By Jessica Stitz, MBA, SHRM-SCP


What comes to mind when you hear the phrase “tough conversation”?

Many conversations feel tough when they involve giving employees or co-workers negative feedback or disagreeing with them. And, there’s a lot at stake! For most people, it’s a conversation that makes us feel uncomfortable—especially if it takes place at work.
If these conversations are mishandled, they could lead to disengagement, negatively impact your relationships, and create distrust.

That’s probably why over 60% of people say that they avoid having difficult conversations.

Did you know that there’s one skill every single job needs, but it’s hardly ever spelled out in the “required skills” section of a job description?

You probably guessed it—it’s navigating tough conversations, and it is one of the most underdeveloped skills in the workforce.

When I think of successful people at work and in relationships, they all have one thing in common: they’re able to have these tough conversations and move forward while allowing people to feel comfortable and supported in the process. That’s why I’m happy to share a process that will stop you from avoiding tough conversations and leave them feeling successful.

Here are my eight steps to navigating tough conversations at work.


Part 1: Before the conversation takes place

Before having a tough conversation, there’s some essential preparation or “pre-work” you can do to set yourself up for success. Thinking through the following 4 steps can make all the difference!


1. Define your intention

First and foremost, you should define your real intention for having the conversation. Why? Well, people can usually sense what your real motives are.

For example, if you take a moment to think through your intention and realize that it is to prove your boss wrong and that you are right, you will want to avoid the conversation altogether. It is likely not going to get anyone anywhere.

If you intend to help your boss see that the path she is planning to take on a project will likely harm the customer and your business, then move forward with the conversation.


2. Decide what outcome you want before you even start

Before even talking, it’s essential to know what you want to get out of it.

If your outcome is to keep a good relationship with your boss while helping to make positive progress with a key customer, then make sure that stays top of mind. Keep the outcome in mind while you are engaged in the conversation—especially if emotions start getting high.

Emotions have the habit of ruling a conversation and pushing aside the logical brain. When we feel threatened or defensive, our brain resorts to our fight-or-flight instinct to avoid danger. This reaction in our brain is helpful if a bear is chasing us, but not so much during a conversation at work.

Remembering your desired outcome can help you continue to think clearly and avoid fight or flight mode. If you find yourself there, take a pause from the conversation until you feel calm and logical again.


3. Decide what’s fact or fiction

So, you’ve decided to have a tough conversation and know your intentions and the outcome you seek. What’s next?

It’s time to separate the facts from your thoughts and feelings about the situation.

In all my years in HR, I’ve learned that this step makes the most significant difference in conversations and relationships.

For example, if your new employee is late on a project, you might start thinking that they are not invested in their job and are incompetent. The fact is that they are late on the project— you don’t really know that they are not invested or are incompetent. Those are thoughts and feelings at the time.

Remember not to let your thoughts start driving your actions. Ask yourself, “what do I know for sure?” And watch out for the opinions, ideas, or emotions your brain tries to trick you into believing.


4. Be aware of non-verbal communication

Before you begin your conversation, please remember that 55% of communication is non-verbal, 38% is vocal, and only 7% is the actual words you speak.

So think about it like this. If you tell your employee that they are doing a great job, but you have a scowl on your face, and your tone is harsh, what do they hear from you? They will not hear that they are great if 90% of your communication says otherwise.

Please be conscious of what your body and tone are relaying— it can make all the difference.


A manager and his employee look happy after having a successful tough conversation with a good outcome

Part 2: During the conversation

Now that you have done the pre-work and are ready to hold the conversation, use the following tips to have a successful talk.


5. Create psychological safety

Psychological safety is essential for a productive conversation. So, what does that mean?

To create psychological safety in a conversation, you must listen openly, be respectful, show empathy, and avoid blaming. Safety allows people to stay in their executive brain function (not the fight-or-flight feeling!) and have an open, honest discussion with a much better outcome.

If people feel unsafe in a conversation, it’s likely just to make the situation worse and cause someone to shut down or become very defensive. You can spot when someone doesn’t feel psychological safety because they stop participating in the conversation or begin to push their points forcibly.

If you become aware of this, it’s best to stop the conversation. I suggest saying something like, “I feel like we are stuck not hearing each other; maybe we should take a break and come back to this conversation.” Or, you could try to restart the conversation by stating your intention and what you are hoping to achieve.


6. Listen openly

Remember to be open and curious during the conversation, with a growth mindset. The opposite of that is entering a conversation thinking that you have the only correct answer and there are no other possibilities.

Have you ever had a conversation with someone so set in their beliefs that they weren’t hearing anything you were saying? And how productive was that conversation?

Don’t let yourself be that fixed mindset person! Instead, be curious and listen without judgment. I promise it will serve you well.


7. Be clear

“Clear is kind—unclear is unkind.”

Many people think they are kind by avoiding negative conversations or sugarcoating feedback to employees or colleagues. Unfortunately, that couldn’t be further from the truth. As Brene Brown says, “clear is kind—unclear is unkind.”

I’ll paint a picture with this example: Imagine you thought you were doing a fantastic job at work and hadn’t heard anything different from your boss until your review and they tell you that you are not meeting expectations. You are shocked, hurt, and hear nothing else your boss is saying as you attempt to make sense of this new information.

In our line of work, we see this situation frequently. Managers think they are kind by not giving negative feedback until they can’t take the poor performance anymore. Or, they sugarcoat constructive feedback so much that everyone leaves the conversation confused.

On the flip side, sharing clear, constructive feedback gives the person an opportunity to improve and make changes.

We once had a manager come to us ready to fire an employee because they were such a poor performer. I asked about their performance reviews, and the manager said they didn’t want to impact the employee’s wage increases negatively so they always gave them a rating equal to meeting expectations.

When I asked if there had been any conversations about performance concerns, the manager responded, “well, I have given them some dirty looks that should have told them I was upset with their performance.” When meeting with the employee they had no idea they weren’t meeting their manager’s expectations.

The trick to clear communication is simple: Remember to treat others how you would want to be treated, and stop avoiding tough conversations. Think about what you want to know, and let that guide you.

8. Practice

You may think there’s a lot to remember when navigating a difficult conversation, and that’s even on top of the subject matter! But, after watching many people grow throughout this process, I can attest that working on this skill will benefit you in the long run.

The key to mastering any important skill is practice. Find someone you trust and practice having a difficult conversation. Ask them to give you constructive feedback on what your body language and tone are conveying. And test if your intent is matching the effect you were hoping to have.


Tough conversations are worth it

Getting into the practice of having tough conversations—and not avoiding them— will help everyone you work with in the long run. After many years of practicing the craft myself, I can promise that you won’t regret it. You will regret the conversations you didn’t have more.

Remember, doing your pre-work to understand your real intentions and the outcome you are hoping for will set you up for success. And before starting the conversation, define what is fact and fiction in the story you are telling yourself about the person and situation.

When you’re ready to talk, establishing a sense of psychological safety is most important. Keep an awareness of your body language so that your words match the nonverbal cues you give. Then, make sure you are listening openly without judgment and being clear with the things you say.

Lastly, practice having a tough conversation with someone you trust and ask them for constructive feedback; there’s always room to grow!


Having tough conversations is one of the core skills in our Fast Track Management Training, which empowers managers to bring out the best in themselves and their employees. Our team at Turning the Corner is well versed in this, and we’d love to practice with you. Our next session starts on August 23, 2022— learn more here!


At Turning the Corner, we believe that meaningful work that we enjoy is one of life’s greatest rewards—it’s why we do what we do! Our mission is to end suffering in the workplace and empower businesses to thrive through various HR services and training opportunities.