Keeping Remote Teams Connected with Tim Hickle

Lindsay Tjepkema.: To say that we've never been here before, doesn't really do this whole thing justice, does it? Coronavirus, COVID- 19, quarantine, social distancing, it's all uncharted territory, folks. It's got many companies around the world going remote, including Casted. In fact, I'm recording this from day one in our official mandated work from home time, where our entire company is now remote. While there are many, many, many important things to be thinking about right now, you're listening to a podcast about branded podcasts, which leads me to believe that your mind is on marketing at least for the moment. So, let's do it. Let's talk about, that at least for the next half hour or so. I'm Lindsay Tjepkema, CEO and co- founder of Casted, the first and only marketing platform built for branded podcasts. This is our podcast. If you're like a lot of marketers, you're likely one, working from home right now, and two, seeking ways to stay connected with your audience and customers and prospects, of course, but think about how you're connecting with your team. Today, I had the pleasure of speaking with Tim Hickle, Head of Demand Generation at Woven. As you'll hear, he's also the guy behind the scenes of their podcast, Scaling Software Teams. But, Tim also runs another show for Woven, but you won't find it on Apple, Spotify, Google, or any other player. That's because I'm talking about Woven's internal podcast, meaning it's private, shared only with the team's members. You see, Woven is a fully distributed team. They have no office. They all work remotely, always have. So, they have been working to close the gaps between each member of their team all along, just like so many of us are working to think about right now. Listen in as Tim talks about how they are using podcasts to be intentional about creating structure for those special moments that build relationships and establish deep care and trust amongst a team, not to mention sharing internal knowledge in a way that is engaging and simply more fun for everyone.

Tim Hickle: Hi, I'm Tim Hickle and I am the Head of Demand Generation at Woven and I am the show runner for the Scaling Software Teams podcast.

Lindsay Tjepkema.: Awesome. I'm so happy to have you here, Tim, because we are actually going to look at a whole new side of podcasts today. Before I spill the beans, tell me the two different ways that you are using podcasts at Woven

Tim Hickle: The Scaling Software Teams podcast is the second podcast that I've produced for a B2B company. It was something that I came in wanting to do, but the thing that's different about Woven, compared to other places I've been in the past, is Woven is 100% remote workforce. We are all distributed. We've got employees in Chicago and we've had employees in Ohio. A lot of us are based here in Indianapolis, but we've got somebody up in South Bend area. We even have a full time- employees that work out of India and Africa. So, managing a remote, global, distributed workforce, even for a company as small as ours, we're 12 full- time employees, somewhere in that ballpark. Managing a global remote workforce, like that is really difficult to keep everybody on the same page. You've got Slack, you've got email, but a lot of times the most powerful moments that we have are audio and over video. It's a lot easier to convey some of those ideas if you can actually hear them as opposed to reading them in Slack. One of the things that we did, a couple months after we launched our external podcast, is we actually launched an internal podcast that is private, password- protected, that everyone on our team has the login info for. We use that podcast to share everything from sales calls, like we'll upload sales calls that go really well. We'll upload customer calls that go well, or sometimes even that go poorly, but we'll also do low- fi audio recordings of a conversation between you and a coworker about something important. We can upload that. That's something that we've used as a team to help all of us stay on the same page and help communicate things more globally throughout a completely distributed organization.

Lindsay Tjepkema.: That's great. Right now, I should mention that we are recording this March 16th. Today is the first day that Casted is 100% remote. Anywhere, we are very, very lucky that we are a SAS company. Working remotely is nothing new to us, but heading into the scenes that we're all experiencing globally, this whole coronavirus situation, we are officially as an entire company remote today and for an indefinite amount of time, and so looking at these unique ways to communicate and to stay really, really connected as a team with each other and then also with our audiences podcasting, obviously I, and we are biased, but it's a really interesting way to say," Okay, look, we have this medium, we have this channel. What other ways can we use it to bridge that gap?" So, I'm really interested to hear how you've been doing it all along.

