
Topics include: Courage in pursuing a vision, outsourcing tasks, and resolving conflict.
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A
Happy Monday, everybody, and welcome to another edition of Three More Questions with David Novak. I'm Kula Callahan. This is David Novak, and we're talking about your interview with Hayden Brown, who's the CEO of Upwork and an incredibly dynamic and amazing female leader. I am a huge fan of Hayden. I was before, but especially after this episode.
B
I mean, I love the fact that she came up in the organization and after nine years, became the CEO and has taken the organization to a whole different level. And just so articulate. I mean, she is so smart. You know, I'm finding a lot of these CEOs that start out as consultants are truly amazing, you know, because I think they're able to really understand strategy, the importance of structure, the importance of culture, and then they're just so good at communicating. And she's like a poster child CEO. I mean, she's really impressive.
A
She's incredible. David, I'm excited to break down some of the concepts you and Hayden talked about in today's edition of Three More Questions. So let's get going.
B
All right.
A
Question number one in the interview, Hayden says, we can't just build what customers ask for. We need to build toward a bigger vision. Even if customers aren't there yet. How can leaders build this courage and the conviction to pursue a vision that others might not see, See right away, or maybe they don't even know that they need it.
B
I think the most important thing is to understand your customers better than anybody else in the world.
A
Even better than them.
B
Absolutely. You need to know your customers even better than they know themselves. You need to know what their biggest problems are that occur most frequently. And you got to go about solving those every single day. And that'll help you come up with things that your customers could never, ever envision. But once they see them, they're going to go, oh, wow, this is exactly what I was looking for. But they didn't even know it. And that's what I think you got to do.
A
It's so funny, I was watching a clip on YouTube the other day of this professor who teaches the psychology of marketing, and he talked about how, you know, before Starbucks came around, no one would even dream about paying $3 for a cup of coffee and walking down the street with a Starbucks cup before Uber started. No one would ever dream about getting into the car with a stranger to go from point A to point B. You know, there's all these companies and ideas that came about before people would ever even think to do that thing or to use that service. And I Love this idea of kind of anticipating what people really need that they don't know they need. It's the key to unlocking just tremendous growth and disruption.
B
Well, those are two great examples, Kula. And I think as leaders, I think just knowing that your job is to create and envision and imagine around customer issues and opportunities, that's the key. And the leaders who do that best, they're the ones that change the world.
A
Question number two. Hayden describes this shift in employee makeup towards smaller core teams of full time employees and then bigger freelance networks. On this concept of full time employees versus freelancers, David, how should leaders think about what belongs to that core team versus what can be outsourced to freelancers?
B
Well, I think I asked Hayden that question in the podcast and she says it starts with the work. You have to define what the work is that needs to be done. And then you say, okay, what's ongoing that you got to be attacking every day, and you need to have the continuity in the person every day. And then what's something that you can do and get done without having to bring on someone full time? So the key is to start with the work. And by the way, I think that's the key to really building a great organization anyway. Start with the work. What needs to be done? What skills do you have to have? What do you need to make sure that you can execute the strategy that you have from a people capability standpoint, then, you know, go find those people, and some can work for you full time, some can freelance. But if you start with the work, you know, you're solving for the big problem. And that's the critical thing here.
A
How does culture play into how you decide who is full time and who is a freelancer? Like, if there's a great freelancer that you have who has the vision and is a great culture fit and brings this dynamic nature to the team? Is there ever a point where you say, okay, that person is a freelancer, but because. Because of the value they add to the culture, we should bring them full time?
B
Yeah, well, you know, what's really interesting is that freelancers are people too, okay? And you know, freelancers, they want to be a part of the organizations that they work with, even though they're not full time. So your culture should be felt by your freelancers, your suppliers, the people that you work with every day. And that should ultimately become a competitive advantage, because what do you want? You don't want just the ordinary freelancer. You want the best freelancer. And so, you know, treat the freelancers like that they're a part of your organization, because they are, and make sure that you bring on the people that are going to work with your organization in a way that's going to elevate the entire team and not necessarily bring them down. The worst thing you can do is hire people from the outside on a part time basis and they don't do what needs to be done and everybody's pointing fingers and all that. You know, I think that the culture should be something that is a driver for your permanent workforce, your full time employees and your freelancers. And you want people, you know, working together with the same spirit. And I think that's possible.
