Ever watched a conversation die a slow, painful death while you nodded politely but checked out inside?
Strategic interruption might be your secret weapon–it’s one of the most underrated communication skills is interrupting.
No, I'm not talking about that guy (and let's be honest, it's usually a guy) who steamrolls over everyone without a second thought. That’s the typical interruption: a person completely lacking in self-awareness who starts talking over someone else without letting them finish their thought, completely ignoring what they were saying.
I mean interrupting to deepen and improve the quality of the conversation.
Boredom is the conversation’s cry for help
I once saw a founder notorious for always being on his cell phone during meetings. He justified it: "I'm not getting much from the meeting, and I have other stuff to do."
Brutal honesty, but at least he admitted the problem (while missing the meeting’s call for help).
Another founder I coached was much more polite in conversations, nodding and making eye contact, but complained that he was dying of boredom and completely disengaged on the inside.
Sound familiar? You're physically present but mentally scrolling through your to-do list.
LEADING THE CONVERSATION
We addressed this in two ways: Inner Game and Outer Game.
Inner Game: Rewriting Your Mental Script
The Inner Game involved surfacing the implicit narrative in his head, the one running the show behind the scenes.
It often sounded like this: "This person isn't interesting, and this conversation is going to suck."
This turned into a self-fulfilling prophecy. When he thought that, he didn't take any action to change the trajectory, a mere passenger along for the boring ride.
It was time to Lead the Conversation.
Step 1 was exploring alternative beliefs and stories he could tell himself. He started with, "There is absolutely something we have in common–so let me find that thing." As a lover of learning, he also tried, "There's something I can learn here that will be useful to me."
Outer Game: The Strategic Interruption
Still perplexed by how to lead the conversation when someone droned on about something stultifying, I offered a new interpretation and a tool:
Boredom is a signal the conversation is sending you that something vital is missing.
Your boredom isn't just an inconvenience—it's valuable data.
If you are dying of boredom, interpret that as the conversation begging you to inject some life into it.
And then interrupt–with a question.
Ask something that takes the conversation in a direction that interests you.
"That reminds me of something I've been wondering about..."
"I'm curious—what do you think about...?"
When we interrupt, we can do so in ways that are focused on ourselves or others. While it's not inherently bad to focus on yourself, you can lead the conversation in a way that engages both or all parties by sharing something interesting to you and asking others to engage with that.
Next time you feel your attention drifting during a conversation, don't reach for your phone. Instead, interrupt with genuine curiosity. You might just turn a forgettable exchange into a memorable connection.
Either lead it–or leave it.
What conversation will you revive with a strategic interruption this week? Reply to this email and let me know how it goes!