Luis:
Welcome, ladies and gentlemen, to another episode of the DistantJob Podcasts. I am your host Luis, as usual, and we are here to talk about how to build and manage awesome remote teams. With me today is Kieran Flanagan. Kieran is an author, startup advisor and mentor, and the VP of marketing of HubSpot, a marketing and sales software company. Kieran, thank you for being on the show.
Kieran:
Yeah, thanks for having me. Excited to be on.
Luis:
It’s awesome to have you. Obviously I’ve already given my introduction, but tell our listeners a bit more about yourself and what you do.
Kieran:
So I work at a company called HubSpot that’s a marketing and sales and customer success platform. And I’m based in Dublin. The majority of my team or my group, which is about 55 to 70 people, is based in different places in the world. Some based in Dublin, some based in Berlin, I think a couple of people maybe in France, Singapore, and the majority are actually based in the States. And so, yeah, I think that is what… I’m based in, I think I said I’m based in Dublin, Ireland. So pretty a distributed team.
Luis:
So how has it being a distributed team? How has remote work made HubSpot’s business possible or help you make it better?
Kieran:
So there’s a couple of things. I think that remote work’s been a really great initiative for us to both hire and retain people. So I think a lot of people that we have within our company either have wanted to move at times, so they’re not based within our office. And we can keep those people retained working at HubSpot, so they can better manage their work and life and how they want to do that. It also widens the talent pool that we can also hire from. So I think that’s another really great advantage of remote work and that it allows you to hire from a lot of different locations and not just a couple of cities that everyone seems to flock to.
Kieran:
Remote work makes you a lot more streamlined in terms of your communication process. You can’t really rely on just tapping the person beside you on the shoulder and asking them, “Hey, what’s the update on this?” Or, “How are you doing on this?” Trying to get progress reports that way. So you have to streamline your communication and get lot more advanced at that. And I that’s one of the advantages of remote work. And I think that more and more as we progress into the future, people are going to value their time a lot more, and they’re going to want to build their work around how they want to live. And I think for companies who embrace remote work, it just better positions you to be an employer of the future.
Luis:
Well, I agree with that, but then again I’m biased because my business is about recruiting people remotely. So I guess I would say that, but it’s always nice to get some validation from people that are in successful businesses. So I want to tag a bit at the communication thread. Because I was reading a piece that you wrote, it was about marketing because that’s your area of expertise, mine as well. But you talked about something that I identified with, where you said that the big problem for marketing is analytics because on one hand, it allows us to validate what we do, but in the other hand, it gets us focused on the results of analytics. And we tend to only want to do the things that are getting the most results and that doesn’t leave a lot for creativity and experimentation, which could potentially open up highly successful avenues of marketing.
Luis:
Now, I want to twist this a bit into the communication part because I do get that sense that a lot of businesses, especially now we’re in the COVID-19 era and a lot of businesses are doing this for the first time. And I do feel that a lot of businesses are trying to make up for the lack of face-to-face time with documentation and to getting people to measure everything that they’re doing and report everything they do. And I also feel that this is somewhat stifling in terms of creativity, because what I see happening is that a lot of people, by the time they’re done with their documentation and their reporting, they don’t really have the mind space needed for actual creative, innovative work. How do you feel about this dilemma?
Kieran:
I think there’s a balance in everything. And I don’t think this is actually specific to remote work. Documentation is good, in general, to help you better organize people around a mission, better organize people around playbooks that work. So what we try to do in HubSpot is document playbooks and document the things we’re doing, so we can actually describe those things across the rest of the group. We can share those things with people. People can learn from them. We can have a living, breathing document of how we’re optimizing and iterating on those playbooks. So I think some level of document documentation is really good. We also communicate our ideas through memos. So rather than going into a meeting where everyone collaborates together in realtime and tries to riff on ideas and come up with solutions, and it’s a really unstructured way of doing things.
Kieran:
And it also gravitates towards people who are better at communicating in groups, whereas there’s really smart people who don’t prefer to communicate way and prefer to have some time by himself to think through things. So what we try to do is have people document their ideas with a memo, share with a group. We can go back and forth and communicate on that within the doc, and then use those meetings just to decisions on areas that people can’t decide on or agree on. So I think documentation is really good, but the challenge with companies who first start going remote and it’s new to them is they over document, it’s not that they’re over documenting or they’re trying to get people to create too much documentation, it’s that they don’t trust that their teams are actually doing work and they start to micromanage those teams.
