Melissa Waters of Upwork
How Are You Creating Your Company’s Culture?
"FEARLESS CREATIVE LEADERSHIP" PODCAST - TRANSCRIPT
Episode 221: Melissa Waters
Here’s a question. How are you creating your company’s culture?
I’m Charles Day. I work with creative and innovative companies. I’m asked to coach their leaders and their leadership teams, to help them succeed where leadership has its greatest impact. The intersection of strategy and humanity.
This week’s guest is Melissa Waters. She is the Chief Marketing Officer at Upwork. They describe themselves as the world’s work marketplace.
For any business, if your success depends on unlocking creative thinking and innovation, you have to be competitive in the talent wars. The leadership rules for that used to be simple. Create a compelling culture built around in-person experiences.
But how do you lead when a company’s culture is no longer built around physical space?
“But it was interesting, the first time that I went into our office in San Francisco, after working here for a number of months, and I thought, wow, our culture is not here. It was weird. It was the first time I've ever had the opposite experience of starting remote, going into a physical location, opening the door to the office, and just having this feeling of like, oh wow, the culture I associate with this company is actually in my laptop.”
Tens of millions, probably billions, of the currency of your choice have been spent by business owners to build offices conducive to collaboration, creativity, and innovation.
I’ve owned some of those businesses and spent some of that money.
We did it to create a culture. To provide an environment that would help unleash the creativity of the people that worked for us and convert that into economic return.
Physical space wasn’t the only element to building a culture. Beliefs and behaviors mattered as well. But all of them were connected by the fact that, day in and day out, human beings came together and shared ideas and experiences, and learned from each other.
But without the physical structure of an office to provide the day-to-day container in which culture incubates, the responsibility to create those connections falls squarely on the leader.
Who are your people? What do they think, care about, love, loathe? Are they happy or not? Fulfilled or not? Interested, enthused, excited or not?
Do they feel connected to what matters to the company or not?
And if your answer to any of those questions is “I don’t know,” then it might be time to ask yourself whether your leadership is adapting to the needs of today’s talent. Or not.
Here’s Melissa Waters.
Charles (02:56):
Melissa, welcome to Fearless. Thank you so much for coming on the show.
Melissa Waters (03:00):
What a delight. I'm so happy to be here.
Charles (03:03):
When did creativity first show up in your life? When were you first conscious of creativity playing a role in your life?
Melissa Waters (03:10):
You know, when I think about creativity, I think it's really easy to first think about craft. Like, we all go to a place of creativity equals being creative about something. But when I really look back and think about my early childhood, it wasn't about craft and creativity, it was about space. And what I mean by that is, I grew up in a really small town, at the time actually it was being built - so, it wasn't even a full town yet - outside of Houston, Texas. And it was wide open spaces. It was country. It was one Billy King traffic light and a place being developed. And what happened in those formative years is that I spent a huge.… It was also a different era of modern childhood, because it was very wide, you know, free-range childhood.
The way that many of us grew up in. That is not the case today. And I spent a huge amount of my time outside. My parents famously used to put a jug of water, lock the door, put a jug of water outside. So, it was like, you know, it was truly free-range childhood. And so I grew up in nature.
And so, when I think about creativity, I think about it actually more from a place of letting your brain roam. And the process of letting your brain roam allows you to think differently about a problem, about an opportunity, about a situation. And so, I don't think about creativity from the lens of like, how did I apply that thinking, that type of thinking? I think about it more fundamentally around what was true in those formative years that I still hold dear today, which is, do I have space to let my brain room? And I say to my team all the time, it's rattling around, just let it rattle around. It's got to incubate in there for a little bit, and then it will come out, there will be a thing. But the process of getting to create, through creativity, or the creative process, I guess, is something that I'm deeply reverential about around the freedom of roaming.
Charles (05:13):
This is a question not specifically about lead—, well, I guess, a different kind of leadership. Where do you think parenting changed? I mean, to your point, that is such a specific way of parenting, and has a direct consequence. Where do you think parenting changed?
Melissa Waters (05:26):
There's actually an excellent book on this topic. It's called All Joy, No Fun. And it was written by a woman who took a look at all the different chapters of parenting. And, it's interesting that we're even using that word. Because the word parenting actually didn't emerge until the last few decades. If you think about the origin of childhood in kind of modern history, it actually comes out of, there was industrial… agrarian society to Industrial Revolution.
