Most of us have a conversation we keep putting off. Maybe it’s about who takes over the business, what happens to the family lake house, or a colleague who isn’t pulling their weight. We rehearse it in the car and in the shower, and then we find a reason to wait another month.
Our founder, Christina Wing, has spent decades helping families and leadership teams get through these moments. In a piece for Big Think adapted from her book Unspeakable: The Taboo Topics We Avoid and How to Talk About Them (Harvard Business Review Press), she makes a point that’s easy to forget: talking about the things we’ve been conditioned not to talk about is a skill. You can be coached in it, and you get better with practice.
The article lays out eight practices for building that skill. Here’s a quick look at them.
Before the conversation
Know what kind of conversation you want. Christina separates a dialogue from an announcement. If you’ve already made a decision, like ending a relationship or letting someone go, you’ll listen politely, but you aren’t there to negotiate. If you’re hoping to solve something together, that’s a different conversation. Know which one you’re walking into.
Don’t ambush anyone. The breakfast table, the ride to the airport, a text message. Christina has seen people try difficult conversations in all of these places, and it rarely goes well. She suggests setting an appointment, ideally a day ahead and in person when you can. She often recommends doing it by email. That way you can choose your words carefully, and once it’s on the calendar, you’re committed to having the conversation.
Practice with someone you trust. Rehearsing in your head only gets you so far, because the other person never sticks to your script. When Christina role-plays with students and clients, she’ll often get defensive on purpose. She’s noticed that people tend to start out arguing like an attorney giving a closing statement. After a few rounds they get quieter and start asking questions. Curiosity usually gets further than a well-built case.
In the room
Set ground rules. Phones off, no interrupting, and an agreed amount of time. She suggests an hour, with the option to meet again if you need it.
Find a goal you both share. Nobody should feel like they’re there to lose. Sometimes the shared goal is simply getting the facts, intentions, and feelings out where everyone can see them.
Pay attention to your body language. Crossed arms, eye-rolling, or a litigator’s tone can undo careful words fast. Lean in, listen, and pause before you respond. As Christina puts it, “I get it. Do it anyway.”
After the conversation
Write down what you agreed to. People are often surprised by how differently two people can remember the same conversation, especially when emotions ran high. Before anyone leaves the table, capture the main points and ask, “What do you see as constructive next steps?”
Follow up. Thank the other person. Think about what surprised you. Then put the next conversation on the calendar, because one talk rarely settles something that’s been building for years.
Why this matters to us
At Wingspan, we see what happens when these conversations get postponed. The issue doesn’t go away. It comes out sideways, usually with the wrong people and at the worst possible time. Families that can talk openly about succession, money, and roles before there’s a crisis are in a much stronger position than families that wait.
What we appreciate about Christina’s approach is that it doesn’t ask you to have the perfect script. It asks you to prepare, show up, and keep going.
Read the full article – 8 rules for navigating a difficult conversation – at the link below.
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Learn more about Christina’s book Unspeakable at christinawing.com/book.
For more Wingspan content, check out our Insights.
