What Can and Can’t Be Taught with Sean Gabrus

Jordan  00:00

Hello, this is Jordan, the owner and CEO of Greaser Consulting. On this episode, we have Sean, who is the Director of Shared Services at Outreach. He might even hit me for reading out his full title. Essentially, we’re talking about team building today. He has a great success record of just folks that have gone on his team and elevated, shifted positions, grown into different places all within the same company. So this guy is a team-builder through and through. Even from the day I met him when he was an individual contributor, he was talking team and build and community, art and science, and challenge. I mean, it was just, just fantastic. And so I think you’re really going to enjoy this episode if you’re thinking about how do you design a winning culture. How do you manage the right direction? Sean’s got a lot of great, great insight on that. I hope to bring him back someday, quite frankly, to talk more about it. So lean in, enjoy. And here we go.

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Jordan  01:18

Hey, crew, we got Sean with us. Sean, introduce yourself.

Sean  01:23

Hey, y’all, Sean Gabrus here. I am a Director of Professional Services at Outreach, where I get to work with hundreds of customers and awesome sales leaders across the world, helping them with their sales execution, and offering some fun services along with that.

Jordan  01:43

Well, I know the topic of the day is just around team building, what it takes from a management perspective, and everything else. So I appreciate you coming on. And I always like sort of starting each of these with, how do we get here, right? And we were talking about this just before we hit record today. And one of the really neat things that I remember about you specifically; obviously, we both came from Outreach. I remember a conversation with you where you’re like, “listen, like, I want to lead people here. I want to help them get to where they want to go.” And that was back into like, you’re just in the seat, maybe more than just in the seat. But you, you were running the consulting position. And then today, you’re what three years removed? And I mean, how many different teams are you working with today?

Sean  02:33

Yeah, so I have three teams that roll up through me right now. We have a technical consulting, technical services team. We have our core shared services team, which handles all of our scale customers and a lot of our mid-market commercial customers. And then I have managed services, which is all of our augmented outsource staffing and more long-term customer care that we can provide. And yeah, that’s kind of all grown organically from one team of eight splitting in half into two teams, and then adding the third team over time. And it has very much been my focus since I got to Outreach. Like, I wanted to get in as an individual contributor, do the consulting job and prove that I knew how to do it, and then lead a team yes. So that… as that conversation went, like that was definitely exactly how I wanted things to go. And I’ve been very fortunate for it to play out that way.

Jordan  03:33

Were you a manager in any position before coming to Outreach? Or is this like your first foray into the management sphere?

Sean  03:43

Yeah, I’ve had manager experience. I’ve had lead experience in the past. And then I think, generally, through my life, I’ve always been able to be in positions of leadership, like through, whether it’s through things at school, right? Different organizations, getting elected into leadership positions there, whether it was through sports, getting elected and the positions there. And then even going into college and working for a college basketball team and being in a position where I was younger than a lot of people that I had to manage, in a sense, get them to the right place on the right time, make sure they had the right stuff, manage our travel as we flew from one place to another. And so that set me up when I did enter the corporate world to where even if I wasn’t in a formal manager position, I was always thinking about the team and trying to lead even if it was just by example, right? And then when I was at Coding Dojo, I was lucky enough to get into a leadership position there, manage a team with Chad Ross, who you actually know. And then we both ended up coming to Outreach, which was pretty funny. 

Jordan  04:55

Anytime new managers sort of step into the position, and you can tell me if you agree, disagree, maybe in which way you fell. I always, I always say, if a new manager is going to make a mistake, they go one of two directions. They either go into the direction of assuming since they’re a manager, they’re now an authority figure. Now everybody just has to listen. Right? And you get a lot of, “Hey, I’m your manager, do it.” Okay? The other mistake is the other end of this the pendulum here, swinging the other way is, “I’m just going to be your friend.” Right? Like, “it’s okay. Like, I mean, if you can get to it,” and I mean, sort of take this position, like, I just want to be, you know, whatever. As you stepped into management, I’m super curious, like, did you swing one way or the other? Or was there, are you like, actually, that’s the wrong dichotomy there’s like four other items too?

