WFH: Leading Through Mission, Not Proximity

The nature of leadership has changed as we’ve all moved from our offices to our living rooms. For the Paranoids, that means adjusting how we all grow together.

Join this conversation to hear about:

• Our Approach (2:18)
• Squads, Organizing and Leading Remote Teams (6:12)
• Tea Time, Fostering Relationships  (11:11)
• Defcon, Getting Together (13:30)
• Remote Culture Requires an All-In Approach (18:47)

Host: Steven Asifo (Technical Security Manager, Governance, Risk, and Compliance)

Guests: Will Chilcutt (Manager, Community Driven Security), Jeff Larson (Sr. Manager, Behavioral Engineering), Josh Schwartz (Sr. Director, Proactive Engineering)

Chapters

• 2:37 The Paranoids Approach
• 6:31 Squads, Organizing and Leading Remote Teams
• 11:30 Tea Time, Fostering Relationships
• 13:49 Defcon, Getting Together
• 19:06 Remote Culture Requires an All-In Approach

Transcript

Speaker 1: 0:38

Hello everybody and welcome to another edition of the Paranoid podcast. My name is Steven Ascio and I am very lucky to have some amazing individuals with me who will be talking about remote work, remote culture. So as everyone knows, if we've gone through a number of different changes just as a working world, the Paranoids have themselves as a remote first team, and we're very fortunate that our company has been supportive about the way that we've worked. So we're wanted to have a conversation with some of the leaders within the parents to talk about how that's changed within our teams. What are we doing differently on a day to day basis and some, some of the different challenges that we've maybe

Speaker 2: 1:17

Had

Speaker 1: 1:17

To navigate as a, a part of being a remote working world. So to do that, I've have some wonderful people joining me and I'll have them introduce themselves. Will Chicot, Jeff Larson and Josh Wort. So Will, if you want introduce yourself, Uh, title and what do you do here?

Speaker 3: 1:34

Hey everyone, I'm Will Chico. I lead the community driven security team, uh, within larger pro security organization. And I'm responsible for Bug Bounty, our security champion program called Debbie Paranoids, our dynamic analysis effort in our pro sec, uh, lifecycle program.

Speaker 4: 1:52

And I'm Jeff Larson. I'm a senior manager of what we call behavioral engineering. You can think of that at like security awareness on steroids, but really what we do is measurable behavior change to drive security outcomes.

Speaker 2: 2:07

Hey, and I'm Josh Schwartz, Uh, senior director in the proactive engineering organization. Includes, uh, Jeff's org and mostly I have, uh, lots and lots of meetings. And today I guess we're filming a podcast, huh?

Speaker 1: 2:20

We're we're filming a podcast with my, uh, you know, fellow paranoid here. And so since we have you, Josh wanted to kind of hear from you as like the senior director within the paranoid on the paranoid current stands on remote work or, and just what have you seen of some of the key advantages of doing that?

Speaker 2: 2:38

Yeah, I mean, I, I think you said it right. We are, we are fully remote, a remote first team. You know, we, we span across time zones. I'm on the West coast, I've got peers out there on the East coast. We have employees all over the world. And I think it's, you know, something that's created a more level environment for, for all of us, you know, compared to when we were all, you know, sort of half remote in different offices. Uh, I think that now we're sort of able to all just connect virtually rather than having these little pockets and silos and offices. And, you know, personally I don't, I don't see us going back.

Speaker 1: 3:12

Yeah, I was thinking about this the other day is that if I did go back into office, my team is based on the East Coast Dublin and stuff, so I'm technically still virtually interacting with them in some way or another. And I'm curious also for Jeff and Will, cuz you guys are, you know, leaders within the paranoid, How would you describe your guys' approach to leading teams remotely? Have you guys also seen the same kind of advantages?

Speaker 4: 3:36

You know? Yeah, I think it's funny it, when you're in an office as a manager, there's like a, a pull to sort of track people's hours, right? Because you can see them face to face. And one of the gifts that remote, uh, work has given, has given us as, you know, the world as an industry is the fact that like we have to focus on outcomes. We don't, there's literally no way for me to tell if my employee or my colleague is in, in their seat at nine o'clock and frankly, I don't care. Right. I don't care anymore. I only, so we're not, so we're not using Keyloggers Exactly. Right. I only care about the outcomes of the work, right? I like to tell my team, I don't manage your time, I manage the work. And that's really sort of focused us as a team. It's made us more, um, both collaborative, um, and, uh, you know, more efficient because it's really, it's like a clarifying whole remote work is like, you know, kind of this beautiful gift, uh, that makes managers less persnickety. It also makes teammates less persnickety about where you are, Right? Um, and it's freeing for folks, right? I know that, uh, will has, um, you know, I'm a father, uh, fellow father on the call, right? I know that will has a lot of, um, you know, sort of ideas about this too. So Will, why don't you sort of take, take away?

