TECH TITANS: Emotional Firings & Tough Conversations with Brendan Wovchko, CTO at Ramsey Solutions

(Intro Narrator at 00:00:00) Today, we're bringing you an episode of Tech Titans, featuring our most valuable leadership insights from Ramsey Solutions CTO, Brendan Wovchko. You're listening to Joel Beasley, Modern CTO.

(Brendan Wovchko at 00:00:17) So the uncomfortable conversations topic kind of came up originally as a curriculum. It wasn't really like a stage talk. So I used that curriculum to teach my group of 42 leaders at Ramsey, like, how to have uncomfortable conversations with people, right? Because it's a leadership skill that's hard to do and hard to learn. Our live events team, our EntreLeadership team, took notice of some of the internal training I was doing, and they said, "Oh, hey, this would be great if you did it at one of our events."

(Brendan Wovchko at 00:00:47) I ended up taking this four-hour, six-part training thing that I developed for my leadership team and condensed it down to like a 45-minute talk. And I've done it a couple times at our EntreLeadership events. So it's an interesting thing because there's a short version of it, and then there's a really long version of it, depending on what you're doing. But I was going to suggest, if you wanted to focus in on this topic, there is like a download that we could actually give.

(Joel Beasley at 00:01:18) We can put it in the show notes. Give people...

(Brendan Wovchko at 00:01:20) Because there's enough to talk around the topic, but really the piece that people find most valuable is like this conversation guide on how to actually construct an uncomfortable conversation. You know, it gives them options. They can check things and circle things and fill in the blanks, and it will build a storyline or a template that you can bring into an uncomfortable conversation with you if you're really freaking nervous, which most leaders are.

(Joel Beasley at 00:01:54) Yeah.

(Brendan Wovchko at 00:01:55) So I actually think that's kind of what made the topic popular, because it wasn't just this esoteric, philosophical talk on the importance of doing uncomfortable conversations. Although that's in there, there's like hard tools to teach you how and how to practice doing it. So yeah, if we're going to talk about the topic, you know, offering the download would be pretty important because if you try to just verbally talk through the format, it gets pretty jumbly pretty quick. You know?

(Joel Beasley at 00:02:27) I want to know about the day that you decided you needed to make this.

(Brendan Wovchko at 00:02:33) Well, okay. So it's pretty interesting. The day that I decided that I needed to make this was not like one of those really bad situations where I'm in the middle of an uncomfortable conversation and I don't know what to do. It was actually the exact opposite of that. So I was sitting on my couch one night with my wife, and she gets a text message. Not unusual for us. We get text messages at night just like everybody else does. But I see her look down at her phone, and you could kind of feel the air change in the room. And I was like, "Oh, wonder what she just got," right? And she kind of paused for a second, looked at me, looked back at her phone, and then just hands me her phone. And there is a text message on her phone from a woman named Anne, and I had just fired Anne's husband that morning.

(Joel Beasley at 00:03:26) Oh, no.

(Brendan Wovchko at 00:03:27) And all the text message says is, "Hey," right? And then, you know, you get that little animation on your iPhone that apparently some brilliant designers and engineers at Apple came up with to signal to you that somebody is typing a really long message on the other end.

(Joel Beasley at 00:03:43) Mine is off.

(Brendan Wovchko at 00:03:44) Right?

(Joel Beasley at 00:03:44) Yeah. Yes, sir.

(Brendan Wovchko at 00:03:46) Yep. And so my wife and I are both sitting there looking at her phone like in suspense. Like, "Oh my gosh. What message are we about to get from Anne?" You know? Because there's that fear, like, you're about to get your doors blown off because, as unfortunate as it is, I had to let her husband go. And the message that I got back—I mean, it's not a direct quote, but these words are kind of seared into my mind, right? She said, "Our husbands just finished walking an uncomfortable road together." And she said that the outcome was tough, but the process was loving and fair. And she said, "I hope we can still be friends." And I remember particularly that part that said, "The process was loving and fair." It just kind of rocked me, you know, because up until that point in my career, I've been doing leadership for about 10 years. Every time I ever did an uncomfortable conversation, it was brutally bad for me. It was brutally bad for the other person. And this was the first time I had walked through something like that, and somebody, in a subtle way, almost came back and thanked me. And, you know, Anne's going through this moment where her family's in total turmoil, right? Her husband just lost his job. It was a bad situation. But she took a moment to acknowledge how we handled the situation. And as a leader, I don't think there's almost—I don't think there's a bigger win than that, right? So that caused me to kind of wake up and realize there was something I did right this time that I've never done before.

