How do you feel when you hear the words “we need to talk”?
For many of us, that phrase sends a shot of anxiety right through our bodies, especially if you’re non-confrontational. No one likes being on the receiving end of bad news. But here’s what I’ve discovered through my years of coaching high-achieving women: what people really don’t enjoy is being the one who has to deliver bad news or start a tough conversation.
The number one issue clients call me about—the thing they’re truly, truly stuck on—is having to have a difficult conversation with someone. They’re genuinely worried it’s not going to go well.
Sound familiar?
Why These Conversations Feel So Hard
Business leaders are often visionaries. We do our work, hold ourselves to high standards, and move through life with purpose and intention. But even though we’re in leadership, we still find ourselves having to manage other people’s behaviors or deal with situations that are less than ideal.
This shows up everywhere. In our intimate relationships. Our friendships. As parents. And professionally—whether we’re managing teams, running our own businesses, or delegating work to others.
I have so many conversations with women who tell me things like, “I would just rather not have that conversation. I’m non-confrontational. I’m not aggressive. I’m not someone who wants to call people out.” Or they say, “I just wish this would go away or blow over, or that they would just do what they’re supposed to do.”
I’ve heard this both personally and professionally. But here’s the truth: people aren’t mind readers. There can be so much miscommunication simply because there’s no communication at all.
Let’s Talk About Confrontation
Confrontation has kind of a bad rap. People think you have to be aggressive to have difficult conversations. But that’s not true at all.
You just have to be transparent. Honest. Someone with integrity.
Here’s what I want you to understand: people actually want to be around people they feel they can be their best and truest selves with. These difficult conversations? They can actually be incredibly helpful in building stronger relationships. They let people know you’re putting yourself out there to make sure there’s no miscommunication—and that you value the relationship enough to honor transparency and authenticity.
When you look at a conversation you might label as “difficult” and shift your mindset to see it as an opportunity to come together in cooperation, growth, and learning… it really can be beneficial for everyone involved.
A Real Story: When Caring Makes It Harder
One of my clients, let’s call her Moira, came to me feeling really stuck because she had an employee who just wasn’t doing her job well. The employee seemed distracted, wasn’t putting in 100%, and really wasn’t supporting the company in reaching their goals.
When Moira called asking for help, she had already decided in her mind that the conversation was going to go badly—that she was essentially going to break this employee’s heart.
Moira really cared about this woman. The employee had been with the company for a long time. It was only in the last six to nine months that her performance had declined. Moira was incredibly sad and frustrated because this person meant so much to her. She felt like family. The last thing Moira wanted was to hurt her feelings or crush her in the work environment.
So I challenged her with a question: How could this difficult conversation actually empower and support this employee? How could it be beneficial not just for her, but for the company as a whole?
By looking at it that way, she no longer saw the conversation as delivering bad news. Instead, she saw it as an opportunity to open communication. To say, “Here are the things I need, here are the things I’m seeing”—and then ask the employee how she could support her in reaching those goals and improving the quality of her work.
It was a simple shift in perspective. Rather than seeing the conversation as something negative that was going to hurt this woman, it became something positive that would empower both of them to improve the situation.
This Applies at Home, Too
You know, I’m a mother of young adults. And let me tell you—I have to have a lot of difficult conversations with my kids.
They’re coming into their own, finding their independence, and challenging boundaries. They’re doing a lot of discovery about who they are, what values they hold, and what’s important to them. And that doesn’t always align with what my husband and I want for them.
Rather than looking at those conversations as “laying down the hammer” or coming down hard on them, we use those moments to have meaningful conversations about support and growth. We work to understand who they are as individuals while also stating who we are as parents—what our concerns are and what our agreements are about what we do or don’t allow in our home.
The point is this: having difficult conversations doesn’t feel good. Nobody wants to talk about these things. But when you label a conversation with a negative outcome before you even have it—when you’re already assuming it won’t go well—you’ve kind of set yourself up for failure.
My 5-Step Framework for Difficult Conversations
I’ve developed a five-step process that I follow in any conversation I might label as “difficult.” This helps me outline how I want to show up and keeps me focused on the goal: cooperation, understanding, and growth.
Let me walk you through it using Moira’s situation with her employee.
Step 1: State What You Need
What do you actually need in this situation? Use “I” statements.
When I asked Moira this question, she said: “I need specific tasks done on time. I need consistency. I need reliability. I need accuracy.”
Notice how all of those are “I need” statements—not accusations about what the other person is doing wrong.
Step 2: Establish What the Relationship Means to You
I asked Moira, “What does this relationship mean to you?”
She told me: “She means a lot to me. She’s been with the company a long time. We really care about her. We know her background, we’ve seen her struggles, we’ve seen her grow. She feels like family. And previously, her work performance has always been great—so I’m really concerned. I see this shift in her performance and it worries me.”
This step is so important because it establishes that you’re invested in this person, not just the tasks they perform. You care about them as a human being.
Step 3: What Is the Message You Want to Convey?
Moira said: “The message I want to convey is that we see a decline in her work, and we’re concerned. We want to know if there’s anything we need to do to support her—because we need accuracy, dependability, and reliability, and we need these jobs done.”
