation is to reach an understanding first. If you already have your solution in mind, there’s nowhere for the exchange to go. 

Entering the conversation with an intention to be flexible can help you both see eye-to-eye quicker.

3. Work on your listening skills

When we expect a conversation to go a certain way, we might rehearse it in our heads ahead of time. While that helps many people define their perspective, it could hamper your listening, too. 

Listen intently and aim to understand the person you’re talking to. Ask questions as needed and care about their answers. Make a concerted effort not to think about your response while the other person is sharing.

Active listening can help you find common ground and reach a solution. Working with a coach is a great way to intentionally develop your listening skills.

4. Take care of yourself

Tough conversations can be emotionally draining. It’s crucial to take care of yourself to keep a difficult conversation from turning into a fight.

Take stock of when you need a break. Step out for air, drink some water, or pause the conversation and sleep on it when you need to. If you feel your empathy or compassion dwindling, continue the conversation later.

Remember, you don’t have to come to a conclusion right away. Take the time you need to have a respectful and intentional conversation.

5. Brainstorm solutions together

Even if you already have an end goal in mind, coming to a solution is a joint effort. 

You may believe you have the right solution to fix a problem, but you may come to an even better conclusion with your conversation partner.

Explore solutions or walk away, both agreeing to disagree. If you can reach an understanding, create a plan or roadmap toward a solution that works for both of you. 

End the conversation when you both know that you did your best to find a resolution.

Personalized development helps leaders and their teams thrive.

What to do after a difficult conversation

Challenging conversations take a toll on us, even if we get the outcome we were hoping for. 

Don’t expect everything to work out perfectly simply because you had the conversation. There may be a long road ahead of you to create a solution that works. 

Even when a tough conversation ends, we can still benefit from having it. But, we need to be intentional about self-reflection and keeping the lines of communication open after the fact.

First, prioritize your self-care. These conversations don’t always end as well as we expect. Take time to calm down, take a walk, and reflect on any unexpected feelings you experienced.

It takes courage to learn and practice how to have a difficult conversation. Pat yourself on the back for prioritizing healthy communication.

Next, reflect on the conversation and use this as a growing experience. Consider what you did well in the situation and what you can do better in the next difficult conversation. Reflecting on your conversation can expand your self awareness. 

If you’re learning how to have difficult conversations with employees, explore how you can get better at offering feedback. Giving better feedback more often can reduce the likelihood that you’ll need to have tough conversations later on.

If you’re learning how to have difficult conversations with your boss, consider how you can be more open with your boss in the future. You may find new access to confidence from this conversation.

Reflect on these conversations with a BetterUp coach to find ways you can become a stronger communicator.

Learn how to have difficult conversations

Difficult conversations are part of maintaining good relationships at work. 

But when you aren’t sure how to have difficult conversations, even the idea of conflict can seem overwhelming. Now, you’re equipped with the tools you need to manage meaningful conversations successfully. 

Great leaders are experts at having difficult conversations. Developing your conversation skills can make navigating workplace conflict much easier. 

A BetterUp coach can help you hone your conversation skills, so you’re always ready to have the conversations you need to have. 

Start working with a BetterUp coach today to create a more peaceful work environment.

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Published June 4, 2021

Erin Eatough, PhD

Sr. Insights Manager

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