Great Conversations Break the Rules
Momma said, “Don’t interrupt.” Let people finish. Pause. Make space.
Master the habit of letting people finish before you speak. But the rules experts make up get in the way of great conversations.
6 Ways to Break the Rules and have Great Conversations
Break the good habit of letting people finish. Give yourself permission to interject.
Great conversations are a dance. Turn-taking is less important.
#1 Interject to Show Interest
Jumping in shows engagement. Try saying:
- “Wait—did you say…?”
- “Hold on, that seems important.”
- “Do you mean…?” (Stay aligned.)
#2 Circle Back to Preserve Value
Don’t let good ideas slip away. Use phrases like:
- “Before we go on, I’d like to go back to…”
- “That reminds me of something important.”
Ideas expire quickly. Share strong thoughts before they fade when they contribute to momentum.
#3 Get Nosey
“Tell me what you really think.”
“How did that affect you?”
“What do you really think about that?”
“What are you not saying?”
#4 Overshare a Little
“The same thing happened to me.”
“I’ve felt like that.” But don’t steal the conversation. Don’t assume you understand someone.
#5 Judge Gently
“You’re kidding.”
“I can’t believe it.”
#6 Have Fun Speaking the Truth
Exaggeration works when trust runs deep.
“You’re nuts.”
“Have you lost your mind?”
“I think you’re way off base.”
4 Undeniable Laws of Great Conversations
#1 Powerful conversations bounce. Interjections energize when done with curiosity.
#2 Follow the #1 improv rule: “Go with” when you jump in. Be willing to change your mind. Don’t hijack conversations.
#3 Many conversations are all business. When you’re the boss, great conversations are rare. Sometimes they are completely inappropriate.
#4 Location matters. Offices kill great conversations. Take a walk. Have coffee.
Which conversation rule would you love to break?
Which one would you never break?
3 Ways to Energize People during Conversations
Become a Better Conversationalist




Dan – Hi – I’ve read and benefitted from your blog for years; thank you for the tremendous number of insights and thought-provoking posts.
Today’s post is also thought-provoking. While I (like to think I) appreciate the nuances of what you have above, I consider the thought of interrupting someone as abhorrent and, unless we’re dealing with a cooling rod overheating, unacceptable. For years, I have trained team members to at least allow the other person to finish before they respond with their pre-conceived notions. As you can imagine, that statement helps to spur a further conversation – in private, of course.
But, if I interrupt someone, what’s to stop that person from interrupting others in team meetings? And, when (not if) that happens, what leg do I have to stand on/upon/grammar is hard? So…listen, take notes, be thoughtful (all at the speed of thought, of course) and then respond. For me, that’s an inviolate rule.
Again…long-time fan, first-time caller.
Thank you for being a longtime reader, Dean. Your thoughtful note means a lot. You’re right to highlight the value of patience, respect, and focused listening. That’s gold—especially in a world full of noise and half-listening.
You raise an important concern: what’s to stop a culture of respectful interjection from turning into a circus of interruptions? The answer is leadership.
Leaders model curiosity and restraint. The kind of interjecting I’m advocating isn’t about cutting people off to push an agenda. It’s about jumping in to stay aligned. It’s about saying, “Wait—did I hear that right?” or “Hold on—that seems important,” because you care enough to get it right in the moment.
If someone abuses that openness, leaders step in. If someone’s hijacking meetings, it’s a coaching opportunity: “Interjecting is fine—when it builds momentum, not when it shuts people down.”
Also, I should I been more explicit about the context. I’m focusing on 1:1 conversation. I practice interjecting when someone talks on and on and starts covering multiple topics.
I think of interjecting as a skill to learn, after mastering silence and pausing.
Thanks again for the note. You have my appreciation.
Keep making space and making sparks.
It’s interesting the feedback gainst your latest post on what I call “honorable interuptions.” I think different personalities will respond differently and of course the fun-loving conversational skill of the leader is paramount. I actually bristle when my leaders have no interjection or emotional connection with the discussion. After all it is a discussion not a one way “counsel” session where the proverbial leader therapist says, “mmm hmm, I see, ohh, that would be challenging etc.” I always those leaders to as disconnected and fake.
Leadership is not counseling, and advising is not leadership. Leadership in the context above is a one-to-one sharing relationship that moves carefully outside the realm of just getting business done. It’s a type of friendship. So, the idea of properly engaging and drawing out the persons real needs stand out to me in this last post.
Perhaps what scares us is that most positional leaders (I’ve been fairly accused of this a lot while in management) don’t let anyone have a say at all (as to Dean C point) so the concern is that they may not have mastered any form of listening and will take the advice above and misapply it. That risk of abuse aside, your advise seems more cogent than ever.
Always learning! I find your posts invigorating and useful all the time.
Adam Hrebeniuk
Coach, Hrebeniuk.com