This week we’re excited to share our conversation with Meaghan Williams, the Remote Work Inclusion and Program Manager at Hubspot. We chatted about what remote work looks like at Hubspot, what she does on on a daily basis and what she's learned from working within one of the world’s leading remote first companies.

Hubspot embraced remote work early, and continues to innovate on best practices. They are helping lead the charge in building a large business around a remote first mindset. It was great to dive into what a “remote first mindset” looks like for them, practically speaking. Meaghan is truly at the forefront of what a successful remote first company looks like, and I’m sure we’ll see other large remote companies follow in Hubspot’s footsteps in hiring for a similar positions to Meaghan's. 

This conversation was a wakeup call for us in the sense that leading technology companies are embedding remote work in their DNA. Anyone who is interested in promoting a healthy remote first culture, or is searching for tips and tricks on what to do first in building a successful remote team for companies with limited resources, should pay attention to what Meaghan has to say. We certainly are taking her lessons to heart!

Hubspot is hiring remote workers all the time. If you’re interested, you should check out https://www.hubspot.com/jobs

Meaghan's book she'd force everyone to read: The first Harry Potter book: Harry Potter and the Philosopher's Stone

Make sure to follow Meaghan on Linkedin and make sure to check out hubspot.com and find out how their moving remote work forward!

Thanks for listening!

Matt H.: 00:06 Hello everyone. My name is Matt Hollingsworth and welcome to another episode of The Remote Show where we discuss everything to do with remote work with the people who know it best. Thanks so much for listening. The Remote Show is brought to you by We Work Remotely, the largest community of remote workers in the world. With over 220,000 unique users per month, we Work Remotely is the most effective way to hire.

Matt H.: 00:25 My guest on today's show is Meaghan Williams. Meaghan is the Remote Work and Inclusion Program Manager at HubSpot. Her goal is to help support and scale the remote population by managing the rollout of a global philosophy around remote work at HubSpot. That includes high level company-wide guidelines as well as team-based flexibility based on business needs.

Matt H.: 00:48 Meaghan, thanks so much for being on the podcast, really appreciate it.

Meaghan W.: 00:51 Thanks for having me.

Matt H.: 00:53 So really excited about this one, HubSpot is one of those ones where we've been wanting to talk with somebody from there for so long. Really excited that you're able to spend the time today to talk with us.

Meaghan W.: 01:02 Awesome. I'm excited to be here.

Matt H.: 01:04 So the first question that I have been asking my guest is, what is it that you've done over the past 12 months that you are most proud of?

Meaghan W.: 01:12 Yeah, it's a good question. It's a timely one for me because I took on this role of Remote Work and Inclusion Program Manager at HubSpot in January. So I'm about to hit the one year mark. And I think just taking on a new role at HubSpot and really creating the remote programming at HubSpot has been something that is ever evolving, but something that I am so proud to take on. And I think will be one of the biggest accomplishments of my career as we continue to scale it.

Matt H.: 01:39 Yeah, totally. And that's one, it's a title that I don't think I've actually come across in all of my work here at We Work Remotely. So was that a matter of HubSpot to having that role already or was that something that you sort of fell into because of your experience or how did that role sort of start?

Meaghan W.: 01:55 Yeah, so it is a new role for HubSpot as well. I think as we've scaled the remote population at HubSpot from just a couple in the early years to over 200 today, they realize that in order to really scale and support the population, they needed one person to be the sole individual that is focused on remote. And sort of the DRI on all things remote as they start to think about how to make a remote culture, how to do remote hiring, remote training, et cetera.

Meaghan W.: 02:24 And so the role popped up. I was already working at HubSpot but was also concurrently studying for my MBA, focused on HR and organizational transformation. And so it was kind of just the dream role and the dream moment. In the sense that I had a company, I loved a topic that I really believed in and was doing research on. And an opportunity to combine those two things at once was really incredible.

Matt H.: 02:48 Yeah, totally. It's a really exciting thing to see, especially from a company like HubSpot, which is obviously one of the bigger ones around in this space. And it's interesting to think about what the future could hold for companies in a similar position. And it's probably giving them something to think about. The fact that you and the HubSpot team have this role in place.

Matt H.: 03:05 It seems like such an important role, but it's also not something that I really know what you would do during the day. So what do you find yourself doing most of the time in your role right now?

Meaghan W.: 03:14 Yeah, that's a great question. Every day looks a little bit different as you can imagine. So the setting for one can change up, so I work in the office in the Cambridge headquarters one to two days a week. And then three to four days a week I'm at home. But during those days I work on everything from really high level company guidelines, thinking about what is the process that an individual needs to go through when requesting to move from in the office to remote? And how can we make sure that that process is really clean as automated as possible, but also can give that employee a sense of comfort knowing that changing your role, changing to remote life, perhaps moving states, that's a lot to take on your shoulders. And we want to make that as comfortable as possible.

Meaghan W.: 03:57 So sometimes it's just pure process improvement and workflows that way. And then on the flip side, it's also thinking about the inclusion piece, which is why that's even included in my title. And just thinking about how can we take the feedback from our remote employees and iterate on that and make sure that with everything we do as a company, are we allowing our remote employees not just to perhaps be present and watch a meeting or watch an event happen. But to really engage and feel like they're a larger piece of that HubSpot fabric. To feel like they are as much involved as somebody might be if they were in the office. So sometimes it is more individual level or culture based, but everyday keeps me on my toes, that's for sure.

Matt H.: 04:40 Yeah, for sure. It sounds like too, it's one of those roles where you are able to figure it out as you go along to a certain extent. Is that what you've been finding a little bit? Is that just because there's not really a playbook that you can follow with this sort of thing. Is that kind of one of the pieces that you enjoy about the role?