Sean  05:46

Ah, no, I actually think that’s really funny, because I was having a discussion yesterday about this exact topic. Um, we were talking about the book, Radical Candor and kind of that chart that they have within of, you can have radical candor or you can have ruinous empathy. Where you just care way too much, and you’re too nice or you can have obnoxious aggression, where maybe you don’t care enough and you just hammer them with your opinion and feedback, and it’s not really coaching, right? And that’s where if you get to that upper echelon of radical candor, where you can show them, “Hey, I care about you. And that’s why I’m always giving you positive feedback.” And saying, “Hey, great job, Jordan, I really enjoyed how during that last meeting, when you know, Becky, and Jim got a little tense, you stepped in and helped them kind of focus back on the goal. That was awesome, right?” So that way, a week later, when you mess up on a call, and I say, “Hey, oh, Jordan, maybe next time, let’s think about a way we can approach this differently.” It’s not just one-off, one-time thing. And I think that I’m lucky because being around college athletics for seven years, not only was I lucky to have like, our head coach and our coaching staff that I got to see, how did they operate? How did they give coaching, and that truly is coaching and not just feedback. I got to be around a lot of other coaches in different sports. And for me, so much of that translates so well to like just the corporate world that we’re in. Because humans are humans, right? And like, they just want to know that you care about them. They want to know that they have a purpose and that they matter. And then they want to improve. So they need to hear things that aren’t just good. And so I think I was lucky in that because I had done the job, you know, I had done 300 implementations at Outreach. Right? So like managing people, and then working them through challenges was the fun part for me. So yeah, I mean, I think at times, I definitely am a little too friendly, especially earlier. But I think you’re spot on: those two categories are the ones that like if you can find the right balance, it can work out. If I had to tell a new manager, which one to lean into, I don’t know, caring about your team can lead to a lot better outcomes, in my opinion, and assuming things and telling them what to do.

Jordan  08:31

Yeah, I hear you. But I just spoke to, actually one of the guys on my team. He’s stepping up and take on some leadership roles. And he was talking about, you know, years ago, managing at a restaurant, and one of the pitfalls that he ran into was just wanting to be the friend. And he was saying how like the waitstaff, for example, when they weren’t waiting tables they were supposed to, to roll forks and knives and all like, you know, into napkins and whatever. Yeah, they don’t, they don’t really get paid for that the same way they do if they get tips, right? And he was saying, like, he could never get them to do that. But he would always be like, well, “I mean, I know. And don’t worry about it. And I’ll just do it for you” and all this kind of stuff. So, but actually, like it is part of the job, right? It’s not the glamorous part of the job. It’s not the part you want. And as the manager should you roll that for them sometimes, yes. But also, it’s not efficient over the long term for you to be caught up in those tasks if you’re the manager, right? And so, I feel like today, I could be wrong on this, but I just have the impression that in years gone by, if you were going to make a mistake, it was like you’re the authority figure. And it seems like today if you’re gonna make the mistake, it’s because we’re, like over sensitive to like the feelings of others and all this, like, we’re going to lean toward being friendly because we don’t want to offend, which can then sometimes undercut that like, like, hey, but I do need to sort of push you and, and so it’s just, it’s such an interesting balance. Anyway, I just, thinking about you coming in and taking on that role. I’m always just curious like, which way did you tend to lean right out of the gate? And if I have to be honest, like, I’m probably guilty of trying to be friend first, like if I gotta go one way or the other, which leads me to just another question I’ve heard some folks say, and I know this is like, we’re here to talk about team building. But first in team building, you think about how do you manage the team. I’ve had some folks say, if you’re going to be somebody’s leader, you need to recognize you can never actually be their friend because there’s a power imbalance. And there’s all these things in between and whatever else. And in some degrees, like, I understand what they’re saying, but I’m curious to get your take, because, like, it’s a pretty big statement. And I know if you want to lead with empathy, how does that fit in?

