“Kathy, how do you think about timeliness?”
It was one of my first meetings with my board chair after I took over as CEO. I had no idea what he meant. So I said… “We should be on time?” 🤷♀️
He meant meetings. He’d spent over a decade advising and investing in companies, and he rarely missed a beat. He’d noticed I often ran late. He’d noticed my predecessor did, too. And instead of quietly keeping score, he asked me to name a window.
I sat there doing the math. Two minutes, definitely not enough. Four, still no time to grab water or run to the restroom.
We landed on seven. Seven minutes early or late, no note, no apology.
A tiny norm. And yet you cannot imagine how much resentment builds when people are left to wonder why you’re late to their meetings, week after week.
This came up Friday on our first Ask Me Anything call for paid subscribers. A leader wrote in anonymously asking how to build trust with a new boss while everything around them was on fire.
My answer started somewhere that felt almost too simple: Say the question out loud.
We assume that asking “how should we work together?” lowers our status. That it plants doubt. I think that is complete BS.
And here’s what most leaders miss. Psychological safety doesn’t only flow down. It flows up. Your new boss is also wondering whether they know what they’re doing. They are also feeling the pressure to perform. If you feel stretched, they probably do, too.
When you open that conversation, you give them room to be real.
Paid subscribers can watch the full session, including how to prepare for that conversation, the three topics I’d raise before you need them, and a live conversation about choosing a niche or a broad career.
If you’re reading this as a free subscriber: leading can be lonely, and it doesn’t have to be. Paid subscribers join a live call each month to work through real situations together, plus a monthly mini-guide drawn from my coaching process. Every call is recorded, but only paid subscribers have access.
Our next session is Friday, November 20th at 11am ET. $20/month or $200/year, and founding members keep that rate for life.