Kieran:
And that comes out in probably asking for too much documentation, because they’re just unsure or they do not trust that the work is being done because they can’t see those people in a physical office. And I think that manifest itself through lots of requests to do lots of documentation. So like everything, there’s a balance. I think documentation is great for teams, helps to collaborate, helps to foster great ideas, helps to foster great creativity. But I think if you’re experiencing remote for the first time and your natural reaction to that is to start to micromanage your team, then it’s not really documentation. That’s a problem. It’s the fact that you may not trust your team to do the work that you want them to do because you can’t physically see them.
Luis:
Yeah. That’s definitely a situation that happens a lot. Especially I know some cases of this recently when it comes to sales. A lot of companies, as modern as we’ve become over the past year, there’s a lot of companies, even technology companies, still require on-field sales. And even in my family and people that work in field sales and they feel lost now that they have to basically do sales, but do sales from home, essentially. So I do know that you’ve talked about this in the past. So, and that was actually something that I was cherishing the opportunity to talk with you about, because I don’t get a lot of people talking about sales here in the podcast and how to manage a digital sales team, let’s say. How do you think that the current situation of people having to work from home forcefully is going to affect the world of sales?
Kieran:
I think that’s one of the core shifts we’re seeing within our customer base and within the people who were coming to HubSpot at the moment is there’s a lot of companies struggling with moving their sales team online. And as you said, a lot of companies still have field sales teams, and now they’re trying to operate as a inside sales team. I think that shift is going to, for the most part, like stick and change the way companies think about sales. I suspect that a lot of companies who have field sales teams we’ll see that they do not need to have people knocking on doors and being on the road. For some roles you may need to do that. That kind of personal sense of connection may be really be important. That face-to-face experience may be really important. But for the most part, you can replicate the experience of sales online.
Kieran:
There’s a really good book around this called Digital Body Language that the CEO and founder of Vidyard introduced me to, Michael Litt. And we were talking about this on a recent podcast. And I think the thing that companies need to get really great at is trying to figure out how they can replicate their… Like if you’re a sales person, the thing you’re really great at in person is figuring out cues from body language, so you can read body language. And that’s generally why sales like to be in person with people because they think that’s a real skill and that it is. And for companies moving online, you need to try to figure out how to replicate that strength in terms of noticing digital body language of your prospects. And you can do that through their engagement on your website. You can do that through engagement with your product, if you have a free trial or a freemium tier.
Kieran:
And so there’s ways that you can replicate the offline experience and the skill sets you have to be a great field salesperson with online. And you can also replicate a lot of the personal elements. So we’re really fortunate now that we have things like Zoom or Google Hangouts or Skype, or all these different ways to do video chats, and you can be personal on those calls and you can create connections on those calls and you don’t just need to be in person to create those connections and sell your product and services.
Luis:
Yeah. So want to plant a flag in the in-person body language versus digital body language, because that’s something that I definitely want to come back to. But I want to get a bit deeper into the sales model. So I used to work with a salesperson. He was a very good salesperson and he told me this a lot of times that’s a lot of sales, and he worked in technology so he was dealing with modern companies. But a lot of it was about the after party. When he went to conferences, he was like, “Okay, so maybe I’ll get a few leads or something in the conference, but it really is all about the after part. All about having fun with people in a physical location and getting to know them.” And as people develop those personal connections, they’re more likely to give you to give you their business.
Luis:
And this is something that is really hard to replicate even if you’re not talking about sales. Just in businesses in general, it’s really hard to replicate just for a cultural sense. Here at DistantJob, we try to do online gaming. We try to do Zoom birthday parties and that, it usually works. And we feel that it’s helping us build our culture, but it doesn’t come as naturally as doing the thing in presence, in real life. So how would you solve this dilemma? How do you think that the sales people can build more personal relationships while being stuck at home?
Kieran:
Well, I think there’s two things. Are you asking how they build personal relationships with the people they’re trying to sell to, or build personal relationships with their teammates?
