Leading In The Time Of Virus
"FEARLESS CREATIVE LEADERSHIP" PODCAST - TRANSCRIPT
Episode 207: David Lee
This episode is our seventh of Season 2 - which we’ve sub-titled, “Leading In The Time Of Virus”.
These are shorter, focused conversations in which we discover how some of the world’s most innovative and creative leaders are adapting their leadership to our new reality.
These people are among the world’s best problem solvers.
This episode is a conversation with David Lee, the Chief Creative Officer of Squarespace.
David talked about the importance of creating opportunities for spontaneity, about getting away from a meeting culture, and about where ideas come from.
Here’s David Lee.
Charles: (0:50)
David, welcome back to Fearless. Thanks so much for coming back on the show.
David Lee: (0:54)
It's good to be back here, Charles.
Charles: (0:55)
Tell us where you are, where are you living at the moment and who are you with?
David Lee: (1:01)
I am with my wife and six year old daughter, and we are right smack dab in downtown Manhattan, in Tribeca. So there's a been a little bit of cabin fever, but sounds like this is the new norm for the foreseeable future. So we're just trying to be cautiously optimistic in both work and life right now. So, yeah.
Charles: (1:25)
How has the company responded? How has your team responded?
David Lee: (1:29)
We just had like a company, all hands, like a week ago. And I have to say, like knock on wood, we wake up every morning and are pretty thankful that we have a business that is primarily online. And in some ways, we haven't even skipped a beat kind of working remotely, almost to a point where we actually think we've been more productive having almost 1100, 1200 people work remotely. So, like knock on wood, we have a cautiously optimistic view of things, but we always prepare for the worst. But I think our mission in some ways has always been about helping entrepreneurs, creatives and this independent workforce, and providing them the tools to be able to do that online.
So I think our mission, more than ever, is probably like really important and we're trying to do everything we can to help people transition some of their small businesses online. We are trying to help businesses that are in need by getting one-to-one financial support. We're trying to do more content and education. So we're trying to do our best at this moment in time, but things are good, but we always have that lens of being prepared for the worst if this goes on for much longer. But so far, so far so good, yeah.
Charles: (3:05)
I imagine it must be helpful, emotionally, for you guys to feel like you're helping people build towards the future and you're building your business towards the future. There's so many people who obviously who are in hanging on mode, they're just trying to hang on to some version of what they had. But to your point, your business has always been forward facing and you're about helping people look towards new possibilities and what's next. That must help you guys emotionally.
David Lee: (3:30)
Yeah, and I think more than ever. I mean, the reason why I came to Squarespace in the first place was that I wanted to know that I worked at a company that was effectively providing value into the world. And I could sleep well at night knowing that what we're trying to build is a suite of tools to allow people to go after their ideas or passions, their businesses. But to your point, I think, you wake up now every morning and you feel that even more than ever how important that is. And yeah, I think emotionally, it's kind of kept the mojo of the company at a good place despite all the horrific headlines and clickbait kind of things that you see out into the world, that you just got to sometimes just look in your lane and do what you have to do, and know that you are working on something that's hopefully providing value back out into the world in this time right now.
Charles: (4:32)
Yeah, for sure. What are you finding that your people need from you most at the moment?
David Lee: (4:36)
it's so strange that I think the first week where we started to do this remote work, everyone was a little confused and especially for people who have children and families where both partners are working at the same time. I think the first week was just a little bit of a haze that productivity was pretty low. But like I said before, we kind of just hit our stride, I think, in week two, where for some reason, we've actually never been more productive than ever before. And I think one of the main things that the leaders at the company, and including myself, are trying to do is that people need to take breaks. You don't even realize what day it is anymore.
People have obviously, for good reason, canceled all their travel plans and vacations during this time. But people are actually just working through and even into the weekends right now. And I think it's part to do with pure boredom, having something to do. It's partly to do with, I don't even know what day it is today. And so I think more than anything we have to tell people that, A, it's okay if you're having to take big breaks and if you have to do childcare at the same time and be a first grade teacher on the side.
But not only if you're in a living situation like that, but if you're just alone and you're just working yourself to the bone, you have to take breaks. And you have to take a step back and get your mind off of this because if you do this full throttle for too long, you will burn yourself out. So surprisingly, in a lot of the conversations we've been having is about how people are so productive, but I feel like burnout could happen quite quick if we continue at this pace. So people need to take a step back, I think, every once in a while and look at the other wall in their room or take a walk, go for a run, which is something that I've started to do as well.
Charles: (6:52)
Yeah, I think you're absolutely right about that. I think it's also interesting how people are getting to know each other in different ways, aren't they? I mean, a lot of people have talked about the fact that we see each other at home and you start to get a sense of somebody through that lens. Somebody said to me yesterday, very interestingly, they work for a company that has a lot of younger employees. And a lot of those people went back to their families, went back to their parents when this happened, right, which I think is very natural. And they said and they've moved back into their childhood rooms. And so what they're seeing are not only these people at "home", but in fact in their original home, and in the rooms that they had as kids. And so you see them through another dimension, which I think is just fascinating. I imagine you're getting to see your people in a different way, as well as getting to know them in a different way.
