In this conversation, Rich Kaplan shares his experiences and insights from his time at Microsoft, particularly during the Y2K crisis. He discusses the importance of leadership, effective communication, and the need for clarity in meetings. Kaplan emphasizes the significance of personal priorities and how they influence decision-making in a corporate environment. He reflects on the lessons learned from influential leaders like Bill Gates and Steve Ballmer, and the impact of good leadership on organizational culture and success.

Chapters

00:00 Introduction

01:21 Leadership and Vision

03:31 Effective Communication in Leadership

05:32 Meeting Management Techniques

07:43 Feedback and Guidance in Leadership

10:01 Personal Experiences and Life Lessons

11:35 Health and Priorities

13:50 Philanthropy and Giving Back

15:54 Y2K and Crisis Management

18:02 Innovative Marketing Strategies

20:06 Reflections on Technology and Society

27:12 Navigating the Y2K Challenge

30:09 Establishing Support Policies

33:42 Customer Commitment and Reputation

36:39 Leadership and Accountability

38:19 Influencing Without Authority

49:57 Executing the Y2K Strategy

51:21 Y2K Strategy and Execution

52:58 Confidence in Preparedness

57:04 Lessons from Y2K and Security

01:02:05 Leadership and Culture at Microsoft

01:04:40 Influence of Key Leaders

If you listen to any of the following shows, we're sure you'll love this episode: The Diary of a CEO (Steven Bartlett), The Shawn Ryan Show, The Lex Fridman Podcast, Masters of Scale with Reid Hoffman, How I Built This with Guy Raz, The Mel Robbins Podcast, The Tim Ferriss Show.