Luis:
Yeah. So I was thinking more about the people they’re trying to sell to. How to create that rapport, that’s an essential part in sales.
Kieran:
Yeah. Well, again, coming back to what I said previously, maybe some jobs do need to be in person. Maybe there are some sectors where you still need to go to the party, or you still need to go drinking with your clients, or you still need to go to the conference and shake hands with people and you can’t replace those things over a Zoom call. And so there’s no thing that’s going to replace the physical interaction you can have with someone. And if the fundamental part of your sales process is having that physical interaction and you can’t sell that in remote work. And I see so many people trying to brainstorm how to solve the water cooler moment, which is the favorite conversation to have about remote work.
Kieran:
And it would be easier if everyone just admitted that you can’t. And that if the water cooler moments are really important to the company and the person, then they shouldn’t work remote. And similar to sales. Let’s just be realistic. You can’t replicate in-person contact over Zoom or over remote. And if that has a fundamental way that you sell and that is a fundamental part of your sales process and how you make your clients happy and how you sell your product or service, then you shouldn’t do it remotely. You should, hopefully, after this all calms down, go back to your office and go back to selling in that way.
Luis:
Yeah. So that’s super interesting point that you made up there, about the water cooler moment. I’ve never heard that point. So I want to explore it a bit. A lot of people, including many guests that I’ve had in this podcast, just assume that the water cooler an important, maybe not vital, but an important part of working at the company. And that you need to find a way to replicate it online. And, as you pointed out, many times many of those efforts feel forced. So what makes you say that the company, it can be equally successful without that water cooler? What are the things that water cooler provides maybe it’s not so essential?
Kieran:
So I’m not saying that they can. I’m saying maybe you are a company that those things are pivotal to how your team work and those water cooler moments where people have organic conversations and personal interaction with them is fundamental part of your company success. And if it is, for the most part, you should probably work within an office. We may as well, just be honest that remote work isn’t for every person or every company. The thing I would say about water cooler moments is everyone uses that jargon to say, “Well, that’s the thing that remote work really misses.” But if you break down what water cooler moments are, you have to really think cautiously or carefully about what people are actually saying. The water cooler moment could be broken into two parts. It’s a physical interaction you have with someone organically within the office.
Kieran:
The other part of that is that you’re building a personal connection with someone and talking about things outside of work. And that’s the two general paths that people describe when they bucket things under the water cooler moment. If your thing is, “Hey, can I build personal connection to my team? Can I make it feel more like a team that aren’t just talking about work all the time, where we’re getting to know each other, where we’re building something a little bit more than just talking about the latest charts or the later processes or the latest work things, you can certainly do that on remote. I think it starts with good leadership, good management, good remote work hygiene, where you have things like at the start of the meeting we talk about what we did at the weekend, we talk about the latest sports game when sports used to be a thing and actually what’s happening in the real world.
Kieran:
You talk about the latest movie. You have Slack channels where you talked about the latest shows and you can have these organic conversations about things that are non-work related. However, if your thing is, “What’s essential to me as an employee is physical personal interaction where I can get to hang out with someone in person. I can look at them. I can interact with them like across a table. And that’s just critical to me feeling happy and critical to me being a successful employee.” Then you shouldn’t work remote because you cannot replace physical interaction on a remote work call or in a remote work job. And I think that’s where we should start being honest and try to break those things down and be really clear that if you are really unhappy you don’t get to have physical interaction with someone and you don’t get to spend time physically with someone, you will probably not be happy with remote work, unless you can build those connections in your community you live in and spend some physical time with people outside of your workday.
Luis:
Yeah. I 100% degree. And the point that I like to make, and this makes me sound mean to my colleagues, but that’s not my intention at all. But there is no rule that says that you need to be friends with the people at your work. You should be able to separate your social life. And the people that you play and talk in a meaningful fulfilling conversations with from the people whom you work with. Now, obviously, that’s not to say that you shouldn’t care for the people that you work with, the more you care for them, the better, but work doesn’t need to be the place where you seek emotional and social systems.
