41. Bad Managers and How Not to Be One with Rachel Windzberg and Dave Lifson

The Estee Show - Product Management & Business Insights

Mastering the Art of Management: Insights, Challenges, and Strategies

In this comprehensive episode, we delve deep into the multifaceted world of management. Drawing from personal experiences and professional journeys, Rachel, David, and other speakers examine the defining traits of good and bad managers, highlighting the impact on mental health and job satisfaction. They stress the importance of trust, clarity, and genuine care in manager-employee relationships and explore how effective one-on-one meetings can boost team dynamics and psychological safety. The conversation also touches on the role of managers in aligning team goals, acting as multipliers, and navigating challenges. Topics such as the pitfalls of promoting untrained high-performing ICs to managerial positions and the effects of organizational changes like removing middle managers are also discussed. This episode offers valuable lessons for both managers and employees aiming to foster a collaborative, productive work environment.

00:00 Welcome and Introductions

00:34 Discussing Management Styles

01:55 David's Management Experience

02:43 Good vs. Bad Managers

03:13 Personal Stories of Bad Management

04:29 Characteristics of a Good Manager

10:36 The Importance of Collaboration

14:44 Values and Autonomy in Management

17:11 Reflecting on Management Challenges

17:46 Building Trust and Empowerment

22:09 Effective One-on-One Meetings

26:46 Navigating Organizational Dynamics

32:50 The Role and Value of a Manager

39:42 Challenges in Large Organizations

51:29 The Importance of Good Managers

56:47 Concluding Thoughts and Reflections

David Lifson has led high performing teams at startups, public, and private equity backed companies, delivering high impact outcomes through clear vision, validated product strategy, and collaborative culture. He’s gone 0 -> 1 multiple times, as well as led teams supporting $350M in revenue. His experience leading teams spans 15 years, including four as CEO/GM and eight as Head of Product & Engineering. Dave has a bachelors and masters degree in Computer Science from Cornell University, and is based in Austin, TX.

Rachel started her path to product management as an Engineer in the semiconductors industry. Prior to that, she was a Digital Marketing and Product Specialist at Fiverr, where she was one of the first members of the team to focus on marketing and product research. As a strategy consultant at BCG, she focused on private equity and operations. Rachel joined YouNow as a Product Manager where she focused on broadcaster experience and internal tools, and joined DataDog to lead monitors and alerting product. Rachel holds an MBA from Columbia and a BSC in Electrical Engineering from Tel Aviv University.