How to be a Holistic Leader (And Why We Need More Holistic Leaders in Tech)

Melanie Margolin
Chief Legal Officer
Automatic Summary

A Truly Holistic Leadership in Tech: Expanding Boundaries and Breaking Status Quo

Lead by Melanie Margolin, the Chief Legal Officer at Thumbtack, this conversation revolves around embracing a holistic leadership approach. Melanie shares her threefold secret including connecting outside boundaries, intentional guidance, and advocating and representing others with pride.

Melanie Margolin: A Holistic Leader

"Every single one of us is a leader,” Melanie says. We all have distinct attributes that make us leaders. From being a mentor to being an executive, a team player or an ardent advocate - serving a holistic role becomes the success cocoon. Melanie calls upon everyone to explore their capabilities and venture into holistic leadership in the tech world.

The Tech Industry’s Leadership Dilemma

The tech industry does not lack leaders, but authentic leaders who can inspire us, improve us, and care about our career goals are in short supply. Melanie suggests, we need leaders who are more interested in service than power - guides not dictators. Good leadership is a human calling that requires passion, dedication and resilience.

Introduction to Holistic Leadership

Imagine your role not as a box but the hub of a wheel, connecting ideas and people, Melanie suggests. A holistic leader does not stick to their lane but serves where they are needed. Melanie encourages eliminating corners and stepping up, even when it's outside your job description.

Three Pillars of Holistic Leadership

Melanie summarizes the approach into three principles:

1. Connect Across Boundaries

"We need to build a network that reflects our belief that we have something to offer everyone,” she says. Melanie encourages everyone to break out from their silos and connect on a broader scale. The diverse connections we build can help in choosing the right people for our team and result in a thriving, diverse work culture.

2. Guide with Intention

A holistic leader leverages formal mentorships for continuous growth. Melanie views mentorship as a chance to guide and be guided. With her ongoing career development plans, Melanie has managed to connect her team more to the company and its objectives.

3. Represent Others with Pride

The trust of people, Melanie says, is quintessential in leadership. She insists on being a champion for others by giving visibility to people like their contributions and achievements.

In Conclusion...

Holistic leadership is about looking at the bigger picture - raising diversity and inclusivity issues, being inclusive, and uplifting others. By adopting this leadership style, we can foster a more inclusive and successful tech industry. As the conversation ends, Melanie encourages everyone to tear down silos, think beyond their job descriptions, and acknowledge and appreciate their teammates' contributions.


Video Transcription

Melanie Margolin, my pronouns are she her, hers? And I'm the Chief legal Officer at Thumb Tap. We're a technology driven platform that helps people care for their homes. From top to bottom being the chief legal officer at Thumbtack is only one role I play there though.I'm also a mentor, an er g executive sponsor and an outspoken ally across the entire organization. You could say that I'm someone who rarely stays in my lane, which is something I credit for much of the success I've had in my career. So I wanna dive right in. I'm gonna ask you a question and feel free to just think about it for a moment. Normally we could put it in chat or I could see raised hands, but I don't have that opportunity here. So just think how many of you here would consider yourself a company wide leader. When I ask people this question, one on one, I often get tentative looks and very few acknowledgements that they are company leaders. But what I hope is that by the end of this talk, everyone will feel like they're company leaders and you'll all be raising your hands to dive right in because whether it feels like it now or not, every single one of us is a leader. I don't care what your job title is or a list of projects that you're working on day to day. We're all leaders. And today I want us to start thinking of ourselves as the right kind of leaders.

Because what we all know from sometimes painful experience is we have a leader shortage in the tech industry. Well, let me be clear about that. We have no shortage of people who think they can just tell us what to do and how to do it. But that is not what great leaders do. And we don't have an abundance of leaders in tech who inspire us or make us better at our work. We don't seem to have folks who care about what we want from our careers or how they can help us be our best. So instead of relying on the status quo leader, we need to focus on what good leadership is and how we can help cultivate it in others. To me, it's pretty simple, good leadership is interested in service, not power, good leaders guide and support. They do not dictate and good leaders ask what can I do to help you be great? Not what have you done for me lately? I have 25 years of business and legal experience and I've been an executive for about 10 of those years, but I only just joined the tech industry in 2020.

