The Crossover Episode: Behind the Scenes with Drift's Podcast Hosts

Matt Bilotti: Hello and welcome to the Growth podcast. I'm your host, Matt Bilotti.

Maggie Crowley: And welcome to Build. I'm your host, Maggie Crowley.

Sean Lane: Welcome to Operations, my name is Sean Lane.

Matt Bilotti: And we are all here today, the three of us. We're on podcasts here at Drift. And we were thinking that we could do something special to wrap up the year of 2020, get all three of us on a podcast together and talk about what it's like to record a podcast in addition to our full- time jobs. And maybe some of the stuff we've learned along the way. We're just winging it here and we think it will be useful, so we're going to roll with it.

Sean Lane: This is so exciting. I don't think we've ever, the three of us, got together and actually just talked about the experience of doing this.

Maggie Crowley: Yeah, I agree. I feel like there's a lot of Slack threads here and there, but not a lot of actual discussion about the lifestyle of the side hustle podcast.

Matt Bilotti: Yeah, love it. So we all supposedly wrote our own few questions that we wanted to toss out to the group and talk about. We can open up with starting point one, which is so we've all done, at least Sean, you've recorded at least 50 episodes. I don't think you've launched all of them yet?

Sean Lane: Yep.

Matt Bilotti: So we've all done 50. I would love to get a sense of how you think about the podcast today versus how you thought about when you first started. How has it shifted or changed if at all in the topics, the mindset you have or anything like that? So Maggie, why don't you kick us off if you have something?

Maggie Crowley: Sure. That's a good question. I'm curious to hear, Sean, your answer because from my perspective, your podcast is more structured than mine was definitely at the beginning. I know that I started just with an idea that I would talk about all the topics that we talk about in products. And I would try to find some smart people who could come on the show and I could learn from. And there would be a mix of solo episodes and interviews and not even really sure what I would get into. So that's really where I started. And now that I've done I think I'm on 65 episodes. I'm much more interested in targeted conversations, going deeper into specific topics and trying to get into examples. I feel like the first season or so of the show was high level," What is product?" And now that I've done all that content, I'm really more interested in," Okay, well now what? How do we go deeper? How do we get better?" So I think that's changing the show.

Sean Lane: Yeah, I think my approach has been pretty similar. I think those first 10 episodes, you're still feeling it out and trying to learn how to even have the conversations and what questions to ask. And you want to play to your guest's strengths as well. But I think since then, it's more been trying to find a specific theme or topic that can encompass the entire episode. And you can bring multiple topics inside of that. But if you have one larger umbrella theme that you're trying to tackle within that conversation, that to me has generated the best conversations or the best episodes. And it's funny to look back at some of the episodes that we've done. And I don't know if it's like this for you Matt or for you Maggie, but I can look back and I can basically trace what I was working on internally at Drift through the episodes." Oh yeah, this is when we were working on this." And I can tell that because I had an episode about it.

Maggie Crowley: I couldn't agree more. I was thinking about that. The arc of the show overall absolutely matches," What am I working on? What do I think I don't know how to do?" And then I match up," Okay, crap. I have to go work on this thing. Let me find someone to tell me about it." And then we take a bunch of notes and go do that when I have to go present to Craig.

Matt Bilotti: Yeah, I feel like having the podcast is a bit of a cheat code to connect with somebody that is an expert or could be a mentor in any given thing that you're working on. In addition to what we're just talking about here. I also love the clarity of starting, because you both said you started the podcast with rough ideas, and now over time it has turned into each episode is a deep dive. And I've seen the same thing. I thought about it early on of," Let me just find really smart Growth people and have good conversations and they'll be interesting." And now I think of it much more as," I want to create a library, which is the 101 or deep dive on any given growth strategy, tactic, whatever it might be." Which I think seems to be the natural progression of these types of shows. You start with a broad theme, you get the basics out of the way. And then you go into how can somebody look at your library and pick the thing off the shelf, whether it's tomorrow or three years from now and say," We're trying to do this thing. Let me go take this episode because that's the one where I'm going to learn that from."

Sean Lane: Matt, I feel like people who listen to your show might not know that you are also the MC of our company. You are the host of Drift in so many different ways. And so I'm curious, what does your prep look like when you're getting ready for one of those episodes that you're trying to build out that library? Do you do something similar for some of your internal hosting duties at Drift that you do with the podcast? What does your prep look like?

