Speaker 2
And I love that story. And I love how you kind of frame it that way. And it is, I think it's like life goals, founders goals, right? To have all your, do you have your parents like go vacation together?
Speaker 1
Yeah, yeah. It's a special thing. That's great. But it's also, you know, that's on the personal side, but like you also have to like know what context you're in so when we are in work mode in the gusto mode we don't think about any of that stuff that stuff doesn't matter right it's like we are now wearing different hats as leaders in the company and we act that way as well right and so and and that that's really important too to not bring like too much of like your personal connections into a professional environment. That's something that you have to be really diligent about as well.
Speaker 2
Yeah. You talked about different hats and I think that different hats is also another leadership skill. Is that something you think about in the rest of your leadership as well?
Speaker 1
Yes. I have to wear many hats and many leaders have to wear many hats. You know, I have my hat as the head of technology at Gusto, but I also have a hat as a board member at Gusto or a leader in our executive team. And I think it's really important to know what hat you're wearing because you're representing like sort of a different role to the company. Sometimes I'm like actually very explicit about that. Like literally will say, I'm taking off Eddie's head of technology hat and I'm wearing my board hat right now. And here's what I have to say. Like, just so it's very clear to others, like why I'm responding in this way. I guess that's another thing that I realized is that when you have multiple hats, it's also very important to sometimes be very clear on what hat you are wearing in that moment, sometimes in a very explicit way. Yeah.
Speaker 2
So people understand.
Speaker 1
People understand.
Speaker 2
Yeah, totally. I think it's so important. You talked earlier about how you learned management skills, and now you're talking about some other skills that you have around compartmentalizing and understanding the need for different hats and putting on one hat and taking off another hat and also telling everybody about that. There's a lot to it to be a manager. I guess I'm curious, what was the easiest for you to learn and what was the hardest for you to learn in terms of your management skills? The
Speaker 1
hardest one for me was really like giving up the hands-on keyboard hat, right? There's some hats you have to take off and never put on again. And I know myself well enough now that if I pick it up a little bit, even for a day, or like we have a hackathon and like I decide to participate in it, then that hat stays on. And then the other hats like don't get worn. And so for me, I don't know why, but like, it's almost like a drug kind of thing where like addiction is like, you have to know yourself well enough to like, just stay away from it, you know? And like, that was a very hard lesson for me to learn of all things for some reason. I mean, everything else was really just honestly years of experience and making mistakes and learning from them. And I still make mistakes all the time and still learning all the time. And just every time something doesn't go right, seeing that as an opportunity to get better next time. I think that's probably the most important thing. And that's kind of a key to just learning how to wear other hats and getting really good at all these different aspects of being a good leader.
Speaker 2
Yes. What were some of the lessons you learned around hiring executives, hiring your senior people, especially in your organization, or, you know, being part of the hiring team that hired, you know, their peers around you, executive peers around you? So
Speaker 1
in some ways, it's no different from hiring anybody else, especially when it comes to making sure that there's a strong alignment, values and motivation. Again, it's the reason why we have them go to the same interview as every single other person. So there's no difference in that sense. But in other ways, yeah, it's very different. I think executives, I've learned you have to be very, very patient in finding the right person because the wrong executive hire can be very bad for the company. And then so knowing that like when there isn't a good fit and just having like a direct conversation that, hey, it's not working out, right? How do you know it's not a good fit? Like,
Speaker 2
what are some signs for you either earlier or late in the game that they're not scaling or it wasn't the right fit? There's
Speaker 1
so many different ways I think it could be not a good fit. It's hard to like kind of, I think every case is a, little different. Some are not able to scale. Some are not good at inspiring others. I think probably the common theme that I have noticed is, well, I think it's really important to have skip levels and talk to the folks that directly work for this person and get a sense. And it's not just like, oh, do you like this person or not? But really trying to get a sense. I think you can learn a lot from skip levels and how someone is performing.
Speaker 2
What kinds of questions do you ask skip levels?
Speaker 1
I sometimes just don't, you know, with skip levels, I really don't try to come in with like too much of a agenda. I try to just learn a little bit more what they're doing, what they're working on. And I think you could just tell sometimes in conversations, is the team healthy? Are they productive? So yeah, I really try to come into skip levels without really any agenda and try to listen as much as possible to what that skip level is saying. And then you kind of infer based on those conversations on how this particular leader is doing.
Speaker 2
Yeah. Now, Eddie, any founder over a decades-long journey like yours has had ups and downs. Can you think about what was maybe one of your highest highs and one of your lowest lows in this journey of Gusto? Hiring
Speaker 1
a good leader is like one of the biggest highs ever. I never like thought of myself as like someone who could enjoy sales, but like, and not to say like hiring someone is like a sales process, but there is an element of like, once you found the right fit, you need to get that person excited about what you're doing as a company, right? And so there is like a little bit of like salesmanship of like, hey, let's do great things together. And like, here's what we're doing as a company, you can be a part of this, right? And the best people, they have multiple options, like, they don't have, they don't need you, they don't need to join your company and sometimes that whole conversation like can last weeks and you're getting to know them and when they say yes to join the company it is like in my mind like one of the like best feelings in the world and so those are like kind of sometimes the biggest highs that I can remember and so yeah I think a lot of the highs and lows in my world right now, like have to do with finding great people to work with.
Speaker 2
I love that. It's so, it's so also interesting that you're the guy that has trouble getting your hands off the keyboard, but nonetheless, you know, the value of hiring a really good person.
Speaker 1
Yeah. I mean, it's, I think it's something I've learned over the years, right? Like when you're just starting out and you think that like, you know, you could do everything yourself and you are the best person to do the task, right? But then as you grow, like you have to realize that it's such a team effort and you have to do it with other people and with other great people.