(Brendan Wovchko at 00:05:17) So I kind of walked the situation backward and just started writing down, like, what did I do? What sequence did I do it in? What do I want to repeat? And when I got all that stuff down on paper, then I was actually amazed by how much information I was able to kind of regurgitate. And then when I started bringing that to other leaders, they started to treat it like gold, you know, because to me, one of the hardest parts about leadership is basically learning how to model for other people things that were never modeled for you. So for me, in my experience, you know, I've worked with lots of great people over time, but I come from that generation of technology folks, you know, I'm the first generation of the web. And there were not a lot of people in my experience along the way who were able to give me really great leadership advice. We were all kind of figuring it out at the same time. So one of the challenges for me being that first-generation web guy is now I have hundreds of people who work for me. I've got 40-plus leaders that work for me. And a lot of those folks are a little younger than me, you know, the next generation. So I've had to figure out, like, how do I model for them what has never been modeled for me? And that's a tall order. You know, it's hard to do. So the uncomfortable conversations topic is one of the first times I really stepped into that and said, "Okay, I've identified something here where I've got some success. Let's make sure that I get that out for other people to learn too."

(Joel Beasley at 00:06:49) I want to talk about—I want to give like a specific scenario.

(Brendan Wovchko at 00:06:52) Yeah. Yeah.

(Joel Beasley at 00:06:53) That way we can work through it. So the details are going to be in the worksheet, which we're going to attach to the conversation so people can walk through the formula. But just conversationally here, one of the toughest conversations anyone has to have as a leader is letting someone go, right? And so what is like the high-level milestones that you think of when you're going through that process?

(Brendan Wovchko at 00:07:13) Right. So it's funny you bring up that example, because that is the most frequent thing that people bring up. And if you're not careful, and this happened to me when I first started teaching on this topic, when you start giving people tools about how to have uncomfortable conversations, wouldn't you know it, the first thing that they do is they're like, "Oh, great. I finally have the tools to fire this guy or fire this gal," right? And I figured that out pretty quick when I started teaching this. And I really had to get everybody to pump the brakes and be like, "Whoa, whoa, whoa. I didn't give you these tools so you could just start firing people. I'm giving you these tools so you can take 10 steps backward and hopefully avoid ever having to fire someone," right? So the way I kind of break it down in my head is there are really five types of uncomfortable conversations, but six things you have to do. And when you're dealing with somebody and you've got some maladaptive behavior going on, you have some unwelcome behavior, the first thing that you've got to do that most people don't pause and do is get really, really clear about the problem. Most of the time, when you're sitting down to talk with someone about a problem, you're really just kind of boiling up all the frustration that you have as a leader. Like, they didn't do this, or they disrespected me in some way, or they didn't follow instructions, or, you know, whatever it is. And you're actually acting pretty emotionally. And the first thing you've got to do, like the first step of everything, is just stop, calm yourself, get really clear and concise about what the problem is. And then after you're at that point, then you can kind of walk through a process of having different kinds of uncomfortable conversations with people. So the first one, the first uncomfortable conversation, I call first contact. So first contact is the uncomfortable conversation you have with somebody where you're addressing the maladaptive or the unwelcome behavior for the first time, right? It's also the hardest of all the uncomfortable conversations because you're broaching that elephant in the room, you know, and it can be really uncomfortable. Once you have that first uncomfortable conversation with people, you then want to walk into a pattern of coaching. So, you know, you've identified the problem in that first contact conversation. You've probably identified some action steps of what needs to happen.

(Joel Beasley at 00:09:34) Can we make it more real?

(Brendan Wovchko at 00:09:35) Yeah.

(Joel Beasley at 00:09:35) You can fire me. All right.

(Brendan Wovchko at 00:09:37) So, okay. Here we go.

(Joel Beasley at 00:09:38) My performance—I'm a leader of your team.

(Brendan Wovchko at 00:09:41) Oh, okay.

(Joel Beasley at 00:09:41) Product, right?

(Brendan Wovchko at 00:09:45) Is that an option?

(Joel Beasley at 00:09:47) I'm a product, and my performance has dropped. I started out strong.

(Brendan Wovchko at 00:09:50) Right.

(Joel Beasley at 00:09:51) We're three months into it.

(Brendan Wovchko at 00:09:52) Right.