Matt Bilotti: Yeah and I'd love to ask the same question of both of you. So my prep generally is first find the guest, which is a whole lot of head hunting just people who I think have done really interesting things or have really fascinating backgrounds. And then the prep looks like I get on a call with them for 15 to 20 minutes, talk through what topics maybe they have top of mind that they could bring on the show or that they have worked on a lot. And we pick out something that could be a really good fit. And then I basically just put together a rough outline of questions that I want to make sure that I cover. And it's more meant as a guide to the conversation rather than how the conversation actually goes. I send it to them a few days ahead of time and give them a chance to redirect it or add stuff or remove things. And some guests prep a lot, some don't really, and either way, it's fine with me. But I wouldn't say my prep is all that insane for it. I build a rough draft of it and then we go into it together.

Maggie Crowley: Yeah, I agree. I do a very similar thing and it's interesting. There are some people who generally speaking it aligns with what their title is. So CEOs and founders typically don't want to do any prep and just want to hop on and see what happens. And then someone who is maybe more of the same level as me, or maybe more junior, whatever, might want to do a lot more prep, which is always interesting. But I also have realized over time that when I first started just the idea that if I just got a smart person and we just had a conversation, it's definitely going to be interesting. It's just not true because relying on that level of serendipity is so dangerous because you might just have a really boring conversation. So I spend a lot more time making sure I have a backlog of questions just in case, because I want to make sure that no matter how the conversation goes, I can move it forward.

Sean Lane: So I think the only thing that I would add to what you guys are saying about your prep is I actually have found it really helpful to have a pre meeting with the guests, talk about some of those potential topics. And so the thing that I found most helpful about those pre- meetings doesn't have anything to do with the prep that I've done. It's more that I can learn more about what they are working on at that moment in time. And that's usually where I've got the best topics, where I just start by saying," Look, I've done a bunch of research. I have a handful of potential topics that we could talk about. But before I even go into my research, tell me about what you are passionate about. Tell me about what you've been working on recently within your company." And that has always for me generated the best topics. And so by the time they start talking about that, it's more often than not that I actually try to stop them and say," Okay, I don't want to hear anymore. Let's save this for when we are actually doing the recording." And so those 30 minute pre meetings usually are what have started to generate the best episode topics for me.

Maggie Crowley: Yeah, I super agree with that. I want to ask a different question though, because we've skipped into how we all do the show, but I'm really curious because I don't think I've ever asked either of you this. Why did both of you decide to audition for the show?

Sean Lane: Yeah, that's a really good question. I don't think I've ever told either of you this, but even in that process of quote unquote" auditioning" and just to give people some context, our CEO and our VP of marketing had their own show. One of the pieces of feedback that we got from this great community that they had built up was that people wanted more function specific lessons. And so we decided as a company that we were going to double down on the show that we had before called Seeking Wisdom and start to build out these function specific tracks of podcasts at Drift. And to be honest with both of you, my original pitch to DC was to do a sales podcast. I was convinced that no one would listen to a show about operations. And so my first couple of guests, my audition, my submission to him was all with sales leaders and he emailed me back and he's like," Why are you doing this about sale? You should be doing this about what happens inside of hyper- growth companies, within operations teams." And I think like a lot of that came from the fact that I had just not seen operations stories told very well before. And once we actually crack that open and started to talk to these smart operators inside of these fast growing companies, my perspective completely changed. But at the beginning I was all in on doing it for sales because I was just convinced no one would listen to a show about operations.

Matt Bilotti: That's amazing. Whenever we get feedback from David Cancel, it's always insanely helpful and that is certainly no exception. For me, I had auditioned because from prior things that I've done, I've learned how much benefit you can get from just being able to pick the brain of really smart people. And it just seemed like an amazing opportunity to do that. And additionally, the growth topic came up as one that we wanted to run the podcast for. And I had just moved into a growth type role for the six months prior to that. And I remember spending a lot of time poking around on the internet, looking for other podcasts that were about growth or blog posts and everything was fragmented. And I couldn't find a really good library of content on it. And so I felt a little bit lost and it just seemed like there was a really clear gap and space for content in that. And I felt like I had, through the internal Drift MC skills and all the other stuff, I felt like I had a decent set of tools to be able to build that up by bringing on awesome people. So that's why I jumped on.

Maggie Crowley: I think for me it was probably a similar, Matt, to you. Just wanting to have a place where a better resource for operators in products. Just because there's a lot of how to get into product content and a lot of content around the role. But not a lot of," Okay, I'm a product manager, now what?" type of stuff. So, that was definitely part of it. But I think the other part for me was it was totally outside of my comfort zone. Super scary. I had no idea how it would work. And I often find when those opportunities come around, I try to run towards them because it always means I'm going to learn something. So I think I remember when DC was like," Oh, we're going to open up auditions." And I immediately was like," Oh no." And then I said," Wait, I should probably do that."

