Finding the Right Force Multiplier

Learn to Lead, First

One of my first jobs after graduating college was as a financial controller. The new job was great! I mean, I even had an assistant right away! Of course, I wasn’t exactly sure how to navigate that relationship, and often had her fetching me coffee, filing, and faxing documents for me. At the time, that’s what I thought assistants did. 

Just a few years later, I left the corporate track to go all in as an entrepreneur—I became a REALTOR® and built a real estate team. I quickly realized that if I wanted to achieve the levels of success I had envisioned, I would not be able to do it alone. When I began my career in real estate, I really started to understand the importance of leveraging to a great assistant. It wasn’t just about handing off miscellaneous tasks, it was about creating a mutually beneficial relationship. I focused on sales and my assistant focused on her strengths—handling marketing and client services and creating systems and processes to make my business run smoothly, which was good for business for both of us. 

Over the next four years, as I was building my real estate team and later launching a real estate franchise, I went through several assistants, none lasting longer than eight months. It wasn’t anyone’s fault per se. I was relentlessly driven, incredibly fast-paced and impatient, with an overall lack of leadership skills. The assistants I was hiring fell more in the reactive, rather than proactive category. I didn’t really understand how to properly hire talent back then, and I paid for it with high turnover.

Eventually, through trial and error, I started to get it right. I had a great real estate marketing assistant working beside me—let’s call her Maya—and we were handling clients, contracts, and communication together well. The real estate team was growing, I was adding more agents, and it was time to expand and scale. At that time, the plan was to promote Maya to Executive Assistant, so we would put out a job ad for a real estate marketing assistant to take those duties off of Maya’s plate.

Hiring the Right Force Multiplier for the Right Job

Maya and I went through the hiring process, and eventually extended an offer to Hallie. Maya began to train Hallie on handling transactions, listings, and clients, while she prepared to take over more of my day-to-day business and personal life as Executive Assistant. Maya and Hallie worked well together and things were going great!

But something felt off… I was watching how they interacted with the team, clients, and of course, with me. Maya was amazing with clients and transactions and tended to default to working on anything related to that. Meanwhile, Hallie was curious. She dove right into problem-solving mode and initiating change and was very interested in whatever I was doing. For example, she immediately began reading the same magazine, newsletters, and books I was, as well as learning everything she could about running a real estate team. I had a gut feeling that they may be the right people, but on the wrong seat on the bus. So, I kept my hypothesis in mind, and I continued to watch and see what showed up.

After about three months of working together, I knew what I had to do. Maya and Hallie were in the wrong roles. Damn. Who would have thought after all my trial and error with assistants, that I would now have two strong individuals, who may both leave my organization after I talk to them!?

But, I’m an entrepreneur at heart, which means I’m willing to take necessary risks for the good of my team and company. I don’t shy away from tough conversations. I knew I had to talk to Maya and Hallie. I made peace with the outcome and called them both into my office.

To this day, Hallie still tells me she remembers almost everything about this moment. I sat behind my desk in my corner office overlooking Lake Champlain and the Adirondacks. Maya and Hallie sat in matching black club chairs in front of my desk – Maya on the right and Hallie on the left. They both held notebooks, unsure of what this meeting was about, but suspecting something was about to go down. I didn’t beat around the bush (not my style), and just said, “I think you both may be in the wrong roles. Hallie, I think EA may be a better fit. Maya, I think you would be a better fit for the real estate marketing assistant position.” And then I stopped talking.

They looked at each other and started nodding. Hallie spoke first and told me she agreed, and Maya did too. Hallie later told me she had that visceral feeling of excitement, nervousness, and desire to make that transition happen. She saw the Executive Assistant role as a catalyst for her own career growth and was excited to dive into the unknown. Maya was a bit relieved, and then ultimately thrilled that she could continue to do what she did well—work with clients and handle the streamlined real estate transactions. Phew! No one was leaving!

I want to take a second to point out two important things here:
  1. As an entrepreneur and leader, you must be willing to have the to have the tough conversations that others are not willing to have. There was a lot at stake by having this meeting with Hallie and Maya. I could have left that room with two less employees, and a huge headache on my hands. Instead, we made what appeared to be a minor change, but was ultimately a transformational transition for both myself and Hallie.
  2. When hiring, taking behavior and personality styles into consideration is key. Maya’s natural behavior leaned more towards consistency, stability, people-orientation, and structure. Meanwhile, Hallie’s behavior was marked by assertiveness, drive, project and task orientation, and creative problem-solving. They are both wonderful behaviors to have on your team—you just need to make sure the individuals with those behaviors are in the right position where they will thrive and be able to contribute at their highest level.

Be Willing to Grow, Together

As Hallie and I began to develop our leader/Executive Assistant partnership, I believe she taught me just as much as I taught her. I mean, that’s what partnership is all about, right? Within our first year of working together, I finally experienced what it meant to have a true strategic business partner—a Force Multiplier. I would argue that all leaders need a Force Multiplier by their side—particularly entrepreneurs, who should make it their first hire. I know first hand that it’s one of the most important hires a leader will make. 

Hallie has been by my side in the business each step of the way since 2010, pissing me off by challenging my thinking, helping me set up or dissolve companies, creating content and events, hiring staff, keeping everyone on track, co-hosting a podcast, supporting me in my personal and business life, and more. While Hallie is no longer my Executive Assistant (she replaced herself in that role in late 2017), she served as a combination of Chief of Staff, Executive Assistant, and Personal Assistant to me for over seven years. 

Today, Hallie is my Chief of Staff, but really, Force Multiplier and Business Partner more aptly describes her role in the company. The value of a Force Multiplier is not lost on me. And, if you’re at all on the fence about whether or not you need to make that hire for your company, don’t be! Our book, The Founder & The Force Multiplier: How Entrepreneurs & Executive Assistants Achieve More Together will be your guide every step of the way.

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