Meaghan W.: 04:53 Yeah, there's no playbook that is for sure. So we're learning a lot as we go along. I think I do enjoy that in the sense that one of the things I love about remote work is that it is just inherently unique and personal. And so I think even if there were a really standard playbook, the reality is best practices. If you think about something like remote management though, best practices for remote management might differ depend on if there are different time zones involved, the disbursement of the team, is the manager remote as well. And so there's all of these different things that we need to take into consideration and the more that we scale the remote population, the more of these situations come to light.

Meaghan W.: 05:30 And so it's fun to think about. There's always going to be a very standard levers, communication, inclusion, collaboration. But it's fun to think about how we might use each of those levers in each individual situation. And how we can empower our employees to learn about those and be able to start to do that on their own.

Meaghan W.: 05:47 One thing I'll say about just the remote industry I guess I'll call it, is that everybody has been very open, very welcoming with wanting to share ideas. I think we're all trying get to the same goal. And so it's been really incredible, especially as my title even on LinkedIn has changed. The amount of people that have reached out wanting to connect to share their ideas, their best practices has been really incredible. And there's also a lot of really great remote conferences out there where we can all sort of brainstorm with each other, learn from each other's mistakes, as well as what's worked well. So I've been very fortunate to be able to connect with other companies.

Meaghan W.: 06:21 The reality is, again, because remote work is so unique in its individual experiences, we can't make assumptions on what we think is going to work really well and is going to resonate with people. What we have to do is try our best, ask for feedback, did it work, and then do our best to pivot it from there. And so I'm fortunate that our remote community is really great about giving me transparent feedback, actionable feedback. And you know, we have certainly, there've been things that worked really well. There have been things that didn't work so well and we've learned from both.

Matt H.: 06:51 Hmm. That's really interesting. Have you found that there's something that comes to mind when you think about what's surprised you over the past, it sounds like it's been about a year since you've done the role. Was there anything that you didn't expect that you were maybe surprised by since you've taken on the role?

Meaghan W.: 07:06 I think in terms of what surprised me, it's often just how unique each situation can present. So I think when I first started the role, I did have this kind of mindset that here would be the playbook for management, here would be the playbook for training, here would be the playbook for the process of going remote. And the reality is that you can again create as much of a template as humanly possible, but because it is just so personal in its nature, there's only so much you can automate. There always has to be a little bit of a human touch. And so for somebody that really loves operations and could be in an Excel sheet all day. Every now and then, that can be a surprise for me. But I think that's also what makes it so unique and I think our approach there is really important in making sure that we don't lose that human side in any kind of programming we create.

Matt H.: 07:57 Yeah, it's one of the things I think about with remote work and for myself personally where it can end up being where you don't feel like you are the type of person to need that level of human interaction. And all of a sudden when you do realize that you maybe need to get ahead of these things when it comes to things like isolation and just human communication and connection in general. You find that you're kind of having to dig yourself out of a hole to get back to maybe a starting point of comfort level where you're working. Well, at least that was my experience.

Matt H.: 08:24 Do you find that you have to do anything preemptive, I suppose, in the sense that you're getting people involved before the issues of remote work start to present themselves when it comes to things like isolation and feeling now part of a team?
Meaghan W.: 08:38 Yeah, absolutely. So we've got some things that are just set up on, you know, more of the community level. So for example, to combat the isolation and loneliness factor, we've got a Slack room dedicated to all of our remote employees. We host a weekly water cooler, we just had one today, over zoom where it's just, you know, a drop in stop by say hi type of conversation.

Meaghan W.: 08:59 We have monthly mixers where our remote employees get randomly matched with each other to maybe have a coffee chat over zoom. So some of those things we know will already be there and we let them know before they go remote that they can engage in those practices if they want to and not for everyone.

Meaghan W.: 09:14 But another way that we think about it, again on that more personal level is we have what's called a setting expectations guide. What it is, is it's a pretty lengthy document to be fair created by our HRBP team, myself and our management and leadership team.

Meaghan W.: 09:29 And what it does is it walks through remote employee and their manager through a conversation to address all of the things you just mentioned, right? How will I engage with the team? How will we use our Slack room appropriately? How will I make sure I'm meeting new team members? How often and when will we meet? And it's meant to get those wheels turning so that we have managers and remote employees partnering together. To make sure that they're thinking ahead on those things.

Meaghan W.: 09:54 But we also encourage them a month in, three months in, six months in, talk about it, give feedback. If it's not working, make sure that you're pivoting as needed. Because I think that isolation and loneliness especially can definitely be a roadblock for people, particularly if they came from the office.

Matt H.: 10:10 I think it's something that you need to solve when you think that you're one of those people that's okay with being alone a lot. And you're okay with the fact that you don't need to be seeing people on very often and then all of a sudden you realize that maybe you do need that and you need to be a little bit more intentional and get out there and talk to your coworkers or talk to somebody else or what have you.

Matt H.: 10:29 So I guess my point is that it requires, I think, the remote worker to learn and know about them themselves and the way that they work. In order to be successful in a remote role. Is that something that you sort of talk about or think about or encourage people to like have that level of self reflection when it comes to the individual and how they work? And how do you approach that?

Meaghan W.: 10:47 Absolutely. Yeah. I think the reality is remote work isn't for everyone, right? There are people that love to be in the office every day and that's where they get their energy and that's where they work best. And I think to your point, there's a lot of people that might like alone time, but they don't necessarily like working alone and they're very different things. And so I think one way that we encourage people to think about that is because we are a flexible company before going remote, if possible, you know, work from home a couple of days. Work from home for two weeks if you want and get a sense of is this the right choice for you? It's not correct for everyone. But I think that if you can start to be really honest with yourself about are you going to be effective, happy and successful in this role while remote and while on your own. It's something that you really need to experience in order to be able to answer that question.

Matt H.: 11:36 Yeah. So how do you approach people who haven't necessarily worked remotely or maybe you don't hire people that haven't worked remotely already? And if you haven't then I would be curious to hear how you approach that decision and if not, and how you bring somebody on to have that sort of level of testing? Like if you bring somebody on and it's specifically for remote role, if that doesn't work out, do you have other options for them in case it's not a successful work environment for them?