And children were labor, very much so, and seen as kind of an extension of family legacy, in that our family will still be alive if we have a lot of kids. And many of them still survived, you know, going through life. And then when you move past World War II into the '50s when society got a lot more stable, if you actually look back at all of the women's magazines, women's publications, things talking to, you know, women in the household back then, it was all about housekeeping.
And people often refer to that generation as kind of a “be seen, not heard” generation. And so parenting as an active way of being in a household was actually not even present in that era.
Then you had these chapters of women becoming more educated, having higher education, even surpassing men in college enrollments. And then the hypothesis is that as women became more and more educated over those preceding decades, that they started to apply a lot of that application into the household. So then you get this emergence of kind of helicopter parenting in the '80s, the '90s, the early 2000s, etc., which is still alive and well today.
And the modern kind of more recent rhetoric is like, how do we try to let our kids fail and be kids, and all those things? But yeah, there's… the concept of the word parenting actually is a pretty recent term and it's a pretty recent phenomenon inside of households. So, I think about that as one generation of moving from, you know, put a jug of water outside and lock the door, to living with three children, you know, today and parenting three children today. And I try to bring a healthy bit of skepticism to like, do you need me involved in this? I don't think you do. Why don't you go figure it out? And try to get them a little bit more latitude to operate on their own.
Charles (07:45):
So, you feel your parents’ influence in how you parent?
Melissa Waters (07:48):
Oh, yes, very much. There are a lot of things I wouldn't do. But, absolutely, yeah. I mean, I grew up with my dad as a cop, and my mom as a teacher. And there's no escaping the effect that both of those professions had on my life. And my father was a ex-Marine officer turned police officer.
So you just add those things up. And growing up in Texas. And growing up in a deeply religious family. Like, there's no shortage of layers of complexity of all of those elements that comprised who I am. No question.
Charles (08:22):
What do you think is the link between how one parents and how one leads?
Melissa Waters (08:26):
Actually quite similar. I think about it a lot, actually. How do I.… When I think about leadership, I think about setting a vision, I think about creating stability, I think about clarity. I think about, how do I ensure people know where they stand so that they have all the rules of the game and the rules of the road? They're not questioning, there's not a lack of psychological safety around, am I safe? Am I in tune with my leader, in tune with my boss, in tune with what the organization needs? So if you break all of those down, they're all human elements that you could absolutely draw in a complete parallel to parenting.
Are people in your household feeling like they know, your children feeling like they know where they stand? They know what's expected of them. They're safe, their parent is taking care of them. So I think there's a huge amount of overlap. The way that I lead teams, which is a very human based approach, and the way that I parent…. You know, I say all the time, like, "You wouldn't find a different me if you showed up at my house on Saturday morning versus Monday morning." I'm the same no matter the folks I'm around.
Charles (09:34):
How do you define success?
Melissa Waters (09:40):
I'm very motivated by impact. And I don't mean just business impact. I mean the impact on humans. So success for me is, from a leadership standpoint, is when people say, “I learned so much from you.”
So, really, we're all just passing on knowledge to the next generation. We're just taking our cumulative experience, drawing a lot of conclusions across it, handing those lessons to people who are coming up behind us, and helping smooth the path that they're on. I don't think there's anything magical about it. I think it's just that simple.
And I have been, I have benefited so much from people who have done that, who have shepherded me through all the chapters of my life. And so, when I think about turning back and looking at the group that's coming up behind me and the people on my teams, success to me is when people say, "You helped me a lot get where I'm going. I still draw lessons from my time with you."
Charles (10:40):
And there's a tension, isn't there, between that and driving business success? I mean, there are times when those two things just feel anyway, like they're at odds. How do you reconcile those moments? Do you lean one way or the other?
Melissa Waters (10:54):
No, I try to integrate them as much as possible. And goodness, we're all going through this exactly right now, right? So, you've got business after business after business having to make really hard choices about teams because of the macroeconomic environment and the climate. So, business is having to go through incredible, you know, incredibly tough moments of talent layoffs, and team layoffs, and restructuring, and all that good stuff.
And that is not a situation in which it's just a cold calculus of how to change the numbers on a spreadsheet. It's humans, it's human lives, it's livelihoods. So, I don't know any other way to lead except to be incredibly transparent with my team about what's going on in our business. And to explain the rationale I have for any move I make on any front, good, bad, mediocre, whatever.
And I find that that builds trust in our organization. And even when we have to make tough calls, even when we have to divest out of programs that we've spun up, or change team constructs, or, you know, make hard decisions, I feel some level of comfort that people will not say, "Oh, I didn't understand that. I don't know why it's happening."
