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EntreLeadership

The 5 Step Framework for Addressing Difficult Employees

EntreLeadership

Ramsey Network

Business, Management, Entrepreneurship

4.74.4K Ratings

🗓️ 2 March 2026

⏱️ 19 minutes

🧾️ Download transcript

Summary

Hard conversations aren’t optional—they’re part of the job. In this episode, you’ll learn how to handle the five types of difficult conversations leaders face with clarity and confidence—so you can lead decisively instead of tiptoeing around problems. Next Steps: 🎥 Watch our video The 3 Mistakes People Make in Hard Conversations (and How to Avoid Them): https://www.youtube.com/watch?v=UBsV1vHu7rY 📋 Get the framework for addressing your difficult employees: https://ter.li/ravdz3 📞 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

We've talked before about how to have hard conversations as a leader, but not every tough talk

0:13.6

talk is the same.

0:14.5

So today, we're breaking down the five types of hard conversations you'll face and how to approach each one with clarity and confidence.

0:25.2

Because when you know which type of conversation to have and when, it helps you communicate the

0:30.2

problem clearly. Keep your team on the same page and make those tough moments a lot more

0:35.8

productive. Ramsey's chief technology officer, Brendan Wojko, joins Entree Leadership's John Falcons

0:43.2

to share some practical ways to handle these moments well.

0:47.2

So you can lead your team forward instead of avoiding the tension.

0:51.2

So, Brendan, we've talked a lot about how to have a difficult conversation. And we've

0:57.1

got resources on that. So if people want that, they can click the link in the show notes. But today,

1:01.9

we really want to get into the different types of difficult conversations. So could you help us

1:07.2

unpack what those different types are? Yeah, yeah. Usually when people ask me about uncomfortable conversations, it's all about, like, how to have them, like how to have a successful uncomfortable conversation. And the reality is that there's not just one. What I found is there's five distinct kind of uncomfortable conversations. The first one is what we call first contact. The first time you actually address a problem with someone, right? And in that conversation,

1:29.1

like, I mean, the biggest thing is just to make sure that you really clearly state the problem

1:32.8

in a way that they understand what the problem is. Okay. You know, I always joke around and say,

1:36.8

like, your articulation or the problem should be so clear, like your fourth grade, you know,

1:40.9

English teacher should be proud of you, right? The reading level should be a low number, right? The reading level should be low, and the statement should be really short. Okay. And it should be about observed behavior. Like, John, I see that you've been showing up late to work, and that's not okay. Yeah, this is getting personal fast. Right. Yeah. I mean, it's, you want to be really clear on the problem. The second part of it, you want to make sure that they're really clear about the process you're going to walk out next. Okay. Because you're typically not having uncomfortable conversations the right way when you sit down with somebody and you kind of like swoop and poop. Like if you, you know, if you swoop into the situation, you kind of drop a

2:17.6

problem on their lap and then you're gone. That's not a productive, uncomfortable conversation, because the person, if they just become problem aware, it doesn't mean that they know what to do, it doesn't mean that they're going to get the coaching they need. It doesn't mean that the problem's actually going to get fixed. All it means is you dropped a 10, 10 ton, you know, concrete block on them, which is you got a problem.

2:34.6

And so in that first contact conversation,

2:37.0

we want to make sure that we really click as you dropped a 10 ton, you know, concrete block on them, which is you got a problem.

2:34.6

And so in that first contact conversation, we want to make sure that we really clarify the problem.

2:39.0

And we want to help them understand like what happens next.

2:42.8

Okay. And usually in that conversation, I'll say to people like, listen, we're going to walk through a series of like coaching conversations because it's great that in this conversation, this first contact conversation that we've made the problem clear.

...

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