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Megan Chinburg on building and managing engineering team at help scout remotely

by Pushpak Mundre August 25, 2021

In this episode, Pushpak & Megan discuss about building and managing the engineering team at HelpScout remotely. Megan Chinburg has been an engineering leader since 2004 and loves empowering resilient, successful, remote-first teams. She is currently the VP of Engineering at Help Scout and has been living abroad in Italy for the last 4 years. When not in front of the computer she can typically be found mountain biking somewhere between the Ligurian sea and the Alps.

This podcast is hosted by Pushpak Mundre, Pushpak is Marketing Specialist at CrewScale



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Be Remote Podcast . Episode 11






Hello, everyone. Welcome back to another episode of Be remote podcast. I’m your host Pushpak. And today we have with us, Megan. 

Megan is a VP of engineering  HelpScout, Welcome to the show. Megan, how are you? Thank you. I’m doing well today. Awesome. Awesome. So let’s start with a short introduction about you and like what you do I tell you?



Yeah, it’s short. So I am the VP of Engineering at Helpscout. I’ve been working with Helpscout for the last five and a half years, and two and a half of those years have been in my current role. I’ve been leading engineering teams since 2004. and managing remote or remote hybrid teams in some capacity since 2007. So I’ve been doing this for a while I love working remote. I love empowering people to be the best team and version of themselves that they can be. And I’m very passionate about leaving the tech world better than I found it particularly for anyone with identities in the margin. Awesome.


Pushpak : 

Why move to Italy from the US 


So I’m really curious to know as we’re not talking here as well, like, you’re from the USA, and you’re staying in Italy, like most of the people I know like they moved to the USA to work in, you know, tech. So like, why you chose to move to Italy and wholeness things. It is to know about this.




I knew coming in to help scout that it was a remote company. And I was looking to just change locations. I was living in Portland, Oregon, and was looking for a change. And my partner and I started considering different areas around the world. And we had a friend who suggested Italy as a place to try out. There are lots of hiking and mountain biking trails, which is something that I enjoy, especially up in the northern part of the country. So we made the leap, and now we’re there. And luckily being remote. This is not a difficult thing to manage when it comes to working with a team.


Pushpak :  

Manage meetings with different time zones 


Yeah, so actually, that was my next question. I wanted to ask you about your team, like most of your team must be in the USA, right? And you’re in Italy. So how do you manage your meetings? And how do you, you know, sync up with your team? How do you take scrums and all like to go because you guys are in different time zones?




I don’t have the exact numbers offhand. But we have, I think something like 60% of the company is in North America. And then everybody else is somewhere else we do tend to not necessarily have core hours across the company. But we don’t have people as far east as the Eastern European time zone. And that stretches over to the west coast of the United States. However, we also have people in Australia. So that is sort of the one outlier in our time zone. 


Pushpak : 

Managing team


So, How do you manage your team? Like, you’re the VP of Engineering at HubSpot, and you’re the tech leader in the company. So how do you manage your team remotely? That’s like must be the challenging part. Right. So how do you do it?



Sure. I guess I’ll just start by mentioning that Helpscout had a bit of an advantage going into the pandemic. And we’ve been a remote company since the beginning. So we weren’t having to learn anything new when it came to working. Right. So while we had to manage the stress, the global crisis, we were pretty lucky because we were just pros at remote collaboration. As a company, we default to asynchronous communication so we make heavy use of slack Dropbox paper for documentation, we use videos a lot. So meaning video recordings. So if we have to share something, either a team meeting, or we’re explaining how and you know, the design of a new feature, we’ll record it. And usually in the loom is one of the tools of choice that goes, and then share it publicly and broadly within slack. We encourage communication to happen in public as much as possible. So everybody has the context across the team. One thing we have implemented is core team hours. So each team across the organization is allowed to designate their four core hours. So depending on where people in the team live, there are four hours that you’re always going to be available for meetings, or, you know, being able to hop on a call or discussion about anything. And that helps a lot. We do not require that people sit within a certain time zone on the team. But we do have conversations about it. So we try to be intentional about where people on the team live. And if we have someone who’s an outlier, like everybody is between the east coast of North America and maybe Europe, if there’s one person sitting over on the west coast, we might have a conversation with them to make sure that they are okay. With the work-life balance that is, you know, will be interrupted to work their team core hours. On top of managing time zones as a company, we’ve committed fully to using ours. So objectives and key results. So I think it’s a great tool. A lot of people might roll their eyes at it, but I think it’s very powerful. We can agree on the objectives. We’re all aligned. So from a leadership position, like I know that if the cars are hit, and we’re getting like, you know, roughly, you know, somewhere between 70 and 90% of those objectives, I know that people are doing the right work like I don’t have to manage the details. I don’t need to, you know, get into how I’m just caring about the what, and that’s pretty powerful because it provides a lot of autonomy for the teams to, you know, figure out the implementation.