Charles (12:10):
I mean, you're ahead of the curve from that standpoint, from my experience. Because people are moving towards that view of leadership and that recognition that that's what modern leadership needs to be built around. But where did it come from for you? Where did this ethos, right? I mean, it's an absolute core set of fundamental beliefs from your standpoint. I can see it in the way you describe it.
Melissa Waters (12:30):
Yeah.
Charles (12:30):
Where did it come from for you?
Melissa Waters (12:33):
You know, I think it's deeply ingrained in my human-born personality. So I'm a believer in using tools to discover who you are as a person, before I feel as though I've really unlocked my leadership style. I've done a lot of analysis of who I am. So, pick your tool, use many of them. I tend to use the Enneagram, more than others.
But understanding who I am and the composition of who I am as a person has allowed me to then apply that same set of principles, to then, you know, apply it to leadership. And so, when I think about what I have learned about myself over the decades of being alive, is that truth-telling is actually really core to me. I don't operate well on, in any relationship, whether it's a business relationship with my boss, or my team, whether it is a personal one with my family, whether it is a friend, group, etc., I don't really navigate, I don't navigate the world unless I understand that I'm kind of operating in a place of radical truth.
And so, I don't know that.… I think that's totally inherent to who I am. Yet, I've also had to over the years learn how to harness that need for truth to be productive inside of companies. Because you can't just always be, you know, letting it all hang out around all the things that you want to say and being unfiltered in any way. So I've learned how to be a diplomat.
And so I think about this balance of need for truth, need for clarity, need for transparency, with the idea that, of course, there's moments in which the way that that gets delivered has to be very, very nuanced. And so I think about applying it in a diplomatic sense. And if you think about the world's best diplomats or the world's best negotiators, they're not hiding in the shadows of untruths.
They're actually working with truth to be able to forward an agenda. So that's kind of the way that I think about applying it. And I've watched other people before me, and people I've worked for and around, and just been incredibly perceptive about ways in which they have used the same kind of techniques and tools to further an agenda inside of organizations. And I feel like I've just tried to learn some of those lessons from others, as well.
Charles (14:57):
Yeah, I'm always interested in the number of times I talk to leaders and say to them, you know, let's talk about developing a set of leadership values. And they'll always say, not always, but most of the time, somebody will say, “Honesty, pure honesty.” And that's a difficult trait for leadership to actually present all the time, right?
There are certain circumstances where your fiduciary responsibility alone prevents that from happening. How do you reconcile what you've described as a need for absolute truth with the challenges of actually running a business?
Melissa Waters (15:28):
Absolutely. I think you can have truth at the heart of what you're working on and the, you know, the nuances of how it gets communicated to which audience at which timeframe can both be in sync with one another. So, of course, I have way more information than my team about a lot of things. And that's acceptable. That's an okay construct and contract inside of organizations.
I'm going to be in the most inner circle of information because I'm on the leadership team of a company and close to the board. And I know what's going on with all the nuances of this business. But we run a publicly traded company, and we have a very large team. And so, how you navigate which audience knows which thing at which timeframe, is actually the contract of running a business.
So, I don't find those in congress with one another. I don't find the concept of, I need to operate from a place of truth, at odds with the fact that it cannot be open and radical truth at all times. It has to be distributed in a right sequence. Just the same way that I expect that my boss can't tell me, you know, our CEO, can't tell me every little thing going on in her orbit.
Because she's got a lot of things on her plate that I'm not privy to yet, or may never be. But that's a contract. I understand that. And so that's not at odds with the concept that between she and I on things that are pertinent to me, that we do have that truth and that honesty with one another.
So, I think there's a fair bit of stakeholder audience management on who knows what, when. But that doesn't feel at odds with the concept of the principles around being a open, truthful, transparent leader. I don't find those to be at odds with one another.
And my team, if I said that exact same thing to my team, they'd say, "Oh, yeah, totally, makes complete sense. And we always know that when you can tell us the right thing, or the most information, that you will."
Charles (17:25):
You said that you learned to be diplomatic. Were there times before you learn that, that radical truth got you into trouble?