I quickly realized that we're not doing nearly enough to demand and provide good leadership to our people in this field. This slide shows some women who I love as leaders and role models. While we do see some examples of inspiring women and people of color and leadership roles.

If we look hard enough, there just aren't enough of us, especially in tech. And frankly, this strikes me as kind of crazy because the quality of leadership can make or break a company. I would argue this is true even more than our products and services. At times, we can use technology to build amazing things, but we simply cannot automate good leadership. It's a human calling, a passion, something that sets some of us on fire in the morning and it's hard. Let's be honest because when it's done well, it's an intentional act and one where you not the bot have to show up every day as I have tried to show up every day, there are two pieces of advice I've heard over and over in my career. One I try to follow and the other I intentionally disregard. The first is don't be afraid to try something new. And the second is stay in your lane. Do these sound familiar? The first is clearly better for you than the second. But I want you to take both to heart. I want all of us to walk away this afternoon fired up to lead and to figure out how you can be the kind of leader that anyone can come to and someone who everyone seeks out. So I believe these two pieces of advice, both the one I follow and the one I definitely don't show us how to be the highest possible form of leader, a holistic leader.

Now, what do I mean, when I say holistic leader, I mean, someone who uses their job, not as a box to live in, but as the center of a wheel or a great connector of ideas and people and platforms. When you think about the wheel, it's one of the simplest yet most profound inventions that we have. It has a hub at its center. And from that hub, there are spokes or blades that expand out in all directions because there are no corners, every part has to move in sync together. And because of that, when the wheel revolves, it takes you and all of your spokes anywhere you wanna go. I often tell people that being a holistic leader means living beyond the four corners of your job and considering the whole highway, your length. But the larger truth is as you lead, there should be no corners at all. You should seek to serve in every capacity where you can, where you're needed in places where gaps exist on projects or initiatives that ignite your energy regardless of whether it's your actual job description or whether it's in your lane. The chances are that things that make you the happiest as a leader are those things that have the absolute highest impact for your company and the people with whom you work and the people you serve. Take Megan Rapinoe, for example. Well, she is an incredible soccer player.

Her social activism and equal pay work are her long term passions and what a difference she has made by stepping outside her soccer line. Well, we can't all be as cool as Megan Rapinoe. Let me start by giving you three straightforward ways. You can start being a holistic leader today. The first one is to connect across boundaries. I think one of the biggest threats to our society right now is fear. We're afraid of each other. We don't trust each other and we don't even talk to each other even though we have the power to connect to anyone and everyone. 24 7, we don't always do that and when we do it, we don't always do it. Well, we choose what we know and we stay in our silos. I get it. It's nice and safe in our silos. I'm actually from the Midwest. I lived in Indiana for over 20 years. We have silos everywhere. Silos are great for storing things and from shielding them from the elements. But maybe you've noticed no one lives in a silo. So why should someone work in one and what kind of leader can you possibly be? If your entire world is inside a silo, we need to be better than that. We need to build a network that reflects our belief that we have something to offer everyone. We need to connect across boundaries and learn from everyone. These connections can be life changing.

I take my personal connections and network very seriously. And some of the dates all the way back to when I was in college or law school. So it's never too early to start building your network connections with other people are what drive good business as an example, I've created a diverse network of professionals in my life who I always think about and for whom I like to make connections. This includes people who I may not initially have had that much in common with. As you can imagine, these connections come in handy a lot, especially when we're trying to work our way through career decisions and complex problems at work. And also when it's time to hire someone throughout my career, I've developed a process for making connections and building high performing diverse teams. It's one of the things and recognitions. I'm most proud of across my whole career at thumbtack. We turn this process into something we call simply higher life melody and quickly, here's what I do. First, I treat hiring like a mission. The end goal is to find a top notch person for the job. Next I build a candidate pool as much as I can through my network and my team's network. The hiring process is not a lottery. It should not be a game of chance.