(Joel Beasley at 00:09:53) Had good references, but my performance has dropped.

(Brendan Wovchko at 00:09:55) Right. Okay. Well, can we make it even more real?

(Joel Beasley at 00:10:00) Okay.

(Brendan Wovchko at 00:10:00) Okay. Let's say that you're a leader on my team, and you have a team member that's not performing well. And you came to me recently, said, "I feel like I need to go put this guy on a 90-day plan," right? So you've now put him on a 90-day plan. And I got an email from this person who's on a 90-day plan last night that they are 50 days into their 90-day plan, and you've not checked in with them. You've not given them any coaching. Other than having them sign some sort of document that says, "Hey, this is the behavior change you've got to have," you're kind of ignoring them. So I've got to sit down with you and say, "Oh my goodness. I knew you were new in this 90-day plan. I knew you were walking into some disciplinary action with a team member, and you were letting them know, like, 'Hey, some things have got to change.' But I don't really feel like you're holding up your end of the bargain as a leader. You're either intentionally or unintentionally participating in leadership neglect. And your neglect of this team member is going to cause this team member to lose their job." And I mean, that would be a pretty on-point way to describe the problem. And again, we got a template for all this. You know, the first thing that I like to tell people is, if this were a real scenario between you and I, and I call you into my office, you know, there's a power dynamic there. You've got to acknowledge the power dynamic. So the first thing I—and, you know, when the power dynamic happens, people aren't thinking logically, right? They move back to their limbic system. They're in fight or flight. So the first thing you've got to do when you're having an uncomfortable conversation with people is you've got to get them out of the limbic system. You've got to get them up to their prefrontal cortex where they're actually thinking, right, logically. And so when somebody comes into my office, I don't make small talk. I don't ask them about their weird pets, or their kids, or their spouse, or anything like that. Within five seconds of somebody sitting down in my office to have an uncomfortable conversation, I let them know two things. I let them know, "Hey, this is going to be an uncomfortable conversation, and don't worry, nobody's losing their job today." Within five seconds, I've kind of set the tone with the person, and I've addressed the elephant in the room. And then, you know, once you've gotten that out of the way on the front end, then you can move into talking about the severity and the impact of the situation, stating the problem, you know, and getting through some conversation about the issue.

(Joel Beasley at 00:12:30) Okay. I like that.

(Brendan Wovchko at 00:12:31) So that's the first contact conversation. Okay. Once you move past that first contact conversation, now we're going into a coaching pattern with someone, you know? So I would probably say toward the end of that first contact conversation, "Well, hey, let's get together again tomorrow. I want to help give you some coaching." And what I tell people about coaching is, "Hey, coaching's going to go really well if you do two things. One, you've got to actually apply the coaching that I'm giving you. And two, you have to share my urgency around how important this is to fix," right? And if you're really clear with people and give them that level of clarity, like, "Hey, this is going to work out. This coaching is going to go great if you apply my coaching and share my urgency." You have now set the rails on the coaching conversations you're having with people, and so you're able to come back in your second coaching conversation or your third coaching conversation, and you're able to ask them, like, "How well do you think you're applying my coaching and, you know, how effectively do you think you're sharing my urgency?" You actually compare some notes. And the other thing I'll do in coaching conversations too is bring in the feedback of other leaders. So let's say there are a couple of other leaders that are working closely around you and they're also aware of the situation where you're kind of unintentionally flubbing this guy's 90-day performance plan.

(Joel Beasley at 00:13:56) Okay.

(Brendan Wovchko at 00:13:57) Right? I would probably reach out to some of those leaders that work closely with you and say, "Hey, are you noticing Joel spending a lot more time with this team member? Are you noticing Joel coach this person? Are you noticing Joel giving this person a disproportional amount of his attention? And do you see the person benefiting from it?" And, you know, I reach out to some other leaders that work around you, and I'd ask them to kind of score you on it, like one to five. Are you doing those things? And are you sharing the urgency?

(Joel Beasley at 00:14:28) Is this just conversationally, or is there an actual like document?

(Brendan Wovchko at 00:14:30) No. There's actually—I can include that in the download.

(Joel Beasley at 00:14:34) There's a—

(Brendan Wovchko at 00:14:34) There's a real format that I use. Oh, cool. And then I bring that into the conversation with you too. Because if you're not careful in an uncomfortable conversation situation, it's really easy for the conversations to become unnecessarily adversarial.

(Joel Beasley at 00:14:48) Oh, yeah.