Speaker 3: 5:02

Yeah. And, and I totally agree with Jeff that, that it's awesome, you know, not having to focus on having that, that set start stop time, you know, being able to do your job and, and deal with everything all, uh, also going on at your home. Um, uh, like Jeff said, uh, you know, I'm a parent. Uh, you know, I, I've dealt with all those things that come along with that. I, I think, um, there's really like three, um, key things that I think about whenever, uh, I'm thinking about like leading a team from home. Uh, that first one is, you know, uh, being flexible to what's going on, uh, in your background. Uh, you know, whenever we started out, I had two kids at home and had a newborn. And the leadership, uh, you know, from, from my manager all the way up, uh, through Yahoo, uh, was very supportive of all of us, uh, parents and all the things we had to take care of. Um, and you know, fast forward two years, uh, later and that support's never really ended. Um, and now I get to be part of that support for my team. So, you know, no matter if it's, you've got that kid running around the background or you got a toddler that you're just trying to take care of at your desk, uh, just so you can get through that last meeting of the day, that's not like a, a big deal to anybody. You know, everybody's very understanding and, uh, many of us have been there at some point, um, or maybe you're like me and have like a, a bathroom model, bathroom remodel going on in your background. I don't know if you guys can hear it, but, uh, that's going on and a lot of solid noises going on. Um, but, uh, yeah. And, and the second thing I, I think of whenever we're thinking about like leading a team remote, I is, uh, meeting fatigue. I, I know a lot of us have felt that. And, um, the, the ProTech leaders, uh, really felt that, uh, last year. And so we made a big change within our ProTech organization where we switched to this, uh, self-managed, uh, team model, we call it squads. Uh, one of the benefits of doing that is that we switched over to, uh, these squads determining when they wanted to meet. Uh, so we switched from having, you know, everybody having to go to these large daily standups to, you know, determine when your squad wants to meet and, and there's a little lead for each one. Um, so they get to determine that and kind of reduce that, that meeting fatigue. Um, and, and then the last thing I, I'd tell you about, like leading a team remotely, uh, that's awesome is, you know, we get to tap into those, uh, talent pools that we didn't necessarily were able to before because, uh, they weren't near a, uh, office. So that's been great to bring in people that we haven't, uh, been able to before.

Speaker 1: 7:33

Very well said. Well, cuz I have a puppy right now. Not saying it's the same as a child, but you know, sometimes I do gotta take him out so he doesn't leave me a present in my office cuz sometimes the present smells. But one thing I I was kind of thinking about as you were talking about talent pools is, uh, how has it changed? Kind of like creating that connection amongst your different teammates. Cuz Josh, you and I, we used to sit next to each other. I, I would think we were, we were pretty close pals at that time. But I guess how do you think about the shift to remote work has changed that interaction?

Speaker 2: 8:04

Yeah, I mean we were pals we, we could high five each other in the office and now we get less, less high fives perhaps

Speaker 1: 8:10

Emojis.

Speaker 2: 8:11

Yeah, I mean the shift obviously has created more freedom for us. I know I was personally, I was in a living in a, an old van for a while and traveling around the, the west coast while we were, while we were remote.

Speaker 1: 8:22

That is a different episode. Talk about that.

Speaker 2: 8:26

That's kind fun. You have more freedom obviously, but you know, there, there are some things that you lose, right? You lose that in-office culture, you lose that sort of serendipitous ability to have these little conversations with your, with your colleagues that are sitting next to you and those colleagues maybe aren't on the, the same team as you. And there's sometimes connections in these, in these, in this ability to talk to the person next to you and you get information about other teams that you normally wouldn't have a meeting with. You normally wouldn't be able to connect with them. And I think we did lose that having, not having that in office water cooler conversation, but you know, it's kind of a benefit, you know, that you lost it so that you can go and you can take some, some conscious effort to replace that. And you know, personally I've gone and, and just scheduled one-on-ones with more people outside of the team. Um, we have recurring one-on-ones, not just within my direct uh, management structure. Um, and the paranoid themselves. I think as an organization we have this protege program that's fostering and creating more of those opportunities. And so rather than before where we would have it so that everyone, uh, that's sort of forming these bonds is in the same office now you have these inter team connections between different people and they aren't even in the same office on different teams and different locations, things like that. And I think that we also had to, I think we did this right away, like right during the beginning of the pandemic we started icebreakers and the icebreakers are just like a little question, a little short thing. The first five or so minutes of the meeting we used to just chit chat just to talk about ourselves, just to kind of get to know each other and uh, you know, it's, is it awkward? Yeah. At first. But that silliness and that awkwardness, I really think, um, you know, replaces some of that silliness and awkwardness that used to be in the, in the in office in person

Speaker 1: 10:23

Especially cuz it was called Ice Ice Breakers. Shout out to Vanilla Ice.

