Sydney Hockett of Evergreen On Authentic Women’s Leadership

You will question yourself and face pushback.

When you lead authentically as a woman — and if you’re doing so in a male-dominated industry — you will inevitably be confronted with a common dilemma. Over and over again you will ask yourself: am I letting stereotypes get to me? Am I acting too emotionally, or am I not being ruthless enough? What would my male counterparts do in this situation?

These are good questions to ask, but listening to them at the expense of being authentically yourself can be damaging.

Intoday’s dynamic world, the concept of leadership is continuously evolving. While traditional leadership models have often been male-dominated, there is a growing recognition of the unique strengths and perspectives that women bring to these roles. This series aims to explore how women can become more effective leaders by authentically embracing their femininity and innate strengths, rather than conforming to traditional male leadership styles. In this series, we are talking to successful women leaders, coaches, authors, and experts who can provide insights and personal stories on how embracing their inherent feminine qualities has enhanced their leadership abilities. As part of this series, we had the pleasure of interviewing Sydney Hockett.

Sydney is a member of the M&A team where she helps lead Evergreen’s inorganic growth, focusing on managed IT and application management businesses. Sydney spends her time identifying and talking to business owners, and bringing in new platforms and add-on acquisitions.

Prior to Evergreen, Sydney was a Manager at AlphaSights, an expert network, where she oversaw the Middle Market Private Equity book of business and a team of associates.

Thank you so much for joining us in this interview series. Before we dive into our discussion about authentic, feminine leadership, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

Even before I started college, at Notre Dame, I had an interest in business and private equity. I just wasn’t quite sure what a career in that field would look like. As an economics major, there were a couple of obvious career paths — Big Four consulting and investment banking — but neither totally appealed to me. The interview process for consulting jobs left me cold, and I also knew I wasn’t interested in the day-to-day financial modeling side of PE, or the classic investment analysis role. So with college coming to a close, I wasn’t sure where to turn.

I was lucky, in this period, to get a job at AlphaSights, an expert network provider. My role at the company involved connecting our clients — PE and consulting firms — with industry experts during the due diligence process. As an extrovert, I get a ton of energy from other people, so I loved that part of the job. I also loved getting to closely examine a wide variety of different industries. And, just as I’d hoped, I was working with large PE clients. It was kind of the perfect situation.

My time at AlphaSights was essentially a crash course in PE, which I came to realize drives a huge portion of our economy. I became fascinated by the entire process of buying a business — all those moving parts, all those different personalities. For the first time, I was gaining a deep understanding of deal-sourcing roles and investor relations and found myself extremely drawn to the more people-oriented side of PE.

Fortuitously, I came across Evergreen through a recruiter. Their “Hold Forever” model was very important to me in a sourcing role, and I felt good about the story I’d be “selling” to founders. Plus, the company was small — a start-up backed by Alpine. I was excited to be there early on and felt I could meaningfully shape its culture.

Can you share the most interesting story that happened to you since you started your career?

I can’t exactly say why, but ever since I was young I’ve dreamed of spending time in London. Just one of those little fantasies that nags at you from time to time and that you probably care more about than you consciously admit. I did almost get the chance to spend time in London through my first job but had to give that up when I decided to join Evergreen. Joining the Evergreen team was more important to me, but I can’t say I didn’t experience the slightest twinge of regret.

Again, when I joined up with Evergreen, it was very early days. The founders had an incredible vision, and I was confident we’d get there eventually, but we were very much still laying the foundation. Part of that involved writing articles outlining our vision for the company and where we saw ourselves in five years. Inevitably, I mentioned London in mine. For a new hire at a firm with no overseas ambitions, this was a bold move, but such is the naïveté of the young.

The next few years were largely about building and getting settled in our industry. London did occur to me occasionally, but there was too much on our plates to dwell on it. Now cut to 2023. We’re established, we have a lot more latitude to experiment, and suddenly we start to see several UK opportunities come across our plate. At first, it was almost a running joke, as my partner and I kept bringing these UK opportunities to leadership. But eventually, it got serious: leadership told us to put together a real case for why international expansion was a good idea.

So we got to work. My teammates and I spent months market-mapping the space and assembling a real case for UK expansion. And then, three months later, the dream finally came true: we acquired our first business in London with an incredible team. Now, we’re about to close on our second business in London, I’ve hired a London-based teammate to spearhead efforts there, and — after all these years of hoping — I’m spending weeks at a time in my dream city.