Tim Hickle: I'll be honest. There were some times that we were better about this than others. There've been times when we've been good about the external podcast, getting that updated and the internal podcast usually tends to be one of the things that falls off our radar. It's hard for us, but I think that being, the more people are going full- time, remote, more important things like this become. One of the things I've found that make it really easy is, we don't try to make it too fancy. When we do our internal podcasts, we will, I will oftentimes upload entire sales calls, just audio of an entire sales call or I'll upload the audio of a conversation from a Zoom call and I can upload the entire audio piece. I don't go in and do any editing. I don't do any go in and do any cutting or clipping. I will go through and identify the timestamps for highlights so that people know, Hey, I have this great conversation with Lindsay. We talked about this at this timestamp, this at this timestamp, this at this timestamp, just wanting to make sure you guys were able to hear it. But, one of the things that I think has been effective for us is not trying to get too fancy with it. The times when we've been really bad about keeping it up to date have been the time when we're going through and saying," Oh, I should edit this call down. No one needs to listen to the whole hour. I should edit this down just to the five minutes that people really want to hear," because then that adds another to- do on the plate and that pushes back something getting distributed. I mean, we make it raw. We make it uncut. We make it unfiltered and we try to use timestamps to make sure that people are calling out the highest points.

Lindsay Tjepkema.: Right. That's a good option to use. For myself, for one of these cases that we have actually in communicating with our board is that we use the key takeaways within Casted. It's very meta. We use Casted to speak to our board of directors, but yes, I do a podcast and then I actually break it up into the key takeaways and do a private page so that my, at that point, an internal audience can go through and catch each clip the way that you're referring to as like each timestamp and understand what's happening when, so that they can skip to the part of the episode, that's most relevant to them. Then you can also attach the relevant resources, the related resources right there on the page too. Podcasts, they're not just for external audiences anymore. Right?

Speaker 3: Right. Well, and we also, we have an internal, we have a Slack channel for our internal podcasts where people can upload whatever audio files they want and we'll upload them to the internal podcast. That's nice too, because I'm able to crowd source the work. I'm just, I'm there as a conduit to make sure it gets posted on the channel, but people are able to upload things and then also it lives in two spots, right? That's the other nice benefit, is even if there's a delay on me getting something uploaded into the internal podcast feed, there's a shared Slack channel where everyone's seeing that audio. It's also been great for onboarding new team members. We've added three new employees in the last three months. Two of them started in January and adding new team members in a fully remote environment can be really challenging. One of the things I was able to do though, I was able to give them the login and fell in and say," Hey, go listen to a bunch of these episodes. That's your task for the next day." It was just go through. You can listen to actual sales calls that people are doing. You can listen to actual discovery interviews that we've done, conversations that our CEO has had directly with customers, directly with investors, directly with prospects. You can listen to those yourself, and I can give you some highlights and takeaways, but you're hearing from the horse's mouth what is the most important. Yeah, I think it's been really powerful for us when it comes to helping scale a fully remote team.

Lindsay Tjepkema.: What kind of topics are you covering and what's the thesis, I guess, of your internal show? What all is the purpose?

Speaker 3: That's a wonderful question. There isn't one. I think that if I was doing this right, there would be. I think the best world, let's say that my full- time job was managing podcasts, like I could make the internal podcast a really heavy focus. The best world is one in which you've got thematic episodes. You're able to make sure that you were releasing episodes about things that align with your cultural values, that you're releasing episodes that aligned with value props of your organization. For us, it is literally just a audio distribution vehicle. It is just, we are as a team, constantly having conversations that shouldn't exist just between two people. They should exist between the entire company. We should have a transparency and as a result, this is one of the easiest ways for us to do that. If my CEO and I have a conversation about our go- to- market strategy, and we want the rest of the company to hear it because we want them to understand how we came to a decision, that information should be available to everyone. That accomplishes two things. Number one, it helps everyone on the team understand what direction we're rowing in and why. But then it also holds me and my CEO accountable, because we know whatever we say to each other is going to be public in front of the rest of the company. It forces us to come correct. It's a good forcing function for us. I think step one is using it as a vehicle for getting everyone on the same page and then step two is how do you take it to that next level and make sure that it aligns with your company's values?

