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The CEO of Upwork Reveals the #1 Key to Success in Work & Life — Transcript

by How Leaders Lead with David Novak · 11,922 words · 1,692 segments · language en · Watch on YouTube

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0:00As a leader, we have to start with a
0:02clear and shared narrative of what's the
0:05market and what's our situation in the
0:07market and what's the problem to be
0:08solved or the job to be done. If we
0:10don't know what problem we're solving or
0:11we don't know who we're solving it for,
0:12we can do all these other steps and they
0:14will not move the needle on our ultimate
0:16goals. If you've ever felt like your
0:18team is working harder than ever, but
0:20not really getting anywhere, it might
0:22not be an effort problem. It might be a
0:25clarity problem. Welcome to How Leaders
0:27Lead. I'm David Novc and every week I
0:29have conversations with the very best
0:31leaders in the world to help you become
0:33the best leader you can be. My guest
0:36today is Hayden Brown, the CEO of
0:38Upwork. Now, if you aren't familiar with
0:40Upwork, they help companies find and
0:43hire top freelance talent. And leading
0:45in that space, Hayden has real expertise
0:49on two topics every leader is talking
0:52about right now, remote work and AI.
0:56You'll hear her insights on both and
0:58they're terrific. But I also want you to
1:00listen to how Hayden creates clarity for
1:02her team. If you want to cut down on
1:04confusion and give your team more
1:06direction and confidence, you're in the
1:08right place. Here's my conversation with
1:10my good friend and soon to be yours,
1:12Hayden Brown.
1:18[Music]
1:19Now I understand that you have actually
1:22learned a lot about how to run your
1:24business by studying dating sites. You
1:27know tell me about that.
1:29>> You know a big function of what we do at
1:31Upwork is, you know, connecting
1:34businesses from the Fortune 100, you
1:36know, companies like Microsoft, Airbnb,
1:38Cloudflare, all the way down to your
1:40local mom and pop company. We connect
1:42them with the most in- demand talent in
1:44the world. And of course, that's a large
1:47part of matchmaking. That's really where
1:49we're kind of finding the exact match
1:50for not just the company, but the hiring
1:52manager, the project, the specific issue
1:54that they're trying to solve and going
1:56into our tremendous talent pool to find
1:58that person. So, there are a lot of
2:00analogies to dating sites and kind of
2:02matchmaking services generally. And
2:04certainly, we always try to pull from
2:05the best to figure out how we do that
2:06matching better and better every day for
2:08our customers.
2:09>> What do you think has been the biggest
2:10insights you pulled from the dating
2:12sites that you've transferred over? You
2:14know, I think one thing that makes
2:15dating sites an an interesting analogy
2:18for us is um you know, unlike e-commerce
2:20where someone can come into uh a website
2:24and kind of browse a bunch of products
2:26and then you know many people could
2:27order that same product, you know, they
2:29have thousands of that product on
2:30inventory. In the world of dating sites
2:32and the world of Upwork, every uh person
2:34is unique. There's no two people are the
2:36same. There's no two, you know, orders
2:39you could make of the same thing through
2:40our platform. And so we really look at
2:42how dating sites uh kind of bring
2:44forward the uniqueness, the specialness
2:47of every person and find those very
2:49specific attributes that become part of
2:51the matching algorithm to get the right
2:52person to that uh to that individual.
2:55>> Tell me about the origin of Upwork and
2:57and what it is today.
2:59We were founded about 20 years ago
3:02really through two very good childhood
3:05friends who grew up in Greece and one of
3:08them moved to the US and he really
3:10wanted to work with his good old friend
3:12from Greece who was still back in that
3:13country and yet he found in the early
3:162000s it was not easy to do this and in
3:19fact his employer was pushing back and
3:21saying well we don't know this person
3:22and how do we trust them and how do we
3:24know they're doing real work for us and
3:25that really led him and his friend to
3:28start OD odesk which was basically a way
3:30to connect remote talent together with a
3:32trusted kind of paradigm where there
3:34were things like screen captures hourly
3:37work guarantees on both sides and all
3:39the infrastructure to make remote work
3:41safe secure and appetizing for both
3:43businesses and talent so that was the
3:45early story of our business we've gone
3:47through a ton of chapters since then
3:49merged with our you know arch rival
3:50Elance and become Upwork in 2015 but
3:53really this is a business that's I think
3:55at the beginning of the next huge
3:57journey and I'm sure we'll talk about
3:58that But AI is changing everything to do
4:00with work and we are certainly at the
4:02forefront of that uh both our with our
4:04product and for our customers.
4:05>> Well, there probably isn't a company in
4:07the world that knows more about remote
4:08working and how to make it work than you
4:10and I can't wait to really get into that
4:12as we go through along. But I'm going to
4:13ask you lots of questions about how
4:15you're leading upward. But I'm going to
4:16take you back, you know, and what's a
4:18story from your your childhood that that
4:20shaped the kind of leader you are today?
4:23>> You know, I've been an entrepreneur
4:24since I was a really little kid. And the
4:27story there was I grew up in this small
4:30town in Massachusetts, a blueco collar
4:31community. Everyone knew everyone. And
4:34when I was 6 years old, my older brother
4:36was paralyzed from the neck down very
4:38suddenly. He's fine today, but he got
4:40this rare autoimmune disease called
4:42goneret syndrome and suddenly was in the
4:44hospital for six months. And there I
4:46was, this little kid loving and
4:47idolizing my brother and trying to
4:49figure out what can I do for him? How
4:51can I make his life better when he's in
4:52this situation? And I got this idea
4:55because he was a huge car nut that when
4:57he got out of the hospital, I wanted him
4:59to come home in a stretch limousine.
5:01Like this was the thing I wanted to do
5:03with his friends inside this big
5:04surprise, this big moment. And yet my
5:07allowance wasn't going to cover that.
5:08Like I had no way to fund that type of
5:10car rental. So, I got started collecting
5:13bottles and cans, turning them in to the
5:15recycling center, getting 5 cents each,
5:17and thousands of cans later, I had
5:19enough money to pay for the surprise
5:21limo trip for him home. But what I
5:24really got from that wasn't just like
5:25the joy of seeing him in that
5:28experience. I realized how powerful it
5:30was to have earned money as like a
5:32little kid, to be able to actually do
5:33something with it that really made
5:34someone else's life better. And that led
5:37me to go on and get a paper. I was
5:39probably the youngest in my town to do
5:40that, to start a small business called
5:42Hayden's House Cleaning. I went around
5:44the neighborhood doing chores for
5:45people. I went on and started a summer
5:47camp for local kids. Like all of these
5:48things were important to me, but the
5:50throughine was that early experience
5:53where I saw the good that I could do as
5:55an entrepreneur and seeing my parents
5:57who were nonprofit people and were
5:59working in communities around the world.
6:01We moved to Nepal when I was 11. We
6:03lived in cotandeu and they taught me the
6:05importance of not just doing work but
6:07doing work with a purpose doing work
6:09that really has a positive impact on
6:11people's lives which is what they
6:12dedicated their lives to and so that
6:15whole experience led me to want to be in
6:17business and create new things create
6:19new products but do it in a way that
6:20really tied back to personal impact
6:23human impact and that's really one of
6:25the big reasons I'm at Upwork today.
6:26>> Yeah that's fantastic story and you
6:29lived in Nepal.
6:31What what was the the biggest thing you
6:34took out of that experience?
6:36>> You know, about a year after we had
6:39moved to Nepal, I remember my first trip
6:41back to the US. So, I was 12 years old.