David Lee: (7:38)
Absolutely. I think one of the things that's happened with, again this transitioning to remote work, is you start to really look at just the cadence of the week and you start to look at your calendar and kind of go, you start to realize that maybe half of the meetings you had on the calendar weren't really necessary as well. I think there's been a really quick, like let's just find the hardworking muscle and let's get rid of the fat right now. So I think that's been really reassuring that people are just being more productive. But at the same time, as a manager, you have to do your one-on-ones and make sure that your team is emotionally still there outside of all the work stuff. So we've had, for the most part, we think our company has been, and specifically my team, has been doing quite well.
But we do have a younger workforce. A lot of our staff from my team are probably in situations where they've never experienced something like this before in their entire lives. So it's all new. I mean it's new for me so it's probably new for everyone in the world. So I think there's an emotional tax that, it's emotionally taxing I think for a lot of people, including myself. So I think as a leader, you just have to make sure that you're there if someone wants to talk to you about this. And for all of the other leaders in the organization, it's just to make sure that you have kind of like an open door policy if someone needs to chat about this stuff. Yeah.
Charles: (9:22)
Are you finding people are actually reaching out to you proactively to take advantage of that?
David Lee: (9:26)
Yeah, I mean it kind of comes and goes. You have the people that you normally do your kind of like one-on-one meetings with, and then I tend to like doing skip levels and things like that, just to try and get a sense of the heartbeat of my team and the company. So it's been a little bit of a mixed bag, but I think we're doing our creative all-hands tomorrow for like 120 people, and have a packed agenda. We hold Q&A sessions virtually. And yeah, it's just to make sure that there's constant kind of continuity of making sure that there's some thread to what everyone knew of their work life in the past, and making sure that everyone's kind of taken care of. So we're trying our best and we're certainly learning as well, as an organization, on how to deal with a situation like this as well.
Charles: (10:30)
What are the biggest problems you're encountering? What are the biggest challenges that you're trying to solve for?
David Lee: (10:35)
I can talk specifically about the creative team at Squarespace. Although we're being productive, I think what we miss are a lot of the serendipitous kind of moments and conversation, like these fleeting moments that happen when you're all kind of in the same workplace. A lot of times, that's where the magic actually happens. And it's kind of hard to do that over Slack and Zoom or kind of Google Hangouts. So it's like, how do you find that magic? Working remotely has been a little bit of a challenge. I think there's inherently, this looming kind of aura in the world right now when you see unemployment, kind of like numbers kind of shoot through the roof. Where even though we tell everyone that the businesses is stable and we're going to do everything possible to keep this ship stable, I think there's still, it's emotionally taxing just hearing all this stuff.
So I think trying to keep optimism alive is probably one of the most important things that we're trying to work with right now. It's hard being a New York City kind of headquartered company, where obviously we've become the epicenter of COVID-19 and it's hard to turn off the news. And you turn off the news and then your phone gets a notification over here and then you turn off the TV and then you get it like somewhere else. So yeah, it's emotionally taxing. So I think the hardest thing, to your point before, is that it's the emotional part that we probably are trying to make sure that everyone here feels safe and they're being productive, but have all the reasons, if they need to take a sizable break, that they can. So yeah, I think those are kind of the things on the top of my mind right now.
Charles: (12:57)
I think that notion of spontaneous connection is kind of the next phase of challenge to this, isn't it? Because I've heard from a lot of people exactly what you've described, which is, there is real focus and in fact efficiency coming out of this. And certainly there has been until this point. And people I think, have really come together and tried to support each other in a very human way, and I think that's positive. I think your point about where does the spontaneity come from, is going to be a very important question to solve, going forward, because I haven't heard anybody actually get to that. People are task-oriented at the moment and kind of initiative or project oriented. And where does the original thinking come from that is not connected to something specific, is going to be a challenge because I suspect we're going to have waves of this for a few months. We'll get released. We'll probably have another version of this as the numbers spike again, I suspect. So I think what phase two and phase three looks like is going to be important to figure out.
David Lee: (13:53)
Yeah, 100%. I think that's probably, for myself and probably for the creative team, is like where does that lightning in the bottle, where do you find that and when? It's kind of like we've been cooped up in our homes for a month and it does work well when there's a roadmap of things that you know you have to do. I think to your point, any task-oriented kind of like project right now, they're doing really well. If you know what you need to build, if you know what you need to code, if you know what you need to design and these are all the things that are coming up, then those seem to be going very well and are being very productive. But yeah, the creative part of it is, where do good ideas come from now, is an interesting conversation because ideas are subject to what you kind of intake as experiences.
And for me, our family are like prolific travelers. Like that's how we would get inspiration. And we're definitely not doing that anymore. So how do you find inspiration in your four walls at home, is a challenge. And then how do you interact with others to collectively try and crack something, is something that I don't think anyone's really cracked just yet. But it's probably like the next phase of creative ideation and thinking is like, how can we bring a little bit of that serendipitous thought back into the work process somehow because it's hard, it's hard right now.
