– Welcome, everybody to today’s Building My Legacy podcast, I have with me Christopher O’Donnell. He is just fascinating because he’s Senior Vice President of Product for HubSpot, he is an innovator, he is a speaker. he is, does a lot of work with MIT in talking about team and culture development. He is also very interesting ’cause he’s strong in music and continues to follow that passion that he has as he continues to also develop his business. So he has taken HubSpot product from startup, which was a $50 million company in revenue, and had it publicly traded to about $600 million in revenue. So he is a man who has a great deal of experience building, growing, innovating and developing. So, with Christopher, we’ll get started. and if you wanna add anything that I missed and what you think is really important about who you are, please share it and then we’ll get into our discussion.

– Well, first of all, thanks for having me Lois, I’ve really looked forward to this and just excited to see where the conversation takes us. What a time for us to be engaged in conversation about legacy and team building, it’s something I’m very passionate about.

– So Christopher, you talk a lot about team building and culture. Let’s start with team building in times of tremendous uncertainty we have right now, what I call the blended workplace, you have people working at home and in the workplace where we have people shifting back and forth trading, some working at home for a period of time and then trading places. So different days a week been in different places, or we just assign people to certain spots. So, given what you know about team building, how do we navigate this new world of what we’re going to experience?

– Well, I mean, what a timely topic. As we sit here having this conversation, it’s what, it’s early June, we’re in the first week of June here. The world is, has never been, you know, or perhaps it has, but, you know, certainly in my lifetime, the world has never been a more complicated and challenging place, you know, Vis-a-vis how to wake up and make a contribution. It’s becoming foggier I think, you know, there is the the pandemic, obviously, threw us a lot of curve balls and with, you know, the heightened race relations conflict right now, we’re really hitting pause to wrap our heads around, around these challenges intellectually and emotionally and also put our arms around each other, you know, to try to figure out how we say something and do something while also executing on our mission, which, you know, in our case, I think is a very meaningful one in terms of giving people economic freedom and giving them the tools to really build careers, and so forth, and we don’t wanna lose that. So that balance is not something I think that’s very mature for us, you know, if I’m totally honest. I think the part that’s more mature for us is the aspect of what you mentioned around this blended workplace. That for us is maturing quickly, you know, we have eight physical offices around the globe, and as we launched our ninth office in 2019, the location of that ninth office was remote. And, you know, we doubled down before COVID, we doubled down on remote hiring, perhaps people transitioning from in office to remote, and many of us I have to say have a gone and obviously with COVID, you know, we’ve gone entirely in the direction of full time remote. But this idea of hybrid, you know, this idea exactly of, I love that word blended, I found myself starting to split my days before COVID, and, you know, trying to be smart about my energy levels throughout the day, trying to be smart about my commute, you know, I mean, on one hand, the idea that we all need to live in suburbs and get in our cars at the same time in the morning, sit in traffic for an hour and 20 minutes at the same time, so that we can sit at desks for the same hours and then, you know, do the whole thing in reverse is, in a lot of industries, it’s a little silly, you know, it just doesn’t make a lot of sense, you know, we all need to, to rush in and pack like sardines, you know, it’s not necessary. And in COVID, you know, I hate to say that there are blessings here, but I think we can take from it the positive of investing in making that work, you know, here we are on zoom talking to each other, and this is much more natural than it would have been. And, you know, everybody in my life is now used to doing this. As a musician, I can take lessons with, you know, 10 times as many teachers because people are more open to that format. And so in a sense, the world has kind of opened up in all of these different dimensions, which is, which is really interesting, so many different communities strands have moved online, and I suspect a large part of that will stay forever. You know, I noticed that it’s not necessarily that employees, you know, pandemic aside, it’s not that employees these days are full time remote or full time in office, though certainly either of those are kind of possible, but, you know, if I’m meeting with, in the office with the three or four people who sit physically next to me in the conference room that is physically next to where we sit, I noticed that one of those people will be on zoom, you know, one of those people will be video conferencing because life happens, and I think that’s a huge part of modern leadership, is embracing that life happens, you know, the days of having to file PTO so that you can go to the dentist or having to explain to people because your kid is, you know, throwing up first thing in the morning or something like that, that’s very quickly going away, you know, it just doesn’t make a lot of sense, and it’s not necessarily even an aspect of altruism or employee culture and retention, it’s really, it just doesn’t make sense from, from a capitalist perspective to be niggling and diamond people on every minute of the day when, what you want and what drives the company forward, and yes, what helps retain great employees is those people feeling like they can do their best work when they’re ready to do it, you know, capturing the imagination of creative people, getting them motivated to execute on a mission, and so much of our work is done in the shower or walking the dog or, you know, while we’ re sleeping, you know, and of course, the collaboration and the heads down time reading and writing is still a massive part of any, you know, “information job”, but the world has just absolutely changed, I think COVID has accelerated that change, and I see a massive new normal, where wide swaths of certainly our country and beyond our borders will be partially remote or distributed forever.

