Here’s What I’ve Learned Working for the Same CEO for 10 Years

On October 6, 2020, I celebrated my 10 year anniversary at Adam Hergenrother Companies. When I was first hired, I knew very little about real estate and building businesses, but I did know a thing or two about being an Executive Assistant. And I knew a lot about working hard to get results. I was hungry and ready to be challenged. When I met Adam, I finally met my match.

When I first joined Adam’s company, he had a successful real estate team and had recently opened a Keller Williams franchise. I was hired because his team was growing and they needed a marketing assistant to help with real estate listings and client care. I had always had a passion for real estate and had even completed the real estate licensing course in New York during college. Being as risk-averse as I am, I figured I would join his team as an assistant, learn the ropes and then become a high-profile agent like the ones I’d seen on Million Dollar Listing. As an assistant, I worked closely with the agents and clients, and quickly realized that not only would I not enjoy being an agent, I wouldn’t be very good at it! But the administration? The operations? The leadership? The organizational physics required to run a business? That was totally my jam.

Transitioning to the Executive Assitant Role

Within a few months of being hired, Adam called me and his new Executive Assistant (who had hired me to help out on the team) into his office. Was I getting fired already!? Nope. Adam simply pointed out that he thought we were in the wrong positions. Right people. Wrong seats on the bus.

He saw something in each of us that pulled him to ask the question if we were in the right roles and ultimately reorganized our team. I became the Executive Assistant for the team and for Adam, and the woman who hired me took back over my job managing listings and clients (which she was way better at than I was!). If Adam hadn’t been paying attention to how we were each showing up at work (and more importantly, if he hadn’t been bold enough to bring the conversation to light), then I wouldn’t be where I am today. That was a critical tipping point in my career.

From there, the rest is history, but by no means a straight line of success for me, for Adam, or for the companies! Ten years later, two companies have turned into a portfolio of companies (with endless iterations and startups and pivots along the way). I’ve done everything from delivering lasagna dinners for clients after closings to speaking on stage with Gary Keller and Jay Papasan to showing and managing rental properties to legal set up for new entities to creating marketing flyers to writing a book to managing social media to schlepping boxes during office moves to hiring key leadership staff to organizing and planning agendas for company meetings to creating blogs to packing protein bars and markers for Adam’s speaking engagements to navigating the internal and external communication during lawsuits to creating courses for our training organization to facilitating strategic company planning, and so much more!

That list can seem like quite the random list of responsibilities and projects (and at times it was!). However, the common denominator was this: acting as the right hand to the Founder & CEO to ensure his vision was organized, communicated, and implemented.

Career Lessons as Chief of Staff

My role today looks much different than it did 10 years ago. Each year as the company grows, Adam and I grow as leaders, business professionals, strategic partners, and humans. Here are 10 important career lessons I’ve learned over the past 10 years:

# 1. It’s okay to be human.

Believe it or not, I’m not a robot. Maybe someday I’ll be working with one, but for now, I have come to accept that I am simply human, and that’s okay. I have feelings. I need time to rest and recharge. I need to stop and eat lunch. This was hard for me to admit in the early days of my career. I could work longer and harder than anyone to get done what needed to get done. I could share my thoughts and ask questions and logically argue either side of an issue. But feelings? Hell no. It didn’t matter if I was overwhelmed or tired or scared. Just. Keep. Going. Over the past few years, I’ve come to realize that being a whole human and bringing that whole human to work actually makes me a better employee and a better human. It doesn’t mean that I bring a slew of personal issues to the office, but it does mean that I tune into my inner voice and insights when needed.

#2. Ask for help.

I didn’t ask for help for a long time. I thought it meant that I couldn’t handle it or that I was “less than” in some way. But asking for help (whether in the form of additional resources or staffing or delegating) does not mean you are not competent and capable. Believe it or not, you don’t have to do it all and someone else often can do it better than you, depending on the task. Easier said than done, I know. When asking for help, come with a specific request and a plan. And then once help is there, get out of the way and let them actually help! I should have asked for help much earlier in my career. I had reached my max capacity and was actually holding the company back by trying to do it all on my own, which was the exact opposite of my intention. To reach the next level for the company and my own personal growth, asking for help was necessary.

#3. Hire people who are better than you.

If you don’t hire people who are better than you, you won’t actually get the leverage you are looking for. The first few direct reports I hired were not as talented as I needed them to be, which meant I was always having to check their work or push them along to get their work done. Instead of freeing up my time and brain space, I was often double or triple checking that things were getting done. These sub-par hires were a totally ego-driven move on my part. If I hired someone better than me, than what would the company or Adam need me for, right? Well, after failing forward on that a couple of times, I started to let go of the ego and hire the right people. People who intimidated me just a little bit (a sure-fire sign that they were the right people) and who truly took the role from me. And, guess what? The company still needed me and I was able to truly contribute from my strength zone and operate in my flow. I won and the company won.

#4. Don’t take notes during meetings.

Not taking notes sounds counter-intuitive for an assistant, right? But listen to me for a second. If you’re in a meeting transcribing everything that is being said, then you’re not really “in” the meeting. As you’re trying to capture what is being said, you miss the subtleties of the conversation, you miss the spaces where things aren’t being said, you miss the opportunity to share an idea or bring an issue to light that no one is bringing up. Sure, jot down a few action items, but stop transcribing. Use your technology for that. Instead, sit at the table. Then listen. Contribute. Make notes of any action items. And then follow-up. This will immediately raise your visibility as an EA and allow you to provide value to the organization in a new way.