Meaghan W.: 12:01 Yeah, so it depends on the role. I think in terms of hiring, of course ideal hire is somebody that has remote experience and knows that they work well in that environment. But I think we can also start to glean whether or not they'll be effective from other examples. So how have they been in a globally dispersed team where maybe they were in an office but they still had to communicate asynchronously through online channels or through Google Docs, through Slack, et cetera. And so that's some of the things that we look for if there isn't pure remote experience. We start to think about how else have you been able to demonstrate working independently or perhaps collaborating across time zones and across channels.

Meaghan W.: 12:40 So that's more on sort of the hiring end. And then you know, if we have a hire who it turns out they get into a remote role and they're not happy in that role. We certainly work with them to try and figure out what is it about this role that's not working and what levers can we change? Based on where you're living, right. And what your situation is to make that situation work well for you. But we try to make it as clear as possible upon hire, what the experience is going to be like so we don't have those surprises.

Matt H.: 13:08 Yeah. It's one of those things and there's no one right answer for it, but I'd say it's an important one for people to think about, I think.

Meaghan W.: 13:10 Absolutely.

Matt H.: 13:12 So with your role, because it's so specific to remote work and so specific to the culture piece and also the inclusion in there as well. How do you think about your own success in your own role and what does that look like to you? So if you were to look in six months from now and think this was a successful month, what would that be and how do you measure that?

Meaghan W.: 13:31 Yeah, so in terms of my role, there are definitely metrics that all look at, right? There's hiring rates, there's employee net promoter scores, there is attrition rates, performance data, survey responses, and those will be the metrics that I lean on to gauge whether or not we're moving in the right direction. But at the same time, I think to be fair, success in this role is ultimately just going to be more nuanced, especially in that inclusion piece.

Meaghan W.: 13:54 So one of my overarching goals and something that I'm constantly pushing myself on is really trying to ensure that remote work is ingrained in our culture as opposed to running alongside or running separately from it. I want it to be something that people naturally think about on their own without having to create a separate plan for remote employees. And I think we're getting better and better about that every single day. But those are some of the pieces that I think we'll be a little bit harder to measure six months from now.

Matt H.: 14:22 Yeah, for sure. You mentioned there a awhile ago that you wanted remote work to be part of your culture. So culture is obviously one of those big topics I think a lot of people have to think about these days. It's one of those things where I think it's kind of buzz wordy in the sense that nobody really, again has the right answer here for things like culture and how to build a successful culture. For you and for HubSpot, what does that mean? Like what does having remote work part of the culture mean exactly? And how do you think about just building a culture that people want to be a part of? Is that sort of within your job description and if so, how would you approach something like that?

Meaghan W.: 14:54 Yeah, and so I think you're thinking right to one of our biggest challenges in this role and with remote community in general, which is ensuring that what we can promise in the office, which is this amazing and dynamic place to work, is also what we deliver to remote employees. And I think one of the challenges in the context of remote is that we have to remove the aspect of the physical setting that we're in.

Meaghan W.: 15:16 So, yes, our offices are incredible and we have all of these great things around us. But for me, what I think about is that culture is more than just stuff. It is more than just the setting that you're working in. And for me it's more about the feeling, right? It's that feeling that I can use my voice, that I can stand up for myself, that I can connect with everyone up to the C levels comfortably. And that I can freely engage and have my ideas heard and pivot my career based on those experiences.

Meaghan W.: 15:46 And so I think there's still challenges there, right? With the remote community in the sense that being able to create those same networking and collaborative, engaging experiences is a little bit hard when people are dispersed throughout six countries. But that's really what I think about when I think about building the remote culture is making sure that they feel just as empowered and just as important as a Hubspotter who might be in the office because they are. And so it's just about creating that experience and helping them to really believe in that, but also create the channels for them to continue to engage that way.

Matt H.: 16:22 So with that, having your voice heard piece, is it something that's shifted for you in the sense that you have different ways of approaching it? Like how has that sort of piece of your job evolved? I suppose, and I guess maybe we can go back from previously when you weren't working in this role, but just in general with HubSpot. As you've grown, I would love to hear about how sort of remote work and how it's approached has shifted both for you and for the part of the company that you 
can speak for at least.

Meaghan W.: 16:47 Yeah, so I think in terms of the ways that remote work has shifted at HubSpot, I think 10 years ago we had a handful of remote employees, right? But I think it happened organically. I think it evolved organically and so as that was the case as there were smaller groups of people, I think it was very much just sort of figuring out one to one how things worked. There wasn't necessarily any processes in place. We weren't thinking as a company about the remote population.

Meaghan W.: 17:15 I think in this role and with the creation of this role, what we're thinking about is this is basically an office or a population of their own. And so how do we make sure that they are able to network accordingly, that we have the technology in place for them to communicate with each other. Whether that is over a video call, over Slack, over Google Docs. We want to make sure that that communication can happen really, really easily.

Meaghan W.: 17:41 And we also want to [inaudible 00:17:42] the in-office folks to think about it in that format. So if everybody's on East coast time, but have one remote employee on Pacific time, let's hold those conversations that might happen via Slack at 9:00 AM Eastern time until later in the day. When we know that our Pacific time employee is going to be online. So sometimes there's this little things that we can think about from the office to make that-
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Meaghan W.: 18:03 Sometimes there's just little things that we can think about from the office to make that a more collaborative experience. I think that shift in mindset, it's everybody's responsibility to support remote employees, is really where we've made a huge change, and I think it's shown a big impact for the remote population.