Speaker 2: 10:28

Yeah, thank you. You like that

Speaker 1: 10:29

<laugh>? I did, I did actually<laugh>. And so I guess Jeff will, I'm not sure if there's anything else that you guys do. I, I know for my team try to include more things as well, like, so on Fridays try and do, um, you know, songs, songs of the week. So we have like a running YouTube playlist of just songs that we've listened to or just like really resonated with at a certain time that again, if we were maybe in person and that would've just been like the local thing, but now everyone kind of checks in for that and try to do on once a week. Also like a different icebreaker as well that everyone can collaborate to. So, and I think that does help just having those different things. And I think also you guys have put on like movie nights and stuff like that, so that's been pretty cool. Yeah.

Speaker 4: 11:16

Yeah. I echo Josh's, you know, sentiment that you have to be like really sort of like constantly creating these serendipitous moments so that you, you know, colleagues can connect. So like we do a tee time every week where it's like not a meeting, right? Where we just talk about life. I also think, you know, because I hold the bag for again, like behavioral change and, and security awareness, um, we've shifted our strategy, right? We, we, we no longer hold in person trainings on things like using our password manager or, or meet and greets with the paranoid, um, large that's changing a little bit, um, which we'll talk about in a second. But we've also shifted security awareness towards things less towards things like t-shirts and swag and more towards things like meeting backgrounds that, uh, you know, can go viral and like really create this sense of security culture across the entire company. So not only has it like shifted the personal connections, but it's also shifted a lot of how we work, uh, in general. Um, I think, uh, and I don't know, you know, I want to sort of like also point out the protege program. Josh, you sort of like touched on that a little bit, but that has been a real level up in terms of like providing mentorship because something that you miss out out of the office is speaking with, you know, your more experienced colleagues. Um, and that mentorship sort of happens serendipitously again in the office, but you have to be really, really sort of like focused on ensuring that that happens.

Speaker 1: 13:03

And I'm not, so, I'm not gonna lie, I, I'm a big fan of the remote first situation. I don't live too far from the office. And when I did go into the office for like our company's global volunteer day, I'm not gonna lie, I kind of enjoyed seeing people, not just paranoid, but like other people from different teams there and just checking up and I think everyone kind of felt the same way. I was like, Oh, it's good to see you. Like I remember when we used to do this more formally there. So like, I guess my question is like, are there opportunities where we as paranoid, like meet in person and have those type of powwows?

Speaker 4: 13:37

I think, you know, there's a couple that come to mind. Like, uh, a lot of us, um, are Bay Area centric or can travel to the Bay area, so, so generally like dinners and meetups after hours. But the big one this year for us is we made the conscious decision even though it was still a little, you know, on the tail end of sort of the pandemic that we've all been dealing with, um, to get everybody to Defcon, right? Um, so we offered everyone who wanted to go, whose threaten, whose risk model sort of like, was okay with spending a few days in in Vegas, uh, to go to, you know, to go to Vegas and really meet in person and realize that like we are not just posted stamps on a Google meet screen or a Zoom screen and uh, uh, really start building those personal connections like, oh hey, you are both smaller and taller than I thought you were

Speaker 1: 14:42

<laugh> and can we put some respect on, you know, the Las Vegas sw? I like, we didn't just go there for anything. It was like one of the largest and biggest, um, it was also, yeah,

Speaker 4: 14:51

It was devcon. I don't know if I said Dcon, right? Um, I just, well,

Speaker 1: 14:54

You know, in the paranoid party itself was topnotch just, yeah,

Speaker 4: 14:58

We also, we also came back in full force with a paranoid party, um, that was really fantastic. And if you scroll back in our Twitter feed, uh, enough, you will see some highlights from that. Um, you know, it's been a hard couple of years. It was a little bit of healing for every everybody and it really showed that we have investment in our people, right? Like building those bonds that you talked about as c o and Josh that you might have had, you know, in the office, like reinforcing that again, right? Like we're not just tiny, tiny faces on a screen.

Speaker 2: 15:31

Yeah. It's not cheap to get everyone to Defcon, but I think it definitely was worth it. And for a lot of the folks on the team, it was the first time that they even got to see their colleagues in person. Like people were, we, we worked for two years together and it's the first time meeting people and I think, you know, being able to do that maybe once a year or something like that, especially in a remote first environment, it's gonna be really important. I think it's gonna be a part of our, of our DNA where it's like, yeah, we're remote, but every once in a while we gotta get together, you know? Cause we can't just be little boxes on screens like the Brady Butch. We gotta be, we gotta be people. And, and every once in a while we gotta cough each other's faces and shake hands and things like that.