6:43I got off the airplane. Within a few
6:45hours, I found myself in a US
6:48supermarket, you know, probably a stop
6:49and shop in Massachusetts. And I'll
6:52never forget the kind of wonder that I
6:54had walking down the aisles and seeing
6:5712 brands of toothpaste, you know, 55
6:59stereotypes, like all of this abundance
7:02that previously I had just taken for
7:04granted growing up in the US. But now
7:06having been overseas for a while and
7:07seeing obviously such a different level
7:09of access and opportunity in common, I
7:13realized as Americans, we are so
7:15privileged and we have so much access
7:17and and things that we just take for
7:18granted the rest of the world would, you
7:20know, literally move night and day and
7:22like do anything to access. So that was
7:24a huge wakeup call for me really seeing
7:26that disparity and and understanding
7:28firsthand the privilege of being an
7:30American. It felt like I I was born with
7:31a lottery ticket because of that and
7:33starting to figure out how can I help
7:35others in the world have access to this
7:37incredible opportunity that we have here
7:38in the US.
7:39>> That's that's uh that's so great. You
7:40know, people always ask me what my
7:42biggest break is and I always tell them
7:43that being born in the United States of
7:45America and the son of Charles and Gene
7:47Novak. It sounds like you you have the
7:49same same kind of belief that I have on
7:52that.
7:53And you know, you you you go to
7:54Princeton and you graduate there, great
7:58school, and then you start up your
8:00career at McKenzie, you know, when you
8:02think about leadership and and and and
8:05making an impact. What did you learn by
8:07being a consultant?
8:09>> You know, I'll share you I'll share this
8:10lesson with you. I don't I don't know
8:12how how appealing it will be to people,
8:13but actually it was such an incredible
8:15experience to be 21 22 years old and
8:19asked to go in and work with some of the
8:21biggest companies in the world on core
8:23strategic problems that they were
8:25struggling with that they did not have
8:27answers to. And that was exactly why
8:28they were we were there as a firm and
8:30why I was being asked to do analysis or
8:32research or prepare a presentation that
8:34summarized various things. And what I
8:37really saw from that is it demystified
8:40business and business leadership for me.
8:42It made me see that even the people at
8:44the top, the most admired and successful
8:46people in the world, they too have
8:48questions. There's things where they
8:49need help. There's things that they
8:50don't understand or don't know how to do
8:51and could benefit even from someone
8:54straight out of college coming in and
8:55providing some information or
8:56perspective that they needed. So I think
8:59for me that really opened up this idea
9:01that like anyone can be successful in
9:03business. we can all have a shot at it
9:05and there's nothing especially unique
9:07about people who are already very
9:08successful like they got there through a
9:10hard le lessons learned but also are
9:12still learning every day and that that
9:14journey is never done
9:15>> and you you know were in this huge
9:17company Microsoft for for a while uh
9:19what did you what did you glean from
9:21that that experience that that you've
9:23taken with you to to Upwork
9:26>> culture is everything you know I was at
9:28Microsoft at a time when you know there
9:30was that famous cartoon of like the
9:32different divisions pointing guns at
9:33each other because it was just it was
9:35very fraught internally and there was a
9:37lot of internal competition and yet I
9:39was privileged enough to join a team
9:41that was nothing like that. We had this
9:44small team that was kind of this ninja
9:46force first working on M&A and strategy
9:49for the online business which was this
9:51new thing at the time and then going on
9:53and working on the biggest corporate
9:54strategy deals in the company's history
9:56including things like the 40 plus
9:58billion dollar acquisition bid on Yahoo
10:00uh the investment in Facebook etc. And I
10:03saw that the culture of our team which
10:05was so different than the broader
10:07culture of Microsoft was really a huge
10:08motivator for me and a reason I stayed
10:10and did that work and just loved it and
10:12grew so much. Whereas once I realized I
10:14wanted to go into product management and
10:16do something else with my career, I knew
10:18going into the rest of Microsoft at that
10:20time in that culture was just not
10:21appealing at all. And so I I've carried
10:23that with me in thinking about how do I
10:25build at Upwork the right culture that
10:27really attracts and retains that gets
10:29the best out of people and is not
10:30political is not you know discordant
10:32internally but really has us all moving
10:34in the same direction.
10:35>> And when you think about culture at
10:37Upwork what do you think is the single
10:39most important
10:41behavior that you're really trying to
10:42drive that'll get results?
10:44>> We have a value called build and break
10:46fearlessly. And we have a number of
10:49company values. We have we have uh five
10:51total values, but this one is the one
10:54that I think really animates our culture
10:56and our reason of being the most because
10:58we're a company that's built to break
11:00the status quo to create possibilities
11:03for people and businesses that did not
11:05exist before and would not exist without
11:06our platform. So, we need to be fearless
11:09every day examining what needs to change
11:12not just in the ecosystem outside and
11:14where we're trying to influence, you
11:15know, stakeholders, customers, etc., But
11:17how do we need to build and break our
11:19own culture or our own ways of working
11:21or our own practices to actually achieve
11:23these goals for our customers? So this
11:26value for us cuts very deep and shows up
11:28in all aspects of our work and is I
11:30think the thing that keeps us innovating
11:32at the edge of kind of the comfort zone
11:34and kind of pioneering our space in a
11:36way we could not do if we weren't so
11:37anchored on this value.
11:39>> When you're talking to your team about
11:40the importance of break and build, what
11:42what's what's your favorite story you
11:44tell?
11:45>> There's so many. I mean, we just had a
11:47huge announcement on on Tuesday, which
11:50was around this new business unit and a
11:52brand we launched called Lifted, and we
11:55created this business through two
11:57acquisitions plus our own uh existing
12:00enterprise business put together in this
12:02new structure. And I will say this is
12:04probably the biggest build and break
12:05fearlessly moment that we've had because
12:07this required us not just to uh do
12:10acquisitions or change our product or
12:11change our sales strategy. It's it
12:13actually caused us to restructure our
12:16business and create this um unit and and
12:19kind of completely change our operating
12:21model in order to be able to serve our
12:23customers the way we knew they needed to
12:25be served. And so this one I think is a
12:27great example of how we went deep inside
12:29and not just outside in terms of how we
12:30apply this value and really did the hard
12:32work to set us up for this next next
12:34great chapter.
12:35>> And as I understand it, when you when
12:37you joined Upwork, you were the head of
12:40uh product. you know what what does head
12:43of product mean in a in a in a company
12:45like Upwork? What did you do?
12:47>> Yeah. So, I joined the company in 2011
12:49actually as a product manager. I found
12:51uh the head of product at the time was
12:53willing to take that bet on me
12:55transitioning from strategy and M&A and
12:57this other part of my career into
12:58actually being a builder. And uh then I
13:01grew up to be the head of product and
13:02then ran marketing uh before becoming
13:04CEO five and a half years ago. But what
13:06I saw with being in product was this was
13:09such an amazing throughine between
13:11really understanding customer needs very
13:13deeply and then being analytical and
13:15focused about how to action those needs
13:17and also being very creative in terms of
13:19solutioning design you know product
13:21development. Uh and then of course
13:24closing that feedback loop by seeing
13:26what happens when you ship those
13:27products, how customers engage with it,
13:29how they respond and then using that of
13:31course to come back to the beginning of
13:32the process all over again. So, I loved
13:34how I got to be so front and center with
13:37customers, understanding their problems,
13:38and then applying them directly into
13:39changes in our business to address those
13:41problems.
13:42>> You know, one of the things that I think
13:45is the case, and you can correct me if
13:46I'm wrong, but you you you have a big
13:48perception of being this company that
13:51hires freelancers for creative projects,
13:53but yet you've expanded over time to to
13:57human resources, IT, finance. H how
14:01challenging was that for you to take
14:03people with you to to broaden your your
14:06offerings?