Pushpak : 

How you manage to communicate without daily scrums


Yeah, it makes sense. So I truly wanted to know about you said video parts you communicate through video, like by making a video. So like, you don’t like daily scrums and all? If, if you want to explain something to someone, like your, your colleague or someone like maybe a developer, so how or like, do you like to get on a call with them? Or, as you said, like to do videos as well, you make videos. So how does this work? So I want to know about this?



Yeah, I think we use every tool or medium at our, at our fingertips, right. So if it’s something really small, or maybe, you know, has a lot of detail, we probably write something down. So put it in the paper, maybe in Slack, depending on if it’s ephemeral, or if it needs to be saved. And we might start there, and then ask for a call if people’s time zones align, and that can work out. But usually, that’s only if you need to have some sort of back and forth. If you’re just sharing something, then usually recording a short video and dropping it in the team channel is going to be successful, like people love to interact with videos and hearing someone explain the work that they’re doing. I think it’s more powerful than just reading about it. Yeah, let’s say it depends on the situation




there. So because you know why I’m asking this because I have noticed, I have personally observed this, like some of the managers in my company, they wanted to explain something to their, to their intern, but they’re not understanding it, you know, or like, in adult one time, so they have to explain them repeatedly, again, and again. And then they get kind of pissed off. Like someone, some people take time to understand things, right. So this is a good idea like just create a video that explains everything. And they can watch videos multiple times, right? So the manager won’t have to worry about explaining again and again. So this is a really good insight point. Yeah,




Pushpak :

 Unique Experience while working remotely


So many unique experiences you had like while working remotely like by management, or like, by talking to your colleagues, like, you know, like go maybe some, like as I explained to like support, someone made some mistake and then any miscommunication or like any unique experience you had while working remotely and more to learn from it. Maybe some if something comes to your mind.



Sure. I’m not sure if unique would be like I don’t know if I could come up with a unique thing. So I think all of us as he Humans as we’re working remotely like we sort of run into the same challenges. Yeah. I think, you know, miscommunication happens all the time failure happens all the time. And then I think the superpower to deal with it is vulnerability. So being able to acknowledge that like, oh, something, something happened, something went wrong, there was a miss. So acknowledging that and having a very, like a transparent conversation with whomever you experienced this miscommunication with or failure with. And moving on and sort of committing to move on together can be a really powerful tool. I believe that vulnerability and trust are key ingredients for a successful team and company. So I lean very hard into a building that I talk about my mistakes publicly, I share them with the entire organization. I think demonstrating that I can fail regularly and talk about it and talk about how I’m moving on is I’m trying to demonstrate the behavior I expect to see across the whole team. I think that works well, for managing a lot of situations, because the more trust and vulnerability you have amongst a team, the easier it is to recover from, you know, anything that goes sideways. So while I don’t have a unique example, there, there are several that happened, I feel like daily that you know because you can have that trust and respect and vulnerability, it just makes it easier to get work done.


Pushpak :

 Challenges faced while working remotely 


 So what kind of challenges do you face while working remotely?




Yeah, so I think our biggest challenge is not dissimilar to everyone else’s big challenge. Zoom is not the best way to communicate as humans. You know, we do a lot better communicating in person where you can read all the body language and the energy. Also, you don’t have the weird interruptions and having to wait to see if someone’s going to go. So that’s, that’s all, I think a lot of people’s biggest challenge. But for one challenge, I would say our biggest challenge is that it’s been so long since we’ve had any in-person connection. Typically, you know, in the past, we would get together every six months as a whole company, we’d go to some, you know, retreat somewhere, either in North America or in Europe. And we would spend a week doing a little bit of business-focused work, but mostly just connecting and having fun. And I think that relationship building and being able to see your coworker as a full human is deeply important for doing hard things together. So we try to recreate that as much as possible, by being intentional about fun things for the teams to get together. And do. We try to spend time just talking to our co-workers, not about work, we have practice, we use a word that we borrowed from Swedish, which is called FECA. Where we will just schedule random chats with people throughout the organization, we use a tool called donut in slack. And it just pairs you with different people randomly in the organization, you set up a 30-minute phone call, you talk about anything you want, but you can’t talk about work, or you shouldn’t talk about work. And we have a channel in slack where people might take screenshots and have the conversation and talk about share what they talked about. So we encourage people to, you know, share with their co-workers Connect, have some fun.