Kieran:
Yep. Yeah. And I think, because I talk about remote work a lot, everything is through-the-lens of remote work. But most of this is not just specific to him at work. Some people enjoy working remotely because it fits their lifestyle. Some people enjoy working in an office because they really enjoy those physical connections. They enjoy getting it out of the house. Meeting people. Some people don’t like working remotely or in an office, they prefer working outside. And so this is more around how you structure your work around the life you enjoy and what remote work is is just another option for people to be able to better structure their work around whatever part of their life they enjoy. And you should do that. If you want to work in an office, you should work in an office. If you want to work remote, you should work remote. If you want to work outside, you should go try to figure out how to do that.
Luis:
Yeah. All right. So since you’re talking about structure, I’ll take the chance to jump into something that I usually like to ask, because it’s something that I think about. It’s about workday structure and workweek structure. So why don’t you take me through how you structure your week and each individual day, and start by describing a bit about your team. How many direct reports do you have and how do you structure the management of your team in a daily and weekly basis?
Kieran:
Yes. So in the group I have, I have six direct reports and everyone else reports up to those and they have managers and those managers have some managers. And so the way that I structure my week is unusual because of the way that my teams are structured. All of my direct reports are remote to me. So I have some people in the office in Dublin, but they actually report to some directors on my team or some managers on those directors team. All of my direct reports are based in the States, a one based in London and one based in Singapore. And so the way that I break up my day is I have a real advantage that I can take the first part of the day up until about 12 or 1:00 PM my time, Irish time, to actually do work, which is a pretty amazing thing.
Kieran:
When you’re you’re managing 65, 70 people that you can do a lot of real work and not have to just spend your time in meetings. And I think it’s a real advantage because I can just power through the things that I really enjoy doing. Then I have the second half of my day going through all of the meetings and catching up with people. And so the way I try to structure my week, I used to try to structure my week so I have no meetings on Friday, but I actually work pretty well having half and half. That works really well for me. The way that I communicate with my team. So we break it into like an annual plan where we forecast across the year.
Kieran:
And I don’t know if we want to get into specifics in that, but like we have that forecast broken into monthly metrics. We have a strategic doc that talks about the growth pillars we’re going to focus in for the year. And then each and every month we have goals against those growth pillars and we have weekly check ins. And then we have a monthly kickoff where we all get together and look at the progress we’ve made. Within that time, if there are specific projects… The way I manage my time is when you’re managing that many people, you cannot be that involved in all the things. And that’s actually a bad thing for you to do, if you have senior people in your team like senior directors and directors, you should trust them to do great work.
Kieran:
So the way I split my time is I pick a couple of things each month and I try to over-index my time in those things. And the way I communicate on those things that I have my attention on is I usually ask for memos, strategic doc progress on how we’re tackling those things. I get weekly to monthly updates. And so I guess the easy way to describe that is we have annual goals, an annual strategic doc, monthly goals, monthly goals against that doc, weekly check ins with my direct reports and a monthly kickoff where we look back and look forward in terms of things that have gone well and things we want to do well the next month. And then outside of that, there’s specific strategic projects I’m focusing on. There could be additional documentation, like memos, additional meetings around those things. And really just try to keep it very fluid. One of the things I definitely try to do is have as few as meetings as I can. Try to kill as many meetings as I can and try to make meetings productive. Now, I don’t always do a good job, but it’s one of my ongoing goals.
Luis:
So you don’t always do a good job. And I can definitely relate to that because I have the same feelings and I sometimes I don’t feel I do a good job as well. What would the good job be for you?
Kieran:
I think for the most part meetings should have clear agendas and you should be trying to shift decisions. If you’re having to meet and just to catch up, if you have a meeting that there’s no specific outcome you’re trying to get to in that meeting, then you probably can do it through a document. You could probably do it through an email, a Loom update, Soapbox update, whatever the means of communication is. But if you’re using meetings just to communicate information, there’s better tools to do that. And I think meetings are best served when there’s a clear agenda and that agenda leads to a decision being made within that meeting. If you think about meetings and how much of people time it takes, and those people are paid a certain salary and then how much a meeting is costing you per minute. You can shift decisions within those meetings and I think it makes them a lot more valuable and a lot more impactful.
Luis:
Okay. Yeah, that’s pretty much my usual approach and that’s usually my intention, but I find that, sadly, I’m not always up to the standard that I would like to hold myself to. All right. So let’s talk a bit about your team specifically, marketing team. So let’s talk a bit about quality control. What are the challenges when you’re dealing with direct reports that are directors and, I assume, they are doing most of the quality control in the work. How do you quality control those directors’ quality control, let’s say. How are you sure that they’re making the right decisions with the people on the ground level?