Sean  11:01

Yeah, for me, I think it comes down to what is the definition of friends. So let me look this up real quick: “a person whom one knows and with whom one has a bond of mutual affection, typically exclusive of sexual or family relations,” right? Not those things, just, hey, stronger than an acquaintance or an association, right? To me, if you care about your team, and you hired someone because you want them to be successful as a person, you want them to learn more and grow in their career. Right? You obviously want them to, like, make more money and be successful financially, and then, like, buy a house and do stuff like that, right? Like, isn’t that what you want for all of your friends too? Now, with that, there’s obviously some formal lines that have to exist, right? But as you know, depending on the culture, depending on the type of organization you’re within, those lines may vary greatly. As we know, sales teams, their manager sometimes have a lot of fun with their actual team, but that may be different than director may not. Right? It may… or the VP may not, right? Um, so yeah, I don’t know, it’s, it is an interesting thing. I do think that the best people leaders are able to find a really strong balance there. But like, am I hanging out with my team on the weekends? No, I’m not. 

Jordan  12:58

So here’s a question for you. Again, since we both lean sort of, toward the empathy, and we think a lot about like the quality of the team, the culture of the team, and all of that. Quite frankly, this, the question I’m about to ask you is something that I in the past have struggled with how to deal with. Just because of the way I’m wired and the way I think about, like, the team is more than just performance. It’s also how do you feel when you’re performing and you know, all of these things. What do you do in a situation and in the vein of team culture, where you have the team, sort of culture player, and you know what I’m talking about the person that’s like, the heartbeat of the team, folks love that individual; they’re fantastic. And man, they just can’t get the job done. But like, you like ‘em, so to speak, everybody else, there’s such an encouragement, you know, they sort of keep things going like, like, as, as a manager in that scenario, and again, I’m legitimately asking this for my own edification, because this is an area that I’ve had a hard time with, like, what do you do?

Sean  14:09

Yeah, I love that scenario. Because that’s like, a big part of why I feel like I’ve been successful at Outreach. Is I have oftentimes found a lot of people in scenarios like that and pulled them to my team. And that’s where it’s like, I’ve also had some people I’ve hired that maybe didn’t launch as fast or struggled out of the gate, or, you know, were really a great fit on the team, but maybe weren’t a perfect fit for that role. And that’s for me, when I have to go back to like, why did I hire them? What were the original skills that we were excited about? What passions do they have? And like, are there other roles that might be a better fit? Because if they really are that great of a team fit, if they bring the energy, if they get along really well with everybody, if they’re checking all the values that you care about, there’s got to be a slot for them somewhere, right? And sometimes it’s just not the right role. And like my career has played out that way; when I was in a hardcore sales role where I had to do 40 card drops and 40 cold calls every day, I literally hated my life for a year. I did fine at it, but I hated it, right? And I was a good fit with the people around me, they liked me, they wanted me to grow and succeed. But that job was not for me. And with that company there, there wasn’t really other roles that I think would have worked either. But like, if there are, it’s always worth doing that. And that’s where my team is fun. Because I have former Technical Support Engineers, I have former CSMs, I have former SDRs that are now four times certified Salesforce experts leading the largest implementations, we have. Rigsy. And that’s the fun part for me is because he has all the values; he’s got grit; that man made 100 cold calls a day, of course, he’s got grit. He’s got the hungry craftspeople mentality; he wants to learn all the time. “Cool, come learn Salesforce; I’ll teach you.” You know, and that’s where I’ve been very fortunate in that I’ve hired people who, they want to invest their time and energy to get better. So I’m willing to pour that back in. And we’ve done that. And it’s been really fun, like my favorite stat: I’ve hired or I’ve had 32 people work for me at Outreach; 31 are still there. And that is because they help each other grow. They’re willing to admit when they make mistakes because we all do. My favorite joke is that my first five Outreach customers are not Outreach customers anymore. I don’t know if it’s true, but it feels true. And that’s how bad my first five implementations felt because it was like “here you go, figure it out.” And I was like, cool, let’s do it. But now looking back, I’m like, ooh, if I could do those again. But everyone feels like that at some point, right? And being able to remember what it felt like to not know Salesforce, not know, Outreach and be faking it till I make it. It’s helpful they didn’t hire people and remember, oh, that’s what it’s like to be new.

