Difficult Conversations Done Well
April 21, 2025
We’ve all been there—dreading a tough conversation and quietly hoping the situation will resolve itself. But avoiding those difficult talks can lead to misunderstandings, mounting tension, and eroded trust. Whether it's delivering bad news at work or raising a sensitive issue with someone close to you, how you handle these moments can shape the strength and direction of your relationships.
Anticipating these conversations can be anxiety-provoking, but with preparation, you can help ease those feelings. Don’t give in to the discomfort—allow yourself to move through it. Be clear about the purpose of your conversation and the key points you want to convey. I’ve seen firsthand how clients confronting hard topics with clarity and empathy are more centered and steady in the moment. I’ve also seen the relief that follows—and the quiet pride that comes from facing something they deeply want to avoid but recognize it’s too important to leave unaddressed.
Delaying important conversations can be unsettling, confusing, and stressful—for both you and the other person. Imagine you're drowning in work and want to let your boss know you're too overwhelmed to take on additional tasks. Avoiding that conversation leaves your workload unmanageable and sets you up to feel burned out, all while continually being assigned more responsibility. Addressing it promptly signals respect, transparency, and a willingness to engage honestly. In personal settings, delaying hard truths—like admitting there’s a strain in a close friendship—can allow resentment to take root. Speaking up sooner gives everyone involved the chance to begin moving forward.
Before diving into a hard conversation, take a moment to slow down, gather your thoughts, and plan how to share what you’re feeling in a way that reduces defensiveness and creates space for a productive exchange. When expressing something that may be disappointing or sensitive—like turning down a promotion—offer enough context to help the other person understand without sounding overly critical or impersonal. Know that being clear and thoughtful makes it easier for the other person to stay connected while you’re saying something that might be hard to hear.
These conversations can stir strong emotions. That’s why it’s so important to be kind, direct, and compassionate—so the other person is more likely to hear and understand you, and less likely to shut down. Resist the urge to rush through your message, as moving too quickly can lead to missing key points or leave the other person uncertain about what you meant. Like I tell my clients: you’ve had time to prepare. The person you’re speaking with hasn’t. Give them the space they need to absorb what you’ve shared and ask any questions they may have.
And finally, remember that not all difficult conversations are the same. A conversation with a colleague about performance looks very different from telling a child about parents separating. Each situation carries its own emotional weight, influenced by the relationship, the stakes, and the readiness of the people involved.
Tough conversations are a part of life, and while they may feel daunting—especially when you’re upset with someone—they also have the potential to strengthen relationships and build trust. It’s understandable to want to avoid them, but facing your anxieties head-on transforms discomfort into personal growth. Not only will you increase your chances of enhancing your relationship, but you’ll also learn firsthand how difficult conversations are done well.