Overcoming Resistance to Coaching

In my latest episode of Cutting Through, I had the privilege of diving deep with CEO and executive coach Dan Auerbach into one of the most challenging aspects of leadership development: how to coach people who don't want to be coached.

Dan brings a fascinating background. He combines 20 years of experience as a psychotherapist with decades as a CEO of his own Enterprise Assistant Program company.

He now shares the insights from these experiences as he coaches other CEOs.

He's developed a brilliant framework that completely reframes how we approach resistant leaders:

The Autocratic Controller – understands their fear of losing control and everything falling apart
The Aloof Analytical – recognizes their need for perfect answers before speaking
The People-Pleasing Avoider – sees their terror of damaging relationships through confrontation

What struck me most was Dan's insight that resistance isn't personal – it's psychological.

Instead of fighting these defensive patterns, he's learned to work with them by understanding the underlying safety needs.

His transformation stories, including a senior executive who overcame years of harsh leadership once they understood how childhood bullying was unconsciously driving their behavior, show just how powerful this approach can be.

Timestamps

03:16 – The Psychology Behind Resistance – why we need to take an “other-oriented view” instead of getting personally triggered by coaching resistance

05:29 – The Three Defensive Leadership Types – breaks down resistant leaders into autocratic controllers, analytical aloof types, and people-pleasing avoiders

06:40 – Speaking the Controller's Language – how to approach leaders who fear losing control by validating their frustration with lack of cut-through

08:12 – The Origin Story of Control – how controlling leaders often learned to be the “organized one” in chaotic family environments

13:06 – Understanding Intellectual Aloofness – why some leaders withdraw and want perfect answers before speaking, and how to work with this pattern

17:27 – The Seed-Planting Approach – a gentle method for encouraging analytical leaders to share their intellectual gifts with the team

18:45 – The People-Pleaser's Authority Gap – how accommodating leaders lose their voice while trying to maintain relationships

22:41 – Leaders Already Know the Problems – most leaders have deep understanding but lack productive ways to share insights

25:23 – Elevating vs. Eliminating Traits – transforming defensive patterns into leadership strengths rather than trying to eliminate them

27:28 – Powerful Transformation Story – Dan shares how a senior leader overcame depression and harsh leadership by understanding childhood trauma triggers