14:07>> This happened really naturally for our
14:09platform actually. We started with a
14:12really strong um foothold in technical
14:14work. So we had a lot of Eastern
14:16European talent and others around the
14:18world doing web and mobile software and
14:20application design all of that work kind
14:22of in the early 2000s. And then you're
14:24right, we also had this very stronghold
14:26uh big stronghold with design and
14:28creative work. But what we saw is
14:30customers would come in, you know,
14:31they'd have something in mind like build
14:33a website, but that was not something
14:34that just a designer or a developer
14:37could do in isolation. They needed
14:38design, development, marketing, you
14:40know, they needed the full spectrum of
14:42skills to execute these bigger projects.
14:44So very naturally, they started looking
14:46for and finding talent on our platform
14:48that drove that flywheel where now we
14:50have over 130 categories of work,
14:52250,000 AI specialists globally. I mean,
14:54and that the composition of our
14:56marketplace continues to shape shift
14:58based on client demands, which is an
15:00amazing aspect of our marketplace.
15:02>> And you know, here you are now, you're
15:04the leader in the industry, but you have
15:06companies like Fiverr and others who are
15:09trying to to do the exact same thing or
15:11or or even better, you know, how do you
15:14think about competition? You know, we
15:16stay focused on solving our own
15:19customers problems. And of course, we
15:22look at what others in the marketplace
15:23in the ecosystem are doing, but we have
15:26such a unique solution that actually no
15:28one has replicated. There's no one that
15:30does what we do. You know, our we do
15:31complex large project work. We have deep
15:34relationships being fostered between
15:36clients and talent on our marketplace.
15:38This is not small transactional stuff or
15:40throw it over the wall to somebody
15:42talented. So, you know, our distinct
15:44value proposition and kind of market
15:46positioning is something that we see as
15:47a huge asset that we can continue to
15:49expand on with things like our AI
15:51features and what we're doing there with
15:52things like this enterprise expansion,
15:54what we're doing there. And we see
15:56ourselves bringing to the market
15:58solutions that no one else has and
16:00frankly are really disrupting some of
16:01the legacy players who've been around
16:03for a long time but aren't tech enabled,
16:05don't have marketplaces, you know, don't
16:06have the set of talent and other
16:08capabilities that we have.
16:09>> Yeah. And you know, so h how do you how
16:11do you stay in touch with the voice of
16:13the customer and and and
16:16balance giving them what they're telling
16:18you they need versus versus giving them
16:20sometimes things that they don't even
16:22know that they need?
16:24>> It's a great question. I mean, we talk
16:26to customers every single day. I mean,
16:28we're on the phone, on Zoom, you know,
16:30in person. I do an AI uh customer
16:33council every month where I gather
16:35customers who are focused on AI and are
16:37using our platform for AI and talk to
16:39them about what's current and on on
16:40their minds. So, we have a ton of these
16:42channels for getting that feedback. But
16:45you're right, David. You know, one of
16:46the things I think is critical about a
16:48product manager and about a product
16:50company is we can't just build what
16:52we're asked to build. We have to go
16:54beyond that and have a bigger vision for
16:56where we're headed that customers may
16:57not even, you know, fully grapple with
16:59yet. they might not may not even be
17:00there yet, but we've got to be building
17:01that vision and making it real for them.
17:04So, we also do a lot internally in terms
17:06of u putting stakes in the ground around
17:08how we see the market evolving in the
17:09next few years where things like AI will
17:12transform our opportunity, visioning
17:14that out, and then building a roadmap
17:16that is giving incremental wins to
17:18customers along the way. So, they're
17:19seeing those benefits. We're not waiting
17:21until that big reveal, but we're
17:22building towards something that once we
17:24get there, everyone will look back and
17:25go, "This is totally different. This is
17:27totally transformational." Yeah, I want
17:29to get into how you're leading in the
17:30world of AI because there are very few
17:33people doing it as well as you guys are
17:35doing it. And uh but you spent almost 10
17:38years at Upwork before becoming the CEO.
17:42You know, not many rise to that position
17:44of CEO, being at the top of the
17:46organization.
17:48If you had to pick one thing that really
17:50was the key driver of your own personal
17:52success as a leader, what do you think
17:55it would be?
17:57I think clarity is probably the most
17:59important thing if I look back and at
18:02every step of the way I really focused
18:04on bringing clarity to hard problems
18:06that we didn't know how to solve or or
18:09you know hadn't resolved yet. Also
18:11bringing clarity to what's the actual
18:13situation in the business because as a
18:15leader we have to start with a clear and
18:18shared narrative of what's the market
18:21and what's our situation in the market
18:22and what's the problem to be solved or
18:24the job to be done. Then we have to
18:25articulate that vision of what could it
18:28be? What are we driving towards? Where
18:29are we trying to get to? And then the
18:30third thing is executing that plan,
18:32building and mobilizing the plan and the
18:34people to get there. So for me, it's
18:37always started with clarity. If we don't
18:38know what problem we're solving or we
18:39don't know who we're solving it for, we
18:41can do all these other steps and they
18:42will not move the needle on our ultimate
18:44goals. And you know what you're really
18:46talking about is the first
18:47responsibility of leadership which is to
18:49define reality the reality of the the
18:51the workplace and then create these
18:53innovative solutions. Can you share an
18:56example of where you provided clarity on
18:59a really complex problem that that that
19:01really helped the trajectory of your of
19:03your company?
19:04So in January of 2023,
19:07you know, basically two months after
19:09chat GPT had had started to land on the
19:11scene, we sat as a leadership team and
19:14had a discussion about what did AI mean
19:16for our business. So you know, if we
19:18remember at that time, two months in,
19:20tons of open questions, plenty of
19:22healthy skepticism. There was a raging
19:24debate within our own team of should we
19:27try to act on these uh kind of new
19:29technologies? Should we be incorporating
19:30them into the roadmap that we just built
19:32for that year? You know, we just
19:34finished that whole planning process or
19:36do we wait and see? And there were
19:37advocates on both sides. That was a
19:39moment where I felt it was critical to
19:41step in and really have a strong voice
19:43and clarity around my view, which was
19:46this technology will change everything.
19:49We have to be a first mover, not a last
19:51mover here. We can't wait to see what
19:53others are doing. And the only way we're
19:55going to be successful is if we get our
19:56hands dirty and start to learn by doing.
19:58Now, at the same time, we couldn't just
19:59throw out our whole road map and start
20:01over again because we had a ton of goals
20:03to achieve. We knew a bunch of problems
20:04we needed to solve with existing
20:06capabilities. So what we did was isolate
20:08a small team to basically go off-site
20:11essentially in our in our kind of
20:12virtual mode and just focus on the
20:15question how would we build Upwork today
20:18and what would it look like if we built
20:19it premised on an AI foundation and that
20:23work and that team came back with some
20:24incredible insights huge inspirations
20:27for us from a vision standpoint in terms
20:28of putting stakes in the ground of where
20:29we were going in the medium term and
20:32then we gradually pulled pieces of that
20:34into the road map and started to build
20:36kind of chunks of that idea as part of
20:38our our AI strategy. But that was a
20:40defining moment for us in terms of
20:41making that pivot and really uh
20:43committing to something that at the
20:44time, you know, there was still a lot of
20:45question marks about.
