Navigating Difficult Conversations: Practical Strategies for When You Need to Speak Up
We’ve all played a difficult conversation over and over in our head – often before it even happens. But not in a helpful, planning, way; more in a work ourselves up, catastrophize it way. Sometimes, this cycle in our head creates enough doubt and anxiety that we continue to avoid the conversation altogether.
It’s common.
You know you need to have that conversation with someone—a team member whose performance is slipping, a colleague who keeps overstepping boundaries, or even your boss about your unmanageable workload. You rehearse it in your head, you plan to bring it up, and then... you don't. You put it off another day, another week, another month, forever.
Avoidance, however, doesn’t serve us (as much as our survival instinct tells us it does).
We are bombarded by difficult conversations, however, most of us were never taught the skills to feel comfortable addressing and navigating them. We're expected to know how to deliver difficult messages, address sensitive issues, and manage people's reactions – all successfully. In a way where we maintain our composure, ask great questions, don’t get triggered and preserve the relationship. The kicker is that in addition to not learning the skills to do this successfully, most of us learned by watching others do it poorly, which then exacerbates the skill divide. The examples we reference in our heads; that we try to mimic, are ones which don’t give us a good base to build from.
For most people, these conversations feel uncomfortable, but it’s not too late to add some skills to your toolkit and increase your comfort level.
Why Difficult Conversations Feel So Uncomfortable
While there are a myriad of reasons why we dread these conversations, three are particularly powerful.
Our Brains Work Against Us
Everything that enters our brain gets processed through the limbic system first. That's the emotional center, the part scanning for threats. When you're heading into a difficult conversation, your limbic system doesn't distinguish between "having a tough talk with my employee" and "facing an actual danger." It perceives conflict as a threat. The emotions of fear, nervousness and anxiety are similar, and that is what it recognizes.
When you're in that stressed or emotional state, your prefrontal cortex, the rational thinking part of your brain, becomes inaccessible. You can’t access ration when you are stuck in emotion. So, you're trying to navigate an important, nuanced conversation at precisely the moment when your brain is least equipped to help you do it well.
We're Worried About the Relationship
We value our relationships, and fear of damaging them (or of being rejected) often leads us to avoid having the conversation. We worry that they will get angry, cry, shut down completely or hold it against us. While these fears are real, avoiding conversations and letting resentment build is almost guaranteed to ruin a relationship.
We also don’t want to be seen as the “bad guy.” Many of us were taught from an early age that “if you don't have anything nice to say, don't say anything at all.” And we equate bringing up challenges and concerns as not being nice. Addressing issues and concerns in a caring fashion is mature and relationship-saving, though.
We Never Learned the Skills
Most of us didn’t take classes where they taught us to manage these conversations. If we fought with our siblings, we were told to stop fighting, but we weren’t sat down and taught how to resolve the conflict. There weren’t classes in school that broke down these skills either, so we’ve had to learn through trial and error (often lots of error), or by watching others (not always the best examples).
So here we are as adults, expected to skillfully navigate these crucial conversations, but we're essentially improvising based on some questionable examples.
Five Strategies for Navigating Difficult Conversations
Understanding why these conversations are hard is useful, but what really matters is what you can do about it. The following five strategies can help you approach difficult conversations with more confidence and skill. They work best when you're the one initiating the conversation and have time to prepare, rather than when you're caught off guard, however, they are still useful if you find yourself unexpectedly in the middle of one of these conversations.
Before the Conversation
Strategy 1: Prepare Your Message and Know Your Goal
When your brain is stressed, clear thinking becomes harder. So do your thinking beforehand, when you're calm. Write out your main points—not to memorize a script, but to clarify what you actually want to communicate. What's the core issue? What specific examples illustrate it? What change are you hoping for?
Just as importantly, start with the end in mind. Before you walk into that conversation, ask yourself: What does success look like? Are you trying to change a specific behavior? Set a boundary? Repair a relationship? Reach a mutual agreement? When you're clear on your goal, it helps you frame the conversation effectively and recognize when you've actually made progress, even if things don't go exactly as planned. If things go off the rails, it helps bring you back to what you want to accomplish.
Strategy 2: Get on the Same Side
How you begin a difficult conversation sets the tone for everything that follows. Start by clarifying your positive intent. If it's a work relationship, you might say, "I really value working with you, which is why I want to address this." If it's personal, perhaps, "You matter to me, and I want to work through this together."
Then think about alignment. Instead of positioning this as you versus them, how can you make it you and them versus the problem, or you and them working toward a shared goal? Maybe it's, "We both want this project to succeed" or "We're both trying to make this team function better."
This even extends to the physical setup. If possible, don't sit across a desk from the person—sit beside them or at an angle. It's a subtle signal that you're working together, not in opposition. You're literally on the same side.
During the Conversation
Strategy 3: Manage Your Stress in the Moment
Even with preparation, you'll likely feel nervous when the conversation starts. That's normal. What helps is having tools to manage that stress in real time.
Take deep breaths. If you feel yourself getting overwhelmed or activated, pause. It's completely acceptable to say, "I need a second to gather my thoughts." The conversation doesn't have to happen at breakneck speed.
You might even try naming your nervousness out loud: "This is hard for me to bring up, and I'm feeling a bit nervous about it." It sounds counterintuitive, but there's real power in acknowledging what's happening. It humanizes you, it often helps the other person relax because they realize you're not attacking them, and it can actually calm your own nervous system by bringing the elephant in the room into the open.
Strategy 4: Lead with Curiosity
Curiosity can de-escalate a situation. Consider the difference between stating, "You always interrupt me in meetings," and asking I've noticed I get cut off sometimes when I'm presenting. Can you help me understand what's happening there?"
Curiosity opens up dialogue. Accusations shut it down.
Similarly, focus on specific behaviors or situations rather than making it about someone's character. There's a difference between saying "You're irresponsible" and "The last three reports have been submitted late." One is an attack on who they are as a person, which will trigger defensiveness. The other is a factual observation about a specific behavior, which is much easier to hear and address.
When you approach the conversation with genuine curiosity, you might learn something that shifts your perspective too. Maybe there's context you weren't aware of. Maybe there's a systemic issue creating the problem. You won't discover that if approach the conversation from a blame or accusation standpoint.
Strategy 5: Use I Statements
This is a communication staple for good reason. "I" statements allow you to own your experience without blaming the other person. Instead of "You make me feel undervalued," try "I feel undervalued when my contributions aren't acknowledged."
The first version puts the other person on the defensive—you're essentially accusing them of causing your feelings. The second version describes your experience and links it to a specific situation. It's much harder for someone to argue with your feelings than it is for them to defend themselves against an accusation.
The format is simple: "I feel [emotion] when [specific behavior or situation]." This keeps the focus on the impact rather than debating someone's intent, which is usually unknowable anyway.
Moving Forward
Difficult conversations are challenging for a reason. They might not ever feel easy or comfortable. But with these strategies, they can feel more manageable. You don't have to use all five—choose the ones that resonate with you and feel authentic to your style.
Avoiding these conversations often creates more problems than having them does. Issues fester, resentment builds, and relationships deteriorate from lack of honest communication. On the other side of these difficult conversations is often real growth—in your relationships, in your leadership, in your work, and in yourself.
So, if there's a conversation you've been putting off, maybe this is your moment. Prepare, lead with positive intent, stay curious, and remember: the conversation you're avoiding might be exactly the one worth having.
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