None of this seemed likely when I started at Evergreen. Now it’s hard to imagine us functioning any other way. Our UK and broader international expansion has become a cornerstone of Evergreen’s growth and has the full weight of the firm behind it. All of which is to say: you never know when your personal and professional stars might align if you want something badly enough.

What do you think makes your company stand out? Can you share a story?

Evergreen is a holding company: we never sell the businesses we buy. They join the Evergreen family for life. That means that we approach the growth of our businesses and the people who work for them with a very distinct mindset. These founders trust us to carry on their legacy and life’s work, and we take that responsibility very seriously. Building their trust is core to how we operate.

Part of that trust comes from how we operate our companies. We use a decentralized operating model, which means we’re not rolling up and integrating them, as is standard in PE. We also tend to weigh attributes over experience when evaluating companies and founders, in both our portfolio and at the holding company. Many of the people who work here at Evergreen are young and have been given the opportunity to step into a big role early on. Being able to pay those kinds of opportunities forward is one of the best parts of the job.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Number one: humility. When I started at Evergreen, I knew very little about the businesses we were investing in. I had to pick up the relevant information on the fly, in a highly pressurized environment. I could have just bluffed my way through meetings and pretended to know more than I did, but I realized early on that that approach wouldn’t work. What I’ve learned is that a willingness to acknowledge your blindspots while demonstrating a real interest in rectifying them can go a long way toward building trust with your colleagues. Certainly, it’s been critical to my career success.

Two: communication. This might seem obvious, but you really can’t overstate its importance. The better your communication skills are, the better off you’ll be. In my job, you’re constantly dealing with people, and being able to adapt to very different conversations and environments is essential.

Three: comfort with ambiguity. The fact is, in business, you’re often driving blind. There’s no established precedent, no rulebook to guide you out of a jam. Being comfortable enough to ask questions, take responsibility, and make decisions with limited data is the only way to be successful here. Knowing when to ask for help and when to plow ahead and experiment has been critical to my success.

Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader? I’m curious to understand how these challenges have shaped your leadership.

Without speaking to a specific example, I can say that virtually all of the tough choices I’ve made in my career have involved dealing with other people. Learning to balance empathy with expectations isn’t easy, and the way you communicate can make or break a relationship. Through countless tough interactions with colleagues, I’ve learned so much about how I work, what causes me stress, where I draw my boundary lines, and so much more. Sometimes you just have to take a bet and accept that you’re responsible for the outcome. It can weigh on you, but it also teaches you how to step up, articulate your position, and take responsibility when the time comes. In the end, whether you’ve made the right or wrong choice, what matters is how you handle it before, during, and after. Even if you’ve made the “wrong” choice, you can still feel good about the path that led you to it. From there, the job becomes learning from your mistakes.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Can you share a personal experience where embracing your unique leadership style, which might not align with traditional expectations, led to a significant positive impact in your organization or team?

When I first joined Evergreen, I struggled with a raging case of impostor syndrome. I was young, I was inexperienced, and I felt, at times, like I’d been handed all this responsibility by mistake — like I’d be found out at any moment and shown the door. Being a young woman in a decidedly male industry contributed to these feelings in a major way. Growing into my own, and realizing I did deserve to be there, took a long time, and was the culmination of hundreds of small moments of self-assertion. I started to realize that when I spoke up, people listened — and that they actually appreciated my perspective. It took the help of countless mentors, managers, and friends to make me realize that not being my authentic self in a professional context might have been hindering my success. That’s not to say it’s been smooth sailing ever since. I’ve tripped up along the way and will continue to do so. It’s part of the job. But as far as I’m concerned, few things feel more powerful than acknowledging that fear and acting despite it. I’m able to make decisions with my gut, as my authentic self, because after all this time, I can trust my intuition.

In your journey as a leader, how have you balanced demonstrating resilience, often seen as a masculine trait, with showing vulnerability, which is equally powerful, but typically feminine? Can you give an example where this balance created a meaningful difference?

There’s no doubt in my mind that vulnerability is a powerful asset. That doesn’t mean it’s always an asset. There’s a time and a place for it. But if you can find that perfect balance of vulnerability and resilience, you’ll be set up for significant success.

