This is the first part of the series Work in Progress. Subscribe to get the next part in the series.

In 2011, I joined as the 6th employee of a small, ambitious startup called Privia Health, with an entry level title of Operations Associate.

Twelve years later, I left as the longest-running employee and Senior Vice President of a $2B+ public company that served thousands of doctors and millions of patients.

The experience was an odyssey, far different from what I expected. There were highs and lows and multiple internal revolutions in the pursuit of personal mastery and company building.

Like any startup, the company went through challenging times and repeated evolutions from birth to maturity. To survive, I had to do the same, evolving rapidly to keep pace with the stage of the company. These were my hard-won lessons learned.

Establishing Myself

When I joined Privia in 2011, we were an early company seeking product-market fit. Working to bring our ideas to life was part glorious, part bewildering. While Privia was trying to find its way, so was I, a young 20-something trying to create a name for myself in the world.

Pick the people, not the company

It’s embarrassing to admit, but when I joined Privia, I had zero projection about the future of the business. I didn’t ask about revenue, business model, investors, customers, or whatever else smart people ask about when evaluating a startup.

I liked the mission, but I mostly remember thinking: “woah, these are some of the smartest people I’ve ever met!” It was the people that made the decision for me: Jeff Butler (Founder & CEO), Dave Rothenberg (President), and Tom Peterson (consultant who would go on to found Evolent Health).

I later heard that early-stage investors pick the founder, not the idea, because it’s too early to validate an idea and good founders figure it out. 

If you are figuring out what to do with your life, picking the people to work with is a good heuristic; at the very least, you’ll witness what great work looks like.

Find career leverage

People and businesses can use leverage - such as code, labor, or capital - to create outsized returns relative to the input. At a personal level, I believe there is “career leverage,” where certain opportunities yield greater return than others.

I recognized high career leverage immediately at Privia, which became an enormous accelerant for my career. 

It’s easy to detect the roles with the worst career leverage: dead-end jobs, where no matter what you put in, you won’t get back out more than the minimum.

Less obvious are roles with low career leverage. These roles may seem attractive (high pay, high status), but they lack leverage because your upside is limited to predetermined guardrails set by others before you.

High career leverage can feel very open-ended. It’s joining something fast growing, where out of necessity, anyone half-way competent is thrown into more accountability and visibility among leaders. Low career leverage is when you are relegated to some sub-part of a big company and while you are safe from risk, your work barely makes a dent.

High career leverage is bosses who care about your performance and capacity to take on more. In fact, they are desperate for you to have both. Low career leverage is bosses who care more about hierarchy, years of experience, number of credentials, and want you to “stay in your lane.”

If you don’t have high career leverage, you might want to keep looking.

A season of hustle

I use the word “season” deliberately, because I don’t think you should hustle hard across every season of your life. But the foundations of my career were built on intense, hard work, so it would be insincere to recommend anything else.

At the start, it’s all about building credibility, because you have none. And ironically, the easiest way to build credibility is to work hard.

By working hard you are trying to overcome your deficiencies in experience, skill, and reputation. You are signaling to others that you are all-in, that you will do what it takes. When times got tough at Privia, I worked even harder, despite other people questioning the path and dropping out along the way.

That perseverance, loyalty, and reliability were critical for creating my credibility at Privia. I like to think that my commitment was unquestionable and that reputation resonated to others.

Scaling Myself

In 2013, we started Privia Medical Group, which would go on to revolutionize the company and propel us through years of epic growth and scale. While the beginning of the startup felt like finding my way, the scaling part felt like holding on for dear life.

Shift from personal success to team success

The transition from individual contributor to team manager was painful.

Many of the things that got me to this point, started to hurt me now. I had built my career on individual performance, relying on hard work, control and direct influence. I could get it done myself, so any limits to success were my own.