Jordan  17:13

Yeah, let’s linger on that stat for a second. 31 of the 32 that have worked for you are still at Outreach. You are in a, ya know Outreach has historically been a hyper-growth company growing ultra fast. Like that is a statistic that I don’t think I’ve heard anywhere else ever before.

Sean  17:35

And it just, it was 32. So I’m still, I’m still crawling through the emotion.

Jordan  17:40

Yeah, you’re still going through the emotions. So what’s the, maybe you’ve already talked about it? And I don’t think it’s, I don’t think you’re trying to make it a secret. But how in the world in an environment that, and it’s… this isn’t an Outreach environment, let me be really clear. In a company that is growing really fast, people get stretched, sometimes processes change, sometimes the job you signed up for no longer exists, okay? Like things like this happen all the time. And what so, the reason I’m saying this is not to paint some brush on Outreach of like, oh, it can be a tough place. I’m saying any company that is growing at any scale, right? Yeah, you’re going to have things and issues and process or whatever. So how in the world, is it that you’ve had a basically a 97%, you know, stay rate at Outreach with the folks that you’ve worked with?

Sean  18:40

Ah, yeah. A lot of luck. And then a very perfect recipe and balance of opportunities for growth, which you need for people, right? Like if, if the people that really want to become leaders don’t have opportunities to lead, it’s going to be hard to keep. If the people that want to become experts, in a subject don’t have a chance to get that senior title and show that they’re an expert, it’s going to be hard to keep, right? I’ve been fortunate enough to have that and then through the various re-orgs we’ve done and then building out the specialties, to your point, my team has not at all had the same job they signed up for. When I hired them, they were client engagement managers; that job title doesn’t even exist anymore. What has been nice is because when we hired, we focused on values, we focused on do you have a passion for this product and the market that we serve? Cool, let’s ride. And that, that has been what is nice with everyone is, everyone is so down with chaos. They’re down with ambiguity. They’re down with figuring it out and just rolling up our sleeves and understanding that, hey, we may make this decision today, but we may have to pivot tomorrow because XYZ may happen. Finding people who want that and that’s why they want to come to a company like Outreach, that was always key for me. Um, and then I think, you know, investing in internal hires and people that want to grow and have kind of hit the, the end of the length of the road in the job they’re in. Hey, you know, two years of Outreach as an SDR, that’s a very valuable skill set. What if you could go consult with new customers and teach them all the stuff that you just learned for two years, from your amazing Outreach SDR interests? Wow, that’s super valuable; I can teach you the technical stuff. Right? Um, and so that’s kind of been the magic, magic sauce. And then, you know, we’ve had a lot of people go from my team up to the field team, and now they just work enterprise and do all that. And that’s been a fun growth path for them. But it’s been nice because they had hundreds of implementations with, with customers: SMB, commercial. And that really allows them to then go, lend such a broad market expertise with these other customers. And that’s just it’s been fun. Yeah, I’ve been, I’ve been very lucky. And I think the main thing is hiring people who want to help each other and are open about that.