Melissa Waters (17:31):
Yeah, I mean, I've learned that over the years that just saying what's on my mind without thinking through, you know, everything from everyone else's point of view can certainly land in ways that are unintended consequences, you know. And I think that that's actually part of, when I was saying before that I've done a lot of work to get to know myself. What has unlocked for me on the difference for when I say certain things, or how I say them, is doing the work of getting to know the people around me. Because as soon as I know more about them, their motivations, what matters to them, how they like to be communicated with, what's gonna spook them, you know, that type of thing. Then I know how much I have to temper what I might just have said as something that was, I didn't find controversial, but somebody else might find controversial. So, this team, actually, I've done this for a few teams. But this team that I built at Upwork is the… I guess it's maybe the second team I've done this with.
We built the half this team from… inherited a couple of folks and then built the rest of the team. And as we've come together, we've started with, let's start with Enneagram. Let's start with understanding each other's personalities and motivations. Let's start with laying a foundation of just human to human understanding.
And from there, then we can go write an annual plan and go deal with all the business stuff we've got to do. But if I don't understand the composition of this group from a human level, like, to your point earlier, no, let's go way back. Let's start where you were born. Let's start with the origin story.
If I don't know that, I don't have the ingredients to understand how I'm going to deliver feedback to you, or how I'm going to say things that might spook you. Or how I'm going to navigate giving you great news and not so great news. So, that has been incredibly valuable for us to start there. And this team, folks tell me, I haven't done this before in a business, because not every business thinks about starting with humans.
So it's been really, really illuminating for us as an operating team. And also really inspiring to know that we've now used a tool that I hope that they will use for the decades ahead in their careers. And hopefully it helps them unlock some value in future chapters, as well.
Charles (19:48):
I'm not sure I've ever heard anything as true as, “Not every business is started with humans,” because that's absolutely right. The pandemic has changed a frame of reference, I think, because we were living in a business world that was fundamentally formed out of the industrial age. And none of it, nobody's ever really stopped to wake up and realize those traits and characteristics and practices didn't work anymore.
Before I jump into that, and since I have you talking through the lens of radical truth, what's your relationship with fear?
Melissa Waters (20:14):
Yeah, that's a good one. Well, I don't, I think fear and I broke up a few years ago. But the, you know, and as far as relationships go, I think about fear and anxiety as bedfellows who have different kind of dimensions. And what I'm what I mean by that is, like, I'm very in touch with anxiety. Very in touch with the concept of being… scanning the horizon for danger.
If I think about us back millennia ago where we were literally on the savanna looking for whether or not a lion was going to eat us. I think human beings are absolutely…. We are creatures. We are organisms who have grown up and evolved from a place of, anxiety is what allows us to live. So I feel very comfortable and, and close with the concept of anxiety.
I have done a lot of work to harness it in the right way. And to make it work for me instead of have it be debilitating. But the tipping in from anxiety into fear is something that I don't relate to. And I think this is more of just a born trait, to be honest. Because I have siblings, and I wouldn't say that we're all quite the same way.
And I see that play out to this day on anything, a business challenge, a personal challenge. I was having this conversation with my team recently, because we did an Enneagram not just of ourselves, but as a team construct, like, what is our overall Enneagram profile.
And we learned that I'm like, exactly what we've been talking about, this kind of need for the truth. I will wrestle the truth. I want to talk through things. I want to challenge each other. I need for us to have a certain amount of friction in our conversations to feel as though we've gotten to the right outcome.
And the team has more of an avoidant profile. And I'm like, "All right, well, that's probably not going to work super well." So we've got to figure out how to actually co, you know, work well together, with these dimensions and dynamics. So, back to, you know, the concept of fear versus anxiety. You know, I don't feel attuned to fear. I don't feel like I have a relationship with fear.
Anxiety, it's interesting, I never would have thought of that word. I didn't identify with that word. I don't think of like, oh, I'm an anxious person. But I have come to realize over my life that one of my superpowers is actually always scanning for worst case scenario, which is an anxiety driven kind of superpower.
However, I've always done it from the lens of like, I just want to be prepared. So, if I know what the worst case scenario is going to be, then I can work backwards from that, make sure we don't hit it. So it works to my advantage because I just am always thinking through like, how things can go wrong, and therefore, preparing properly for them.
Charles (23:02):
I just want to jump back to your point about being prepared as a superpower. We've all lived through something that none of us were prepared for. How has COVID changed your leadership, if at all? How did you respond to that?
Melissa Waters (23:19):
Yeah, I mean, COVID brought us all to our knees, right? COVID was a pressure point for every one of us, in which any kind of veneer or façade or passivity that we were walking through life, I think just became exposed.