Sean Lane: Maggie, it's interesting because you were the pioneer, you were the first one of the three of us to do it. And so I think, Matt, I don't know about you, but I definitely benefited from watching you and trying to learn from some of your early ideas and the way you are going after guests and things like that. We all, I think have talked a lot about the idea that doing this, as Matt said, it's a cheat code of a way to talk to smart people. Is there a different benefit other than that, that you feel like looking back at your 60 plus episodes that has surprised you as something that you've now taken away from hosting the show that you weren't expecting?

Maggie Crowley: Yeah, I didn't expect that it would have such an impact on the quality of my day- to- day work. So there definitely is the cheat code part. There's a network building aspect that I also didn't really expect that the guests, some of them definitely become people in my network that I talk to regularly. That was a huge surprise. But I think really what I didn't expect was that when I'm not doing the podcast which is not our full- time job, that I would be better at what I was doing. So I absolutely think that it gave me a way to get better at a lot of the core functions of products, especially things like communication and presentation and making choices. So, that from you was a real surprise.

Matt Bilotti: Yeah. I think for me, in addition to all that stuff that Maggie just said, I feel like it forced me to get better at asking good questions because I think good podcasts are only built when good questions are asked. And I have learned that through trial and error in building this podcast. I feel like being in a growth role, product role, I'm sure operations too, in any type of role you are most effective when you can ask really good questions, challenge your team members. Why are they thinking things a certain way? How can we do this thing better? And I feel like the constant exercise of," What are great questions that I can ask where I can learn and many other people can learn from this person that is clearly a wealth of knowledge?" It's just a really good forcing function for getting better at being critical about what is a good framing of a question and where are we going to learn the most.

Sean Lane: Maggie, I think to your point about just the impact on your day to day. The other benefit that I would add to that is we talk at Drift internally a lot about role models. And there's no better way to bring a role model example to the conversation than to say," Oh yeah, well, I talked to the president of Showpad and the way that he runs his professional services program is X." And so again, yes, we're learning for our personal benefit and yes, we're learning for the benefit of our audience, but then to be able to take those specific examples of actually how their companies are run. And when we're trying to solve a problem internally, be able to reference a specific person at a respected company and say," This is how they do that." And know that's how they do it. This brings so much more credence to whatever argument you're trying to make.

Maggie Crowley: Yeah. I love that when I can line up a guest and a problem or something that we're working on internally and say," Okay, we have this thorny strategy question." Okay, I just spent an hour talking with one of the VPs from Box about how he thinks about strategy. And then the thing that doesn't get into the show and I'm curious if you guys do this, is that after we're done recording, usually there's a couple minutes where our files have to upload. And that's when I have saved two, three questions that I need to know where I can be really specific about stuff that I might not feel comfortable sharing in the recording. But that's when I'm like," Okay, this is the real story that I'm dealing with. What would you do?" And so I'm always trying to get some cheat code advice from these people right after I record.

Matt Bilotti: Yeah, I always feel like those post few minutes of recording are when I get some really interesting answers and I kick myself sometimes because, and I joke to them," I wish we had this thing on the podcast." But I think that also goes to the rapport that you build generally leads to better conversations. And so you just that build that up over the course of an episode. And I think it's tricky sometimes where you have episodes where it feels like it starts slow, but then you get some really incredible stuff towards the end. And I release those episodes, I'm like," Man, I really hope people stick with this one." It's hard for me to tell them," Make sure to really listen through the end."

Maggie Crowley: And the other thing that I didn't realize is that it would broaden my employment prospects. I absolutely think that this is the type of thing that I can point to that people can see how I think and could know if I were to interview somewhere, it's really easy for me to demonstrate what I know about because I have this whole library of things that I've talked about. And it also gives you access to those people. So it's a weird job thing as well. And then the other thing is, Sean and Matt, I don't know if this shows up for you, but when we're recruiting, it's really funny when someone gets into an interview and they say," Oh yeah, I listened to this episode when you and Craig were talking about blah, I'm really interested in doing product that way."

