By Madalena Coutinho
When my kids were growing up and I’d tell them about the communication workshops I was delivering, they’d ask: “Mom, do they actually pay you for that?” “Yes,” I’d say. “Why do you ask?” “Because what you teach is such common sense.”
They’re not wrong. Most of what makes a difficult conversation go well is common sense. But there’s a gap between knowing something and actually doing it under pressure. Closing that gap is the real work.
Here’s how I’d approach a difficult message
- Get clear on your intention: Before you speak, know why you’re having this conversation and what you want to happen.
- Use the right opening line: A few well-chosen words can lower the temperature before you’ve said the hard part.
- Prepare for a different impact than you intended: The message will land through their filters, not yours.
1. Get clear on your intention
You may already have the skills to have a difficult conversation, but until you turn inward, you’re not ready to use them. Start by getting honest about why you’re having this conversation and what outcome you’re actually looking for. Skipping this step is how people end up technically saying the right words while the conversation still goes sideways.
2. Use the right opening line
There are real skills, frameworks, and tools you can practice for exactly this moment, starting with how you open. Try something like: “I need to discuss something difficult, because our relationship matters to me.” Or: “I need to address something that isn’t working, because I respect you and I really see potential in what you’re doing.”
Framing the conversation as coming from care, before you get to the hard content, changes how the other person is able to hear you.
3. Prepare for a different impact than you intended
You can’t fully control how your message is received, but you’re still responsible for keeping that in mind. The impact of what you say may not land the way you intended at all, because it’s filtered through someone else’s experience, not yours. Expect that gap. Prepare for it. And meet it with empathy rather than defensiveness.
In my training, we cover the mindset and skills needed for good communication, but I also create a safe space for learners to practice having difficult conversations and sometimes fail – because that’s all part of learning. It’s in the practice that people are transformed.
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Join Madalena on October 29, 2026 for The 4 Stages of Psychological Safety. The 4 Stages of Psychological Safety (11643) – half-day – English/Virtual | Intersol
About Madalena
Madalena (Maddie) Coutinho is an ICF-certified facilitator and learning & development leader who has been designing and delivering training in French and English for decades.
Maddie offers clients training and focused coaching on the topics of communication, psychological safety, leadership & emotional intelligence, among others.