It’s very powerful.


Pushpak : 

How your day look like as a VP of Engineering 


Yeah, this is helpful as well. Sounds good. So how does a day as a VP of engineering look like, what do they know, you know, daily basically? Sure.




Well, I guess, the first thing I do is check Slack, to see if there’s anything urgent. I typically try to keep one very large strategic initiative on my plate during the quarter. And then maybe like two or three smaller boulders, you know, rocks, like one Boulder, a couple of rocks. And so every week, I think through things like, what are my top three priorities, those are going to be the most important things that I could get accomplished that are going to serve my goals. Ultimately, as a manager, you know, I’ve any sort of leader of any organization. Your job is to, you know, deliver high value for the customer and set your team up for success. So, with anything I’m doing, if I’m not actively moving the needle, on either of those two things, I’m probably focused in the wrong direction. So, for example, right now, we are taking a look at our org, our organization structure, and our architecture and how we could better align those two things through domain-driven design. So I’m spending a lot of energy, you know, talking with our CTO, speaking with architects on the team, you know, speaking with our, our product management team and understanding, like where they see the product evolving and their vision so that we can make sure that everything is in alignment. And I just keep that as my main focus for the week, and then sort of everything else just fills in, like, I feel like there’s sort of constant, constant noise from slack. Yeah, maybe some constant noise from vendors, you’re managing vendors, through email, and, and then meetings, I do have to admit, I feel like I spend most of my time in meetings. And while they all feel I’ve got, I’ve done a thorough analysis of all the meetings, they are important, I have to have them, if I try to, like take them out or make them shorter, things start falling apart. So I do feel like communication is the biggest part of my job. When I look at it, I use rescue time to track everything that I do. And you can see that like, you know, 60% of my time is spent either in slack or in zoom calls. So that is, that’s mostly what I feel I do for my job is like talking.


Pushpak : 

Future of work after pandemic?


Talk. And I don’t know, that’s what does mostly like it, like conveying the message and communicating properly. Yes. Yeah. So what’s the one thing which you are curious about remote work? And where do you see the future of work, especially after the pandemic?




I think the thing I’m most curious about is what’s going to happen with all of these companies who are trying to do a remote hybrid approach to work? Yeah, I, you know, I, my hypothesis is it’s going to fail. Tragically, I think now that workers have been able to see how beautiful life can be if they don’t have to commute if they don’t have to sit in an open office plan and be interrupted by co-workers coming by or what’s going on in the break room, like, you’re so much more productive and focused. And you can squeeze that into an amount of time that works to fit your life. And I don’t, I don’t believe that people are going to want to go back to the office. So as much as I love seeing my co-workers, my life is better working remotely. And I think that more and more people have discovered that. So yeah, my guess for the future for remote is that the practices will get better, the tooling will get better. The way that we approach leadership and collaboration will evolve. And I think all of the things that have been happening in the tech space, particularly around, you know, just enablement and empowerment, shifting as much into the hands of the people doing the work as possible, and giving them the autonomy to make decisions and work towards outcomes. Like the less like, I don’t even see the need for you know, even the most micro-manager of micro-managers, why do they need to see the human in the chair, you’re going to be able to see the output of their work really clearly.



What do you think remote hybrid would fail? 


No? Why do you think a remote hybrid could fail? Is there any specific reason?




Um, well, I think mostly because people are not going to want to add the commute and the distraction back into their life. You know, it’s better I believe, it’s a better way to run your life, particularly if you have children, or you’re a caretaker for anyone. There’s just so much more flexibility in how people can run their schedules that I think that that adds an amount of I don’t want to use it. I don’t like the term work-life balance. Because I feel like it’s overused but it’s just the number of control people have. How they spend their time is huge.


Pushpak : 

 What  did you learned from your position of VP 


Yeah, I think especially for families, remote work is so they can spend time with children and everything. So, yeah, so what did you learn from as a VP of engineering, which you wouldn’t have learned anywhere else? Is there anything like that?




Um, so, I think anytime you step up in leadership, things get more and more nebulous. Like, as I’ve grown in my career, I don’t feel like I have more clarity about anything. I feel like I have less So, ambiguity is high. So I’ve learned how to manage ambiguity, deal with ambiguity and find comfort, and come to love it. There’s the same that Nick Francis, our CTO started using, he says your job as a manager is to absorb ambiguity, and spread clarity. So, you know, and I embrace that. And I try to keep that in mind, whenever I’m speaking with anybody, I have to take into account they do not have the context I have, they might not have the same degree of comfort with ambiguity that I have. And I need to tailor how I speak and the information that I share to account for that. So that’s probably the biggest learning. As you grow in your career, things don’t become more clear or easier, they just become, like, harder and less, but you grow more skills to deal with it.