I think about this a lot during the process of negotiating a deal. I’m coming at it from an investor standpoint. I’m trying to determine what the right price is, how to maximize our returns, and how we can get the best possible deal. Conventional wisdom says that things like these demand a willingness to play hardball, to be a killer. But in my experience, that is not always true.

What I’ve found is that building meaningful personal relationships can take you just as far here, if not farther. These founders are selling their life’s work. It’s an emotional process for them, and I feel it’s important to acknowledge that. In my experience, you can be open about the process. Yes, we’re investors, we want a good deal — without neglecting the human feelings of the people you’re negotiating with. Realizing this has changed the game for me.

After all, you don’t want the people you’re negotiating with to feel like they’ve been mistreated or got the wrong end of the stick. It matters to me that I can call so many of the founders I’ve negotiated with friends and that so many of them have become Evergreen’s biggest advocates. It speaks to the importance of striking that balance — cultivating respect while taking care to build rapport.

As a woman in leadership, how have you navigated and challenged gender stereotypes, especially in situations where traditional male-dominated approaches are the norm? What strategies have you employed to remain authentic to your style?

In my experience, the best way to combat stereotypes is to be successful at what you do and to do it in your own way. Trying to contort yourself to fit the norms of male colleagues is a dead-end. The better approach is to demonstrate success not only as a woman but because you are a woman.

Of course, that can be easier said than done. There’s no question that being a woman puts you at a disadvantage in PE, which remains male-dominated — though we’ve neared parity for entry-level jobs, we’re far from reaching that goal in leadership positions. Inevitably, you have to work harder to build the respect that, for your male colleagues, is just assumed. But once you do, you’ll find yourself a lot further ahead than those colleagues because you’ve really had to push yourself.

I view these challenges as a kind of competition. I’m motivated by proving people wrong about their gender assumptions. We might wish for a society in which these toxic stereotypes simply disappear, and we might get there eventually. But the reality is that in the present tense, they do exist, and it doesn’t seem like they’re going anywhere soon. Hard as it is to say, some environments will not set women up for success, and being able to recognize those and avoid them in favor of environments that do care about advancing women is essential.

I would never compromise my beliefs and values, but I do tailor my approach depending on the deal, the meeting, or the relationship. If I’m working with a large, male-dominated bank, for instance, I’m going to come armed with what those kinds of institutions respond to — namely, data and concrete success stories.

Ultimately, it’s important to surround yourself with other strong women but also to seek out strong men who support you and believe in your value.

How do you utilize emotional intelligence and active listening to create an inclusive environment in your team or organization? Could you share a specific instance where these qualities particularly enhanced team dynamics or performance?”

I strongly believe that emotional intelligence and active listening are core to any successful leadership style. Without them, you’ll inevitably struggle to get a firm grasp on your team. This is a people-centered business. If you can’t understand people, and don’t take care to meet them where they are, your effectiveness as a leader will suffer.

I think about these traits often as I ramp new people onto the team and set performance expectations for them. While metrics and “goals” may be relatively clear-cut, how precisely to reach them may be at times unclear. I’ve had to teach myself to read people — to understand what motivates them, how they approach different tasks, and how they view success. This skill set is key to hitting your goals.

What role has mentorship played in developing your authentic leadership style, and how do you communicate authentically to inspire and empower both your mentors and mentees?

Mentorship has played a huge role for me, both formally and informally. The years I’ve spent paying close attention to other leaders — inside and beyond Evergreen — have deeply informed my own leadership style.

Growing up, my dad would always say: “Take what you like from your parents, and leave what you don’t.” In my experience, the same applies in the world of business. As I’ve grown into a leader, I’ve taken so many amazing things from my mentors and managers, but I’ve also gotten a clearer sense of the things I want to do differently, and have been able to integrate both into my leadership style.

As for how to communicate authentically, I think the answer is, quite literally, to communicate authentically. Simple as that. Chances are, you’re working with smart, talented people, who are going to know when you’re not quite being your true self. I’ve always come down on the side of overcommunication vs. undercommunication. I think it’s important to always provide the “why” behind your decisions. I also think it’s important to be able to acknowledge missteps and shortcomings. These are invaluable tools in both directions. They build trust in mentees and help you get a lot more from your mentors.

And by the way, you should never underestimate the usefulness of positive reinforcement. In my opinion, it matters just as much as critical feedback.