Speaker 4: 16:06

Yeah, I think Will and I both join during the pandemic, so especially Josh is a lot taller than I thought he was. Um, as he Shorter

Speaker 2: 16:15

<laugh>. Yeah,

Speaker 3: 16:20

<laugh>, yeah. And, and, and talk about Defcon. Uh, you know, uh, whenever everything first started working remotely, our, our pro site organization was only about, uh, uh, 12 people and we exploded up to like 25 people. So this was like the first time for a lot of people to meet in person. Especially we, we have hired a lot of people in Dublin, so flying those people into the United States and, you know, having those people all to get get together was awesome. Uh, but just a few weeks after that, uh, we had our first, uh, in like two years, uh, first time bug bounty life hacking event, uh, that we, uh, flew a lot of our team over to Belgium for. Um, and you know, we brought together a, a ton of different paranoids, you know, not only the bug bounty team, um, but people from your team, Jeff, you know, people from different, uh, pillars of the Paranoids. Uh, you know, we brought in engineers from our deputy paranoid program, you know, even Angus, the CTO joined. Um, and, and between us paranoid and the uh, uh, uh, bug bounty platform integrity team that we had there, and then the hackers that we all had in person, uh, you know, it was a very intense, uh, event for this team. You know, we were working late into the night to get things closed out, um, from being in those war rooms, uh, to getting things done and then being able to go out to the bar and grab a few drinks afterwards late in the night. Uh, being in person building those, uh, bonds was a huge deal for my team and built a lot of team cohesion. And then, you know, coming outta that life hacking event, you know, I, I really love working remotely and, and the freedom that it gives, but it's really highlighted to me, uh, and and to others that I've talked to about the importance of building these bonds in person. And so, you know, for the going forward I'm trying to do more social things in person. So, uh, I just ha I met with people in the, the local DC area, uh, uh, a few weeks ago. I'm gonna try to do that, uh, near the offices like once a month, get those people together, probably get the coast, uh, together like, uh, every quarter and then, uh, as a team project we're gonna try to get together, uh, once a year we have something that we do ProCon and so we're playing that for 2023. Um, and, and that's great for doing social stuff, but I, I really think coming outta that life hacking event, having people not only socialize but get some work done at the same time doing these like two or three day projects, I think that can kind of be a game changer, uh, for teams working together. Cuz you're like in the, uh, you're kinda in the zone, you know, working there and, and you come out that with some like, you know, uh, stories, war stories about, hey, that was awesome, that was intense and, and there was ups and downs, but we got through it. Uh, and and I think that's really a game changer for remote teams, uh, having those opportunities to do that.

Speaker 1: 18:59

Absolutely. Thank you very much for sharing that. Will, uh, is Josh anything you wanna add in here as we can? Yeah, I mean

Speaker 2: 19:07

Not, there's, there's something I think that's worth mentioning about the the remote culture or not remote culture, right? And it's that it, it sort of only works if everyone's in on it. You know, I, I know that, you know, the idea, it is like we kind of got a, a little bit of a gift in the pandemic is that we were all forced to go remote. We were forced to learn how to work this way. And it was something that I think before this I sort of would've said like, Hey, you know, people wanna be remote. It's kind of tough, you know, it's kind of tough to be remote because when you have some people in the office, they form these like little, these little clicks and these bonds and you've got some people who are remote and it's really tough to come up with a system that keeps everybody included. But now that we're all remote, it works really well. And so I think this, everyone's remote all the time and then every once in a while we all get together is a, is a good model. But something like going halfway back where it's like, well there's gonna be some people in pockets of offices and some people remote. You start to get those little like fractures and stuff and we're sort of all bonded together in this being all remote together. And as long as it's like that, I think it works really well. I mean, maybe we get more meeting fatigue and things like that, but I mean, I think genuinely it works really well

Speaker 1: 20:24

Like it

Speaker 2: 20:26

Van anymore, but it's, it's nice.

Speaker 1: 20:29

I'm glad you're not in the van anymore, but I know that was, uh, you know, by your own free will. I, I I think that is definitely a, a very important observation. I know I'm also a lot happier when I see you guys on like a social line cause like, oh hey look, it's been some time and, you know, physical interaction there over a meal or, or that may be, and I always look forward to the next one cuz you guys are taking people out to Belgium, going to Vegas. Um, so look, we don't have to meet in the office. Let's, let's, let's coordinate, let's talk about that. Um, so I think at this time that's how we feel about remote work culture. I, I don't know if there's anything else. People are like dying to get off their chest, but I think you guys really dug into what that looks like for the paranoid and how we're trying to show up for our teams and how we're organizing. So with that, I wanna thank you Josh, Will and, and Jeff for tuning in and joining me on this conversation. And for everyone else, thank you very much for listening to another exciting episode of the Paranoid Podcast and stay tuned to our next episode.