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

Learn how to transform a challenging leader-assistant relationship into a successful partnership through commitment, humility, and trust-building.
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.
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.
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.
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.
Building Trust
Building trust in a new working relationship, particularly with a leader navigating the assistant dynamic for the first time, requires consistency and transparency. It's about showing up reliably every day and demonstrating through actions that you can be counted on.
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