Lindsay Tjepkema.: That's great. I think, especially for a fully remote team like yours. I mean, teams that have the luxury of being in the same place at the same time, have conversations about nothing or share conversations, or share information that is important for people to know, or you're in the middle of the conversation with each other and you say," Hey guys, come in. Everybody come into this room. We should, probably include you in this conversation," where you can't really do that in a fully remote team. I think that that's important, but it also goes back, marketer to marketer to knowing your audience and to say, who's it for, what's the goal, right? Yours is, who's it for? It's your it's for your team and you're fully remote. You really understand that persona, if you will, really well. What's the goal? Is to just have everyone feel connected, is what it sounds like. Right? Whereas, other teams, it might be different. It might be a little bit more official or product- related or official internal inaudible related or a little bit more buttoned up. But, I think that for you, that sounds really healthy and really pretty strategic

Tim Hickle: Well, and one of the things that I wish we did, we have not done this, but it's one of the things I wish we had, would have done with our internal podcast to date, is make it more about people than about product, because I think that to date, it's been mostly educational. It's really heavily focused on here is some information that you need in order to, if you're selling our product, here's some information you need. Here's a conversation you should be privy to. Here's something that will help you level up within the organization, to help us grow. But, I actually just wrote an article over the weekend, because I've been working for a year and a half as an extrovert. It's a lack of people- time can be a very big challenge for a lot of people when it comes to working remote. One of the things I talked a lot about in that article, that I think could have done with our internal podcast, but didn't do, and I wish we did, was finding time to make more time for just getting to know your coworkers as people, not as business partners. The thing I talk about a lot in that article is like when you're in an office face to face, you have all these little micro interactions that happen throughout the day. I come in, I wave, I say," Hey Lindsay, how's it going?" Then, I walk past you. We don't get that when we're remote. You close a big deal. You come over to my desk, you high- five me. Those little micro transactions that help build trust, that help build comraderie, those don't exist in a remote environment. In a fully remote environment every single one of your interactions is going to be more or less about work. That starts to make your relationship feel very transactional. That erodes trust and it makes it really hard for people to work together as a cohesive unit, because I don't think about you as a three- dimensional person. I think about you as the person who needs this thing from me. Whereas, this is something I think we could have done with our podcast and I think it would have been a better choice if we had made this decision a year ago. But, I wish it would have had episodes that were literally just two people shooting me, shooting the shit. Two people having a good conversation about nothing in particular. One of my employees is a video game streamer and I've gotten to know him very well because I follow his streams on Twitch and Mixer and I'll just tune into them once every couple of weeks I don't watch them every night, but once every couple of weeks I'll tune in and that's helped me get to know him a lot more as a person. I wish I was doing that with every single one of my employees, but I'm not going to ask all of my employees to stream on Twitch. What I can't ask them to do is," Hey, can we have an informal conversation that's just for fun. Then, we'll post that on the internal podcast and other people can get to know you the way I'm getting to know you." I wish I was doing that. I'm not doing that. I think we should change that.

Lindsay Tjepkema.: Let's talk about lessons learned and recommendations. A lot of people are, social distancing is the word of the week, as it should be right now. A, lot of, all of us are wondering, what does that mean for this area of my life? What does that mean for this area of my life? But I'd love to hear your thoughts as this is really top of mind for a lot of people. What do you recommend? Where should people get started? What should they consider? What should they avoid.