A
Absolutely. Question number three. Hayden says that her team has an agreement to resolve conflicts immediately, never letting them roll into the next week. What can leaders do to build that same kind of resolve it now culture on their teams?
B
You know, I think what is it in the Bible is, I don't know the verse, but it's, it's don't go to bed angry and you know, solve what needs to be solved today and don't take that to bed with you. And you know, I think that is such an important thing. You know, don't let things fester. When things fester, they just get worse and worse and worse. So what you have to do is when you see that conflict, you gotta resolve it. You gotta get it all out on the table. You know, one of the great traits that I think the best leaders have is they're able to sniff out the conflict. If they know that conflict resides within their team and that it's not being surfaced, they'll sniff it out, ask the questions that get the conflict out and then seek it to be resolved and resolved quickly so that people can be aligned and go about executing what needs to be done. So many times you develop these little political factions and companies and teams where people go off into their own little island and say, can you believe that person did this or this person did that and da da, da, da da. But they don't really get it out on the table with that person. And as a result, you lose productivity, you lose a lot of what I think could be positive energy that gets filled up with negative energy and many times cynicism, which is the death of any team or any organization.
A
Addressing conflict can feel awkward at times. But I love that Hayden has made this resolve it now such a key piece of their culture. Because if you know that conflict will be resolved, you know, by the end of the week, so to say, then you almost come to expect it. And then it becomes almost a normal habit and pattern that you have week in and week out. So it takes that awkwardness or discomfort of addressing it. It kind of eliminates it over time.
B
Yeah, but the most important thing is, what is it? What is the conflict? Do people understand what is it? I mean, is it really being raised? Is it being identified as conflict? If it is a conflict, then go do the tough sledding to make sure that it's resolved because that's how you're going to drive speed, efficiency and effectiveness in your organization.
A
If you haven't listened to the episode with Hayden Brown, I highly recommend it. David, you asked some great questions, too, about what it's like to be a female leader and how to balance that. And so for all the women listening, I definitely, definitely would recommend it, as I do with all of our episodes here on How Leaders Lead. David, that does it for our edition of three more questions for today. Thank you so much for listening to How Leaders Lead. We're on a mission to make the world a better place by developing better leaders. And if you carve out a little time with us each and every week, we'll help you build the confidence you need to lead well.
B
And coming up next on HAL Leaders Lead is my interview with Klaus Kleinfeld, the former CEO of Siemens and Alcoa.
Podcast: How Leaders Lead with David Novak
Host: David Novak
Guest Host: Koula Callahan
Original Interviewee Referenced: Hayden Brown (CEO of Upwork)
Date: September 15, 2025
This bonus "Three More Questions" episode follows up on David Novak’s recent interview with Hayden Brown, CEO of Upwork. Joined by co-host Koula Callahan, David unpacks three major leadership insights inspired by Hayden's original conversation—exploring visionary leadership, evolving team structures, and building a culture of direct conflict resolution. The tone is direct, practical, and focused on actionable advice for leaders navigating change in modern organizations.
Timestamp: 01:05 – 03:06
Timestamp: 03:06 – 05:51
Timestamp: 05:51 – 08:23
David and Koula emphasize the importance of bold leadership: shaping visionary products, structuring teams for agility, and cultivating a candid, collaborative culture. This episode distills practical advice from Hayden Brown’s leadership into actionable steps for leaders at every level—encouraging listeners to anticipate needs, start with the work, and always address challenges head-on.
Recommended Next Step:
Listen to the full interview with Hayden Brown for more on leadership as a female CEO and balancing authenticity with business demands.