Out of the blue, as I was building Boldly, my father — who’d been a senior-level leader in government for decades — shared something I never expected from someone who barely remembers my birthday:
“You know, the only person I’m still in touch with twenty years after retirement is my executive assistant. We worked together for 25 years. She was my right hand. She knew everything about my life. I really counted on her, and she had my back. She still calls me on my birthday, and I call her on hers.”
The man who rarely shows emotion and tends to keep everyone at arm’s length has maintained one professional relationship for 45 years.
The person from his work life who matters most to him two decades after retirement is his executive assistant.
His words stayed with me, revealing something fundamental about executive support that the business world keeps missing but I hear everyday from our clients.
At the highest levels of leadership, trust matters more than efficiency ever could.
The Rumor That Won’t Die (And Why It’s Wrong)
Our team uses AI tools. Of course we do.
But when clients come to us, they don’t ask for someone with machine-like efficiency and productivity. They ask for someone they can trust.
Someone who will figure out how to get them out of Greece when they’re stuck without a passport. Someone who genuinely has their back during times of high stress and emergency.
That’s what my father found in his EA: emotional safety and steadfastness in a world of immense pressure and never-ending changes, not just administrative support.
And that’s what today’s executives still desperately need (and want, it turns out).
At Boldly, nothing has really changed for us despite all the AI buzz. We’re still a heart-centered company at our core. While others chase the latest efficiency metrics, we believe the world is better when we have real human connections. That’s what we stand for. That’s what makes our team stand out and thrive.
Leaders Choose Humans In An AI World
The increasing isolation of leadership makes human connection more valuable, not less.
Our clients tell us they need someone who will be there when there’s a crisis. When they need both a solution and someone who understands the weight they carry. That’s the kind of support that kept my father connected to his EA for 45 years.
Technology can assist, but it can’t anticipate needs born from really knowing someone. Our best EAs already use AI as their assistant. It drafts emails they personalize. It analyzes calendars while they protect what matters. It takes notes while they read the room. They conduct a variety of tech tools like an orchestra.
The tools make them stronger, but knowing when to trust technology and when to trust their gut is pure human wisdom. Tech simply can’t provide the emotional safety of working with someone who has your back. It can’t offer the peace of mind that comes from genuine human care.
Because at the end of the day, when you’re carrying the weight of responsibility, you don’t need another app or algorithm. You need what my father found: someone you can count on, someone who knows you, someone who still calls on your birthday 20 years later.
That’s not something you can automate. And that’s exactly why it matters.