Charles: (15:46)
Yeah. I think that's such a good point. And I was talking to my wife the other day and I said, "When would you be comfortable going to Italy on vacation? Is that six months from now or a year from now or two years from now?" And to your point, so many of us have benefited and valued being able to travel with freedom and get so much richness from life out of those experiences. And it's really hard to imagine sitting here today, even when society is released, wanting to get on a plane and go somewhere else. And with the threat that you still might get sick and you might get stuck over there or who knows what, right? I mean all of those things I think, come to the fore. So I think we are going to have to get much more conscious about how do we extract more meaning and more inspiration from the world around us.
What do you think, kind of evolving from that thought, what do you think of the good things that are going to come out of this? What do you think will be around a couple of years from now that would have come from our experiences in living this way?
David Lee: (16:43)
I do think there'll be great things that come from this. It's kind of hard to see through the weeds right now, but there's got to be some blessing in disguise that we can use as some sort of North Star. I think for us, this month has been a fantastic experience to work experiment, to kind of just see again, how productive we've been. I think one of the things that we started to realize is how much of a meeting culture we actually had, and how I would just look around and meetings are obviously very important and critical to any business. But I think what we're going to see after this is that A, I think this is quantified that some sort of remote work situation on a semi-permanent or maybe even permanent basis isn't necessarily a bad thing.
That people can actually just be as productive and potentially even in different time zones, and you don't all have to be under the same roof to do great things. I think that's one thing that I'm starting to realize is that I think we are going to be able to work fine on the different coasts of the U.S., and with our different offices. And we've already started to have some remote workers in different cities where we don't actually have a presence. So I think this is only going to validate that we can be just as productive and do great things with that kind of model. Again, with the huge caveat that there is a little magic that's lost if you have a company that's completely remote, like most of the world who's probably listening to this right now. But I do think there's going to be good things that come away from that, there's going to be a lot of lessons learned.
I'm seeing a lot more, just organic, helpful collaboration that I didn't see before. I think the humanity kind of part of it has really, not in some contrived way, but it actually has kind of brought teams closer together. And yeah, I think we take that for granted when things are going great. Like life needs highs and lows to really appreciate it because if you didn't have the lows you wouldn't really appreciate the highs. It's like going through life in like the same gear. So no one wants this, but I think it's going to ultimately, really get us to appreciate the things that we have, in work and in life. And yeah, hopefully, it doesn't just last a month and then we kind of go off and back into our daily lives. But yeah, this has been a strange one. I can't say I've ever seen anything like this since, like 9/11 and things like that. And I think it's going to make people stronger after this.
Charles: (20:04)
Yeah, I think you're right about that. I think we find out a lot about ourselves and to your point, each other in these times. And actually, to that point, how are you taking care of yourself and what are you learning about yourself?
David Lee: (20:18)
So I'm trying to just find some time on my own where, like I said it before, trying to go for a run every once in a while. I used to do it like three, four times a week. And then I think the first two weeks of this stay at home situation, I was kind of struggling to get back into the flow. So for everyone's sanity, make sure that you take breaks and take some time for yourself. Go outside and yeah, just stop, turn off the news every once in a while, which I have a hard time actually doing. The news is something that just keeps creeping up. So I got to find a way to completely turn it off for a week. I think that's what I'm going to try and do.
Charles: (21:08)
I mean, I do think that you can get very addicted to it, can't you? And it really does just start to change the wiring of your brain after a while and everything looks helpless and hopeless if you're not careful. And I certainly have found that I have to, A, limit the amount of intake I have every day, I mean physically limit it. And then the other thing I found is I cannot have it be the last thing I'm listening to at night because my sleep is so disturbed if that's the only thing that I'm dealing with.
David Lee: (21:38)
It's a fair point.
Charles: (21:39)
So I find light entertainment or something just changes the course of my thinking for the last hour before I go to sleep.
David Lee: (21:45)
Yeah. I mean I started having dreams of like a dystopian New York City, just purely based on all the headlines and all the notifications and things that you hear constantly. So, yeah, I might try and do a week of no news, obviously outside of the work related things that I have to maintain. But there's a lot of clickbait kind of article headlines and sensationalized things and a lot of superlatives and it's just getting a little, it's probably a good heads up that I probably need to tune that off a little bit.
Charles: (22:26)
Yeah, I mean I think the people who I've encountered who are doing the best are very much forward facing in terms of how they can develop, whether it's new skills or new understanding or just develop something that they've wanted to work on for a while themselves. And they try to put themselves into the future in a positive way. And so I've tried to emulate some of that as well. And it's difficult because I think we do get sucked into the day-to-day dynamic of the media.
Thank you so much for joining me today and I hope you stay safe, hope your family stays safe and well. And I very much look forward to getting together in person, sooner rather than later.
David Lee: (23:02)
I appreciate it. Thanks for having me on and stay safe out there too.
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