I start with the humans inherently, like, I've always done that. I didn't feel as though that was hard to find. I didn't have to go look for like, gosh, how do I now start to think of my team as people? That was always there. What I found to be so challenging for myself and for everyone around me was just how dire everything felt and how scary things felt.
And how emotionally robbed it was to just get up and try to do anything. Work, take care of your family, navigate the fear in the world. Like everybody kind of went through collective fear around what was going to go wrong. And so focusing on the humans and feeling as though whether it was first taking care of my family, taking care of my team, the focus on the humans was right there for me.
You know, how do we make sure that people are safe? How do we make sure that whatever people's situation is, they're supported in whatever they need? With lots and lots of families, obviously dealing with school closures and working in very strained conditions with kids at home.
And I have three kids. I was right there with everybody. So, it felt very close to home. And I had the same exact experience that all the people with kids did on my team. I had a harder time, you know, like, putting my arms around or kind of figuring out how to really support people who are alone.
Like, how do we go find you where you are, and make sure you feel supported if you're spending all of your time alone? I think that was something that was harder for me to relate to in that moment, because I was living in the cacophony of, you know, a family of five being all piled on top of one another, navigating this.
But I hope that what it did for everyone is bring, accelerate our views of the importance of looking at our team as humans first. And I do believe that that happened. I believe that people really.… It accelerated either our ability to say, we are a collection of people trying to get things done together, trying to have impact together.
And what can we do to hold on to some of that humanity as we go forward? I was at, you know, I was at HIMS actually, when all of this happened. And then I moved to Meta where I've worked there all remotely. And I've since moved to Upwork. And Upwork is a remote first company.
So we've been doing this type of work for 23 years in this format, very little reliance on office culture as part of our DNA. So this place is very oriented around that. It didn't mean though that we didn't go through our own seismic shifts on business health. The whole world went through a shockwave of everybody stopping everything.
So business health, I think, was really something we all navigated, and who knows what this is going to mean for the future of the business. And I also went through the Ukraine war and with this company, last year. And that was a big part of our DNA as a company, as well, and that was another kind of major moment.
And then seeing us navigate all of these crises from a human first perspective, we talked about being people first. And I never totally understood that about our culture until I went through the Ukraine war with Upwork.
And seeing us take care of our people in regions where war was breaking out, was something I will never forget. It was incredibly moving to see how we surrounded the people across Russia and Ukraine and Belarus. At that time, it was just extraordinary.
Charles (27:07):
How often do you get together in person with your team?
Melissa Waters (27:12):
My leadership team that I am on, my first team with our executive group, we get together about five times a year for four day off-sites each. So, significant chunk of time in person. And then my marketing leadership team, we get together a couple of times a year. And everybody kind of does that. Everybody's got their own cadences for off-sites.
There's no rule. It's whatever works for you. Some people do regular off-sites in an office nearby, the majority of their team. We have an office in San Francisco, an office in Chicago. And we have ways in which we work remotely across all sorts of different locations.
But it was interesting, the first time that I went into our office in San Francisco, after working here for a number of months. And I thought, wow, our culture is not here. It was weird. It was the first time I've ever had the opposite experience of starting remote, going into a physical location, opening the door to the office, and just having this feeling of like, oh wow, the culture I associate with this company is actually in my laptop.
It is not in this physical office. Which is very strange. That's like a, such an odd juxtaposition from all the other companies I've been at which had been incredibly.… All the tech companies I've been at, Pandora, Flip, Lift, HIMS, Meta, they're all very physical environment companies where the culture is posted on the wall, and everybody's spent a lot of time building college campus-like experiences and feeding people and all of that. So this has been a really interesting learning about how culture can be built in totally different way.
Charles (28:48):
Have you been conscious that you have to show up differently? I mean, you have a really powerful presence just naturally. I'm struck by your presence just meeting you this way.
Melissa Waters (28:55):
Oh, thanks.
Charles (28:56):
But have you been conscious, or did you have to adapt to what this required?
Melissa Waters (29:02):
I don't know that I've changed necessarily my approach. I think that the piece that I'm conscious of, and I'm still not really great at it, but I'm striving to be better all the time, is that if you can't see your team all the time in the hallway moments, or the sitting at, you know... I'm a big fan of desk drive-bys. I tell my team that all the time.
Like, in IRL world, I would come sit at your desk and just chat with you about whatever you're working on, because that was how I felt close to the team. So I do virtual desk drive-bys. I'm like, if I call you on Zoom, if I call you on Zoom, if I call you through Slack Huddle, do not freak out. Like, I am not calling you for, you know, some emergency. It's always so scary when the boss calls.