Based on your experience and research, can you please share “5 Ways Leading Authentically As A Woman Will Affect Your Leadership”?

1) You will question yourself and face pushback.

When you lead authentically as a woman — and if you’re doing so in a male-dominated industry — you will inevitably be confronted with a common dilemma. Over and over again you will ask yourself: am I letting stereotypes get to me? Am I acting too emotionally, or am I not being ruthless enough? What would my male counterparts do in this situation?

These are good questions to ask, but listening to them at the expense of being authentically yourself can be damaging.

One of my strongest skills has always been reading people — cultivating deep relationships that extend long past the initial scope of work. Part of that means having a deep sense of what drives people. For instance, I’ve found myself in deal negotiations where the other side of the room is pushing a data and numbers perspective. I’ll know, deep down, that I understand the business owner better than anyone else, and that this approach may not be the best one, but I’ll find myself turning away from that path out of a concern that I’ll be seen as leaning too heavily on emotions or established relationships. And nearly every time I haven’t at least voiced my opinion, the deal hasn’t worked out.

It comes down to confidence: being able to believe in yourself, stick to your convictions, and voice your opinion, even when you might be questioning yourself.

2) You need to own the fact that you’re a woman.

In my experience, acknowledging the fact that you’re a woman and that your leadership style might be different for this reason will take you much farther than simply pretending you aren’t. Being an authentic female leader is a strength and should be deployed as such. I’ve found absolutely no value in pretending that my leadership style and approach to work aren’t different, and when I’ve made the choice to harness that difference, it’s taken me much further. I know I have a high emotional quotient (EQ) and good communication skills, and I leverage those every day. Tamping down those traits because they may be viewed as “weak” lessens my value-add.

3) You can’t always change your narrative, but you can pick your place in it.

This might be a controversial opinion, but here it goes: while there will be times when highlighting your strengths as a woman will benefit you, there will also be times when it will land flat. You should never compromise your values or diminish yourself, but it’s important to know you can’t change everyone’s opinion. Developing the ability to pick the right moments to step up and change the narrative is a crucial skill in and of itself, and will garner you a lot of respect.

4) Authenticity always wins.

The more authentic you are to yourself as a woman — whatever that means to you — the more successful you will be, and the prouder you will be of that success. You can’t pretend you’re not a woman, so why bother trying? Every time I’ve made a decision out of a feeling that it was what I was “supposed” to say — what someone wanted, or what someone else would have done — I’ve always wound up regretting it, even if things worked out in the end. Being authentically yourself is a risk, and can be scary, but it’s also so much more rewarding, and it will make the relationships that you build as a leader 100 times stronger than they would have been.

5) Understand your motivations.

As a woman in business, you will inevitably think more critically about each action you take than your male colleagues. But it’s important to learn to distinguish whether you’re questioning yourself because the environment around you has conditioned you to do so, or because an extra moment of thoughtfulness is benefiting you. The former represents the proverbial glass ceiling — what we’re all trying to break through. The latter is when leading authentically as a woman will actually set you apart and advance your ambitions.

Are there potential pitfalls or challenges associated with being an empathetic leader? How can these be addressed?

There’s a risk that people may view you as too emotional or soft. It’s important to find the right balance here — to be empathetic, but also strong. You can meet people where they are without sacrificing your ambitions for your team. And it’s important to point out that not everything is captured in numbers and data. Sometimes a gut feeling can be the turning point in a deal, a sale, or a partnership. Don’t be afraid of leaning into those feelings, but also stay conscious of when you need to draw lines, whether with managers, customers, or other leaders.

This may be the main question facing women in the professional world, particularly in male-dominated industries. Being an empathetic leader can often get you labeled as too “emotional.” But empathy is a form of strength, and when used correctly, it will take you very far. You just need to know why you’re doing what you’re doing and then refuse to back down out of fear that someone will label you a certain way. Ultimately, success is the best way to back up your decisions and to show that leadership styles can take many different forms.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I would create a program that would help funnel women into the corporate role in greater numbers. Nothing would be more important to me than granting more women the opportunity to access the kinds of one-on-ones I’ve had with the mentors and other important people in my life. I wish I could give that to any young woman doubting herself because I know for a fact that I’d never be here on my own.

How can our readers further follow you online?

https://www.linkedin.com/in/sydney-hockett/

Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!