Matt H.: 18:16 Mm-hmm (affirmative) yeah. So you have offices as well as a large remote workforce. Having people in the office as well as having a remote section of your organization. What are the nuances and difficulties that that presents as opposed to having a fully remote and distributed team? And it's one of the questions I hear a lot actually is if you were to approach a company or if you were to approach either taking a company remote or starting your own company, what would be the ideal situation and how would you approach the culture piece differently if you had a semi-distributed team versus a fully distributed team? How do you think about that as a unique challenge that you need to approach and try to resolve? And how is that making it more difficult or easier potentially for you as a company to include a lot of the remote workers that you have?

Meaghan W.: 19:05 Yeah, so I think for all remote companies, the benefit there is that everybody is what we call like on equal footing, right? Everybody is meeting each other over Zoom, everybody is working from home, there is no in-office majority if you will. And so I think in some cases with regard to culture and perhaps collaboration that can be easier from the start. I think for me, HubSpot is obviously what we call a hybrid company, and we have both in-office as well as remote. And then we've got some folks in the middle like myself that work from home four days a week but are in the office one to two days a week. And so I think the benefit there is that as a company we're able to solve for all types of employees, right? People that really want to be in the office and feed off of that energy and work effectively there.

Meaghan W.: 19:50 But we can also work with remote employees who perhaps don't live near one of our headquarters or perhaps just prefer to work remotely full time. So I think there's a benefit in the hybrid model. But in terms of how the hybrid model adds extra challenges, I think one of the biggest places that I see in hybrid companies is that natural instinct within the office to perhaps turn to somebody to your right and just start an organic conversation that then starts to create a larger conversation amongst your team. It's really easy for a remote person, especially if they're the only remote person to be left out of that conversation.

Meaghan W.: 20:28 I think that's where, again, it's so important to, as a company, have that mindset of remote first and making sure that it's not to say you can't have a quick off the cuff conversation, but if we're going to talk as a team, let's spin up a quick at Zoom, right? Let's look the room behind us and make sure that we can get the really valuable thoughts of the remote employee who is also on the team and likely has incredible things to contribute based on that diverse perspective. So I think it's really just to shift in the mindset and it's making sure that it's not just on the employee to create that shift.

Matt H.: 21:01 Right. Yeah, it's interesting the approach of mode first. For HubSpot, you're such a large team now so that you kind of have to approach it in that way where it's not going to be successful if it's just a secondary component of your workforce. It's such a big part of your company now and probably has to be addressed in a real meaningful way, which it does. It sounds like that's your job. It's cool to be able to pick your brain on it, and I'm curious to hear about how you consider your job progresses from here and like do you see companies of your size with remote employees going in similar route and having somebody like you on the team?

Matt H.: 21:32 And I guess it's probably a difficult question to answer and be reflected in this way, but how important is something like your role to a team of such a large amount of people that are semi-distributed and having such a real impact on the remote work world? I'd be curious to hear your thoughts and where your role goes and maybe your team goes over the next maybe year or into the future, if you can answer that.

Meaghan W.: 21:57 Yeah, I think that the value of a role like this is that because remote employees just like in-office employees, there's so many different things that they experience and touch, whether it be benefits and payroll and career growth and training and meetings. And so I think the value of having a role like mine in a company is that you have that one person. It's not just thinking about remote training or just thinking about remote benefits, but it's thinking about how do all of those things intersect and how can we properly set expectations for remote employees for all of the things that they're going to experience and can do as a remote employee or can think about as a remote employee.

Meaghan W.: 22:36 I think with my role as the company evolves, as the population scales, I think I'll continue to do that, but I think I'll continue to expand what I'm thinking about. I think we're becoming more and more focused on our remote population, which means more and more teams, more and more managers, more and more trainings. Also thinking about how are we going to make this more remote friendly. And so I think it will continue to expand in that effort. Beyond that, I'm not sure what the future holds.

Matt H.: 23:04 Yeah. Not an easy question to answer. Yeah, I was just maybe reaching that a little bit. So with a smaller team now, somebody who has the culture and maybe it's a people OPS role or maybe it's just an HR role or whatever that looks like for a smaller company that doesn't have the luxury of maybe hiring for a role similar to yours. If you were that person or if you're giving that person advice as to how to best allow your own employees to feel more part of the team and approach that sort of all of the things we've been talking about when it comes to the downsides of remote work and maybe if you can give some advice to that person as to how to have a successful remote team when that's not necessarily their entire role. Like where would you focus first if you were that person?

Meaghan W.: 23:45 Yeah, so if that wasn't their entire role, I think what I would think about is two fold. One is ask your remote employees if you have them. There's so much value in just learning from experience and being really clear about the fact that you're here to help. And so if there's pain points, if there are things that are challenging, you need to know about them because you can't fix what you don't know about. In my experience, remote employees tend to be very grateful. They tend to be less likely to raise their hand and say, "Hey, I have a problem with this." And so sometimes you do need to pull it out of that a little bit more because they're so thankful to be able to work remotely, but they tend not to want to complain. So I think it's setting the stage that this is for us to improve as a company. This is for us to better support remote employees on the whole and so their experience and their feedback is super valuable.

Matt H.: 24:36 Mm-hmm (affirmative) yeah. I also think going off of what you were just saying there, when it comes to talking about remote work, and some of the the difficulties that arise from it. I think it's partly, at least for me, it was more difficult to bring up the things like isolation and the lack of connection maybe with my employees or my company because it doesn't feel like maybe that kind of conversation you would normally have with your managers or your executive team. Like for somebody who hasn't worked remotely before, that's shifting to a remote role, I think that there's a certain level of being unsure of that as something to bring up at all and it's not this is just a personal problem and it's not the company's issue to bring up.

Matt H.: 25:17 I hope that through this podcast and the conversations we've been having and just that remote community that we've shed some light on the fact that it is something that should be talked about more and if you're feeling that way it should be addressed. How do you approach that when it comes to bringing somebody else on? And you mentioned a few things there with just checking in and things like that, but is there anything that you would recommend for a smaller company when it comes to that piece? Is it just a matter of asking? Is it surveys? How would you approach that?