(Brendan Wovchko at 00:14:49) My role is to be a coach to you. So I tell people, be a coach, not a cop. My role is not to be law enforcement. My job is literally to be on your side of the table trying to help you through this problem. Like, the thing that should be the adversary to you is the problem, not me.

(Brendan Wovchko at 00:15:08) So my job is to come alongside you, coach you, so we can get rid of the problem, and we can continue to walk forward together. But too many leaders, when they get into that first contact conversation or that coaching conversation, put themselves unknowingly in an adversarial situation with the other person. So part of staying out of that adversarial pattern is bringing in feedback from other leaders. Because if the only feedback you're getting is just from me, it just sets us up for an adversarial situation.

(Joel Beasley at 00:15:38) Right.

(Brendan Wovchko at 00:15:38) So do you want me to go through all five? I can rip through them.

(Joel Beasley at 00:15:41) You can rip through them. Yeah, I'm curious.

(Brendan Wovchko at 00:15:45) The first kind of uncomfortable conversation is a first contact conversation. Second kind is a coaching conversation. And, you know, you and I could have one coaching conversation and it goes fantastic, and that's it. We just need one, and then we're done.

(Brendan Wovchko at 00:15:59) Or we might need two or three. I'll tell you what I don't usually do. I'm not gonna do four, five, or six coaching conversations with somebody. If we're two or three into it and the person's not, you know, sharing my urgency and doing their work to solve the problem, we're gonna move beyond coaching to the next level.

(Brendan Wovchko at 00:16:18) And this is a really weird phraseology that we use at Ramsey that you're not gonna hear anywhere else. And I gotta explain it the moment I say it, because you're gonna be like, what is that? We call it an emotional firing. And it sounds really harsh, but it's actually kind of an act of mercy, honestly. What an emotional firing is, is a conversation with a team member where you say, hey, we've been doing this coaching, and you're not applying my coaching, you're not sharing my urgency, this is not going well.

(Brendan Wovchko at 00:16:48) And so I need you to make a choice. I need you to make a choice as to whether you wanna keep on fighting to save this situation, or whether you're ready to tap out and surrender and maybe move along to your next job. So the goal of the emotional firing is to cause someone to have the emotions of a termination without experiencing the material consequences of the termination. And that can sound harsh, but what it's gonna do is it's gonna make real for you the situation that you're in.

(Joel Beasley at 00:17:20) Let's take a moment to talk about Ramsey, the company.

(Brendan Wovchko at 00:17:24) Right.

(Joel Beasley at 00:17:24) Yeah. Recruiting is one of the reasons why a lot of people come on the show.

(Brendan Wovchko at 00:17:28) Because—

(Joel Beasley at 00:17:28) A lot of—

(Brendan Wovchko at 00:17:28) I'm on the show because I like you.

(Joel Beasley at 00:17:30) That's it. I wanna give a plug for Ramsey Solutions. And the reason why I wanna do this is because I came and I got to visit the buildings in person and see the studios. And you gave me a tour, and you had lunch with me, and you had that thing that you really liked a lot. And the guy knew your order.

(Joel Beasley at 00:17:50) Oh, yeah. The Philly cheesesteak.

(Brendan Wovchko at 00:17:53) Yes.

(Joel Beasley at 00:17:53) So the environment was unbelievable. Incredibly welcoming.

(Brendan Wovchko at 00:17:58) Yeah.

(Joel Beasley at 00:17:58) You could see the joy on people's faces.

(Brendan Wovchko at 00:18:02) Yeah.

(Joel Beasley at 00:18:03) The amenities just blew me away.

(Brendan Wovchko at 00:18:05) Yeah.

(Joel Beasley at 00:18:05) Right? And I remember having a conversation with my wife after I got home, and I said, man, I've gotten to visit so many companies and experienced so many teams and talked to so many people. And I go, that is one of the only places I think I would ever wanna work if I wasn't an entrepreneur. Because it just felt like there were so many great people there, and they were all aligned working together towards a goal. It was a great atmosphere, and just everything about it was awesome.

(Brendan Wovchko at 00:18:33) And that's what happened to me. I am a lifelong entrepreneur. Ramsey is actually the first full-time job I've ever had. Ramsey, slowly over a period of a couple years, became my company's biggest customer. And as I got to know Dave and I got to know the operating board and a lot of key leaders at the company, I fell in love with the place.