Sean Lane: Yeah, I definitely have had that happen during the interview process. And one, it shows that the candidate has actually done a little bit of research and gone the extra mile to hear about how we think or how we approach problems at Drift specifically. But also it has brought about, for me, some of the best jumping off points in those interviews and in those conversations because it's something that hopefully if I've put out a full episode on I've thought a little bit about. And then from them listening to it, they are bringing some of their own perspective and it helps you to learn about how they think and how they would approach the problem and how they would be as a collaborator on those types of problems. So 100% agree with you on that, Maggie. And I think the other added benefit in terms of just like networking and personal outreach and Maggie, you told me this was going to happen right at the beginning was you just hear from people who are completely outside of your network. You get to hear from folks who have somehow stumbled across an episode of your show and they give you this amazing story about how they then took that and applied it to their role. I actually had one person who used the episode that they had listened to in an interview at a different company and that helped them get a job. And so that was a wild experience too. And so I think there's a whole bunch of different network effects of being a host and being on one of these shows.

Maggie Crowley: Yeah, that's so cool.

Matt Bilotti: That's the most rewarding part about it, is finding out that this episode helped this team at some company I've never heard of get through a really thorny problem or whatever it might be. I think to me at the end of the day, when I look back on the podcast, I love the fact that I built this library. I love that I get the personal branding from it. But for me, it's the hearing from people that have listened to it and hearing how those episodes have helped them in their day to day or on their team or building a new strategy or whatever it might be. That is really, really what I find to be the most rewarding part.

Maggie Crowley: Yeah, I agree. I think one of my favorite moments of that was I have a friend who constantly mocks me for working in tech and having a podcast as one does. And then eventually texted me one day and said," I'm really annoyed about the fact that I had this question and I knew you had recorded on it. And I listened and it helped. And I'm just frustrated that I have to tell you that." And I thought that was my peak happiness of doing the podcast was even getting one of those people something that's helpful.

Sean Lane: That's amazing. I'm curious, you both talked about the fact that you think your show has evolved since it started. Matt said we're doing this to wrap up the year. As we look ahead to 2021 and beyond, are you guys thinking at all about how your show can take another next step or another iteration? Are there things that you are thinking that you could do to stretch what you do today?

Maggie Crowley: Yeah, I can go first, Matt. I think yes is the short answer, but what I'm really interested in doing is some stuff that I would say is level two podcasting. So if what I've been doing is the safe option, what I want to really focus on next year is I want to have more disagreements. It's really hard to record a show when you don't both agree on the thing. An idea I've been kicking around is I personally really struggle with case interviewing. I think it's really hard and I don't really understand why we do it in product. And so I would love to get someone who does the case interview for Amazon or Google or someone to come on the show. And I want us to argue about it because I want to have that discussion. So I want to do more stuff like that. And then I also want to do more solo episodes. I think those are a lot harder for me. So I want to push that one a little bit further.

Matt Bilotti: Yeah, I'm totally with Maggie on solos. They're definitely more challenging, but they really help you crystallize your own thinking on certain topics. And then I think another thing that I would love to do more of, which I've started doing towards the end of this year in episodes, is I think a lot of conversations could, if you're given any specific topic, could focus so much on the stuff that seems straightforward or is straightforward about any given processor, tactic or campaign or whatever it might be. However, there's always this mess behind it that doesn't get brought up in the blog post or any other given interview where a team is implementing this new strategy, here are the steps that they did. But there's this other side of this story of the fights that they had internally with the leadership on this other team and how many slide decks they had to make to get the buy- in. All that stuff, the real part of it that is the struggle of the day- to- day and not just the glossed over," This is how to do the thing." I really want to get deep on that part of it. So people could really understand that and connect with the it's actually not that easy, this stuff is hard. And here's all the hard stuff that usually people don't talk about.

Sean Lane: It's not all that glamorous on every single one of those projects as the blog post or the product announcement would make it sound.

Maggie Crowley: I don't think it's ever been glamorous.

Sean Lane: I'm with you Maggie on the debate piece. I think the one potential twist that I was thinking about for my show is I would love to bring two guests on who have that differing opinion and we'll let them go at it. I think in ops people have very strongly held preferences around things like the tools they use or the architecture that they set up. And so I would love to bring on one person from one company who loves one version and one person who loves the absolute opposite and I'd let them go at it. And I think there's a way to have that conversation without it being contentious. But that's one of the things I'm looking forward to for next year.

Matt Bilotti: I love that. Sean's like," Hey, you two people, you're really smart, go on this podcast and I'll publish it. I'll just hang out in the background."

Sean Lane: Exactly, it's called being a facilitator, Matt.

Matt Bilotti: I love that idea. I think it's something that you have your own perspective you can bring to the table and you can carry it with your own opinions. But sometimes the clearly different set of experience will just get a really other level type conversation. So that's a great idea. I might do that too.