– You know, I hear from women in middle management in particular, like well, I used to be on the road Monday through Friday for my company. I don’t wanna do that again, I’m finally home for the first time, my kids are now teenagers and I’m getting to know them, right? So you’re right, those are some of the positive, I think coming back into work now, people are gonna come back with some different attitudes, and once, you know, before it was I need a paycheck, I got to go home to support my family. Now they seen I can do a paycheck, I can be productive, and I can take care of my family. So let me do that, right? And I think there’s gonna be some very different discussions, but tell me, with what you’ve done and how you’ve worked with your eight offices in your remote office. How do you develop and build teams?

– Yeah, wow. How do we develop and build teams? The beginning, I mean, just as we think about a customer lifecycle, in say, sales and marketing and, you know, sort of that front office side of the business, we focus on the employee lifecycle and there is an entire arc to that, and you can take every phase of that human experience of being part of the team in the mission, and give yourself an honest grade on how you’re doing and give yourself a grade on, you know, your ability to attract the best people, your ability to retain them, and while they’re on this mission, hopefully for a long time, are they growing, are they developing, and are they doing their best work? You know, so following that, if, you know, one were to sort of buy into that lens, it starts with recruiting. I spend an enormous amount of my time recruiting at all levels, you know, from Associate Product Manager, it’s somebody’s first or second job out of college, you know, kind of thing all the way up to, you know, the vice presidency or vice president level. You know, it’s so critical, and every conversation that you have, in some ways is a career development conversation for you and for the port person that you’re, you know, interacting with, we’re all sharing information, we’ re learning, and that ends up being the best conduit to build the team. You know, I love when people materialize, it’s not as though, I love that word, it’s like, I see somebody in the halls and they have materialized on the team at HubSpot. But we’ve had a relationship–

– What does that mean to you, would you say they need materialized on the team at HubSpot?

– They have been on our radar, you know, and they have relationships with multiple people within our walls, and the day has come for them to join the team. You know, and so it’s, I guess, suppose what I’m illustrating is it’s not a, it’s not just a funnel, it’s not transactional, where you say, you know, here’s a job posting, and we are going to allow people to apply for it and pick one of those people. Absolutely, that’s a part of it, but how do you do that in a really wide, broad, sleek kind of way that is ongoing and that it’s really engaged and where we can be involved in developing people’s careers, even before they work here, you know, and we can find, this is by the way, a massively important motion and sort of perspective toward recruiting for diversity and inclusivity. You know, we want people with different work behavior, we want people from different backgrounds, we want those with different people skills examples that they bring to the table, and, you know, you may not have the right role for somebody based on their personality and their interests and their skills. If you keep that relationship going, you might in six months. And so it’s a very long term approach. I look at my direct reports, and a lot of those folks, you know, I knew for two or more years before they came in joined the team. And so that’s what it means to me to sort of materialize in our halls is to have already been part of, you know, our universe, and then, you know, to teleport into this mission at the right time, you know, and the right part of the mission for that person for them to succeed. And, you know, I think that there’s nothing you can do to build an effective team without getting that right, it’s not enough to just do that, but it’s absolutely the, you know, if you think of Maslow’s hierarchy of needs for team building, I mean, that’s got to be at the bottom, is getting the right people in a diverse mix of people who are gonna push each other, trust each other, and grow in their mission, try different things, have a diversity of experience. And then it’s, you know, from a leadership perspective, it’s our game to lose at that point. How do we create psychological safety and keep people sticking around and excited engaged in doing the best work?

– So here’s something that’s interesting with what you said, you see somebody in the halls and you realize they have materialized, right? Now with blended, the fear is, well, you notice me in the halls, there’s no longer that hall, So how do people get noticed?