Meaghan W.: 25:44 Yeah, so I think it depends on how small the company is, right? If it's so small that you can actually connect with people who are already remote and get a great sample size that way, that's what I would recommend. I think that's where to your point, people are less likely to put in a survey. I'm feeling lonely, so I think that if you can have those conversations and if you can show that you really care about those aspects, they're more likely to talk about it. If you do have a larger company, and it's just not scalable, especially if it's not your only role to talk to everyone, a survey is a great way to do it. I would say ask really specific questions about what are the pain points? What are the challenges? If there's one thing that you could change, what would it be?

Meaghan W.: 26:24 But I think the other thing is my push to people as often try working on really yourself, even if it's not for you. I do think that there is value in having your entire team go remote for a week, or you yourself going remote for a week to understand what does that feel like, what did you not expect that ended up happening and how can you do your part in the office to solve for that? So I think there's value in seeing it from someone else's perspective, and then putting yourself right in their shoes if we can.

Matt H.: 26:58 Mm-hmm (affirmative) it's always fun to think about... We talk about remote work all the time and obviously that's a big part of our community and what we want to accomplish is spreading the word and having these conversations. But it's interesting to think about for us and for me like being reflective of, "Okay, well how does this actually affect me? What are my personal challenges when it comes to remote work? How is this actually in reality effecting the way that I work? And sometimes there is a bit of a disconnect. To your point, I think it's really important for people who are especially who are in a role where they're setting up processes or they're having these conversations and they're not necessarily working really themselves to really step in those shoes of the people that they're trying to empathize with. Because otherwise it's really difficult to get a sense for what the challenges are for a remote worker if you haven't done so yourself.

Meaghan W.: 27:36 Absolutely.

Matt H.: 27:36 I'm taking a step back a little bit and I want to ask you some specific to you questions. With HubSpot, where you working remotely before you stepped into this role?

Meaghan W.: 27:45 A little bit. I was a Customer Success Manager for three years of HubSpot before starting this role and with that role you're on the phone with customers most of your day. And so for me it was a lot easier for me to be focused on the phone with customers when I was at home. So I was not formally a remote employee where I was outside of the office 100% but I did work from home typically two to three days a week and I loved it.

Matt H.: 28:10 Nice. Well, what's your number one challenge when it comes to working remotely? Just on a personal level, what's your biggest challenge when it comes to working remotely?

Meaghan W.: 28:18 For me, I think working remotely, you know the days that I do it because it is so easy for me to focus and because I can get so ingrained in my work 
when I'm working remotely, it's also hard for me to not necessarily separate, I do have a separate room, but it's hard for me sometimes to say, "Okay, it's five o'clock and I'm going to shut my laptop at this point." I think conveniently for me, my team is very supportive of that. There's no expectation, there's no one slacking me after business hours and so the environment is there for me. But for me personally, it's often hard for me to say I've done enough today, particularly in a role where there's always going to be work to do in this role. And so it's hard to say that's enough for today. And I think that's probably more of a personal issue than a remote work issue, but I think in the office there is that benefit of traffic piling up that encourages me to get outside the office. When I'm working remotely, there's none of those signals to help.

Matt H.: 29:19 Right. And that's actually a good segue I think to talk about, one of the things actually was brought up recently with a colleague. Just the idea of setting expectations for being online if you are working remotely and in the event that you are, especially if you're a manager, and you're contacting somebody outside of working hours, how did that affect the dynamic of your work environment? Whereas most people feel like if they get a message from their direct superior, or an executive in the company after work hours, when you're working remotely and if you're a fully distributed team, especially that there is some level of pull towards answering email or answering that message just because the dynamic is such where you feel like you want to make sure that people are aware that you're a hard worker and that sort of thing.

Matt H.: 30:01 I guess this is a roundabout way of asking, is there anything that you do in terms of process for making sure that people have that time to shut off at the end of the day and making sure that people have a life outside of their work and have that level of balance that I think is so important?
Meaghan W.: 30:16 Absolutely. We believe really strongly in this. This is something that just as a company I think we are really serious about. And so there's a couple things that we do to help with this, particularly knowing that our remote employees are all over the world. Nevermind, throughout different times zones, and so what you can't say to an employee in California is don't talk to your manager after their business hours because they're still in their business hours. So the ways in which that we can solve for that, we look at things like Google Calendar has a function where it will tell you if you're trying to book time outside of someone's business hours. So that can help us ensure that even though you might be booking a meeting again at 9:00 AM Eastern Time, that's 6:00 AM Pacific Time. We don't need that person necessarily to sign on.

Meaghan W.: 31:02 But you might not think about that if you don't realize that person is remote. In addition, thinking about things like Slack snoozing, so you can snooze your notifications, minor snooze to beginning at 5:30 at night, which means that if there are remote employees, again in different time zones that want to shoot me a quick Slack while they're still working and in their working hours, by all means, they can do that and feel comfortable because it's not going to disrupt me. I'm not going to get that notification until the morning. They also on the flip side know that I'm not going to respond because they'll get that message that says Megan's notifications are sneezed. So it's a tough thing to navigate because the other thing that we do want to think about is, for me, I work the best at 7:00 AM. It's just when I'm the sharpest.

Meaghan W.: 31:45 So does that mean that I can send out emails or I can't send out Slacks at those times? No. But what I can do is be really thoughtful about that. On the flip side, if you have parents that maybe you want to go home at three o'clock to get their kids from school, have dinner with them and put them to bed, sign back on at 10 o'clock at night to get some work done, we want to support that too. And so really at the end of the day, what we're constantly thinking about is how can you get your best work done when you have the time and the energy to do so? But how can you also be thoughtful about the environment that you're creating and make sure that there's always that common understanding that just because you're sending something out doesn't mean there has to be a response back within that same hour. And I think as a company we've done a really good job of that.