Kieran:
Yeah. It’s not too different from the structure I provided. So I think, for the most part, if you have people on your team who are quite senior, you’ve hired those people because you trust they’re pretty great at their job. They’re pretty great at managing people. And they are very proactive in terms of trying to make progress against goals. So I think my job is to work with them to have a clear strategic direction for the year. That’s something that we all agree on. So I try to make sure that all of my direct reports are, for the most part, part of the decisions we make and if it comes to a disagreement, then I have to make decisions and then sometimes you have to do that. And not everyone agrees on it and that’s fine. But the way I work with them is I have the strategic doc that we work from.
Kieran:
We have clear goals each and every quarter. We talk about those goals. We make sure we’re aligned in them, we agree on them. We have those weekly check ins where we can just talk about any things that are hindering success, any issues across the team, any blockers we have within the company. We can brainstorm them, try to figure out ways to solve those. And then I have all manner of dashboards that I get sent to me each and every day that show me progress against our goals because we have monthly goals. And so we’re able to see daily progress against those goals, which I think is one of the things that have helped to make us successful. We have that monthly kickoff where we can do a look back, a look forward. With my direct reports, we have a quarterly check-in to look to see, are we making good progress against the goals we had set ourselves at the start of the year?
Kieran:
Are there additional things that have come up within the last quarter, opportunities, and should we deviate from our plan to invest in those things? So there’s things that we didn’t know when we planned for the year. Those unknowns may cause us to change path because there’s just better opportunities now to do new things. And then we have reviews every six months to check in and to see how my reports are progressing against both their goals and their career goals and how they feel about life at HubSpot, and if their teams are happy and if there’s anything we can do to make their teams happier. So that’s generally how I do it, but it’s pretty fluid. I don’t have those kind of set model. I think that it changes based upon the month and the circumstances you’re in.
Luis:
All right. Okay. So obviously I wanted to be respectful of your time. We are closing to our deadline, but I wanted to ask if you’re up for a round of rapid fire questions? Where the questions are rapid fire, but the answers don’t need to be. You can expand as much you’d like.
Kieran:
Yeah, let’s do it.
Luis:
So first question, what browser tabs you have open right now?
Kieran:
Which what, sorry? Browser tabs.
Luis:
Yeah.
Kieran:
Oh God. I have at least 300.
Luis:
Okay.
Kieran:
So I think they’re mostly lots of documentation across work. They’re my different email. They’re my whiteboard. They’re my to-do list for today. And there’s a bunch of other things that I actually don’t even know what they are. So who knows?
Luis:
You’re one of those people who do not
Kieran:
I’m not. Yeah. Every day what I’ll do is at some point during the day, I’ll just get overwhelmed with browser tabs, and I’ll close everything down and start again.
Luis:
All right. So it’s the nuclear option for you?
Kieran:
Yeah. It’s the nuclear option.
Luis:
Sounds good. If you had 100 Euros to spend with each person working for you, what would you give them? And just two rules. You can’t give them the money and you can’t ask them for what they want. You need to buy in bulk, let’s say.
Kieran:
Okay. I’d give them all Bitcoin because, okay, if the financial system collapses in the COVID-19 disaster, they have something to spend money on. They have some money in their crypto accounts.
Luis:
Yeah. Then they have 100 Euros in worth of Bitcoin. That’s about like one tenth of a Bitcoin.
Kieran:
Yeah. They’ll be happy with that.
Luis:
Awesome. So what purchase has made your work life easier or more productive in the past year?
Kieran:
That’s a good one. I think my standing desk has been a really good purchase. Yeah. I think my standing desk has probably been my best purchase in terms of my home office. Because at least it extends.
Luis:
Cool. Any specific brand you’re happy with?
Kieran:
I don’t know. It’s not a specific brand, but it just allows me to flex my legs, stand up and sit down throughout the day. So I’m not continually just curl up in a ball. I think that that is, yeah, I don’t have a lot of stuff for my remote office. I have a podcast, so I have a lot of stuff for my podcast. But apart from that, I don’t have… I try to keep my desk as minimal as possible or my workspace as minimal as possible.