– I think that’s a huge concern, it’s a huge concern. I’m personally and I think that my team is, from the data that we have relatively comfortable with a blended environment or a remote environment, with that exception. The bumping into each other at the water cooler aspect of work, the Ad Hoc conversations that pop up, the, yeah, the conversation, you know, on a couch having a coffee that, you know, that was going to be an email that might not have been written for a week that turns into a much more colorful and productive conversation, you know, over that cup of coffee. We have not figured out how to replicate that, we’re trying a lot of different things. So that’s kind of what I would say about it, is we’re in the experimentation phase, our product management team had, for example, a pub trivia night on zoom. And and that’s something that we would have done, you know, in person clearly, and we just decided to move it to zoom and try it. And then, you know, we get a lot of feedback from employees on what’s working and not working. We’re particularly, we’re usually obsessive about it, we’re even more obsessive about it in this world, given how little we know about that, but we worry about that, you know, we worry about losing the water cooler, losing the Ad Hoc conversations. You know, for my part, I’m also experimenting with trying to find blocks of time. For instance, my schedule is typically meetings, top to bottom, trying to find a block of time where I can be more Ad Hoc about it, so that if there’s a slack conversation that can evolve into a zoom conversation very easily. And I noticed there’s some promise to that where it can be easier in some ways to get face to face when we’re all sitting in front of, you know, some sort of portal here where we can magically beam into a conversation, but that’s based on availability. So I think everybody’s trying to figure it out, and I think if you asked me, you totally nailed that, you know, the plot hole with all of this, that really I don’t think anybody’s figured out yet.

– Well, I think there’s two sides to it Christopher, from how I see it. One is I hear as I work with companies, people making the comment, you know what? Anger sometimes over teammates who just are concerned about pushing themselves forward and being politically noticed within the company, sacrificing some key team people. So those people look at what’s happening and go, this is great, I get equal time and I get heard more, people who have succeeded, by leveraging themselves specifically, are probably the ones who get heard more, but they may also be good. So, you know, it’s easy to have a judgment about how people operate without having the data you don’t know, right? So there’s several parts to that that really have to be thought through.

– That’s such a good point, wow. It can level the playing field dramatically, I think, it’s such a good point, I mean, my own work has shifted to be so much more focused on the written word. The entire creative workflow of ideas has shifted and become, for me more transparent and more, probably more collaborative, because it has to live in documents, it has to live in the written word, which provides an opportunity for much more information and symmetry because it’s easier to take a document and invite people in, or publish it on our wiki or, you know, sort of it brought in, you know, the 10th, so to speak of who’s involved in, in that debate or that discussion, much easier than if it’s in a leaders head, you know, and they’re sort of bouncing around their normal orbit having their normal conversations, and I think that’s a wonderful thing, a wonderful thing. You know, I worry from an inclusivity perspective, absolutely, about what you say, you know, the squeaky wheel gets the grease and people who are very good public speakers or people who are funny or people who have, you know, some of these particular traits with which there’s nothing wrong, you know, and there can be a benefit to those things, but they do overshadow unfairly some of the more thoughtful and quieter communication styles and I think in this world of everybody being remote, the written word has become the lifeline for everybody and has the potential absolutely to really level the playing field, I think it’s a great thing, and I think the performance by the way, no surprise, the ideas are better. The conversation is deeper, more people are involved in conversation and it’s crisper.

– So you know what’s interesting about that, if you’re relying on the written word more, do you realize what you have done to diversity and inclusion? You’ve eliminated it as a problem. Because written word has no race in it, it has no gender in it, it has simply the word and your ability to communicate, right? So it’s a at this time with what we’re struggling with, I find that I had never thought of that, that is fascinating?

– Yeah, and, you know, I’ve been experimenting with all kinds of different little frameworks for getting ideas and for starting conversations and for identifying what part of a difficult topic we should spend our in person time on, and in all these experiments, one of the things I’ve started to do is to, to take people’s names off their work, you know, hey, here’s an exercise. Here’s, you know, here’s an exercise for this new product we’ re doing, and we need to figure out the story we wanna tell about it. So, let’s try to each tell a story about this in our own authentic way, and we’re gonna put them in a folder, on a hard drive somewhere in the cloud, and none of us are gonna know, you know, so like, how teachers grade tests, you know, and you take everybody’s names off it. And I think there’s something kind of magical to that, you know, when you do that, because all of a sudden, people are more willing to try “stupid things”, which we all know with innovation that’s where the great stuff comes from, it’s like, hey, I might be crazy, but, and it’s easier to say I might be crazy but if there’s no, you know, hey, here’s just an idea, maybe I wanna do this exercise, maybe I wanna do three of them, and just throw them out there. And it starts to change, this is like a huge culture change that I would love to see across the board, and I would love to live through in my own career selfishly, is just to move away from pride of authorship and to move away from anything, any fruit of that poisonous tree around, you know, joking, right? To your earlier point about, you know, people care about their careers, and people care about credit and they care about looking good, and there’s some reality to that in the workplace of why it makes sense. But there’s the old saying, you know, anything’s possible if it doesn’t matter who gets the credit. And so taking people’s names off the work and sort of centralizing it, has been an interesting experiment.