Matt H.: 32:31 Yeah, it's interesting and it sounds like you have definitely created a thoughtful response and a way of thinking about that because I don't have an opinion in one way or the other, but I think it is important to protect some of the areas that remote work is so good for, which I think is allowing people the opportunity to work whenever it's convenient and whenever they work the best. So like you said, somebody who has other things on their plate that if they log on at 10 o'clock at night and they're working, it doesn't mean that they can't send out those messages. Like you said, I think it's important for the culture to be such that there is no expectation of response from the other person who doesn't have those time frames in those hours. And to make it very clear and obvious that it's not incentivized to show that you're just online to be a good worker and to be somebody who's effective.

Matt H.: 33:19 Do you see that shift moving in that direction? Do you think the culture of remote work is getting to the point where we're not measuring online status as a way of being productive? Is that something you think about?
Meaghan W.: 33:29 It is something I think about and I think especially because oftentimes you can get more work done in the same time frame as a remote worker and so is there value? If you've finished your work for the day, if you're in a role where you have a very clear agenda for the day and you're done, what is the value for you sitting on the computer for an additional hour if there isn't any? And on the flip side, I think the benefit to getting away from that thinking as an industry is that you don't get remote employees trying to prove that they're working just by being online or signing on late at night. I think there's a trust that we need to extend to remote employees that if we hired them to do great work, which we do, that we trust them to do that work wherever or whenever that's going to happen.

Meaghan W.: 34:13 I think if we can create that environment and really empower them to feel like we trust them because we do, they are also less inclined to feel like they need to be online and be present in every waking moment. Because that's not a great way to live. It's not scalable. I think it's really easy to burn out that way. So I hope that the industry does move away from that.

Matt H.: 34:34 It's an important conversation to have for sure, and I've thought about this before and I don't always if it's because I just surround myself with the right kind of companies, the right kind of people and that's the way that they think or if that's truly the way that the remote work community is going as a whole. I don't know. I think it might be a little bit of both, but I hope that it's moving in that direction because I think you're right. I think it's the most effective way for people to be effective in their work and also just have a good work life balance as well.

Meaghan W.: 34:56 Absolutely. I think that's really important for remote workers who their working life happens in the exact same space most times. So being able to really double down on work life balance and support that idea I think is really important as a company. And again, thankfully for us we believe so strongly in that just as a company on the whole that it wasn't a big shift for us to just think about that in the context of the remote workforce.

Matt H.: 35:20 Yeah, no for sure. So one of the things that I have been thinking about more is what managing people looks like and feels like on a remote team. So as part of your role, do you talk to managers quite often as just in terms of how things are working and how best to optimize for remote workers? And maybe this is just something that's part of HubSpot in general, so that it's not something that you need to prove out or convince people out, but I'm curious to hear about how you approach your position when it comes to management within the teams in HubSpot. Do you have remote specific processes that you talk with your managers about, or how do you approach that?

Meaghan W.: 36:00 Yeah, overall at HubSpot, we do have a management leadership team that...

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Meaghan W.: 36:03 Yeah. Overall at HubSpot we do have a management leadership team that is constantly thinking about how they can enable managers ... apologize for the dog barking in the background. Part of remote life. But in terms of my role and how I think about my engagement with managers and how I can support them, what I think about a lot, and honestly some of the conversations I love most are managers who are about to manage their first remote employee and they're thinking about I know what to do in the office, I know how to be a good manager with my team when they're here, I want to make sure I can do that just as well when they're outside the office.

Meaghan W.: 36:36 That can be a little bit harder, and so often the advice that I'm giving them is in terms of what you're looking for out of your employees, it should still be results focused, whether they're in or out of the office. It doesn't matter how long they're sitting at their desk or where their desk is placed. It's what are you looking for in terms of the work that they're producing? As long as you're holding them to those same standards, that's going to be one of the most important pieces.

Meaghan W.: 37:03 But I also think that on the flip side, that more personal management, there are aspects that need to change. I think that you do need to be much more intentional with your communication. I think that you need to be an advocate of your remote worker and I think that you need to make your management style a little bit more personalized to figure out, with earlier conversation, do they prefer to have Zoom video calls in the morning to check in? Would they like to have some kind of additional meeting more than perhaps a weekly meeting because they won't see you as often? What's going to make it comfortable for them to make sure that they get what they need from you and that you can give them that kind of coaching that they need even though they're going to be in a different location.

Meaghan W.: 37:46 A lot of times, again, because it is so unique, that conversation looks a little bit different every time, but I think what I always push at the end of the day is that the results that you're looking for should be the same. The way in which you might coach them and manage them as a person? That might change a little bit, but you need to really communicate with your remote employee to figure out what that's going to look like.

Matt H.: 38:08 Yeah, I'm glad that you mentioned that because it's definitely something that I think people need to think about. Managing a team in general and then shifting that to a remote team, it can be a challenge, and I think that there's things, especially the things that you mentioned there where you have to think about on a personal level, how does this change the dynamic? What do you need to do to make sure that you are setting expectations clear enough so that everybody's on the same page enough so that they can go and enjoy the benefits of remote work and work effectively in that role, but also not forget, because I think it is easy to forget about the more personal component of it, which is because you're working remotely and don't see that person, if maybe it's more easy, especially if you're managing a larger team, it's easier to forget about some of the personal components of what it takes to be a good manager.

Matt H.: 38:53 I think that can come back to bite you and you're having to again dig yourself out of a hole that you may not have had to deal with had it not been that you were more deliberate and focused on that piece of it. I'm glad that you brought that up.

Meaghan W.: 39:05 Oftentimes what I plan to, too, is sometimes it is really just the tiniest little things that setting expectations can make a world of difference. By way of example, when I first started this role I talked to a remote employee and she said, "One of the things that stressed me out when I first went remote from the office was that I wanted to walk my dog around 11:00 a.m.," and probably going to be a 45 minute to an hour long walk. Not a big deal. At HubSpot, we're very flexible. If you want to go to the gym mid-day, go for it and no one asks a question, but as a remote employee, she was concerned that leaving her desk for an hour during the workday, being off of Slack, et cetera, was going to be concerning and that people were going to think that she didn't take her job seriously.