(Brendan Wovchko at 00:18:50) And I ended up selling my company to take a full-time job at Ramsey, which a lot of my friends were like, you're crazy. But best decision I ever made. That was five years ago. Best decision I ever made.

(Joel Beasley at 00:19:01) And are you guys hiring right now in technology?

(Brendan Wovchko at 00:19:03) Oh, yeah. Yeah. I mean, I've got a hundred open developer roles.

(Joel Beasley at 00:19:07) Where do people find that?

(Brendan Wovchko at 00:19:08) Yeah. Ramseysolutions.com. Yeah. We got all of our jobs listed there. Always hiring great engineers, always hiring great product managers, always hiring great project managers, product designers.

(Brendan Wovchko at 00:19:20) You want me to tell you a little bit—yeah. Tell everybody a little bit about the company. So Ramsey Solutions. The background of the company is in 1988, our CEO went through a devastating set of financial circumstances, ended up causing him to go into bankruptcy. He was a young entrepreneur in his twenties, and he had kind of amassed a small real estate empire.

(Brendan Wovchko at 00:19:40) And he did it the way that people are still doing it today, which is he debt financed the purchase of a whole bunch of buildings. And the bank that he was working with got purchased by a bigger bank. And when that new bank was reviewing their books, they said, who's this 26-year-old guy that's got, like, you know, $34 million of debt? That seems pretty risky. So they called his loans, which caused a multi-year domino effect of just financial tragedy. And that created—and, you know, our founder's name is Dave Ramsey.

(Brendan Wovchko at 00:20:10) You might find that name familiar. That created a real awareness on Dave's part about how toxic debt can be to your life. And so as bad as that situation was for he and his family, after he kind of dug himself out of that hole, he decided he wanted to start helping other people that had gone through the same thing, that were in financial tragedy, and wanted to not only help people get out of that financial tragedy, but hopefully, if he did his job right, help other people from ever getting into it. So that birthed a company called Lampo, which eventually became Ramsey Solutions as we are today. So now twenty-five years, thirty years later, post that situation with Dave, you know, we use digital product and terrestrial radio and book publishing and one-on-one coaching and live events.

(Brendan Wovchko at 00:20:57) You know, we're a multi-disciplined company that uses all those different approaches. We reach about twenty, twenty-five million people a week to kind of tell the story of not only just how to get out of debt, but how to stay out of debt and build a future of financial freedom. You know? So that's what the company is all about. It's fantastic.

(Brendan Wovchko at 00:21:17) You know, it's one of the few places—I'll just speak for myself, you know, as an old crusty software engineer. It's the first job I've ever had in my life where I get to go to work every day and hear endless stories of the life change that our customers have helped create for themselves by using the products that we make. And not just change for themselves, but changes for their kids. It's generational change. You know, when people learn how to get detached from the toxic debt culture that we live in in America and learn to live life on their own terms, beautiful things happen in relationships and families and marriages that last generations.

(Brendan Wovchko at 00:21:59) So it's a really amazing, fulfilling place to work. And, you know, you mentioned that having visited, you can tell that on people's faces. You know, we're not doing just engineering work for the sake of engineering work. We're doing engineering work because we know it's changing people's lives, and that's a lot of fun.

(Joel Beasley at 00:22:15) Yes. Back to the Philly cheesesteak. When we were standing in line, an engineer or two walked up to you, and you were just talking with them, and you introduced me. And I went to one of my defaults, which is, hey. What language do you program in? And he goes, whatever language is needed to solve the problem. And I was like, oh, that is great. I was like, that is the perfect—that is the answer.

(Brendan Wovchko at 00:22:37) Yeah.

(Joel Beasley at 00:22:37) So I was sold at that point.

(Brendan Wovchko at 00:22:39) Yeah. We're very, very lucky. I probably don't tell them enough how honored I am to get to work around 250 software folks that are so aligned in terms of the mission of helping change people's lives. It's a different breed. You know, we like to joke and say it's almost like a rare air that we get to breathe at Ramsey.

(Brendan Wovchko at 00:23:03) When you have people that genuinely care about the things that they're doing, it creates an environment that you can't manufacture. You know, it's passion.

(Joel Beasley at 00:23:12) Thank you so much for listening. And if you found this episode useful, please share it with a friend or colleague who you think would get value from it. And if you have topics that you'd like to hear discussed on the podcast, either add me on LinkedIn, or send me an email, [email protected]. Every time I get an email or LinkedIn message, it absolutely makes my day and inspires me to keep going.