And I'm like, "I promise that is not who I am. I'm not, I'm actually quite casual. So, if I call you, it's just because I want to say, “Hello!” and check in and see how you're doing and see what's going on." So I do virtual desk drive-bys. And that has been interesting.
But, what I was going to say, is that because we absorb information in such a different way, it's not all just live Zoom calls all the time. We absorb a ton of information through digital channels. And everybody's in different time zones around the world. Making sure that I can impart what's in my head and communicate it through written and video and other kind of methodologies, and making sure it's distributed, is something that I think there's way more of an opportunity for me to take the time to be better at that. Because you can impart quite a bit of information, tone, lessons, top of mind kind of insights and help….
I really liked the top of mind concept of cascading communications around, here's what's coming out of our exec team to my leadership team, to their leadership team, that really needs to move fast. And so how do you have speed in the way that you communicate so people feel as though every day when they do their job, they've got the most important information at hand in order to do it?
So, I would say the diversity of methodology is something that I think that there's still a lot of room for me personally to get better at. And making sure that that diversity of methodology of communication is as robust and compelling as it would be to sit on a Zoom call and talk through something.
Charles (31:21):
You've had a number of very high profile positions at very high profile companies. Most people will not reach that level. What are those jobs really like?
Melissa Waters (31:33):
You know, I've also… I think an important element of my career is that I've worked a lot for founders. And there is a difference in working for a founder versus working for a seasoned CEO. And I've really only worked for one before, when we were at Pandora, Brian McAndrews came in as the CEO of Pandora.
And the rest of my experience has been working directly with founders. Hayden, you know, I say this to her, too. She's been here for 11 years. So she is so close to this business that she knows more than anybody on it, just the same way that a founder does. And so, what I find to be true about this job, the CMO role, where you are an extension of the brand, you're an extension of the leadership team, you're an extension of the ethos of the CEO, you're out talking with people, whether it's sales enabled businesses like ours or not, you're kind of an as an extension of the company, is that you have to deeply understand who they are as humans and be in tune with that.
And the brand, when you're in a founder-led company, the brand is the founder in many ways. And so that's been one of my biggest lessons. So you ask what it's like. It's like having the EQ to understand what's on the minds of, and anticipating what might be coming down the pike from a founder on what's on their mind, and translating that into operations.
Because really marketing, more so every decade that passes, as we have a proliferation of channels, as we have different methodologies in which we work, it's a sea of specialists, you know. It just is. You've got all these different kind of vertical factions of people trying to get work done. And everybody's very specialized these days.
And so, I think of myself as like a GM of marketing. Meaning I’ve got to help translate from a desire, an identity, an ethos of brands, somebody's hopes and wishes for how they want their business to manifest in the world. And then translate that into operational capability that allows a team of people to be able to run at that.
So the EQ balance, and the balance between desire and desire for an outcome and operating an outcome, are the things that I think about navigating all the time. And so, yeah, I think that that's like sitting in the intersection of those two things is what the job is really like.
Charles (34:13):
Does the responsibility ever scare you?
Melissa Waters (34:16):
No, no. No, I never get scared about the responsibility. I'm critical of myself and my team around how well we're doing at delivering. I feel very in tune with that kind of scanning for the worst case at all times around, boy, we're behind, we need to move faster, we need to do more, we need to improve, etc. You know, in every job, no matter the situation. But I don't generally operate from a place of fear because I can see it. It's just, I choose to not go there because I find myself shrinking.
Charles (34:55):
Mmm.
Melissa Waters (34:56):
I think fear.… I learned a life lesson many, many years ago, early in my life. After witnessing relationships that I didn't love, being in relationships I didn't love, I learned this line that I've drawn upon across every dimension of my life. Which is, make sure you're around people who help you take up space. And the concept, whether it's personal or professional or whatnot, it doesn't really matter, the line still holds.
Which is, if you are in an environment and around people who help you be your best self, then you are going to operate as your best self. You've got the coach right behind you, you know, telling you, you can do it. And I feel like I can sniff that out fast. You know, I can tell when I'm in a spot where I got fear is the thing that is making me.…
Yeah, I can just tell when it's there and its presence. And I have an allergy to it, I guess, is what I'd say. And so, I've also, you know, really drawn upon that line a lot for like, is it my good match with this organization? Am I a good match with this boss? Am I a good match with this team?