See how that opens the door for dialogue? It’s not just criticism. It’s an invitation to problem-solve together.
Step 4: How Do You Want to Show Up?
This one is really important. Before you enter a conversation, you need to think about how you want to show up. Do you want to be positive? Assertive? Clear? Concise? Loving? Compassionate?
This is the time to set your intention.
If your intention is to be compassionate, choose language that shows you’re compassionate and understanding. The last thing you want is to fall into the blame game of all the things they’re doing wrong.
And here’s the key: keep yourself in check throughout the conversation. Ask yourself: Am I being compassionate? Am I being understanding? Am I being clear? Am I being concise? How can I make sure I’m staying on plan and showing up as my best self—the way I intended?
Step 5: Know When to Stop
When you’ve deviated from the goal of the conversation, when emotions are running high, when it’s no longer productive, it is absolutely okay to say: “You know what? This conversation has taken a turn. It’s not going in a productive direction, and we’re not accomplishing our goal here. Let’s put a pin in it, calm down, and come back when we can talk about this with a clear head.”
I find this incredibly respectful. The worst thing you can do in a difficult conversation is allow emotions to take over. That’s when things are said that didn’t need to be said. That’s when the blame game comes up. That’s when words are spoken that can’t be taken back—words that can be more harmful than what the actual conversation was about.
Don’t be afraid to stop, take a break, and start again when you’re in a better place. Then just go right back to step one.
The THINK Test: Before You Speak
Here’s another tool I use before opening my mouth in any difficult conversation. I call it the THINK method:
T – Is it True? Is what you’re about to say actually a fact? Or is it an opinion or feeling you’re presenting as fact? There’s a big difference between “You never listen to me” and “I felt unheard in our last meeting when my suggestion wasn’t acknowledged.”
H – Is it Helpful? Does saying this help you, the other person, or the situation? Or are you just venting? (And if you do need to vent, there’s a healthy way to do that.)
I – Is it Inspiring? Does it improve upon the silence? Sometimes saying nothing is actually the better choice.
N – Is it Necessary? Is this perspective essential to the conversation, or are you piling on?
K – Is it Kind? Honesty doesn’t have to be brutal. You can be truthful and kind at the same time. I call this “loving honesty”—speaking truth in a way that respects the other person’s dignity.
A Secret Weapon: Document Early
When you’re dealing with performance issues or client boundaries, and you’re relying on memory, it’s so easy for emotions to take over. But when you have documented facts—notes from meetings, clear SOPs, written agreements—you can approach the conversation with clarity instead of emotional reactivity.
You’re not coming in hot with accusations. You’re simply saying, “Here’s the roadmap we agreed to. Let’s talk about where things went off track.”
This removes the gray area and keeps the conversation focused on solutions, not blame. (This is also where having a strong work ethic around your systems really pays off.)
When You Need to Say “No”
You know what else counts as a difficult conversation? Saying no.
No to the client who isn’t the right fit. No to the project that would overextend you. No to the commitment that doesn’t align with your values or mission.
Here’s what I want you to hear: saying “no” to something that isn’t right for you is actually saying “yes” to yourself, your values, and your mission.
If you’ve overcommitted, communicate early and honestly. It’s better to bow out gracefully than to push through and deliver poor results. People will respect your integrity.
And if a client isn’t the right fit? It’s okay to walk away or offer a referral. Your reputation and your peace of mind are worth protecting.
When You’re on the Receiving End
What about when you’re the one being confronted—or even criticized?
Stay calm and professional. Don’t respond out of anger. Consider the source and their objective. Take a breath.
Acknowledge the feedback. You don’t have to agree with everything, but you can say, “Thank you for sharing that. I want to understand more about your perspective.” (I dive deeper into this in my post on handling negative feedback with grace.)
Release without resentment. Sometimes a relationship or partnership simply isn’t working anymore. You can let it go without being bitter. You can wish people well while holding a boundary that they’re no longer in your space.
This one took me a long time to learn. But holding onto resentment only hurts you.
Your Turn
So here’s my question for you: what difficult conversation have you been putting off?
Maybe it’s a boundary you need to set with a client. Maybe it’s feedback you need to give—or receive. Maybe it’s a relationship that needs attention… or an ending.
Whatever it is, I want you to know this: you can do this. You have more power in these conversations than you think. And the conversation you’re dreading? It might just be the one that changes everything.
Ready to Lead with More Confidence?
If you’re reading this and thinking, “Okay, I really need to work on how I handle these conversations,” I’ve got a few places to start.
My free Strategic Planning Wheel is a simple tool that helps you audit not just your business, but your whole life. It’s a great way to see what’s working, what’s draining you, and where you might need to step up your communication or set better boundaries. Sometimes just getting it all on paper is enough to spark a real shift.
And if today’s conversation resonated with you—if you’re craving that community of women who actually get it—come join us in the Leading Ladies Facebook group. Almost 7,000 women showing up for each other, sharing wins and struggles, no judgment. Just real talk about building businesses and lives that feel as good as they look.
Want to go deeper? The Hub is my virtual membership for women entrepreneurs who are ready for ongoing support, weekly coaching calls, and a community that will challenge you and cheer you on. Because here’s what I know for sure: you weren’t meant to figure this out alone.
