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EntreLeadership

The 3 Mistakes People Make in Hard Conversations (and How to Avoid Them)

EntreLeadership

Ramsey Network

Business, Management, Entrepreneurship

4.74.4K Ratings

🗓️ 2 February 2026

⏱️ 13 minutes

🧾️ Download transcript

Summary

Most leaders don’t mess up tough conversations—they avoid them.  In this episode, you’ll learn how to face difficult conversations head-on with a clear plan that protects trust, fixes problems faster, and strengthens your team instead of damaging it.   Next Steps:   ·      🎥 Watch the training and use the template to prepare for your next hard conversation: https://ter.li/tiy692 ·      📞 Have a question for the show? Call 844-944-1070 or send us a message: https://ter.li/ask-us ·      📚 Learn about the EntreLeadership System™: https://ter.li/system-p ·      💻 Get EntreLeadership Elite™ for your business: https://ter.li/elite-p ·      ✉️ Sign up to receive tactical tools, advice and resources in your inbox every week: https://ter.li/enl ·      🏢 Attend EntreLeadership Summit: https://ter.li/summit ·      🎤 Attend EntreLeadership Master Series: https://ter.li/masterseries  ·      📖 Order Dave’s new book, Build a Business You Love: https://ter.li/b4kru2   Listen to More From Ramsey Network: 🪑 Front Row Seat with Ken Coleman 🎙️ The Ramsey Show 💸 The Ramsey Show Highlights 🧠 The Dr. John Delony Show 🍸 Smart Money Happy Hour 💡 The Rachel Cruze Show💰 George Kamel   Ramsey Solutions Privacy Policy Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0

From the headquarters of Ramsey Solutions, this is Entree Leadership.

0:14.1

I'm your host Dave Ramsey, with over 30 years of experience leading in the trenches right alongside you.

0:19.8

Most leaders hate having difficult

0:22.8

conversations with a team member. But trust me, avoiding the hard conversations doesn't protect

0:30.0

your team. It paralyzes it. So the best leaders out there don't run from this. They lean in.

0:36.4

That's why today, John Falcons from the

0:38.6

Entry Leadership Team and one of my board members, Brendan Wochko, will show you exactly how

0:43.9

our team has the kind of tough conversations that solve problems, grow trust, and make the

0:49.5

business stronger.

0:50.2

All right, thanks, Dave. Well, Brendan, we have this conversation all the time about difficult conversations, but I know all of your work on that really kind of started with a story, didn't it? Your own experience. Yeah. It's like a fun, not fun story, right? It's fun now. It's fun now. It wasn't in the moment. Right. Yeah. So like one night my wife and I are sitting

1:11.1

on the couch, you know, at her house. It's totally normal. She gets a text message, right? And I kind of barely notice she got the text message until, you know, when I did notice, she's kind of like staring at her phone. And, you know, something about that moment, you could kind of just feel like the air drain out of the room, right? And she didn't, she didn't say anything to me. She just kind of

1:29.3

turns and looks. I grabbed the phone. I look at it and my wife had gotten a text message from a woman named Anne. And I had fired Anne's husband that morning. And it was just like the text message was just like, hey, that's all it said. So you didn't really know what was coming next, you know? And, you know, like, you get the three little bubbles that are, that are telling you on the text message thing, the person on the other end is sending like a really long message. Yeah. And so at this point, my wife and I are both like, you know, sitting there, like staring at her phone, like what the heck's going to happen next? What's the next message that's going to come through? And when the message

2:05.2

came through, it was like not what we expected. She basically said, hey, I know her husbands have

2:11.1

just walked a really tough road together. Right. But I feel like it was handled really well. And I just want to communicate that I'm grateful for that and want to know if we can still be friends.

2:23.1

Yeah.

2:23.4

Okay. That could have gone a very different direction.

2:25.5

It could have gone a very different direction.

2:27.3

And there were like a bunch of lessons in that, right?

2:32.0

Like I think at that point of my leadership experience,

2:35.6

I was like 10 years into my, into leadership at that point. And what was interesting is I kind

2:41.4

of walked away from that, that evening. And I was, I was like, how is it that I've been doing

2:45.4

this leadership thing for 10 years? And I've walked through a bunch of uncomfortable conversations, but I've never had one in 10

...

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