Turning the Tide: A Practical Guide on Shifting from Leader Mismatch to Partnership

So...you don't like your boss. Been there, done that. Now that I've snagged your attention let's dive into the heart of this article.

It's essential for a leader to find an executive assistant who gets them and vice versa. I like to call it "leader pairing." Even if both are fantastic on their own, sometimes the working chemistry just isn't there, making it nearly impossible to function as a dynamic duo. But with the right pairing, becoming a high-capacity partnership becomes a reality.

Like many of you, I've had my fair share of bosses throughout my career, but this one seemed like a total "mismatch." It was like mixing oil and water. Even before becoming my leader, we worked together, didn't see eye to eye, and collaborating was like trying to fit a square peg into a round hole. The big question loomed: bail and find a leader better suited for me, or tough it out? It's a dilemma most of us have faced at some point. This time, though, I chose to stick around and be intentional about making it work. I set up a meeting with my newish leader, kicking off a journey to bridge the gap. I shifted my mindset from merely "making it work" to prioritizing building a strong working relationship. This change transformed what initially felt like a "mismatch" into an incredible journey of cultivating a high-capacity partnership.

Inner Reflection:

While it might be tempting to say, "It just worked out," the truth is that it was more about me than I initially thought. Regardless of staying because it felt right, that pivotal conversation marked a key moment that taught me valuable lessons along the way. Not every journey works out, but join me as we navigate the art of handling what might feel like a "mismatch" in leader pairing and discover how it's possible to change the direction if you're open to going all in, embracing humility, and building trust.

Going "All In":

During the conversation with my new leader, I started that conversation with, "I'm all in." I have no idea what he expected that day because I'm sure I sent one of my famous "Let's Chat" messages. Maybe he thought I would quit or say, "I can't do this." But what happened in that conversation shifted us from a defensive standoff to him meeting me in the middle with so much grace. I don't remember the entire conversation, but I'm sure it ended with him saying something like, "Game on" or "Let's go." So, make a decision and go "All in." You never know what you might miss out on if you don't take the step.

Embracing Humility:

My parents instilled in me the timeless wisdom of "Be humble, Be Kind," and my Dad, in particular, is the epitome of humility. However, stepping into this new role demanded a fresh perspective on humility. Early on, I consciously decided to align my values with my leaders', often calling me to set aside my own ambitions. Making the objectives of both the leader and the organization the top priority wasn't always smooth sailing. Still, I quickly realized that success often hinges on prioritizing others' needs over your own—approaching it with a blend of excellence and genuine care to serve beyond what was required because it was where I was called.

Building Trust:

Building trust in a new working relationship, particularly with a leader navigating the assistant dynamic for the first time, unfolds as a journey of shared learning. While there's an initial level of trust from day one, entrusting tasks is gradual. From travel bookings to navigating the complexities of expense reports and emails, they all serve as reps in constructing that indispensable trust.

I recall one of the initial trips I booked for my new leader—to Atlanta with other leaders. Despite my experience in travel booking and high attention to detail, the seemingly flawless trip took an unexpected turn. The evening he was flying home, I received a call informing me that I had overlooked a small detail in his travel arrangements, booking him on a flight for the wrong return date. Initially thinking it was a joke, the realization struck, and I was panicking on the inside. Despite my freak-out, he responded with so much grace. We laugh about it even today, and he continued to entrust me with his travel plans. He never micromanaged but extended continuous trust, confident I would adjust and learn from the experience. The result? I became meticulous in planning travel and never missed a beat again.

While some tasks are easier to delegate than others, my approach involved an abundance of communication, questions, and consistent follow-through. Trust isn't a one-time achievement; it's an ongoing process. As trust deepens, the partnership evolves to a point where uncertainties vanish. The assistant transforms into someone adept at running plays, handling confidential information, and having your back but also skilled at managing every facet of your daily life. The ultimate goal for every leader and assistant duo is to attain a level of trust where seamless collaboration becomes second nature.

Only you can decide if you want to go "All in" or if stepping into a new job is best for you. I'll be the first to admit that sometimes pairings don't work, but hey, your current leader pairing might evolve into your best leadership match after all. As we wrap up this journey of professional growth and partnership, remember that the dynamic between a leader and an assistant is a unique partnership that, with the right steps, can lead to a lot of momentum and an enjoyable journey. That alone makes it worth going "All in."