Meaghan W.: 39:47 And so it's little things like that where do you want to know if I'm going to be away from my desk for a couple hours or how are we expecting to engage with each other throughout the day? I think it's less about the answers and more about having the conversation so that it's not left to the remote employee to stress out over am I allowed to do this, will they think X, Y, and Z if I go out from my desk for a couple hours? I think just having those conversations even about the nitty gritty little things, setting those expectations early and often does a world of good for just re-establishing that trust and making it a really safe environment to work in.

Matt H.: 40:25 Yeah. No, I think you're right. Do you find that there is kind of a align between checking in often with that sort of thing? What to you is the difference between over-communicating, because I hear that a lot is that you should default to over-communication. Over-communicating and maybe to the extent where it feels like almost micromanaging, is that something you think about at all? The difference between those two things? Because I think on one side I hear that over-communication is a really good thing for remote teams and something that they should default to, especially in the early days when maybe they don't all have the experience, but I think that can kind of bleed into a little bit of micromanaging and constantly having check-ins with your team on Slack or whatever your communication tool is. That could be too much and maybe that kind of is in the realm of micromanagement. Is that a problem that you've had to address?

Meaghan W.: 41:10 It's something I think about all the time because I do think you're right. I think it's a really fine line and I think that's where it's really important to understand what's valuable to the employee, one, but also what is the reason behind any of those check-ins or what is the reason behind any of these setups, and so I think it's really important to constantly ask that question of do you just want to know because you want to know? What does that message convey to you versus something like if it's helpful for your new remote employee to know that they have a half hour every day where they can just ask you these sort of not necessarily urgent questions but that they don't have to worry about interrupting you during meetings and they have that time if they need it.

Meaghan W.: 41:55 If that's available to them, that might look a little bit micromanage-y to start, but if it's valuable for them and there's a purpose to having that set up, 
that, I think, is valuable, but I think again, it just looks different for every relationship and every role really. I think asking yourself the question of whether or not this is micromanaging and whether or not this serves a purpose to either one of us, that is what's going to be the most helpful tool in combating just pure micromanagement versus leaning on over-communication as a tool to build some psychological safety, build trust, and also build an environment where that remote employee feels supported.

Matt H.: 42:35 Mm-hmm (affirmative), yeah. It's definitely a fine line and it takes, I think a real honesty on both sides of that coin to find the right balance. I hope that there's hope people out there are listening to this and maybe will, this will lead to a conversation between them and their managers that will help both sides see better workers, so that's the goal. I think your advice for this one has definitely been a good one.

Matt H.: 42:55 I do want to be cognizant of your time, Megan. You've been so kind to be on the show with us. I do have some more closing questions here for you, if that's okay. The first one here is, so if you weren't involved in what you do now and maybe just technology in general and working in a company like HubSpot, what do you think you would be doing?

Meaghan W.: 43:14 I think ... I started my career in the nonprofit space and I'm still really passionate about the nonprofit space and particularly mental health, so I think what I'd be doing is something related to mental health support initiatives. I think I'd hopefully be working remotely, but outside of the current role I do, which I love, I think that's another place where I could really feed a passion.

Matt H.: 43:35 That probably lends itself well to your role, that interest in the mental health component of your job. It's such an important one. I think it's important for people to think about and talk about because there are real, I don't want to say consequences because I think that's a negative connotation, but there are real considerations when it comes to remote work and mental health, and I think it's really important conversation to have. This is an important one for you. What initiatives are within HubSpot that are approaching the conversation of mental health within their employees? Is that something that's important to you, I'm sure?

Meaghan W.: 44:02 Yeah, absolutely. I think as a company something that I've always been impressed with and something that attracted me to HubSpot was not just how open they were as a company to being honest and transparent and supportive of mental health, but also how many resources there were around that topic. If you follow HubSpot Life on Instagram, oftentimes it's an employee takeover. And it's not uncommon to see an employee and just very transparently saying "Today I went to therapy." It's one of those things where we want employees to feel really empowered to support their mental health, whether that is through therapy, whether that is through yoga, whether that is through meditation. We have a meditation room. We have yoga at the company. We've tried remote yoga, which was really interesting as you can imagine it, but we have a whole health week every year where we focus on not just physical health, but mental health and overall wellbeing as well.

Meaghan W.: 44:57 So I think as a company we've done a really great job of being really open about it, but also walking the walk on it and making sure that it's a comfortable place to work and also feel like you can support your mental health, and so in the context of remote, I think that has been essential in allowing our remote employees again to just be able to create that work-life balance even though I think it's really hard to do that sometimes at home. But I think because we put such a value on it, we've created a better environment for it.

Matt H.: 45:26 What you mentioned there with just how open people are with either therapy or just approaching mental health in their personal experiences, I think it ... I think people underestimate what a top-down approach to being transparent about their mental health can do for a company. If you see your either executive team or CEO or manager and that are being open, and of course it's a personal thing, so you don't want to force that upon anybody, but I think is a really powerful, positive tool that people can use is just being transparent about the potential struggles of their personal experience and having that be okay to talk about. I think it's a really positive, powerful tool.

Meaghan W.: 46:02 Yeah, and I would even add to that that I think for the remote population, on top of just being transparent about mental health and struggles there, I think just thinking about struggles at work or even failures at work, I think, is really important to share with your remote community employees because it's very easy to think that everyone in the office is living their best life and doing the best job all the time, and the reality is we know that everyone makes mistakes. One push that I always have for managers is share your failures and create an environment where your team can talk about not just where did they mess up, but what did they learn to make sure that it's always comfortable to come to your manager as a remote employee and say, "Hey, I messed up today and here's what that looked like" and not feel like that's going to be the end of the world, because that can also be really debilitating, so creating that environment of transparency is huge there.

