When leaders avoid difficult conversations at work, the issues don’t go away. Instead, unspoken words linger, tension builds, and small misunderstandings turn into bigger fractures. Over time, avoidance leads to misalignment, unmet expectations, and frustrated teams. The ability to communicate honestly, especially when it’s uncomfortable, forms the foundation for trust, clarity, and strong working relationships.

Most of us are never taught how to have difficult conversations. At school, the focus is on academics, not on how to communicate through conflict. And at work, hard conversations are usually sidestepped or handled poorly. Many people avoid them not because they don’t care, but because the conversation itself can feel threatening. We may fear conflict, rejection, or simply not knowing what to say or how to begin.

Earlier in my career, I remember standing on the edge of a hard conversation, a tightness in my throat and a swirl of anxiety in my chest, thinking, Why didn’t anyone teach us how to do this? We learn so many important skills growing up, yet one of the most essential life skills, like how to navigate conflict with care, gets left to trial and error. 

In professional environments, the ability to set clear expectations and give candid feedback is essential to building strong, functional workplaces. And in our personal lives, unspoken frustrations and assumptions can quietly erode even the closest relationships. On the other hand, the more we can practice honest, compassionate communication, the stronger our connections become. 

Since navigating these conversations is more of a practice than something we ever truly master, there are a few approaches that can help.

Before I even begin a difficult conversation, I pause. I take a slow breath, feel my feet on the floor, and remind myself that at the other side of this conversation is more information and a more authentic connection. Even if the outcome isn’t what I hope for, reality is still better than operating from assumptions, which are almost never accurate.

To help with not knowing where to start or what to say, I’d offer that a nonthreatening way to begin is to state your intention or how you’re feeling. Something like, “I’m feeling (name your emotion, i.e., sad, scared, angry, insecure, disconnected, confused) and I’d like your help in understanding…” can be a great start.

Phrases like the following have also been useful:

• I’m curious about how/why/what…
• Walk me through your view on…
• Can you help me understand how you see this?
• What feels most important to you about this?
• I want us to find a way forward, but I’m struggling with…

A great book on the subject, offering practical examples and applications, is Difficult Conversations: How to Discuss What Matters Most by Douglas Stone, Bruce Patton, and Sheila Heen. It reinforces that while these conversations may never feel easy, there are tools that make them less daunting. Two important things to keep in mind, which may also alleviate some of the pressure, are that not every difficult conversation needs to be resolved in one sitting, and that it’s okay if things aren’t said perfectly the first time.

Sometimes, taking a break is the best thing you can do. If emotions are running high or if you’re at an impasse, saying something like, “I need some time to think about this. Can we come back to it?” can prevent things from spiraling.

In the book Bridges Not Walls: A Book About Interpersonal Communication, the author John Stewart introduces a concept called “nexting.” The definition might sound obvious, but something about reading it really struck a chord with me. Stewart defines nexting as “doing something helpful next, responding fruitfully to what’s just happened, taking an additional step in the communication process.” In other words, it’s about saying something next that either improves upon what you said the first time or moves the conversation forward in a different way.

Many leaders put pressure on themselves to say the right thing the first time when the stakes are high. This concept was a wake-up call that no one says it perfectly on the first try, and more importantly, no one has to. What matters most is our willingness to keep showing up, keep practicing, and keep choosing conversation over silence.