I recently caught up over a virtual coffee with a former coaching client, Amber. When I reminded her that her biggest challenge used to be getting her CEO to let her help, she looked surprised, then laughed and said:
“Wow, I’d forgotten how hard that was. I can’t believe how far we’ve come.”
Just over a year ago, Amber felt stuck. As a new Chief of Staff, she was eager to support her CEO, who constantly voiced frustration about the inefficiencies in his executive office. He felt overwhelmed and undersupported—but every time Amber offered help, he shut her out.
“He says he’s drowning,” she told me, “but he won’t even let me hold the bucket.”
We started small. We talked about how to build trust slowly, to take on low-stakes work first, and to help him see what was possible with a Chief of Staff by his side. Amber practiced saying things like,
“Some Chiefs of Staff handle this so their leader doesn’t have to.”
and
“I’ll go ahead and get that started for you.”
Bit by bit, it worked.
Her CEO started bringing her into conversations earlier. He’d forward things with, “Can you take this off my plate?” and ask for her input before decisions were made. Several months in, she wasn’t just organizing the coconuts—she was holding the machete, too.
Now? Amber is a critical thought partner. She’s running leadership meetings, refining team operations, and leading cross-functional initiatives that actually stick. The relationship is strong. Strategic. Collaborative.
And it all started with those awkward first months of resistance and persistence.
If you’re navigating something similar—trying to build trust, earn influence, or shape the Chief of Staff role into what it could be—coaching might help. I’d love to support you. Reach out if you’re curious.