20:47>> Yeah. You took this big swing to to
20:50basically what you guys describe, which
20:51I love this is refound
20:54Upwork and and as an AI company when
20:58when others others hesitated,
21:02how did you get the personal courage to
21:04make that call? I think I faced a lot of
21:06tests over the many years not just
21:08leading this business but also just you
21:10know rising up through a number of roles
21:12and uh there was one formative
21:14experience for sure that happened you
21:16know during the really when the outbreak
21:19of the Ukraine war started in February
21:21of 2022 where I think for me you know
21:24that was that was actually for our
21:25business a significant crisis we had 10
21:27to 12% of our talent globally in the war
21:30torn region we had 12% of our own team
21:33internally that we work with also in
21:35that region. So we had internal
21:37exposure, we had customer exposure, our
21:39revenue was at risk like all of these
21:41things and most importantly I was faced
21:43with the ethical question to some extent
21:46of do we continue to operate in Russia
21:48and Bellarus or not and there were
21:51advocates from our customers on both
21:52sides, advocates internally on both
21:54sides. Ultimately, we were the first
21:57company in our space that made the
21:59decision to suspend operations in Russia
22:00and Barus. And that was an agonizing
22:02decision. Through that, I think I really
22:05learned and felt that adage that it's
22:07lonely at the top because there was no
22:09one who could tell me with any
22:11intelligence like what really needed to
22:12happen. And only I had the information
22:14perspective to make that really tough
22:16decision for our customers who were
22:17directly impacted. You know, our
22:19platform is a lifeline for so many of
22:21them. And so turning it off in a certain
22:23market is extremely risky and goes
22:25against kind of our value system. At the
22:28same time, we knew we couldn't operate
22:29and deliver our brand value and our our
22:31purpose in these markets given sanctions
22:33and changing conditions on the ground
22:35that just made it untenable. So this was
22:37a very difficult choice. But I think
22:39going through that and realizing the
22:40full responsibility that I had to our
22:43customers and making that decision with
22:45clarity early on so that they could all
22:48make their own decisions going from
22:49there and we could continue to operate
22:50effectively as a team was essential. So
22:53I think it's been moments like those
22:54David that really, you know, kind of
22:56tested us and our leadership and our
22:58cultural fabric and me in terms of
23:00making a bold and clear decision early.
23:02And I've always seen that those types of
23:05uh decision-making moments play out
23:06better when you can be clear and move
23:08fast and make a good decision versus
23:10wait and wait for more information, etc.
23:13Hey everyone, it's Kula from How Leaders
23:15Lead. And if you've watched our podcast
23:17for any number of episodes, you probably
23:19know that a common theme from all of the
23:21great leaders we interview is that they
23:23are active learners. They had this
23:25commitment to continuing to learn and
23:27grow so that they don't stay stagnant
23:29and so that they continue to see success
23:31in their leadership and in their life.
23:34This theme of active learning is so
23:35important and it's what David's latest
23:38book, How Leaders Learn, is all about.
23:40It's all about helping you develop that
23:42skill of active learning so that you too
23:44can continue to see success in your
23:46leadership and in your life. The book is
23:48really entertaining. It pulls stories
23:50from some of our greatest podcast guests
23:52and pairs those stories with insights
23:55that you can incorporate into your
23:56leadership and into your life right
23:58away. Grab How Leaders Learn on Amazon
24:01or wherever books are sold. And I think
24:03you're really going to love it. You feel
24:04David's personality through the pages
24:06and through his storytelling. And it's a
24:08really powerful way to level up your
24:10leadership.
24:11You know AI is something every leader is
24:13really struggling with right now or
24:15trying to get better making a core
24:16competence for themselves and for their
24:18their organization. What are you
24:20personally doing to to you know up your
24:25game in the world of AI? How how have
24:27you gone about learning about it so that
24:29you can lead?
24:30>> I spent a lot of time myself just using
24:33these different tools. You know I'm I'm
24:34a big chat chat GPT user. I experiment
24:37with Gemini a lot. But I haven't had as
24:38much success with that. And I I look at
24:41and test out um kind of category
24:44specific tools. So I'm not a developer,
24:45but I will watch tons of videos of how
24:48people are using tools like cursor
24:50vzero. Of course, I talk to our own team
24:52all the time about this because we are
24:53using those tools internally, but as
24:55things come out, I'm constantly kind of
24:57reading, experimenting, watching, and
24:59participating in keeping my own AI
25:01skills sharp because I have to roll that
25:03model out for my team. you know, no one
25:04in my company is going to believe that
25:06I'm serious about AI unless I'm showing
25:08up using these tools, pushing on them
25:10where they're not using the tools, etc.
25:12Of course, we also have some
25:13programmatic things in place. We started
25:15an AI effication program where we have a
25:17bunch of initiatives that are really
25:18focused on, you know, targeting and
25:20unlocking this uh this value, but
25:23personally, I feel I need to champion
25:24this both by doing and showing up with
25:26our teams to really advocate for our AI
25:28adoption. Has it been a challenge for
25:31you to take people with you in the
25:32company to get behind this movement or
25:35has it been something that people have
25:36easily gravitated to because you're
25:38you're we're obviously changing old
25:40habits by getting getting used to this.
25:42>> Totally. And and we've seen everything
25:44internally. You know, we've we always
25:45had kind of this uh cohort of early
25:48adopters who were, you know, leaning in,
25:50advocating. We've bought two AI
25:52companies in the last two years. So
25:54that's brought in a lot of like super
25:56forward-leaning AI talent, including our
25:58head of AI who came in from one of those
26:00acquisitions. But you're right, there's
26:01also a long tale of other people who've
26:03been worried or skeptical or feel like
26:05maybe they don't have permission to use
26:07these tools. So we make it a constant
26:10habit. Every week we're talking in our
26:11we have a weekly kind of mini all hands
26:13meeting. We're talking about and
26:15showcasing how people are internally are
26:17using these tools. We've created
26:19workshops and webinars and now really
26:21communicated to everyone that the
26:23expectation is they are using these
26:24tools. So it has taken you know in some
26:26places kind of the snowball needed to
26:28start rolling before speeding up but now
26:30it feels like it's moving really fast in
26:32terms of executing uh on this like
26:34opportunity and getting everyone in the
26:36company involved in it.
26:37>> How important has it been for you to
26:39make it clear to everybody that this is
26:41a this is a bus everybody's got to get
26:43on?
26:43>> It's my top priority. It has been so
26:46important because you're right, there's
26:47skepticism, there's fear, people worry
26:50even in our company about their jobs
26:51being replaced by AI. I mean, this is a
26:53widespread phenomenon. So, I have had to
26:56be very clear and and it's one of those
26:58things like repeat, repeat, repeat until
26:59people are sick of hearing it. And I'm
27:01sick of hearing myself say it, but
27:02repeat what our goals are and really um
27:05reassure people as well as push them and
27:07challenge them in terms of where we're
27:08going going. And this is, I think,
27:10essential for every leader. It's not
27:11going to happen in the business without
27:12each of us really leaning in and driving
27:14this change.
27:15>> You know, you're obviously a leader who
27:17can clarify and you've done that many,
27:19many times. You're a great communicator.
27:22Uh, and you have these obvious skills
27:25and you're at the top of an
27:27organization, which I think is fantastic
27:29and you're a great example for my
27:31daughter and and so many others. Uh, did
27:34you ever find being a female really
27:36inhibited your ability to to take on
27:40opportunities or even get opportunities?
27:42And if so, how did you work through it?
27:45>> I used to be very naive on this topic.
27:47When I was 22 at McKenzie or Microsoft,
27:49I was thinking it doesn't matter that
27:51I'm a woman. Like, that's not going to
27:52hold me back. No one's going to penalize
27:54me for that. And of course, in the last
27:5620 years, I've seen tons of instances
27:58where I'm underestimated. I'm looked
28:00over. uh I mansplain to constantly just
28:04because you know people think oh she
28:06can't know what she's doing or she can't
28:07take this on. So of course I've
28:09experienced that throughout my career. I
28:11think the thing that has been you know
28:14really interesting as the CEO I've
28:16really realized that in our culture uh
28:19there's kind of two types of women
28:20leaders who are stereotyped. There's
28:22kind of the mom who's like soft and
28:24fuzzy but maybe like a little clueless
28:25or can't make those hard decisions. And
28:28then there's I'll call her the jerk, you
28:30know, the person who's like
28:31cold-hearted, like doesn't care, like
28:33you know, just breaking glass
28:34everywhere. And I am neither of those
28:37things. I bring a lot of warmth and love
28:40and caring that's genuine for my team
28:41and our customers. I'm also hard driving
28:44and decisive and bold and analytical.