Maggie Crowley: The other thing that I was thinking about for this is that it's just hard, Matt, for the example that you were talking about. I would also love to get into the messy stuff. But it's so hard to talk about our work without giving so much context on what our business is up to. And that's the thing I struggle with is I want to talk about," Yeah, I had to make 15 versions of this deck and make 17 presentations to finally get this go ahead to do this thing." And Matt, you probably know what I'm talking about, but I can't talk about it because it's not live and it has a lot to do with our strategy. So that's something that I always struggle with is how to get real without giving away all the secrets.

Matt Bilotti: Yeah, that's so tough. And same thing, the guests feel that way too if it's something that is really top of mind and the businesses' prospects rely on that thing working, they're not really going to want to uncover it all. So I've generally found that finding folks that did that type of work three to four years ago and are now onto another role and the company has moved on from that stage, that type of person is more willing to dive into those details.

Maggie Crowley: Okay. So my last question would be what's the number one either lesson you learned from the podcast this year or piece of advice you got from a guest?

Matt Bilotti: Wow. Really putting us on the spot here.

Sean Lane: I'll go first, Matt. So I think the lesson or the story that honestly just blew me away was I had this woman named Karen Borcher who was telling me this story about, I asked the guests at the end of each episode about someone who impacted them getting the job they have today. And Karen, without missing a beat, said," Lin- Manuel Miranda." And I was like," All right, go on." And she basically said that she was out, I'm going to butcher the story, but she was out on a run and she was listening to the Hamilton soundtrack for the first time. And she literally just stopped in the middle of her run to be like," Wow, this is amazing." And as a result of that, she was like," I'm marveling at the work that this person has done. And I'm not marveling at the work that I am doing." And she quit her job. And then she went and found the gig that she has now as a result of that. And she just blew me away as someone who just had this incredibly high standard for what she was doing. And so that was probably a year ago. And it just has stuck with me as one of those stories that I don't know if I would do that, if I could stop myself and be like," I'm not marveling at the work I'm doing." And make a massive life change as a result. And so that was just one of the coolest stories that I've heard from a guest.

Matt Bilotti: That one's pretty amazing. I don't really know if I can top that. I think growth has this broad, overarching, jack of all trades type term to it. It gets used in a lot of contexts. And I've found that even when the context of how growth teams or growth people operate, there's a couple very core similarities at companies, generally a growth team that's spun up gets six months to prove itself at any given company. And I think there are also a couple of people that I talked to, I'm looking at the list now, Christina Rubino, who we talked about the opportunity for podcasts being a growth channel through advertising. That was a really fascinating one. Talked about product led SEO with a guy, Eli Schwartz. And to me, those were just really interesting because they're worlds that I've touched, done a little bit of work on, but there is so much more depth to it than I think I had realized. And talking with people like that, it just shows you that there are specialists that can know something so well that anything that they say and everything that they share is like," Wow, whoa, that's crazy. I didn't even think it like that." And so I think there's just a couple of those that really blew me away.

Maggie Crowley: I think my lessons are probably not as good as yours, Sean, but different because I think the thing I learned this year was that across all of the guests that I've had, the ones who were really amazing at their jobs have this magical combination of curiosity and humor around the work that they do. And it really shows up in how they talk about it and how they're," Yeah, this crazy thing happened and I learned so much and how wild was that?" And they're super flexible and just this attitude that they all have. And I thought it was really cool to meet a bunch of people who were having fun in the work that they do, even when it's really hard.

Matt Bilotti: Love that.

Sean Lane: This was fun, guys.

Matt Bilotti: Yeah, this was great. I'm glad that we did it. And we finished just in time, we got a little bit of a start late because there were power tools going on in my apartment, but here we are and we made it.

Sean Lane: I think we should make this an annual tradition. We'll have to do a end of year wrap up and see what we bring back to the table next year.

Maggie Crowley: I love it.

Matt Bilotti: Absolutely. I have a feeling that we're going to publish this and then we're all going to get a message from DC saying," Why wasn't I invited?" We'll have him on next year maybe.

Maggie Crowley: We'll see.

Sean Lane: We'll see if he makes the cut.

Matt Bilotti: Thank you both. This was a lot of fun and thank you all for listening. We really appreciate it. This one's getting published in all of our feeds. Thanks again. Thanks for following our podcasts, reaching out to us, giving us feedback, whatever it might be. We are all extremely appreciative and we will catch you on our next episodes.

Maggie Crowley: Thank you.

Sean Lane: Thanks everybody.