How to facilitate ‘depth’—a conversation with Oscar Trimboli


e18 / podcast & show notes, wherein I learn a new depth to listening.



This episode sees me share a wonderful conversation with Oscar Trimboli, host of the award-winning podcast Deep Listening—Impact Beyond Words.

Oscar has rich experience as an executive (he headed huge roles at Microsoft) and has cultivated a wealth of empathy and perspicacity as a coach. He shares the same love of questions as I do, and is quite comfortable exploring the ambiguities that exist in the domains of leadership.

I took this opportunity to delve into some of the nuances that Oscar and I share as speakers and facilitators—making this episode particularly apt for anyone looking to help folks arrive at new insight and depth. It wasn’t the kind of thing where we dropped references to articles, books or obscure academic terms. Instead, this episode offered a deep insight into how Oscar approaches the some of the trickier elements of keynote speaking (the opening and close), and how to approach the facilitation of a leadership offsite (with all its politics and perspectives)—all woven up in real stories laced with empathy and warmth.

I’ve been a fan of Oscars’s for many years now, and it’s a joy to bring this episode to you.

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