28:47And people don't know what to do with
28:48that. I think they often can only kind
28:50of look for or see one, not both of
28:53those things at best. So, it's become
28:56clear to me that I need to do a lot to
28:58communicate, as you mentioned, and
28:59really show up and try to educate my
29:02team and our stakeholders in terms of
29:03who I am and what I stand for because
29:05the stereotypes that people really fall
29:07into, especially for women leaders, just
29:08don't apply.
29:09>> What specific advice would you give to
29:12to a female that maybe you wouldn't give
29:14to to a male that that will that could
29:16help them, you know, climb the ladder?
29:19Unfortunately, a lot of women who are so
29:22capable and the the studies have shown
29:24this hold themselves back from that next
29:26step because they feel like h they need
29:29to do a little more, you know, prove
29:30themselves a little more or learn a
29:32little more or go do that other job
29:33before they do the job they want to do.
29:35And a piece of advice I give to a lot of
29:37folks that that come to me and and we
29:39chat is if you're thinking about going
29:41doing that thing, don't do the three
29:43things first. Like go do that thing now.
29:45You're ready. You're capable. Go do it.
29:47That's what that's what a lot of men do.
29:49They don't wait until, you know, they
29:50have that perfect profile or capability.
29:52And I think that's something that as
29:53women, we can constantly push ourselves
29:55on because our culture doesn't
29:56necessarily foster that in us.
29:58>> Yeah, I I agree. And and, you know, it's
30:00it's great to see that that you're
30:02you're leading the way and and showing
30:04people that it can be done in the very
30:07best of way. So, congratulations on
30:08that. And, you know, uh, your company
30:12provides a great service to to your your
30:15customers. And I was just curious, you
30:17know, what advice can you give on on how
30:19to balance between full-time employees
30:22and freelancers?
30:24And maybe you could use Upwork as as an
30:27example.
30:28>> We have about three4ers of our workforce
30:31today is freelancers. And that's been
30:33true basically since we were born as a
30:36as a small startup. We've always built
30:37our workforce as hybrid. And what we see
30:41today in the in the environment more
30:42broadly is a shift where more and more
30:45companies are looking critically at
30:47their full-time employee staff and
30:50realizing the limitations of what that
30:52staff can do for them. Often those
30:54people on on their in their current
30:55payroll don't know how to use AI tools,
30:57aren't maybe moving fast enough up the
30:58learning curve, uh don't have other
31:00critical skills as these businesses are
31:02moving in a very dynamic environment. So
31:04that trend is causing more companies to
31:06have a smaller core FTE group and a
31:10larger group of contingent freelance and
31:12kind of thirdparty vendors that they
31:14work with. And that I think is an
31:15enduring shift we're going to keep
31:16seeing more of. So for every company I
31:19think the the key is moving from a
31:21mindset of I you know in the past like
31:24most leaders have thought like oh I hire
31:26or I do work with the unit of the FTE
31:28that's like the unit of measurement like
31:29I need to add these FTEEs or subtract
31:31these FTEs. That's how work is
31:33comprised. The shift for leaders is to
31:35say these aren't FTE units. Now it's
31:37skills or projects or efforts. And once
31:40we break down the work to be more clear
31:42about what those boundaries and goals
31:44are, we actually may not need a big team
31:45of 10 FDs. Maybe we could have four or
31:47five specialists who really focus on
31:49that project and then we keep going with
31:51them or disband it based on what we
31:52find. And so it's a it's a different
31:54mindset around kind of what the unit of
31:56work is, how you define and scope the
31:58work. And then of course going to this
31:59tremendous pool of freelancers which is
32:01a $ 1.3 trillion economy in the US alone
32:04to find that skilled talent that you
32:06probably don't have to be moving fast
32:08enough and ag most agile you know in
32:11this current environment
32:12>> and how do you go about defining the
32:14scope of a job so that you can decide
32:17okay it's a full-time employee or it's a
32:20freelancer I mean is there do you have a
32:22process that you use to get at that?
32:24>> We do. I mean we start with really
32:26what's the goal here and how what's the
32:28time frame in which we need to achieve
32:30the goal and is this something that's
32:31going to endure beyond that or not. We
32:34also look at aspects of course that are
32:35around kind of compliance and how much
32:38control and direction do we have to give
32:40to this work or is it more kind of
32:42autonomous and we can share context and
32:43then have experts go off and do some of
32:45this work for them. So these are two of
32:47the factors that we look at in figuring
32:49out you know can we do this uh with with
32:52freelance talent but for us David
32:54basically every question it kind of
32:55starts with the premise like why can't
32:57you do it with freelance talent like
32:58that's where we always start is like
33:00this should be something we can do with
33:01a flexible team and if we really push
33:04ourselves to say in places where people
33:05want more headcount like is that
33:06necessary and and they really have a
33:08high bar to justify in order to make
33:10that happen. That makes sense. And and
33:12as I said at the top of the show, you
33:14know, you've been leading in this remote
33:17work environment before people even
33:19talked about remote work environments
33:21and you've been doing this a long time
33:23and it's now the new normal uh for for
33:26for every company. Uh what advice would
33:28you give others on on how to navigate
33:31this? Well, you know, how do you really
33:33be a company that knows how to to lead a
33:37remote remote workforce? The first thing
33:40is I think too often people mistake a
33:43remote first a remote forward workforce
33:45with we don't get together in person
33:48when in fact our model has always been a
33:50combination of yes lots of fully remote
33:52team members lots of flexibility in
33:54terms of when where and how people work
33:56but we still have strong cadences of
33:58getting teams together so they really
34:00build not just business context but also
34:03social context and relationships and
34:05that is really a huge unlock for remote
34:07teams. have to have that as a
34:09foundation. So remote teams have to have
34:11a lot of in-person touch points. It can
34:13vary based on the team and the work, but
34:14that's a key part of relationship
34:16building. And then you also need to be
34:18very clear about what are the remote
34:19work practices. So for example, in our
34:21company in every meeting, cameras are on
34:24for every participant. And that is
34:26really the guiding light as just one
34:27example kind of practically of how we
34:30ensure people are like seeing and
34:31hearing from each other, able to read
34:32body language. It's not about just dial
34:34in on the phone. you have to be like
34:36physically present. Uh those are some of
34:38the things that we do in addition to
34:40like weekly touch points where you build
34:42culture. You've got to build culture
34:43with a remote team that's not in the
34:45office. And for us that means things
34:46like a halfhour touch point every week
34:49where we can put our culture on display,
34:51showcase work that's happening, create
34:53context, and also let people see and
34:55hear about things that are happening
34:56across the business that they're not
34:58hearing about when they're not in an
34:59office, which is what most of our team,
35:00you know, is. So those are some of the
35:02things that really have helped us build
35:04remote culture and remote fabric. But
35:06every company has to approach this for
35:07like what's right for them.
35:09>> We'll be back with the rest of my
35:10conversation with Hayden Brown in just a
35:12moment. Like Hayden, the co-founders of
35:14Warby Parker know how important it is to
35:17move fast. And for them, agility starts
35:20with fast, open, streamlined
35:22communication.
35:24We found that to be successful and to
35:28grow quickly, right? Information has to
35:30flow quickly within the organization.