– So with that, Christopher, you rely a great deal on innovation to keep your company moving and growing. You’ve grown very rapidly, you’ve done very, very well. How do you innovate? How do you innovate with a blended company?

– How do you innovate? Well, you know, if you want really great stuff, you need to have some mechanism for tolerating failure. You know, I think that’s a first principle, I would argue that it’s just a truth, a law of physics. If you want something that is safe, and predictable, it will revert to the mean, or probably below mean. You know, so then the question–

– What’s that?

– You’re right there with Edison?

– Yes, I mean, yes, I mean, yeah, and, you know, truth be told, it stole a lot of people’s ideas, you know, but the failure, the failure aspect of it is, is absolutely critical. And so we can sort of transform the conversation around innovation to one around failure and tolerance, and iteration. So we can kind of build this up for first principles if we want an innovative culture, we need one that tolerance for failure. And to tolerate failure, we need what? Well, we need psychological safety, we need protection, we need trust. And these things sound very, they sound very fluffy, until you have that moment where you can put your finger on it and point it out, and so that’s the thing and leadership that we try to do because we can’t put a team together and say, hey, trust each other.

– Right.

– We can’t do that, no one can manufacture that trust. All we can do in leadership is, you know, we can try to give them a mission and not tell them how to execute on the mission but give them guardrails. Hey, here’s the rules of the game, but you gotta go play the game and you own the result, you know, that’s something that, you know, in the sort of modern leadership, like ISIS has been around for a while now, it’s hard to implement, you know, and why is it hard to implement? Well, because in leadership, we have to actually let teams try things that don’t work. And we have to cover for them when they fail in an authentic and transparent way. That means as leaders, we take the blame, and when they succeed, we need to give them the credit, and also pointing out to them that they succeeded and there’s nothing so small, that it’s not worth pointing out to the team. Look at what you did, look at what you did, and it’s almost like, it’s almost like a Montessori pedagogy where you, you know, you celebrate the child and it’s not about telling the child that they did a good job, but it’s intrinsic motivation and sort of saying, how do you feel about this art that you made? Could you have done that last week? Well, no, I couldn’t have done that last week. Isn’t that interesting? And then the team start to kind of gel and bond. And when that bond is formed, and when the skills are mature, and when the mission is clear, we just have to get out of the way.

– When you talk about having a level of failure that you really accept, you’re a publicly traded company. How do you balance that push from your, you know, looking at what happens with your shareholders and how they view what you’re doing, and that tolerance for innovation is gonna come with some failure, I’ve got to allow it, where do you find that balance for you as the leader because your safety net also is necessary right for you to create that culture?

– And that’s really the ballgame there, you know, guardrails, you know, guardrails. And that’s a huge investment for us in leadership, and you’re right, at the stakes that we’ re playing, there are many guardrails around security and, you know, reliability, these are non negotiable things. We can’t fail at aspects of what we do. And we need to have extremely rigorous discipline and process and levels of quality around those sort of, again, using Maslow’s hierarchy, sort of, if there were a hierarchy for these types of products, you know, the bottom part of that hierarchy is non negotiable. And then, as you start to move up that hierarchy becomes more negotiable, you know, is this new design going to work? You know, well, maybe don’t release it to all of your customers at once. Oh, okay, interesting. And so you can encapsulate the impact of, you know, experimentation, and have that be very controllable and very small. And then from there, think about how do you use those small environments to learn as much as possible? So for us, you know, when we fail, ideally, we’re failing with, you know, five customers only, not 80, 000 customers, but we fail with five customers. And those are customers who have product managers cell phones on speed dial, you know, I mean, some of our customers and we get invited to their weddings, you know, it’s the relationship is that tight. And so it’s not just trusting each other, it’s trusting our customers and our customers trusting us. But the key thing there is to have it be very, very small and very, you know, encapsulated in terms of the level of that risk, so that you can roll it back, so that you can iterate, so that you can kind of pivot around, and then ultimately, when we come forward with a new product, and we talk to Wall Street about it, for example, you know, you mentioned the word publicly traded company, those are things that are not, you know, in the old world of software, you know, where you would ship a bunch of CD ROMs out to millions of people, and you have one shot at it. We’re shipping a much higher quality product than that, because we’ve been able to iterate and move quickly. You know, in the world of CD ROM software, where you’re, you’re shipping box software out every couple of years, which is when my career started, that’s what I worked on, you know, I worked on Windows.exe, C++, binaries that, you know, and today, in our world of cloud software, we ship improvements to customers 1000 times a workday.