#5. Do things you don’t think you’re ready for.

If you’re lucky enough to work with a leader who pushes you outside of your comfort zone like I do, great! If not, push yourself! Look, confidence doesn’t come from knowing everything. Confidence is knowing you can handle any problem or challenge that comes your way. Take on new projects. Volunteer to run a committee at work. Do these things even if you don’t think you’re ready. This is where growth happens! You’ll realize you’re not going to die and you start programming your brain to say “Yes!” to new opportunities faster and with more confidence the next time.

#6. Ask for what you want and need.

What is it that you really need? Time off? Salary increase? More responsibility? More accountability? A flexible schedule? Each person is going to need something different to be fulfilled and operating most effectively in their personal and professional life. The hard part is not asking per se. The hard part is being okay with whatever the answer may be. Four years after working with Adam, I asked for a title change (to Chief of Staff) and a significant salary increase. I came up with a new job description and a proposal for how my new role would benefit him and the organization (not to mention it was for the most part, what I was already doing). Sometimes what you need is a little clarity and validation. There is nothing wrong with asking for that either! Every few months I’ll do a check-in with Adam and make sure I am still on the right track and providing the value he needs. At the same time, I need to know where we are going. I want and need that feedback and future growth conversations to stay inspired, creative, and fueled to take on the next challenge.

#7. Ask a shit ton of questions.

Asking lots of questions is not blanket permission to pepper your leader or other team members with inane requests about things you can and should be able to figure out on your own. But questions in order to gain more context and learn? Yup. Questions to challenge your leader’s thinking and drive clarity in the conversation? Absolutely. Powerful questions to help your leader make better decisions? Definitely. Over the years, my questions have shifted from tactic to strategic, from real estate processes to mergers and acquisitions, from “What are you thinking?” to “Why did you make that decision?” For the past several years, my mission has been to understand how Adam thinks, how he leads, and how he makes decisions. First, so I can better anticipate the questions he may ask and have the answers ready for him ahead of time. Second, so that I can make those decisions on my own.

#8. Let go of the outcome.

Letting go of the outcome takes years of inner work, but man, is it worth it. I am still in the midst of this journey but I’ve already experienced significant personal growth by practicing this. It was a hard concept for me to learn because I’m a driver and I like to be in control. What I’ve come to realize (thanks Adam!) is that letting go of the outcome does not mean you stop fighting for the results. Know who you are and what you want and go after it unapologetically! And when the universe steers you in a different direction, listen, don’t resist, and don’t become the emotions around what is happening. You don’t “need” a certain outcome to be whole and complete inside. If you’re starting position is that you are “okay” with anything, then you just get to go play in the world! For me, that’s through business and there is a hell of a lot of personal growth to be had when you work in a growing organization. I get the opportunity to practice letting go every day. It does get easier over time and I’m able to make decisions and lead with much more clarity and conviction when I do.

#9. Invite yourself to the table.

Inviting myself to the table was one of the things I did from day one and I believe it had a significant impact on my career trajectory. As Adam’s EA, I knew what books he was reading, podcasts he was listening to, the meetings that were important to him, and the conversations he was having. I simply invited myself along. Sometimes with a quick email asking, “I see X call on your calendar, can I listen in?” Other times, I just showed up. The knowledge I gained about the organization, leadership, and how Adam thinks and makes decisions was invaluable. The key is making sure I put that knowledge to good use, such as bringing new ideas to the table once I had context, prepping meetings or presentations on behalf of Adam, or ensuring decisions were streamlined and easy to make. Inevitably there will be some meetings you aren’t needed in or may even be asked to leave. But that will be rare and it’s a great opportunity to work on letting go!

#10. Leadership (particularly self-leadership) skills will give you a competitive advantage.

This year, I hired a business coach with the intention of becoming a better Chief of Staff and leader. Focusing on more leadership growth was the easy thing to do (at least for me). What I quickly realized, with the help of my coach, was that I didn’t need any more guidance on leadership or how to do my job, what I needed was a deep dive into my personal growth and self-leadership. For years I have used my work as a distraction from focusing on myself and I’ve been hitting a ceiling. I thought doubling down on leadership and business training would be the trick to break through. But, the joke is on me. I actually had to do the hard thing… stop using work as an excuse and an escape and work on myself. There is no endpoint for this journey. There is no task to check off. But I have faith in the process and I know that by focusing on my self-leadership I will ultimately get the competitive advantage I’ve been looking for.

The Founder & The Force Multiplier

I am so grateful to have found a career where I am constantly pushed to grow and become a better leader and better version of myself. Ray Dalio just about sums it up, “The people who work for you should constantly challenge you. Don’t hire people just to fit the first job they will do; hire people you want to share your life with.” Even if you are not in charge of hiring, this goes for you, too. Who you choose to work for and partner with matters. After 10 years, Adam and I still have a lot of exciting work to do. I may not always be his Chief of Staff in the future, but I do know that we’ll be working together on something in some way or another.

This is one of the reasons that Adam and I enjoy teaching The Founder & The Force Multiplier Live Course! We have learned so much from working side-by-side when it comes to growing our partnership, and our mission is to share those lessons to help other Founder & Force Multiplier pairs out there accelerate their own growth. If you are interested in this online course, learn more about it here. And be sure to check out our book!

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