Loving Assertiveness | Podcast
Updated: 6 days ago
TL;DR: In Episode 103 of Brain Box - The Leadership Podcast, I got to pick the brains of Omar Khan, executive coach & author of “Loving Assertiveness.” Having worked with leaders across 50 countries - from Fortune 500 boardrooms to post-conflict war zones - the conversation went places I didn’t expect.
Timestamps:
00:43 - The real costs of war
01:25 - Boardrooms vs war zones
03:05 - Dominance as a mask for weakness
05:03 - Loving assertiveness as the "third way"
09:08 - Emotional X-ray vision
12:10 - Most leaders are having the wrong conversation
16:42 - Hiring decisions & cultural fit
19:13 - Key leadership behaviors
22:03 - Communicating with those you disagree
The Insight That Stopped Me Cold:
Whether it’s a our perspective on AI and personal branding political conflict or a strategy disagreement in a boardroom, the underlying dynamic is almost always the same.
Fear dressed up as aggression.
Omar defines "Emotional X-Ray vision" as the ability to look past what someone is saying and find what they most need to be heard on. He shared a story of a senior board member who shot down every idea in every meeting. Everyone had written him off.
Until Omar asked him one question - and the man broke open. His last business had collapsed because of exactly the kind of poor decision-making he was now watching repeat itself. He wasn’t being difficult, he was terrified that it would happen again.
And that one conversation changed the entire dynamic.
The fix isn't a better framework. It's a better conversation. Underneath every act of resistance is a desire or yearning to be heard
The Deciding - Doing Gap:
Omar's research suggests that 80-90% of decisions made in organizations are either inadequately acted upon or simply abandoned. Not because of bad strategy, but because the human conversations that need to follow a decision - about resistance, about power shifts, about what people actually need - never happen.
This concept of Omar’s, sits at the intersection of accountability and care. Not a pushover. Not a bully. Someone who can hold firm on what matters while genuinely wanting things to work out for everyone in the room.
It sounds simple. It is genuinely hard.
His website has free downloadable scripts you can use to practice these conversations. Worth bookmarking. And this certainly is one of those episodes I’d recommend you listen to twice.
About Brain Box - The Leadership Podcast
Brain Box - The Leadership Podcast is hosted by Kaushik Bose and features candid conversations with founders, CEOs, CXOs and business leaders on leadership, entrepreneurship, business and the experiences behind their journeys.
