Teachable moments #48 - The Dillema: Travelling with Leadership

"So I'm flying with our CEO next week," my coachee tells me. "Any advice on what to do or say?"

Most people see this situation in one of two ways:

1. Shrink back, stay quiet, don't mess up

2. Aggressively network, pitch ideas, try to impress

Both miss the mark.

I told her something simple but often overlooked:

"Your CEO is just a person. And all people – especially those in leadership – crave authentic connections."

When you're sitting next to leadership on a flight:

• Don't force conversation if they pull out work or put on headphones

• If conversation flows naturally, follow it

• Ask thoughtful questions about their vision, not just small talk

• Share insights from your role, not complaints

• Be yourself – authenticity stands out at executive levels

The reality?

The higher someone climbs, the fewer genuine interactions they experience.

Everyone wants something.

Everyone has an agenda.

Everyone's trying to impress.

Which means authentic human connection becomes increasingly rare and valuable

I'm looking forward to the outcome when my coachee and I next speak.

The most powerful career move isn't always strategic networking.

Sometimes it's just being the person who treats others like actual humans.