So I personally view every single resume that comes in because thinking ahead, I wanna look back and say I did everything I could to ensure the candidate pool was highly qualified and diverse. Then we don't reach out to one person until at least half of our candidates in the pool are LGBT Q plus or women or differently abled people or veterans or people of color. My whole team follows this process and once we have a diverse pool, then we dive in and start the interview process. This intentional approach of connecting across boundaries, it works. I joined a team of two white straight men in the legal function of Thumbtack in December of 2020 as we built our team up to a small but mighty 10. It's made up of seven racially, ethnically and gender diverse teammates simply by being intentional. Now, here's one last thing to remember about this philosophy. I'm not an hr professional, I'm not certified in recruiting or human capital. And so some would tell me this is not my lane to be in, but obviously, I disagree. This is why connecting across boundaries is so important I have built and I continue to cultivate the kind of network that reflects who I am and what my values are this is a holistic leadership approach to connection.

I'm a better lawyer for connecting with all of these folks through my career. And frankly, I'm a better person for it too. I'm sure you will be as well. If you give it a try and through these connections, you'll find not only new hires but people to mentor people to mentor you and business connections who can help advance your career at some point. So the second way to be a holistic leader is to guide with intention. I'm a big believer in the power of formal mentorship in the workplace. A holistic leader understands the continuous growth of new and traditionally underrepresented talent is a team sport and it happens at all levels through mentorship. If any of you are thinking right now that you couldn't possibly contribute to another person's success, I'm gonna respectfully disagree with you. You absolutely can at all levels and in all roles, if done, right, the mentor and mentee uh relationship can be something where you learn from each other equally because that relationship is not about who's senior and who's junior, which person is more successful and less. It's about providing guidance. It's about helping each other with new skills or seeing blind spots or planning for a future that we're all still uncertain about. Everyone faces those challenges and everyone has a different point of view to share.

That is why I consider mentoring a chance to guide and be guided with intention. Over the years, I've built um unofficial mentor, mentee relationships with people across businesses, financial controllers, engineers, sales and marketing, folks, everything in between. That's the beauty. I think of a holistic approach to this.

I'm always grateful for the time I spend with mentors and mentees. And this is particularly true for every conversation I have with someone outside my lane because those folks add another spoke to my wheel and another skill to my toolbox. So let me give you a few examples of intentionally guiding someone in action. When I was at a previous company, I started a simple 135 year career plan method with my team. This helped them identify and fill their career gaps. So that as time passed, they were getting more opportunity and driving hard on new goals that they had set for themselves, being intentional in their career plans and setting aside time to work through the gaps was new for these folks. And when they started doing this, they were more connected to the company and to the company's leaders than they had been before. They had a real sense of belonging and inclusion in the whole company. When I got to thumbtack, I wondered if I could take this a step further. So last year we launched mentoring with Melanie. It was a five part group mentorship series and showcased to dive into topics that you would normally find in formal mentorship on some of these sessions, we had over 100 and 50 people.

It was clear there was an appetite for this type of mentorship and guidance from people at all levels and through all departments. And I get that I spent years in the legal profession and in the man factoring industry often is the only female voice in the room. And sometimes I was decades younger than those around me. There were next to no people of color and leadership positions and very few. If any LGBT Q plus folks who were lawyers or partners or managers, I want to give visibility to people like me, strong gay female talent or people who are adjacent to me and also underrepresented in their own right. This program did just that I was 15 years into my career before I found a true mentor. It wasn't Jane Lynch, but it was someone who was very happy to yell out through a bullhorn things I should do to improve myself and fill my career gaps. Thanks to her, I became the general counsel of a publicly traded company five years after working for her. Of course, we should recognize that good mentorship will not solve every issue our industry has. But it is a concrete way for each one of us to actively lift each other up, learn new skills and find solutions to problems that we all share. And this leads me to my third point about being a holistic leader. How do you actually represent others.