Tim Hickle: Something I don't think I really understood until I had worked remote for a full year, was that when you're co- located in an office, there are all these moments that seems serendipitous, right? You're at the coffee pot, you're waiting for the coffee to brew and you're talking to somebody from a different team and all of a sudden inspiration strikes. You have this great idea about your next marketing campaign. That seems completely serendipitous, complete happenstance and there's no way to recreate that when you're remote. That's the way I thought for a while, because it's magic. It's serendipity. It's complete happenstance. What I didn't realize is, there are a lot of structural components that make that serendipity possible. You and your coworkers have to share a parking lot. You and your coworkers have to sit next to each other. You and your coworkers have to share a coffee pot. All these structural things are in place that make those serendipitous events possible. What happens when you go to work remote, is you remove all of those structural components and it's your responsibility to replace them with other structural components. Now, that seems counterintuitive to people, because how can I structure serendipity? Structure makes serendipity possible. It's serendipity doesn't happen without structure, so it's important that we rebuild those structural frameworks and that's going to mean a different thing for everyone. One of the ideas, I love that again, we haven't done, is having those casual conversations with people and sharing them out because, so let's paint a picture for a minute of, let's say me and my colleague, Michael. Me and Michael decide, we're going to have a quick 20- minute, informal conversation. We're just going to talk about what we did over the weekend. It's going to be a completely casual conversation, where we don't talk about work at all. We share that out via an internal podcast feed. Other people listen to it. Not only are people going to feel closer to Michael and closer to me, because they've seen our personalities and we feel a little bit more three- dimensional, but just like those conversations could spark interest and inspiration for Michael and I, it could spark interest and inspiration for other people on the team as well. I think that when it comes to working remote, you have to think about what structural frameworks are you removing and you have to think critically about what these frameworks are important, how can I replace them thoughtfully, so that a lot of those micro expressions are happening more frequently. Instead of Lindsay, me giving you 30 high- fives and head nods throughout the course of a week, we've got to do it over the course of a 30- minute call that we do once a week. Oh, that sounds like a bummer, right? It sounds like scheduled fun, but it's important and you got to take it seriously. Otherwise, you lose all of those things that help build relationships, that help build trust and help put you in a position where you can get inspiration from your coworkers.

Lindsay Tjepkema.: Right? I mean, you've got to be intentional about building the structures that allow serendipity to happen.

Tim Hickle: Yes, exactly.

Lindsay Tjepkema.: That makes sense. That makes sense. All right. What, if you had to boil it down, if someone was thinking about specifically podcasting in with what's happening right now and possibly saying," Hey, maybe an internal podcast is something that could be beneficial to my team that's scattered, whether it's throughout the city or throughout the country, around the world", what are some recommendations that you have for them to get started?

Tim Hickle: Start fast. I would, what I would do is, I would literally create a Slack channel. Start by recording a little introductory message on your phone. Make it raw. Make it uncut and start by uploading as many voice memos and things as you can, to that Slack channel. Use that to gauge general interests. I think that will help you get a sense of, is there an appetite for this? You don't need to set anything up. You don't need to set up a feed yet. You don't need to create album artwork. You don't need to overthink this. Seriously, start as simple as possible. Create a Slack channel. If you don't use Slack, you could use something else, I'm sure, where you can upload audio files immediately." Tell people, Hey, this is what we're going to do. We're going to use this." You can even position it as temporary. Say," We're going to do this to stay in touch while we are going through this quarantine phase. Maybe it's something that sticks around, maybe it isn't, but we're going to use it for the time being, just to help us connect." Start there. Upload as much as you can. Reach out to other people on the team to try to get some co- conspirators that are excited about it, because it's a lot easier once people see two or three people that are uploading audio files, then people are more excited about it. The best people I think to go to are salespeople. Salespeople love, when a salesperson gets a good sales call, they want to share it and they want to brag.

Lindsay Tjepkema.: That's really great information to share. I mean, when there's something successful or even a failure, a close loss is a really great learning experience, too.