35:32And similarly, it's got to flow quickly
35:35between the two of us, right? We need to
35:36model the behavior that we want to take
35:38place throughout the organization. So,
35:41we also our office is an open layout. We
35:43sit right next to each other in between
35:45meetings. We're often, you know, sharing
35:46notes with one another. Sometimes we're
35:49the first people that we talk to in the
35:51morning and the last person we talk to
35:53at night. I don't know how much our
35:55wives love that. But again, to be a high
35:58growth company, right, you got to make
36:01quick decisions. And if those are going
36:03to be good decisions, they have to be
36:04informed decisions, which means
36:06information needs to travel quickly. And
36:08we think that our competitive advantage
36:11is having the best data, having the best
36:14information, and having that flow
36:16throughout the company across functional
36:20groups that are in other companies often
36:22don't talk to each other or don't even
36:24exist within the same company, right?
36:26And that's our competitive advantage. We
36:28have direct relationships with our
36:29customers because we sell direct to our
36:32customers through our stores and our
36:33website and our apps. Um, so we're able
36:36to get all this customer feedback and
36:38data, um, and then we disseminate it
36:41quickly across the company, whether it's
36:42to eyewear design or our merchants or to
36:45the technology team or to the CX team or
36:48to the marketing team, right? And then
36:50we're able to sort of move nimly and and
36:52quickly.
36:54Go back and listen to my entire
36:55conversation with co-CEOs Neil
36:57Blumenthal and Dave Gilboa, episode 181
37:01here on How Leaders Lead.
37:04What have you learned about managing
37:07conflict in a remote environment? You
37:11know, you talked about the body language
37:13and you know, but you know, how do you
37:16how do you wrestle tough things to the
37:18ground in a remote environment? So, it's
37:20not just a telling kind of back and
37:23forth mode that way.
37:25>> Two things have really helped us. So,
37:27one is the in-person relationship
37:29building, which again is about dinners.
37:31It's about going on hikes. It's like
37:32when teams get together, they focus on
37:34that. That social fabric then builds the
37:37psychological safety that people can
37:39have conflict with each other and feel
37:40like that's okay. And also when they
37:42hear, you know, a challenge or a push
37:44back from a colleague, they can know,
37:46oh, that's coming from a place of
37:47positive intent because we talked over
37:48dinner and he's a super nice guy and
37:50he's only saying this because he really
37:51thinks it's better for the business, so
37:53let's hash it out. So positive intent
37:55and psychological safety comes from that
37:57relationship building. The other piece
37:59of it which I talk a lot with our
38:00executive team about is you can't have
38:03like one dimension of communication. It
38:05can't be you know only scheduled
38:07meetings. When there's a conflict we
38:09have a a agreement that we will resolve
38:11things quickly. So we'll turn around
38:12we'll get on the phone right away or
38:14we'll set up an inerson meeting right
38:15away or we'll take action so that these
38:17things don't fester and become you know
38:20out of proportion or bigger conflicts.
38:22It's about use whatever tool necessary
38:24to kind of bottom this out immediately
38:25and don't let it wait. So never like let
38:27a conflict roll into the next week for
38:29example and resolve it by Friday.
38:31>> Maybe that's part of your build and
38:32break approach. You know, you're
38:34building the culture and you have to
38:35break down the barriers when you see
38:37them.
38:37>> Totally. And that's why as a product
38:39manager, I love this job. Like I now get
38:41to build the company, not just the
38:42product. And to me, that is everything.
38:45>> Speaking of that, you were a product
38:46manager. Now you're the CEO. You run
38:48every function. You know, how did you
38:50how did you broaden yourself?
38:52>> I'm a huge learner and I'm hugely
38:54curious. So I'm always asking other
38:56people for tips, advice, input, you
38:58know, reaching out to broaden my network
39:00and really learn about the things that
39:02are the next kind of challenges in the
39:04role. So I had the good fortune of doing
39:06a lot of product marketing, you know,
39:08some other things before I became the
39:10CEO. But I've also realized there's al
39:13nothing like trial by fire. And
39:14sometimes you can prepare, you can
39:17learn, but then you just have to go and
39:18do it. You have to get into it. And you
39:20learn a lot by doing. You know that
39:21would be like my first earnings call. I
39:23had never led an earnings call before,
39:25but I I prepared, I practiced, I kind of
39:27thought through it. And actually then I
39:28took like a giant risk and surprised the
39:30street with some announcements they
39:31weren't expecting and it paid off. It
39:33totally worked. But, you know, at some
39:34point you have to kind of set aside this
39:36idea that everyone else knows better.
39:38Kind of like what I learned at McKenzie,
39:40like everyone else is more expert. I
39:41learned, you know, everyone's kind of
39:42making it up. And so it's okay to learn,
39:44be smart, start with first principles,
39:46and then go and apply that knowledge and
39:48then rinse and repeat. Now you're a very
39:50confident person but has there been a
39:52time where you really had some
39:54significant doubt and and if so how did
39:57you how did you work through it? Can you
39:59share that?
40:01>> So two months into the job as the new
40:03CEO and mind you I stepped into a
40:05context that was um you know we were
40:07about one year postpublic. Our stock
40:09price had been faltering. Investors had
40:11some questions. I was put in as this new
40:13CEO. They didn't know yet and I had a
40:15clear idea of what we needed to do with
40:17the business. But some of the things I
40:19felt we needed to do were very risky. So
40:21I laid out my strategy and my plan to
40:24the team. But part of that was saying we
40:26have to act like we're in wartime. We
40:28have to work a lot harder. The bar for
40:30excellence is now going up. And this is
40:32what I'm asking of and expecting of you.
40:35And the thing that I was wanted to do
40:37that I debated was I actually wanted to
40:39make sure everyone at the company who
40:41wanted to be there was there and
40:43committed to this new plan and this
40:45level of effort and that anyone who was
40:47not intending to be there or did not
40:49feel like this was a good idea for them
40:51was out the door. So what I wanted to do
40:54was this thing. We ended up calling it
40:55the graceful leave program where we
40:58offered everyone a severance package
41:00after I had shared this new strategy and
41:02these new expectations and said every
41:03single person if you don't want to be
41:04part of this here's a check here you can
41:07you can go now. But the question for us
41:09was a like what is this going to do?
41:12Like is are we going to have 20 people
41:13left at the end of this? You know who's
41:14going to stay and who's not? Is this too
41:16risky? And also when do we do it?
41:18because I was two months in and there
41:20was a lot of discussion maybe we should
41:21do at the end of Q1 or Q2. Well, it
41:24turned out we did it in February. We
41:26executed this plan. We offered people
41:28severance. A number of people took it.
41:30We also, you know, helped coach some
41:32people out that maybe were not a good
41:33cultural fit. So, it was a huge actual
41:35win for us. But what I realized was the
41:37pandemic hit in March and if we had not
41:40moved fast and executed on that in
41:43February, we would have been in a very
41:44different situation in terms of
41:45executing that type of transformation of
41:47our workforce and our business during
41:48the pandemic when it was like a no no to
41:51to fire anybody. So I had debated and
41:54deliberated the time frame. I got some
41:55great input from people that were like,
41:56"Hey, we know you want to move fast.
41:58Just do it in February." And I did it.
42:00And looking back, that was such a good
42:01decision. And that gave me a lot of
42:02confidence in future decisions about
42:04moving fast, not equivocating, and just
42:06going for it even when the outcome was
42:08very much unknown.
42:09>> Yeah. Well, the graceful leave. That's
42:11another another example of where your
42:13clarity really paid off. You said this
42:16is where we're going. You know, I'm
42:18excited about where it is. I think
42:19there's huge potential there. But you
42:22got to you got to believe it, too. And
42:24if you believe it, we're together. If
42:25not, you know, uh you can leave grace
42:28with. That's that's a pretty good
42:29example, you know. And you you mentioned
42:31you mentioned COVID and you became CEO
42:35right before the pandemic. Uh how did
42:37that accelerate
42:39your your learning just on on remote
42:42work? What have you what have you
42:43learned about remote work because of
42:46COVID?