Well, well, I say we should all represent with pride. The currency of leadership is trust and there are simply no shortcuts there. You have to show up, you have to do the work and you have to earn the trust. People need to know you and see in you someone they can trust and follow. Sometimes that comes in the form of seeing someone who looks like you or has the job you want down the road or someone who simply has that charisma or personality that opens the first door at Thumb Tech. I was immediately drawn to the great culture. It was easy to want to learn the people. I joined our proud tax employee resource group as an executive sponsor and as a member of that community, I was representing this er g in our senior leadership meetings every day, getting to know the folks and being able to help push them forward in their careers. Now, two years later, I probably spend 50% of my time as a holistic leader working on company wide initiatives, not just legal and representing as many folks as possible. I recently became this executive sponsor for our black employee resource group as well.

So I'm cultivating relationships all the time across the entire company. One important part of being a holistic leader is being a champion for others, speaking up and out about people's contributions when they're up for promotion or raises or need more visibility when I first went in house and was working in a corporate legal department. I worked with a mid-level associate at a huge law firm named Lauren. Lauren was super smart and responsive and fun to work with. But her work was really behind the scenes. Eventually, I wanted to bring her up front so that more people could see what she was doing. I made that happen through working with her firm and when she was considered for a big promotion. Years later, I could write a recommendation about the years of experience I had with her being a wonderful client service representative. When I see Lauren now advocating for her own team, I'm filled with enormous pride. Now, would Lauren have gotten to this point in her career if I hadn't represented her or promoted her or helped make her a priority? I'd like to think so because she's talented, empathetic and hard working, but sometimes that's not enough. Sometimes tomorrow's leaders need a champion today. One of my favorite, strong leaders is Abby Wambach. She's a former professional soccer player and one of the most scoring soccer players of all time.

She wrote a book called Wolfpack. And in that book, she says, you will not always be the goal scorer. When you are not, you better be rushing toward her. Sometimes you will be the goal scorer. If you watch of any of my goals, you'll see the moment after I score, I begin to point, I point to the teammate who assisted I point to the defender who protected us. I point to the uh midfielder who ran tirelessly. Every goal I've ever scored belonged to my entire team. So when you score, you better start pointing. In other words, Abby believes you should be a champion for other people's hard work in your companies. What if every day we started pointing? What if we point at the colleague who did a great job but did so behind the scenes. What if we speak up and point to the woman down the hall who never gets invited to lunch? What if we point to all of our underrepresented colleagues who started at the new company ready to give their all? And what if we keep pointing at them and including them and coaching and mentoring them? What if instead of an industry where the majority employees have always had more opportunities than the women and underrepresented ones? What if we all chose to point at our colleagues who make a difference by being inclusive and going out of their way to uplift others?

I have always believed in taking responsibility for my team and giving more credit to them than they may even deserve if something goes right? I think I point a lot for me being a holistic leader and a damn good pointer is about looking at the bigger picture and finding ways to make the biggest impact for me. I like to raise diversity and inclusion issues. When we're making decisions about the business or staffing or initiatives, I'm someone that can be counted on a wheel constantly in motion to represent all of our employees. You can be that too. And I hope that you wanna be quickly in closing. I want you to remember three things. When we connect across boundaries, we create a diverse network with common ground for everyone. When we guide with intention, we foster an equitable learning relationship between everyone, regardless of who's involved. And when we represent with pride, we ensure that everyone is included. Third and over time, we have more diverse leaders who are ready to listen in an act. This is holistic leadership and this is what I've been chasing and measuring myself against all of these years. If you pick only one of these things and implement it at your company, change will happen, leadership will find you and you will find what it is to lead. And I would love to hear about it. Seriously.

Here's my email, reach out and tell me what you did and how it went. Now, let's all get out there, tear down our silos, stay out of our assigned lanes and let's point like crazy to everyone who's helping us be the best leader, teammate and person. We can be. Thank you so much for having me.