Am I a good match with personal relationships? Which, you know, very healthy ones in my life. But, yeah, being around people who help you take up space and be your best self is a good barometer for how to choose the right environment to operate in.
Charles (36:21):
Obviously your career is not over yet. But do you have any regrets so far as you look back?
Melissa Waters (36:27):
A million micro regrets and no macro regrets, that's what I'd say. I certainly think about tons of times in which, boy, I wish I had done that little thing differently. Or I wish I'd made that move instead of that. Taken one path instead of another.
But no, on the whole, I tend to, operate from a place of optimism, operate from a place of possibility, operate from a place of trying to lean into the charge rather than looking back a lot. And so I don't think through the lens of regret. I think through the lens of just constant lessons learned.
How do I, in that micro little way, you know, that I might have done something differently. All right, well, great. Next time can I make sure I apply the lesson that I learned from that time, and to not do it again? And honestly, you asked a minute ago what these jobs are like. I feel like they're, more than anything, they're a collection of patterns.
You know, pattern recognition. when you've been around the block enough times you go, "I've seen this movie a bunch. I know how this is going to end, let's just not do the thing." You know, I've made the mistake before of X, Y, Z, and here's what I learned in that process. So, let me take the learning and apply it again.
And so I feel as though I'm honestly more, more and more just the elder who's like, "All right, well, a lot of these situations are just rinse and repeat situations over and over again for companies." And drawing upon times in which I can look back and say, "Boy, we've made the wrong move on something." I use that as teaching mechanisms all the time. So let's just learn from my own mistakes to be able to do things differently in the future.
Charles (38:07):
And last two questions for you. How do you lead?
Melissa Waters (38:13):
Well, I think I lead from a place of, start with humans first, figure out what the business objective is next, figure out how to operate our way into that, and balance the emotional and rational all the time. And what I mean by that is like, we can write plans on paper all day long, but sometimes people just want to see things because it makes them feel a certain way, you know.
And so, how do we show up and not just deliver the things that are black and white and on spreadsheets, but deliver our work in a way that is emotionally resonant with the executive team or with the CEO or a founder of a company. So I lead from humanity first, transparency, clarity, providing enough stability for the team to get their work done and feel as though they can be successful and know where they stand.
And then balancing all of that with the fact that we are emotional creatures. It's got to be doing it in service of helping everybody feel like we're winning together.
Charles (39:17):
And last question. What are you afraid of?
Melissa Waters (39:23):
I don't know if I feel afraid. But I think that the things that I feel right now are just a weight around, you know, what this world is facing, what my kids are facing, what feels heavy. And there's a lot of stuff in the world that feels heavy. We've got layer upon layer upon layer of, you know, we started with pandemic, then we went into racial reckoning, then we went into war, then we went into a rise in mental health issues. And I'm in California, we've gone through all sorts of environmental disasters. We've got the climate crisis looming. So I think that worry is something that I think about, less about afraid. But, you know, can we get it together?
Can we get it together in a way that's going to make the future better than the past? And I think that is, you know, that is not a sure thing. And I think that I have grown up in an era in which the future was pretty much painted as always going to be better. And I think that right now, we're living in a world of uncertainty around whether that's the case.
And that's worrying for me and for all of us, I think. I'm navigating being a parent of three children. I'm trying to set them up for success in life. You can feel that acutely every day in the house. And trying to help them be incredibly optimistic about what the future holds. It's a real mental challenge, I'd say, for all of us.
Charles (40:48):
Yeah, it really is. I mean, I think I said to somebody the other week that I think that there's never been a time of greater impact on the future of leadership than the one we're living through. I think that leadership is changing in real time, in profound ways. The pandemic clearly triggered an enormous social shift. I personally think we're all of us dealing with massive post-traumatic stress disorder that nobody has diagnosed, and nobody's going to treat, ever in fact. So, I don't know the—
Melissa Waters (41:11):
I agree.
Charles (41:11):
Right? So all of that is going to be a factor. Actually, I do have one other question for you, which a conversation I had last week on the podcast triggered for me. I'm really interested to get your thoughts on this. How do you view disappointing people in a leadership role?
Melissa Waters (41:25):
That's a great question. Inevitable. (laughs)
I mean, it is inevitable that I'm going to disappoint someone. There's no way that I can do my job and not disappoint somebody. It's going to happen. That said, you know, maybe going back a little bit to my just deep need for truth-telling. I tend to, you know, I said to Hayden when I first started this job, I was like, "Listen, what you will get with me is, someone who is incredibly critical of myself. So I'm going to be harder on myself than you probably will ever be on me. That said, please lay it on me. Like whatever you want to say, say it."