42:47>> It's a great question. We because we
42:49were a a hybrid and remoteoriented
42:51company before COVID. We always had a
42:534-1 model in our offices. four days in
42:55the office, one day remote, and then we
42:56had this extensive team of of
42:58freelancers predominantly who were
43:00nowhere near our offices. So, we had
43:01this huge remote workforce. It was easy
43:03for us to flip the switch and go fully
43:05remote when COVID happened. I did learn
43:07how hard it was for other companies and
43:09how much we could help and educate them
43:10with some of our practices. So, that
43:11that was a benefit. But I also learned
43:14to my comments earlier remote work when
43:16it's fully remote and you can never get
43:18together in person which was the case
43:20more or less for the first you know one
43:21and a half two years of the pandemic is
43:24very different than remote work when you
43:25can have these inerson touch points and
43:27I think one mistake we made during co is
43:29you know we grew the business
43:30significantly our our topline nearly
43:32doubled or did double our our employee
43:34base expanded significantly as well but
43:37because we were already so good at
43:38remote work we didn't think about
43:40incepting our team members that we were
43:42hiring with all of the practices with
43:44the level of intentionality that we had
43:46had in the past because in the past
43:47people just come to the office and be on
43:49the road and they kind of learned these
43:50things through the way our culture
43:51worked. They'd be in person sometimes
43:53etc. without those inerson touch points
43:55and without enough intentionality around
43:57what our remote work model was. We
43:59actually kind of backslid at periods of
44:00time where it was like oh this isn't as
44:02effective as it could be. So since then
44:05we've really dialed our dials in terms
44:06of the intentionality in terms of the
44:08communication around what our our our
44:10approaches are. But I think it was
44:11definitely interesting to see kind of
44:12through that period, you know, some of
44:14the struggles that we ourselves had at
44:15moments because of our growth and
44:17because people didn't all understand how
44:18to work in our remote company.
44:20>> Yeah. And and nobody has a crystal ball,
44:21but if you could look out five years
44:24from now, how would you describe the the
44:27remote work world?
44:28>> It's going to keep getting better
44:30because the technology will improve. And
44:32I do think technology enablement, you
44:34know, is a huge driver here of whether
44:36remote work is successful or not. So I'm
44:38an optimist in that sense. Uh I do think
44:41though at this moment everyone is is
44:42recognizing the value of in person and
44:44trying to find that balance again. You
44:46know having many companies swung
44:47extremely remote and I think that's
44:49going to continue. I think we're going
44:50to see more of these hybrid models where
44:53people have a mixed workforce of on-site
44:55and remote folks. But the technology
44:57enablement will mean the remote people
44:59can contribute and be participating and
45:01even higher levels than probably what we
45:02see today.
45:03>> You know I've seen technology where it's
45:06like if you and I were sitting right
45:08across from each other like we're doing
45:09right now. I could basically put my hand
45:12into your screen and it's almost like we
45:14could shake hands. It's like pick up an
45:16apple off your desk or whatever. I mean
45:19it's amazing you know where do you see
45:22that going?
45:23>> I mean I I am sure these things will
45:26continue to come kind of from the lab
45:29you know into reality. That is the
45:30natural technology life cycle. And I
45:32think it's easy to underestimate how
45:35impactful they'll be. I'll give you one
45:37example. we as a leadership team decided
45:40to adopt um kind of we got we got the
45:43like meta 3D glasses and we did some of
45:46our team meetings as during the pandemic
45:48through like a virtual reality setup and
45:51most of it was actually like terrible
45:52because the technology wasn't very good
45:54and there were all kinds of issues but
45:56one thing I remember clearly was the
45:57stereoscopic sound where we could kind
46:00of talk over and with each other more
46:02naturally the way you are in a room
46:04versus on Zoom where it's kind of
46:05turnbyturn talking and then people talk
46:07over each other and they both have to
46:08stop and it's kind of messy. Just that
46:11improvement actually made it feel like
46:13such a better higher quality touch point
46:15for us as a team. So if you imagine
46:18that's just like one small innovation
46:19that can come to all of our remote work
46:21tools and then multiply it times these
46:23more dramatic things you know whether
46:24it's kind of hologram type you know
46:26inerson experiences like the one you're
46:28describing there's a lot there and again
46:30I think that the exponential improvement
46:32of what remote can be based on that is
46:34huge. You know, this has been so much
46:36fun and and I want to have some more
46:37with my lightning round of questions.
46:39Are you ready for this?
46:41>> I'll do my best. I'll do my best.
46:43>> Well, one thing I know is for sure.
46:45We're going to get some clarity here.
46:46Okay. The What are the three words that
46:48best describe you?
46:49>> Bold, analytical, compassionate.
46:52>> If you could be one person for a day
46:54beside yourself, who would it be?
46:56>> I'd want to be one of my kids. I would
46:59love to be a child again and experience
47:00childhood, you know, through their eyes
47:02and also see what kind of parents uh
47:03they think my husband and I are.
47:06>> What's your biggest pet peeve?
47:08>> I have this thing I'm a stickler for
47:10setting goals with dates and then being
47:13clear with metrics using a framework
47:14called from X to Y by When?
47:18>> Clarity again. Who would play you in a
47:21movie?
47:21>> Can I say Idris Elba because he's just
47:23so awesome.
47:24>> Perfect. I love it. you know, uh, how
47:27many languages do you speak?
47:28>> 2.2.
47:30>> What's the point two?
47:31>> Uh, my Nepali used to be a lot better
47:33when we lived in Commando and now it's
47:35definitely degraded.
47:36>> And what's your other language besides
47:38English?
47:39>> Spanish. Oh, and I have a bit of
47:40Japanese, too. So, maybe it's 2.5.
47:42>> What's the one thing you do just for
47:44you?
47:44>> Drive fast with loud music and the
47:47windows down.
47:47>> All right. If I turned on the radio in
47:49your car, what would I hear? you would
47:51hear Gold Gun Girls, which is like one
47:54of my favorite songs uh by Metric and
47:56probably some Taylor Swift. I'm still
47:58like the man and uh You've Got to Calm
48:00Down some of my favorites.
48:02>> Besides your family, what's your your
48:04most uh prized possession?
48:06>> Maybe my house. We we designed that
48:08thing to be so purpose purposeful for
48:10what we wanted.
48:11>> Yeah, that's great. What's something
48:13about you few people would know?
48:15>> I'm a huge design junkie. Like my close
48:17friends know this, but architecture and
48:19interior design, that's like my second
48:21life.
48:21>> And what's one of your daily rituals?
48:23Something that that you never ever miss.
48:26>> Sun before screens. I always have to
48:28look at the sky before I turn on my
48:30phone in the morning.
48:30>> Oh, that's cool. That's cool. All right,
48:33we're out of the lightning round. Great
48:34job. Uh, and I just got a few more
48:36questions for you and we'll wrap this
48:37up. You know, you know, I've heard you
48:39tell stories about the adventures your
48:41parents would take you on as a kid and
48:43you lived in Nepal and you know, how are
48:46you leaning into that same kind of
48:50adventure now? As a parent,
48:52>> it's really important to me that my kids
48:55feel like they're part of a world that's
48:57bigger than, you know, where we are in
48:59California. We do an international trip
49:01minimum once a year with them so they
49:03can kind of see and experience the
49:04world. This year, I also took my uh
49:0610-year-old to Ecuador on a one-on-one
49:08trip because I wanted her to see that
49:10and to have that one-on-one time with
49:11her. So, travel for us is a big thematic
49:14where we're constantly getting out and I
49:16want my kids to have that exposure. I'm
49:18not ready to be an expat with them yet,
49:19but I do want them to feel like they
49:21really are global citizens.
