By AAML Staff

At the 2025 AAML Annual Meeting this past week, Thursday’s keynote speaker Ryan Leak led a dynamic CLE session titled “Working With Complicated People.” Leak offered a compelling framework for navigating interpersonal challenges in professional environments. Drawing from his own experiences and research, he emphasized empathy, connection and attitude as essential tools for working effectively with others — especially when those others are (inevitably) complicated.

Empathy Over Assumption

Leak opened with a personal anecdote that set the tone: “It’s not that I’m bad, it’s just that I can be a little… complicated.” He shared that complexity isn’t a flaw — but a reality — and urged attendees to recognize that “most people’s reactions are a reflection of their pain, not your performance.” Leak encouraged professionals to look beyond surface behaviors and seek understanding, because “complicated people have complicated ‘behind the scenes’.”

Connection Builds Equity

One of the session’s central themes was the importance of relational equity. Leak argued that without genuine connection, difficult conversations become nearly impossible. “It is always going to be difficult to work with someone you have failed to connect with,” he said. To foster connection, he offered a series of strategic questions — ranging from “What’s a job you had before this that would surprise me?” to “What acronym do we use that you don’t actually know?” — designed to spark curiosity and build trust.

These questions, Leak explained, aren’t just icebreakers — they’re tools for creating psychological safety. “The dumbest question you can have is the one you don’t ask,” he noted, underscoring the value of transparency in team dynamics.

Attitude Is Contagious

Leak’s research revealed a surprising insight: attitude — not politics, personality or preferences — is the top factor that determines whether someone is perceived as complicated. “You can’t control who walks into your office,” he said, “but you can control how you show up when they do.” He encouraged attendees to “set the temperature of the room” with their own energy, rather than matching the mood of others.

His advice was both practical and personal. Reflecting on an interaction with a grouchy cashier, he joked “I gave a $10 tip for BBQ sauce just to send a message — you don’t get to ruin my day,” illustrating how intentional positivity can shift interactions. He challenged the audience to own their own power of attitude, rather than let one person or interaction hold the power to set the resulting mood of the day.

Adjusting Expectations

Leak also challenged the audience to rethink their expectations. “We expect people to be simple and perfect,” he said, “but all we ever keep getting are complicated and flawed.” By recognizing patterns and adjusting expectations accordingly, professionals can avoid unnecessary frustration and engage with others more effectively.

Final Takeaway: Ask Twice

Perhaps the most poignant moment came when Leak shared a simple but powerful practice: ask people how they’re doing — twice. “Everybody lies the first time,” he said. “If you ask again, you might just change a life.”