However, as Privia grew, this approach stopped working. I reached a point where my impact was constrained to what I could achieve independently. Even after hiring people on my team, I was still stuck in this mode of “I have my work, which is separate from their work.”

I had to realize that my success was no longer my own, but that of my team’s. I might fail, but if my team was successful, that was a net win. I had to let go of my control and accept what felt like short-term inferior performance.

A mindset shift was required. I had to let go, not hold on, or else I would be held back.

Interview with your head, hire with your heart

One area I’m proud of is my ability to spot great talent. While great talent can be elusive, we were fortunate to have a wealth of it at Privia. There’s a great deal of advice on interviewing out there. Like how being consistent in your interview questions across candidates results in better hiring decisions. So be it. Use your head.

But the most important thing when it was time to hire, was using my heart. Did this person feel right? For the role, for the team, for working with me? Feelings are hard to explain, but there are certain tells that make someone feel right:

• Did I have energy coming out of that interview?

• Did I feel excited to tell other people about them?

• Did it feel more like a conversation than an interview?

• Could I picture myself enjoying working with them?

Let me be clear: feelings can lead you astray, as you can be tricked by your own biases and charisma. But I’m not sure I ever made a hire that I was “iffy” on, that didn’t feel right.

Using your head leads you to safe hires that make sense on paper. You get enamored by their resume virtues. They check the boxes and they’re easy to rationalize to others.

Using your heart leads you to “wow” hires that will surprise and impress you, especially as they grow over time.

Make yourself replaceable

Everyone wants to be irreplaceable. They are special snowflakes and the only ones capable of doing something. Because they are special, they think they are safe, that they can’t get fired. So they hoard information and make sure no one steps on their toes.

I learned that doing the opposite, making myself replaceable, actually made me more valuable.

At a fast-growing startup, there is always new work and new hills to climb. If you don’t replace yourself, you get stuck holding onto the old work and new folks get brought in to handle the new work. By replacing myself, I could hand work off to others, creating opportunities for them, and leaving me open to handle the next challenge.

First, I wrote everything down about every aspect of my work - guides, playbooks, and processes. It was an ongoing joke how most of the shared drive had my name as the owner. Writing it down not only made it easier to hand work off, but the act of writing helped me deconstruct a process from something abstract to something we could deliver on repeatedly.

Then, I delegated my job away. On a spreadsheet, I wrote out everything I did to identify which items I could hand off to someone else. I started with little tasks that were easy to give away.

My breakthrough came when I started delegating away entire buckets of work. Entire projects or teams within my team. At the time, it felt like a scary amount of accountability to put on another person. But something surprising happened… the great people ended up becoming even better than me! I’ll be honest that it doesn’t always work out, but great people have a way of figuring things out.

And the way to figure out if people are great is by giving them more.

Leading Others

After a period of epic growth, around 2017, Privia settled in as a more mature operating company, eventually going public. There was more predictability, order, and with that, more seasoned executives to handle this next stage. I was able to witness many leaders who had influence on my development including, among many others, David Young (former COO), Mark Foulke (Executive Vice President), Dr. Keith Fernandez (Chief Clinical Officer) and Anne Loehr (Executive Coach). While I had proven myself before, this was a whole new arena, filled with unique challenges and potholes.

Learn to work across the org

“Other people think you are a mercenary and you will slit their throat to hit your goal.” - feedback given to me as part of my performance review.

Here again, in a state of evolution. I had become such an intense achiever, singularly focused on the mission, that I got a reputation for discarding or bypassing the people-side of working along the way. Before it was from individual to manager, now from manager to executive.

As organizations grow, they get more complex, requiring more coordination across teams to get work done. There’s more planning, communication, and a boatload of alignment necessary to determine the right work to do and how to get it done. There were more seasoned executives with far more political skill than I ever had. No more just doing things on my own or even within my team.