49:22>> And and what kind of leadership because
49:25you're obviously an excellent leader.
49:27What kind of leadership do you do you
49:29try to take home with you when you're
49:31dealing with your husband and your
49:32family? And how do how do you look at
49:34leadership at home?
49:35>> Leadership at home for me, David, is all
49:38about love. It's all about leading from
49:40a place of love. My biggest goal as a
49:43parent is for my kids to know they are
49:45unconditionally loved. They are it's not
49:47about grades. It's not about
49:48performance. Nothing is conditional
49:50about how much my husband and I love
49:51them. And so I'm constantly focused on
49:54peeling back any layers and just making
49:55sure they know how much they are loved.
49:58And you know, you mentioned
49:59compassionate is one of the words you'd
50:01use to describe yourself and and
50:03compassionate being kind. How do you
50:06balance that with just the
50:08tough-mindedness
50:10it it takes to be a CEO? Like having a
50:14graceful leave policy, for example. I
50:16mean, that took some tough-mindedness.
50:19>> Yeah. You know, it can seem like these
50:21things are at odds, but I actually see
50:23them as interlin because, you know, in
50:26the in the example of that graceful
50:27leave policy, yes, we invited and asked
50:30some people to leave the business at
50:32that time because we knew they weren't a
50:33right fit or we wanted them to self-
50:35select and we wanted the existing people
50:36to to like really opt in. But that's a
50:39compassionate thing to do to give people
50:40choice and to give them agency and
50:42acknowledge that they have that agency
50:44and acknowledge that if they're not the
50:45right fit, this is not going to end well
50:47for them or for us anyway. even if we
50:49play it out a little bit longer. So, I
50:51think a lot of these choices on the face
50:53can seem like they're not coming from a
50:55place of care and kindness, but you
50:57know, one thing I love is like letting
50:59people be free to go find greater
51:01opportunities somewhere else if they're
51:02not a fit here. And that actually is an
51:04act of love.
51:05>> Hey, listen. Every great company has a
51:07north star. You know, there's something
51:09that it's a noble cause. You know, you
51:11go to work and you're just you're not
51:13just going to work to make a paycheck.
51:15You're going to work to really make the
51:17world a better place. you know what's
51:19your what's your purpose Hayden and and
51:22uh how do you drive it deep in your
51:24organization?
51:25>> We are very fortunate because we as a
51:28business have a purpose that is so
51:31evident in everything we do. Our purpose
51:33is to create opportunity in every era of
51:36work. You know we've done this for
51:38businesses and talent through the advent
51:40of you know mobile shifting to the cloud
51:43social media like all of these phases of
51:45work that have happened over the last 20
51:46years. We've been right there helping
51:48our customers transform and meet those
51:50moments. So for us that purpose around
51:53creating opportunity in every era of
51:55work continues to be fresh and relevant
51:59because work is constantly changing and
52:01there's always more we can do to make
52:03work better for all the participants in
52:05it which is like a it's a huge mission
52:07statement if you think about it that
52:08way. So we have this purpose we drive it
52:11through I mean we show it in every all
52:13hands we talk about in every weekly
52:15meeting how the work we're doing
52:16connects back to that purpose and one of
52:18the ways it becomes very vivid is
52:20through customer stories and bring
52:22customers in through video through live
52:24interviews etc to talk about how that
52:27purpose has impacted them directly and I
52:29think that is one of the things that
52:30energizes us all the most
52:32>> you know uh we started out this uh
52:35conversation by talking about dating
52:38sites and what you'd learned uh that you
52:40could apply to to Upwork and and I'm
52:43actually interviewing tomorrow Whitney
52:45Wolf Herd, the head of uh Bumble. Yep.
52:48>> What question would you like to ask her
52:51if you could? It seems like on the
52:54precipice of AI, you know, a lot of the
52:56kind of prior models around dating and
52:58even companionship are changing in terms
53:00of both the tools that can be used to
53:04kind of facilitate matches and people
53:07actually looking for things from AI
53:09tools in terms of, you know,
53:11relationships that they didn't even
53:13think about before. We wouldn't even
53:14have thought about in the past. So, I'm
53:16really curious to understand how is she
53:17seeing her business, not just in the
53:19next year or two changed by AI, but what
53:21does it look like in five years? I think
53:22that would be an interesting
53:23prognostication.
53:24>> All right, great. I I'll definitely ask
53:26her that one. And and you know, thinking
53:28about the future, uh what do you see as
53:30your unfinished business?
53:32>> I mean, Upwork feels like very
53:34unfinished business for me. I mean, we
53:35are at the beginning of unlocking a huge
53:37market and really changing work for so
53:39many more people. So, this is like an
53:42incredible privilege and joy to work on
53:43this very unfinished business.
53:45And what's one piece of advice you'd
53:47give to anyone who wants to be a better
53:50leader?
53:50>> You know, I think people see bold moves
53:53as somehow hard and they hold themselves
53:56back because they want to find some path
53:58that maybe doesn't seem as disruptive,
54:02but the clarity and the boldness and
54:05really facing like what's the worst that
54:06could happen? I mean, we asked ourselves
54:07when we did this graceful leaf, what's
54:09the worst that could happen? And we
54:10said, you know, we'd rather be a tiny
54:12team of highly committed people than a
54:14big team of medium or not committed
54:16people. And I think asking yourself,
54:18what's the worst that can happen can
54:19really unlock for you as a leader
54:21willingness to do these things that on
54:23the face of it maybe seem bold or hard,
54:24but once you think it through, it's like
54:26the obvious thing you would do.
54:27>> Well, I can tell you the best thing that
54:29happened to me today is this
54:31conversation. You, you know, you are a
54:33tremendous leader. I'm so excited that
54:35people will get to learn from your
54:36insights and uh and and be able to to
54:40hopefully up their game like you have
54:41continually throughout your career and
54:43and I I I wish you all the best.
54:46>> Thank you so much, David. This was a lot
54:47of fun.
54:49[Music]
54:53It's probably easy to categorize clarity
54:56as just one more leadership skill you
54:59have to have, but Hayden shows us it's
55:02one of the most important tools a leader
55:04has. Without it, your team will miss
55:07opportunities and be less efficient. But
55:10to give your team clarity, you need more
55:12than good communication skills. You need
55:14curiosity to truly understand challenges
55:17they're facing. You need courage to step
55:19into tough conversations and you've got
55:21to be willing to make bold decisions,
55:24especially when no one else is quite
55:26sure what to do. Hayden models that so
55:28well and it's a big reason Upwork is
55:31able to succeed in a world that's moving
55:33faster than ever. So, here's your
55:35challenge this week. Find one way you
55:38can clear up a situation for your team.
55:40Maybe it's a conflict that's been
55:42festering, a product that's been
55:44stalling, or a big decision that needs
55:47to be made, but there's confusion all
55:49around it. Step in and lead. Bring the
55:53curiosity and courage I know that you've
55:56got and give your people the clarity
55:58they need to move forward. So, do you
56:00want to know how leaders lead? What we
56:02learned today is that great leaders
56:04create clarity for their teams. Coming
56:07up next on How Leaders Lead is Klaus
56:09Kleinfeld, former CEO of Seammens and
56:12Alcoa. So, be sure you subscribe on
56:14YouTube or wherever you get your podcast
56:17so you don't miss it. Thanks again for
56:20tuning in to another episode of How
56:22Leaders Lead, where every Thursday you
56:24get to listen in while I interview some
56:26of the very best leaders in the world. I
56:28make it a point to give you something
56:29simple on each episode that you can
56:32apply to your business so that you will
56:34become the best leader you can be.
56:40[Music]

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