Luis:
Awesome.
Kieran:
My best remote work asset is my Bose headphones, but I purchased those more than a year ago.
Luis:
Okay. Yeah. Good headphones. They help a lot.
Kieran:
Yeah.
Luis:
So what book or books have you gifted the most?
Kieran:
Wow. What books or books have I gifted the most? You know what? I probably haven’t gifted a lot of books. I send a lot more online content than I do books. I recommend a lot of books to people. Maybe I’m not a very good person that I don’t actually gift them, but I recommend them.
Luis:
Okay. That works.
Kieran:
Yeah. Let me see what I have because I actually have a whole.
Luis:
It also works if you recommend your usual online resources. If that’s more your thing, let’s roll with it.
Kieran:
So I wouldn’t even know where I get content from. Because most of my content today comes through Slack and WhatsApp. If I’m being honest, it comes through small groups, which I think is fascinating. I don’t go and look for content online that much. So I think there’s… Actually, you know what, a lot of the content I’ve recently recommended to people, because we’ve been doing some projects in this area, has been around the jobs to be done framework. There’s a bunch of things. There’s a book on jobs to be done. There’s a couple of other things around that. There is a good book I recommend to someone just last week, because a podcast guest talked about it to my brother called Made to Stick, which is about how great ideas take off. And so I think that’s another one. But I have a whole list and I’m generally not very good at remembering what I recommend to people.
Luis:
That’s fair enough. So final question, let’s say that you are hosting a dinner where there are going to come to top tech leaders in the industry. Hiring managers, executives, et cetera. People who are going to sit down and have a round table about remote work slash the future of work. The twist is that this happens in a Chinese restaurant and you, as the host, get to choose the message inside the fortune cookie. So what is the message inside the fortune cookie?
Kieran:
Yeah. Well, that’s a really tough one to come off the top of my head because I’m going to end up saying something silly.
Luis:
That’s why it’s a fortune cookie.
Kieran:
Yeah. So you know what, I would say,” Talent matters, location doesn’t.”
Luis:
You know, for being on the spot, that came up pretty well, I have to say. Congratulations. You win the fortune cookie trophy, I suppose. All right, Kieran. It was awesome having you. Thank you so much for being here. Now is the time to let people know about where they can find you, where they can continue the discussion, where can they find your podcast? How can they learn more about HubSpot? All of that.
Kieran:
Yep. So the place that you can find me is on Twitter. LinkedIn, if you just search my name, Kieran Flanagan, you’ll find me. You can check out the GrowthTLDR podcast, if you like marketing and growth content. And then if you want to check out HubSpot and the platform we have, you can check out HubSpot.com.
Luis:
All right, ladies and gentlemen, that was Kieran Flanagan from VP of marketing of HubSpot. And this was Luis with the DistantJob Podcast, the podcast about building and leading awesome remote teams. Thank you so much, Kieran.
Kieran:
Cool.
Luis:
And see you all next week.
Kieran:
Thank you.
Luis:
And so we close another episode of the DistantJob Podcast. And if you enjoyed the episode, please, you can help us out by sharing it on social media. That would be great. It’s we reach more listeners and the more listeners we have, the more awesome guests I can get in touch and convince to participate in these conversations that are a joy to have for me. And I hope they’re a joy for you to listen to as well. You can also help a lot leaving reviews on iTunes or your podcast syndication service of choice. Reviews are surprisingly helpful in helping the podcast get to more listeners.
Luis:
Now, another thing that you might want to do is go to DistantJob.com/blog/podcast, click on your favorite episode, any episode, really, and subscribe. By subscribing, you will get a notification whenever a new episode is up and whenever we get the transcripts of the episode up, so you can actually peruse the conversations in text form. And, of course, if you need to find a great employee for your team, a great remote employee, you should take the whole world into consideration and not just look to hire locally, not just look to hire in your country. Look around the whole world because that’s the talent pool that contains the best talent. And to help you with that, again, DistantJob.com is the perfect place to start. You will tell us who you need and we will make sure that you get the best possible candidate. 40% faster than the industry standard. And with that a bid you adieu. See you next week on the next episode of the DistantJob Podcast.