– 1000 times what?

– A day,

– A day, wow, wow.

– And so that’s how small the little experiments can be. And we don’t ship 1000 changes and improvements to every customer at every moment. But we are able to, it’s like pick up the candy wrapper, you know, when you’re in the office and you see somebody walked by a candy wrapper, and it’s not their candy wrapper, and they don’t pick it up and throw it away, you know, having that agility allows everybody to stop along the way and fix things when they see that there’s a problem, I mean, we still can fix a customer issue while we’re on the phone with them today, you know, with 700 people in R&D, or what, however many we are 600 people in R&D. Actually I think it’s over 700, we’re still able to do that.

– So you’ve been able to grow and retain flexibility, which is, so you’ve grown but you’ve kept that small mentality of how do we navigate quickly, and I think that is a key that we’re all gonna be challenged with moving forward. There’s something, well, our time has gone just so fast, I have a lot of things I love to talk with you about, and I know our audience would love to hear about, but I wanna hear a little bit about your music and how that has been an integral part in your development, and what you do as a leader and how you build teams.

– Yeah, well, you know, I have a funny background, I actually did my undergrad degree and it was a combination of technology and music. And when I graduated, there was no obvious way to apply that to my life for gainful employment. And I’m very lucky that you know, some years later, at this point, those are the two, in terms of my creative pursuits, you know, outside family, which is number one for me always, but in the rest of my life, those are the two pillars, and they’re so much in common, they’re so, so much in common. I think it comes down to the saying in music that, you know, if you’re the best player in the band, you gotta join a new band.

– Oh, okay.

– You know, and for me in technology, in music, whatever it is, I’ve never been the smartest person, the best person, the best player, the best writer, the best coder, the best designer by a long shot, you know, in whatever room I’m in. With music, you know, since high school or even before high school, I gravitated to the most talented people in schools where I was, and I just sat and I sat with them and I watched them work, and I pointed out when they had great ideas, and ask them questions about what they were doing, and asked if they wanted to roll tape and asked if they wanted to do overdubs over what they just recorded, you know, and that’s, it’s the same job, it’s the same job, and so I’m lucky that on the music side with the band of providers, which people can check out at the providers.com, you know, this is a band where I do write the music, play guitar, sing the songs, and and then we pull in the absolute session players around Boston and the surrounding area. And it’s a delight, I got to tell you, it’s the most fun thing in the world because I just get to be in the room with people who musically are so light years beyond me, and give, you know, me delight and new ideas and so forth. And work is the same way, work is the same way. And we’re talking about this leadership stuff. We’re talking about ownership, it’s exactly the same thing, you know, you don’t hire the best drummer in town to come in to record and you tell them every note to play, you know, why would you, why bother? Why bother? Do it yourself. You bring someone in and you’ve let that person fall in love with the song, and you let that person try three or four or five or 10 different approaches to it, and when they feel really proud of it, that’s when you stop. And in technology, anything else a business, it’s exactly the same way. Yeah, I don’t wanna be the best person in the band, I don’t wanna be the best designer or coder or product person on the team at all. I want to be a magnet, so that the really amazing people think, jeez, if I go there, I’m gonna be able to do my best work, and I want my team to support those people in doing their best work, because it’s the greatest thing, you know, engineers come up with better product ideas than product managers. The product managers are there to tell the story and to lay the groundwork and to help the engineers just like helping the session players fall in love with the song, help the engineers fall in love with the mission, fall in love with the problem, and let them sleep on it, let them try things and then they will come back with solutions that we would have never dreamed of, and that’s the most exciting thing for me creatively.

– What a note to end on, you know, I think that enthusiasm, that excitement of empowering people, which is what you’re really talking about, letting people be their best, and draw that out of them. You don’t need to be the best if you’re surrounded by the best because they’ll just make you better anyway, right? So, Christopher, it has been absolutely wonderful to have you on our podcast today. Thank you so much for being with us. And for those of you who are listening to us today, thank you so much for being with us on building my legacy podcast.

– Thanks so much for having me Lois