Pushpak : 

Apart from work – tasks 


Awesome. So what are you into the outside of your work? So I already told it, but would you like to go in deep into that, like what you do outside of your work? And apart from mountain biking as well? Yeah,



I mean, mountain biking is sort of a deep passion, I took a break in my career. Before joining Helpscout, I spent two years trying to be a professional mountain biker. And yeah, I just dropped out of tech completely and became a cross country mountain biker, it was amazing. I traveled all over the United States and, and different countries as well. I did learn that I do not want to be a professional athlete. It’s not it wasn’t for me. And so I did make my way back to tech. But that was a glorious, two-year, two-year break. So other than mountain biking, I would say anything outside as I love, I love jumping in the water. So Lake river ocean, like if I’m around it, you can’t keep me out of it.




I think those are probably my two biggest passions, aside from learning, I think I love learning anything new about anything from the smallest, like random trivia fact to, you know, something, something deep and you know, going, I would have to go to school to learn it. Awesome.



3 favorite books 


So what are your top three favorite books? Like in terms of business or fiction, nonfiction, anything? Which will be love?




Sure. Um, I think my favorite professional book that I’ve read recently is Bernie Brown’s dare to lead. Okay, I have, there was a lot that she said in there that resonated. And I do try to take her advice and approach to heart and truly like lead from a place of extreme or maybe radical vulnerability. My favorite book, just sort of around engineering team performance, is accelerating. by Nicole Forsgren, just humble, and Jean Kim. It’s a very short book. And it talks about like, what are the four key ingredients or KPIs for a high performing team. And I just really what they’re saying is, if you do these four, if these four things are true, your team is probably going to be motivated and engaged. And that’s going to make them better employees. And that’s going to make your company better. So it’s sort of this virtuous cycle that they create just by trying to push these four metrics for me so I love that. And then there are several wonderful professional development books that I love, and always recommend. But from a fiction side of things, I love the book, the man who fell in love with the moon, by Thomas van Bower is a Portland, Oregon author. And just it’s a very different book from anything I’ve ever read. And it made me think a lot. Awesome. Sounds good.



Top 3 Remote Working Tools 


Check this out. So you already mentioned it, but like, how would you like what are your top three favorite remote tools, which you know, which helps you work remotely, smoothly, musically?




Sure. So it did mention a couple of important software tools, but I think like more important than software tools are the environment that you’re working in. So I have a nice large external monitor that I work with. I have a great chair that I don’t notice. It’s very comfortable. I use a Herman Miller Aeron chair, you know, they’ve been around together forever. They’re kind of the cliche, chair, but like the great, there’s a reason why they’re there as popular as they are. And I also have a sit-stand desk so that I can switch between sitting and standing throughout the day. And that sort of helps me focus. And I, I’m going to add a fourth one, just because I’m good at headphones, being able to hear well and have other people hear me well, through a good microphone is important, and just being able to close out the world and listen to some good music. While I’m working is important. Yeah.


Pushpak :

Message for Engineering leaders  


Awesome. So is there any message that you have for all engineering leaders all over the globe about managing teams and managing their work? Is there any message? Yeah,




That’s a good question. I think I’m just gonna repeat what I’ve already said. But like, you know, you pick the two things, pick one or two things that are important to you for, you know, supporting your team and the business. In my case, I’ve just, you know, I’ve decided that it’s customers and the team. And if I’m focused on making, delivering value to the customer, and value to the members of my team, then I’m doing my job well, and everything else will just follow, like, we will get more customers, our revenue will go up, we will be a more successful business. Like, it’s all I believe, strongly, it comes back to those two things. To find your focus, you know, push hard on those and lean into vulnerability, because I think it is the most powerful tool for building trust on a team and allowing everybody to just move forward without the friction of or I guess, I would say, without that relational friction becomes when you have a lack of trust.




Yeah, I think trust is like the most important thing which comes like, you know, when, you know, working remotely, because India, like, it was remote work wasn’t you know, like, nobody was working remotely and like, people don’t believe like, you know, trust each other. So there was some, you might have heard about it that this monitoring software, so like, some companies started using that and like, you know, toxic culture was happening because of this. So people, though, I think trust is really helpful and investing. Quick if Yeah, if we just, if you don’t trust your employer, just like via working with them, then maybe they. So thank you so much, Megan, your insights are really helpful for all of the people who are working remotely and especially for engineering managers. It was reat talking to you. Thank you so much for giving your time.


It was a pleasure.


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