Jordan  21:25

When you think about hiring, I’ve heard all the time you hire for the skill gap, okay? And what I mean by that is, you know, really practical thing, right? There’s a Dynamics integration; there’s a Salesforce integration, right? So hey, we have Salesforce folks who don’t have Dynamics; go hire Dynamics, right? Oh, you have somebody that understands the marketing world, but not the sales role, go hire somebody; you know, the point is, I keep you hired to round out the team. A question that I have, though, just based on what you’re saying here about the values that look that you look at? Have you ever gone out and hired somebody based on a values gap that you see in your team?

Sean  22:08

Yes, well, maybe. 

Jordan  22:15

Maybe? The confidence.

Sean  22:18

I don’t know I, for me, because I think for me, the values are really important. And like, some of those are so innate that I don’t know if you can really teach them. I think it’s more of personality types. Like what you know, all those tests that put you in the different quadrants and stuff. We love doing those, right? I’m always thinking about how my team balance is there, like there’s like the driver quadrant. I don’t want a team of seven people to be seven drivers, that’s not going to be good. I want people on the other side, on the empathy side, right? And then I want people on the inspiration quadrant, and having a balance of those is the stuff that I’m more interested in thinking about. And then even the skills gap. I used to always talk about when we were client engagement managers, that was the title I was hiring for, like my first big team. I used to always tell recruiting, look, I can teach client-facing, put on nice clothes, you know, do your hair, look nice, don’t use curse words, like, have a talk track, I can teach that.

Jordan  23:31

Yea, button up a little bit. Here ya go.

Sean  23:33

I can teach the management; I can teach you risk management. I can teach you projects, project management, right? I can teach you how to manage customers. The middle piece engagement… that was always my Northstar in hiring. If I had like two really good candidates, and I only had one headcount, it’s going to come down to who’s more engaged to me. Because that as you, like, you’ve got it. That’s 20 years of development as who you are as a person; can you hold an audience’s attention? You don’t have to be loud. I have some folks. Lutzy, you know Lutzy. Front of the room, everybody knows who he is, he’s as loud as they get; he wants you to know he’s an expert. And then I have other people, much more subtle, but when they talk, everyone stops and listens, right? Because they know what they’re saying is impactful. It’s important; it’s going to be correct. And that to me is always my North Star. If I hire someone who’s engaging and wants to grow and has the values, I can teach you Salesforce; I can teach you Outreach, like that’s the easy stuff compared to being a great…

Jordan  24:45

That just makes me think about my college days. I used to go out with a bunch of guys at, like, we would do a Denny’s runs, you know, of all the things right? At like one, two in the morning, we would go get breakfast at Denny’s. Okay. There was a guy named Jesse that used to come with us all the time, actually spoke with a lisp, had a little bit of trouble hearing, here and there. But he used to love coming, and he would never talk, like ever. And he would just laugh his head off. The reason I say this, though, is like every second or third trip, like a topic of real significance would come up, and we would start to talk through, and all of a sudden, he would open his mouth; it would be less than two minutes that he would talk. But literally, everybody sitting there would be like, Jesse’s talking, right? He wasn’t the loudest guy; he wasn’t the funniest guy. Like, the reason I mentioned lisp is, he wasn’t the most enunciative of anybody there, whatever else. But when he opened his mouth to talk, everybody was like, let’s shut up. Because like, this is gonna be… and his topic, like whatever he had to say, that was the thing that everybody remembered even from the three times we met, you understand what I’m saying? So I know exactly what you’re talking about, right? You don’t have to be the loudest person in the room. But are you insightful? Are you thoughtful? You know, do your words have weight, you know, do you draw people in? And I always think about Jesse with that, like, man, he had it. But he used it like, it was like a weapon. Ya know? 

Sean  26:23

Yeah. And that’s like, Jesse is what makes a great manager, like exactly what you just described. You don’t have to be the loudest, you don’t have to talk the most. But if you listen, and you take insights from that, and then when you do speak up, that’s how you get respect from your team and really show them that you care because you’re listening, right? Yeah, Jesse’s got it. That’s great. 