And I had a longtime boss for seven years, Simon Fleming Wood, who I worked for across a couple of jobs. And he always used to say that to me, too. Like, "You're incredibly hard on yourself." And so I guess, usually, I can meet people with a disappointment by saying, "I'm already disappointed in myself for this."
"So, we don't… you know, you're welcome to tell me some dimension I've missed. But here's all the ways that I think that I graded myself on this problem." And that's kind of how I start, you know, any conversation around something that just has gone really wrong. “I just missed it, here's why, here's how, here's what I learned. Here's what we're going to do differently.”
So I feel very in tune with the concept of disappointment as just a normal part of life. Because I think that it's impossible, it's impossible to do these jobs and not disappoint somebody at some point. Leadership is challenging today. But executive jobs are full of complexity, in navigating so many different dimensions and parallels of different people that you're constantly having to balance. That there is absolutely no way that somebody's not disappointed with something. And it's just impossible.
You know, look at the leaders in our politics today. Like, even if somebody's doing things right and on one, for one group of people, or for one dimension, plenty of other people who are saying they're wildly disappointed. And then if that's the case, then you have to know what matters the most. Who matters the most, and what matters the most? If I'm going to win, I’ve got to win across a couple of dimensions, but I can't win across everything. So how do I figure out what matters the most?
And I think that's actually one of the harder things, is that when you're pulled in a million directions every day, you've got a million stakeholders, you've got to be able to filter out, you're really noisy, but if I fail at that thing for you, it's actually not going to make or break my success, or my team's success. So I'm going to let that go. And I'm going to choose to put my energy over here instead.
That's hard to reconcile with. Especially if you're a perfection, natural perfectionist and want to do everything right. It's really hard to say, I'm going to get a failing grade or a C grade at that thing instead.
Charles (44:12):
And it requires an extraordinary clarity of thinking. And also a willingness to put one's own ego aside, and not feel like the thing that most important is that I feel okay at the end of this. Because I think that's where a lot of leadership starts from. And that doesn't work very well.
Melissa Waters (44:29):
Yeah, I think that's right. And I think what can unlock, at least it has worked for me, is to have that contract with the person, my boss, you know, the person who's grading me. Is like, "Look, I’ve got too many things, I’ve got a stack of all this stuff. And I'm going to not prioritize it. Am I missing something? Do you see something that I don't?" Because I could say it all day long. I could say I've decided that this is not going to be my highest priority. But if it comes back later on, and it turned out that it was one of their highest priorities, then I, you know, that's not going to go well.
So I think having that kind of contract around, this is where I'm going to put the focus, and then my energy and my team's energy. And I feel incredibly responsible for the fact that I have human capital, financial, resources. I'm responsible for humans, money, time, energy.
And so, if I've got all those resources at my disposal, then I've got to figure out how to deploy them on the stuff that matters most. And I don't want to miss the movie on what might be important to someone else and, you know, bites me in the ass later. So that upfront contract, I think, really helps.
It's that psychological safety and permission to be able to make decisions on a daily basis, that we don't take for granted. Not every leader can provide that. And not every leader is able to navigate those dynamics. So I really prize leaders who can have that kind of discernment.
Charles (45:54):
I really appreciate you taking the time today. I was really curious about this conversation, looking forward to this conversation, because I'm actually an Upwork client. And I found my… I can't call her my assistant because she's more like my partner really. But anyway, I found Sarah through Upwork.
And she has been extraordinary. And we would never have found each other without Upwork. So I'm grateful to you for that.
Melissa Waters (46:16):
I love that.
Charles (46:17):
Yeah, it's really special, actually. And I'm grateful to you. I think the three-dimensionality of your thinking, I think the rigor of your thinking, I think the way that you look at yourself and explore yourself, there are so many lessons to be drawn for other people in the way that you go about this. So I just appreciate you spending the time and your candor and your insights and your honesty, and especially your humanity. So thank you.
Melissa Waters (46:39):
What an honor. I mean, I feel incredibly just humbled and honored by that statement. And I deeply appreciate it so, so much. You have talked to hundreds and hundreds of leaders and work intimately with a lot of folks around that coaching and leadership development. So I do not take that compliment lightly. And I really, really appreciate it very much. I've loved this conversation.
Charles (46:58):
Likewise. Me too. Thank you so much.
Melissa Waters (47:01):
Thank you.
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