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Executives Unplugged
Keith Cowing
14 episodes
5 hours ago

Welcome to Executives Unplugged, the show for leaders navigating rapid change with limited resources and relentless expectations.

Join operator and executive coach Keith Cowing as he sits down with world-class leaders to decode their playbooks. Drawing on experience leading teams through both failures and multi-billion dollar exits, he skips the idealistic frameworks for battle-tested tactics that will help you:

  • Make high-stakes decisions with confidence.
  • Align your team and drive rapid results.
  • Find clarity in the chaos.

Leadership is messy, but you don't have to face it alone. Executives Unplugged puts the best operators and insights in your corner to help you win and enjoy the ride.

Show more...
Entrepreneurship
Technology,
Business
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All content for Executives Unplugged is the property of Keith Cowing and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.

Welcome to Executives Unplugged, the show for leaders navigating rapid change with limited resources and relentless expectations.

Join operator and executive coach Keith Cowing as he sits down with world-class leaders to decode their playbooks. Drawing on experience leading teams through both failures and multi-billion dollar exits, he skips the idealistic frameworks for battle-tested tactics that will help you:

  • Make high-stakes decisions with confidence.
  • Align your team and drive rapid results.
  • Find clarity in the chaos.

Leadership is messy, but you don't have to face it alone. Executives Unplugged puts the best operators and insights in your corner to help you win and enjoy the ride.

Show more...
Entrepreneurship
Technology,
Business
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Don't Leave Your Moral Compass at Home with Natasha Jaffe
Executives Unplugged
25 minutes 46 seconds
4 months ago
Don't Leave Your Moral Compass at Home with Natasha Jaffe

What do you do when a leader tells you, "You have integrity. That's rare in this profession"? For my guest Natasha Jaffe, it was the signal she needed to leave.

In this episode of Executives Unplugged, I talk with Natasha, an experienced engineering leader and coach who has guided teams at both Fortune 100 companies and startups through multi-billion dollar acquisitions.

We have a raw and honest conversation about the critical mistake leaders make when they chase productivity gains but accidentally "squash the magic" that makes their teams special. Natasha shares a powerful playbook for leading through disruptive changes—like reorgs or the push for AI—by protecting your team's "flow state" and listening to your own moral compass.

This episode is a masterclass in leading with empathy and principle, offering practical advice on how to navigate immense change without losing your team, or yourself, in the process.

Guest:

  • Natasha Jaffe: Experienced Engineering Leader and Coach.
  • Find Natasha's writing at her blog: Nuts and Bolts on Substack

In this episode, we discuss:

  • (1:13) What is "Flow State"? Natasha explains why long, uninterrupted blocks of time are the source of an engineer's most creative and deep work.
  • (2:11) How Leaders Destroy Flow: Forcing teams to prioritize the "important" over the "interesting" for too long erodes curiosity and squashes the magic.
  • (3:40) The Human Reaction to AI: Why engineering teams often react to top-down AI mandates with trepidation, seeing it as "dystopian" and a threat to their craft.
  • (4:35) Fear Kills Innovation: When your team is afraid, they won't engage in the productive risk-taking required to innovate.
  • (5:11) A Case Study in Leading a Reorg: How Natasha turned a messy, demoralizing situation into a success by bringing the team into the decision-making process, listening to their fears, and even choosing a team mascot.
  • (8:33) The Real Path to Moving Faster: Stop telling your engineers to "run harder." Instead, reduce toil and remove friction to "widen the mouth of the funnel."
  • (9:16) The Collapsing Talent Stack: Are we moving away from hyper-specialists and back toward multi-skilled teams who can move with lightning speed?
  • (12:49) The Bell Curve of Team Size: The trade-off between having more minds on a problem and the rapid degradation of velocity and quality when "too many cooks are in the kitchen."
  • (15:01) Your Moral Compass: Why you can't leave your values at home and how the biggest career regrets come from not listening to your gut.
  • (16:35) "They Said the Quiet Part Out Loud": The powerful story of how a single comment about integrity was the signal Natasha needed to make a pivotal career change.
  • (18:41) Key Questions to Ask Yourself: How to get clarity when your job is in conflict with your values, and how to know when it's time to explore a change.
  • (22:08) On Burnout and Recovery: Natasha shares her personal journey of recovering from massive burnout and rediscovering creativity.
Executives Unplugged

Welcome to Executives Unplugged, the show for leaders navigating rapid change with limited resources and relentless expectations.

Join operator and executive coach Keith Cowing as he sits down with world-class leaders to decode their playbooks. Drawing on experience leading teams through both failures and multi-billion dollar exits, he skips the idealistic frameworks for battle-tested tactics that will help you:

  • Make high-stakes decisions with confidence.
  • Align your team and drive rapid results.
  • Find clarity in the chaos.

Leadership is messy, but you don't have to face it alone. Executives Unplugged puts the best operators and insights in your corner to help you win and enjoy the ride.