My lessons come from a volume of mistakes, most of them felt by my colleagues. A few lessons I pulled from my experience:

• Good relationships create bridges - facts don’t change minds, relationships do

• Adapt your style to the individual - if they like when you get to the point, get to the point; if they value personal relationships, show them you're a human; and so on

• Move toward conflict - embrace, don’t avoid; most issues had to do with two people not speaking directly to one another

• Phone over email - I’ve never regretted making a phone call, I’ve frequently regretted sending an email

• Campaign for the customer - it’s easier to get on the same page when you put the customer first

Be a complete team, not a complete person

When you mature, you have a greater understanding of your limits and your weaknesses. You know what you are good at (and not), your preferences (and not), and your personality traits (and defects).

One error some leaders make is to seek out other people just like them. If they are extroverts, they like working with extroverts. If they are operators, they like working with operators. And so on.

Many end up building a team of the exact same person. Great for confirmation bias, bad for creating balance on a team that will need it when running a complex business. You end up with strong leanings toward certain decisions, with little regard for the alternative.

Some of my best bosses or team members were people not like me. They offered a counter balance to my own tendencies. While I was the cold, intense machine, they were people-oriented. While I was conservative, they pushed me to be bolder. While I was building the future, they executed on the now.

I learned that while you cannot be complete on your own, your team can be complete together. By building a complimentary team, you expand the collective capabilities and skills to deal with more problems and opportunities than before.

Believe in someone, before they believe in themselves

I can pinpoint the most important moment of my career. In 2013, we were pivoting our business to Privia Medical Group. I won’t go into all the details, but it was a difficult time filled with risk that created a lot of tension in the company. It’s a story for another day.

In the middle of a particularly painful time, we decided to make a bold change to our business. It felt risky at the time, in a sort of “putting the business on the line” type of way.

Right after, Jeff Butler and Dave Rothenberg pulled me into a conference room. They asked me if I could lead the implementation of the new model.

This would be the biggest thing I had ever done in my career. I had no idea what I was getting into and felt I lacked most of the skills or experience to pull it off. I was responsible for implementing a medical group, with exactly zero medical group experience.

But they believed in me, before I believed in myself. So I naively said, “okay, I’ll do it.” And it was at this moment that my career changed.

The move worked. We ended up launching Privia Medical Group, which would propel us to the multi-billion dollar company it has become today.

For me, the move was a gift that granted me a sense of courage to take bolder risks, to have faith in myself. Writing this, years later, it’s still a memory that chokes me up.

It became the most important leadership lesson I learned: sometimes, the thing someone needs is simply a chance + faith. It became a gift I hope I passed on to others at Privia and hope to continue to do over time.

The Paradox of Work

As I step back from my time at Privia, and reflect on the experiences of others, I keep coming back to this observation: work is both the answer and the enemy.

On one hand, work can be a calling, a path to fulfillment and meaning. For me, work was not only a place where I received a paycheck, but where I received my purpose. Privia was a career maker, and I will be forever grateful for the conditions and people that propelled me to success.

But for many, work can be a curse, a burden to be avoided. While it can pull us up, it can bring us down to the depths of burnout and bitterness and despair. Even the most fortunate can be left skeptical, wondering “what is it all for?”

Work is a paradox. It can bring out the best in us, but also take away the best in us. It offers so much potential, which makes its disappointment so punishing.

It is this paradox that fascinates me now. What makes work, work for some, but not for others?

How do we make work, work for us?

Takeaways

1. Pick the right people, more than picking the right company

2. Find leverage in your career, or keep looking

3. Hustle hard until you have credibility

4. Reframe success to being about the team

5. Interview with your head, hire with your heart

6. Delegate your job away until you are replaceable

7. Learn to work across teams, not just within your team

8. Be a complete team, not a complete person

9. Believe in others, before they believe in themselves

Next up, I’m going to go deeper into being committed to your work - what it feels like and how to get there. Subscribe below to get the next part in the series.

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Note: views are my own and do not represent the views of any companies or people referenced within.

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