Why The Best Leaders Make Wrong Decisions | What We Don't Know with Matt Brittin & Hayaatun Sillem

Leading Through Uncertainty: Clarity, Vulnerability & Decision-Making in a Chaotic World | What We Don’t Know Welcome to What We Don't Know with Matt Brittin & Hayaatun Sillem. The show about better leadership in a truly chaotic world. Across the series, episodes are joined a range of other leading figures, bringing different perspectives to each conversation. Subscribe to not miss an episode! ▶️ ⚡️ Powered by Boxlight.io https://www.boxlight.io/ ------ In this episode of What We Don’t Know, Hayaatun and Matt explore how leadership must evolve to meet chronic uncertainty, shifting from alpha certainty to humility, adaptability, and earned trust. They discuss why clarity of purpose matters more than false certainty, how strategy can provide agency while leaving room for flexibility, and why leaders need faster shared learning cycles and better “intel” from across their networks. Hayaatun shares how the pandemic forced her to blend personal and professional life, show vulnerability, and finally ask for help when she felt close to unraveling, reframing self-monitoring as being “safe to drive the bus.” Matt Brittin reflects on learning decisiveness in ambiguous choices and describes leading Google’s response in Russia after the Ukraine invasion, prioritizing people’s safety and values. Matt and Hayaatun also answer audience questions on fear, decisiveness, resilience, and admitting “I don’t know.” 00:00 Welcome and theme 01:21 Leadership playbook shifts 02:35 Pandemic as pivot 05:02 Strategy under pressure 06:56 Clarity and agency 09:50 Collaboration and intel 12:59 Sandstorm metaphor 13:57 Vulnerability in public 16:09 Asking for help 19:19 Decisiveness lesson 23:35 Russia Ukraine crisis 27:44 Chronic uncertainty stamina 29:41 Personal boardroom 30:31 Cognitive diversity 31:28 Facing Worst Cases 32:59 Welcoming Dissent 34:06 Admitting Not Okay 35:26 Peer Support Breakthrough 39:18 Safe to Drive Bus 40:18 Asking for Help 41:21 Leadership Inspiration 42:23 Learning Model Mentors 44:03 Books Beyond Leadership 45:07 Zak Brown Authenticity 47:51 Dystopian Leadership Lessons 50:25 Sleep as Leadership Fuel 51:57 Audience Questions Rapidfire 53:21 Decisive Versus Right 54:33 Resilience Not Denial 55:17 Leading Without Answers 56:43 Beyond Crisis Identity Credits: Producer: Sunny Winter Producer: Thuy Dong Producer: Jimmy McLoughlin OBE Learn more about your ad choices. Visit podcastchoices.com/adchoices