Matt H.: 46:57 Yeah. No, and I think if you do feel like you can't go to your manager as a remote employee when you made a mistake, that can just compound that level of isolation that you feel because you don't feel like you can talk to anybody else, and if you're alone, that really, really hard one to have to deal with, especially if you don't feel comfortable enough to talk with your team about it.

Meaghan W.: 47:13 Yeah, absolutely.

Matt H.: 47:15 The second closing question here is if you could force everyone to read one book, what would it be and why?

Meaghan W.: 47:20 This is like the hardest question I think you've asked me on this entire podcast. Reading for me, it's one of my favorite pastimes, and so I read a lot, but at the same time, I also think that a book is most powerful when something about that story resonates with you in the moment when you're reading it. I think that's when you have that moment where you absolutely just fall in love with a book, and so on that note, it's kind of hard for me to force one book on everyone at once, but I think if I had to, I'd recommend everyone give the first Harry Potter a try because if you actually give the first one a try, I believe you'll be hooked enough to read the rest, and I'm also fairly confident that in those seven books there's something for everyone to love. There's something for everyone to learn.

Matt H.: 48:06 Yeah, that's so interesting you mentioned Harry Potter, and it somehow got leaked that because I did an AMA for the last episode, so I answered questions from the audience, and it leaked from our marketer Justine, who decided to put this out into the ether and into the world that I wasn't the biggest Harry Potter fan in the world. Before I go any further, it's not like I don't like Harry Potter. I think that they're great and I think this is again, one of those reminders that I should probably go read them myself. I never actually read the books so that's my first problem.

Matt H.: 48:38 And I think the second problem was, is that I have such Harry Potter fans in my family, but it's some level of I'm not going to do that because everybody else is doing it kind of thing, so I do need to, and again, this is a good reminder and I'm glad you brought it up because I want to clear the air about that, first of all, and second of all, I should probably go back and read them from the beginning because otherwise I can't pass any judgment and I'll finally give into my sister's constant reminders that I need to read all of them. So I will definitely put that on my list. I appreciate you that.

Meaghan W.: 49:07 You got to give it a chance.

Matt H.: 49:08 I know I do. I do. You're right. All right. Okay. The last question here before I let you go, Megan, is what is the best advice you've ever been given?

Meaghan W.: 49:17 It's a simple piece of advice, but a really powerful one for me. Our CPO Katie Burke uses this phrase all the time, which is assume positive intent. It's such a simple idea, but I think on a high level it reminds us to just give other people the benefit of the doubt and make the assumption that even if it doesn't feel that way, they are in fact trying their best. I try to remember that when I'm cut off in traffic. I've got to remember that when my dog eats my shoes. I try to remember that especially, I think in the context of remote work where we're often communicating asynchronously, we're communicating just in writing, and I think a lot of emotion, a lot of tone can get lost in those channels, and so I think just assuming positive intent from the start can create a much better communication channel.

Meaghan W.: 50:06 I can help to build trust, especially when you've never met that person, at least in real life, if you will, and you're not able to see that person and see the emotion on their face. That to me has been a really powerful reminder and something that I think back to as much as possible.

Matt H.: 50:22 That's such an important one and you're right, I think it applies so many different parts of life. Just assuming that people's best intentions or the intent behind whatever their action is was, was going to be a positive one and they're trying the rest, because I think that is mostly the case, especially for people who are in your circle. In your work circle, there's the odds of somebody having mal-intent in the business, in HubSpot, or in your life, in your close circles is relatively small, I think, if you're doing it right. If you're surrounding yourself with the right people, I think that very rarely is the case, that people don't have the best intentions and aren't trying their best, so I think it's a really important thing to keep in mind. There is kind of related to that, there's a quote ... this isn't directly related, but it's a quote there. It reminded me of ... it said something like don't ascribe mal-intent to what can more easily ascribed to stupidity.

Meaghan W.: 51:12 That's totally fair.

Matt H.: 51:12 Yeah, and so that's ... another one, too, is that I think that it's more often the case that, especially if somebody has done something not very nice, more often than the case that they didn't know what they're doing in the first place.

Meaghan W.: 51:22 Totally, and I think again that just gets back to failures. We're all here to learn. We're never going to be perfect. But I think if we can believe in each other that we're all trying our best, assuming that positive intent, then we'll be a lot better off for it. It'll be a lot better of an environment to work in as well.

Matt H.: 51:39 No, I totally agree. Well, Megan, I can't thank you enough for being on the show. I think there's a lot to unpack here and we're super happy to have had you on the show and really appreciate it. Before we go, anywhere else that we should be sending people? Any profiles? Obviously we won't be able to go to HubSpot, but anything else that you wanted to point out?

Meaghan W.: 51:55 Yeah, I think let's just say that we are certainly hiring remote employees right now, so for any remote listeners out there that are looking for a great place to work, hubspot.com/jobs is a great place to start, at least in my opinion.

Matt H.: 52:08 Perfect. Yeah, no, we will definitely link to that, and yeah, we're super thankful for you taking the time today, and maybe at some point we can do this again. I have lots of more questions and I'd love to do it again.

Meaghan W.: 52:19 Absolutely. Thanks so much for having me today.

Matt H.: 52:21 All right. Thank you, Megan.

Meaghan W.: 52:22 All right. Take care.

Matt H.: 52:24 Thanks so much again for listening to the show. Be sure to check out weworkremotely.com for the latest remote jobs. If you're looking to hire a remote worker, We Work Remotely is the fastest and easiest way to do so. As always, if you have someone we should talk to, any advice you have, or if you'd like to advertise on the podcast, please reach out to us at [email protected]. That's [email protected]. Thanks so much again for listening, and we'll talk to you next time.