Tim Hickle: Oh yeah. You get, you get salespeople on board, they're going to go through and say," Oh, I want to share these learnings." You're going to get great calls from them. You'll get bad calls from them too. Start there. Start getting those things uploaded. Once you have a decent appetite I would go get a feed ready for this. You can either, if you are not sharing anything proprietary, I don't think you need to make it private. For us anyway, we made ours password- protected, just because we're sharing private conversations we're having with clients, that wouldn't be appropriate for us to share publicly. But if you are only doing voice memos that you're recording or Zoom calls that you're recording with members of your team, where you're having casual conversations, there's no reason that needs to be private and that just creates another barrier to entry.

Lindsay Tjepkema.: Okay. What else have you learned from having an internal podcast that you think is important to share, not only in general, but especially now?

Tim Hickle: The most important lesson that I've learned about having an internal podcast is you have to prioritize it. I think that, this feels very present and top- of- mind right now, but it's almost always going to be the first thing that falls off your plate, because it's not going to generate new business today. It's not going to generate leads today. It's really hard to make that a top priority when there are hard times, potentially, ahead, and you've got to go out and you've got to hustle and it's your responsibility to grow this business, it's really hard to prioritize getting internal podcast episodes up. But, that's why I think the low- fidelity option is so essential for marketers. I think it's hard to do, right? Because we're people who love our craft. We're people who really want to put a good product out and want to do something that we're proud of. The idea of a raw, uncut voice memo, where we stumbled over our words a few times, and we don't have any intro and outro, and there's no thematic constant between these episodes. But, if this is done well, this should feel vulnerable. This should feel you're bleeding on audio for people.

Lindsay Tjepkema.: You don't get authenticity without vulnerability.

Tim Hickle: You don't. You don't. This goes back to, it's really hard. I'm an extrovert. I get my energy from other people. It's really hard to work remote, when you get your energy from other people, because you lose a lot of that human connection, right? When I'm sitting right next to you, Lindsay, I can see on your face. It's like, yeah, I can see on your face, just those little micro expressions of things you're excited about, things you're disappointed in. I can lean into those things. We can have a great conversation. I can walk past your desk and see you're having a rough day and say," Hey, Lindsay, you want to grab a beer after work? I know it's tough today." It's a lot easier to have those moments when you're in person. When you're remote, you miss so much of that. Even if you're on zoom calls on a regular basis, you're going to miss a lot of those micro expressions. You're going to miss that body language. You're going to miss the chance, walking past somebody's desk and seeing that they're really happy and wanting to know what they're really happy about, or they're really sad and wanting to go grab lunch to try and cheer them up. You're going to miss out on all that. Again, you have to deliberately replace it, and the only way you can do that is by being really vulnerable, really aggressively vulnerable. There have been days where I've gone through and I've uploaded audio of literally just me being like," Guys, this was a really hard week. This is a really hard week and here's how I'm feeling right now." Because this side, this thing happened and it sucked, or me uploading audio and this mostly been to the Slack, not to the internal podcast, but uploading audio in the Slack room. Just like" Guys, this was a really great week and I'm really proud of everything we've done." I've been on the verge of tears on audio for this company several times, both positive and negative. I think that when you're a fully remote workforce, I mean I'm a feeler, that's what I am. I got to feel out loud if I'm going to have a ripple effect throughout the organization.

Lindsay Tjepkema.: Absolutely. I think, again, it goes back to know your audience. Who's it for and why are you doing it? This is a great example of that. I really appreciate you sharing so openly and so vulnerably and authentically your experiences with not only podcasting, but internal podcasts, Tim, thank you so much for sharing.

Tim Hickle: Absolutely. Thanks for having, this was awesome.

Lindsay Tjepkema.: This was awesome. Stay healthy.

Tim Hickle: I will. Wash your hands. Use plenty of hand sanitizer.

Lindsay Tjepkema.: That's it for today's show. Thank you so much to today's guest and to learn more about them and see Casted in action, with clips of today's show and related content visit Casted. US. Thanks so much for listening.