Jordan  26:55

Jesse’s got it. Oh, man. Is there anything? Like we’re getting really close on time here. So I just want to give you a chance to kind of talk. Is there anything else when you think about team building? Like we could probably, I could probably sit here for like five hours and riff on it with you know, we could go deep. But is there anything that just for anyone listening as they’re thinking about building out a team, thinking about this empathy? Or even like, the engagement aspect, whatever? Like, is there just anything that like, hey, people need to hear this right now?

Sean  27:24

 Yeah, ah, yeah, I mean, I have, I have, obviously, a lot of thoughts on this. And each company is different, right? And your company’s going to have values or they’re going to have like a slogan, or they’re going to have a model or something that they want people to buy into and follow right? Outreach has our core values; we very much recruit focused on those; it’s very much something we talk about within our culture, we use those for reviews, it is a big focus for us. But even beyond that, I have three specific principles that I always just talk to my team about. It’s a slide that I have in our monthly team meeting that I run with them. And it’s things I talked about during interviews with new hires, those three principles, I think, are amazing for any team to adopt. So I want to talk about that. Number one, is proactive transparency. And that is, I tell my team about a lot of the mistakes I made early in my career. So they feel more comfortable telling me when they’re making mistakes, because I want them to know that it’s okay, everybody’s gonna make mistakes. I love to use the phrase, it’s software, not surgery; nobody’s gonna die if you click the wrong button. Ideally, just tell us as soon as possible, right? And then vice versa. If I’m hearing things, I’m going to tell my team because we’re all adults here. And I treat everyone like adults. And I’ve always respected my leaders the most when they’ve shared information openly with us, because again, we’re all bought in as a team. We’re all trying to accomplish the same mission. And we’re all adults. So let’s treat it that way. So proactive transparency is number one for me. That leads into number two, which is psychological safety; that comes from number one, because we’re so transparent, open with each other, you know, you’re safe. For me, I get to use this stat. Hey, 31 of the 32 people that have worked for me are still at Outreach. We’re not just getting rid of people; I want you to grow. I want you to succeed here. That’s why we bet on each other, we shook hands. Hey, great, can’t wait to work here. And that safety is a big part of what allows people to bring them whole, their whole selves to work and really give their all, and that leads to number three, which is builder’s mentality. Everyone on my team is a builder. There’s always a chance for us to improve a process to improve a service we offer to get better at what we do. Cool, bring that mentality every day, bring your hammer and chisel and let’s find ways to improve what we do. And people are more interested in doing that and being innovative because they feel safe because they know if they make a mistake and they try something new and it’s not good, it’s going to be okay. Just don’t do that again. But you might discover something awesome, cool. Let’s teach the whole team that and now our methodology is going to get updated. That’s what we’re going to do. Boom, you made an impact; you feel like you’re leading, even if you’re not in a leadership role. You’re bought into the team. Everybody’s growing, having fun. And that’s that, that’s how we get it done.

Jordan  30:28

So PMP, yeah, you know me. Alright, Sean, listen, thanks for coming on today. I hope anybody that listened in just had an opportunity to hear, you know, into a window of an individual that I would highly, you know, I highly respect the way he thinks about working, operating. You know, our paths are actually pretty quick. Pretty quickly pass, but, you know, just respected the work he was doing at the time. And, obviously, the data, the statistics, the work, the quality, whatever, you know, speak for themselves. So I hope you were able to glean some things today as you listen in. And Sean, thanks for coming.

Sean  31:10

Yeah, thanks for having me. Always fun. Till next time, Jordan.

Jordan  31:15

Stay out of trouble.

31:17Hot dog. That was a great episode. Thanks for listening. If you want to learn more about Greaser Consulting or any information you heard on today’s episode, visit us online at www.greaserconsulting.com. Be sure to click the Follow button and the bell icon to be notified on the latest here at RevOps Therapy. Thanks and see you real soon.