Executives Unplugged

Keith Cowing
  • 5.0 (6)
  • MANAGEMENT
  • UPDATED BIWEEKLY

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.

Episodes

  1. 2D AGO

    From Burnout to Breakthrough: Master Your Calendar

    Feeling like your calendar is running your life? In this episode of Executives Unplugged, executive coach Keith Cowing shares a battle-tested playbook to flip the script. Learn how to audit your schedule, spot energy-drainers, and make small but powerful changes that double your strategic time without burning out. You’ll discover: How to run a calendar audit step by step The “two truths and two pies” exercise Simple psychological tricks to protect your focus Why just a 10% shift can double your momentum Subscribe for more playbooks to lead with clarity and momentum. Chapters: (00:00) Intro — Is your calendar running your life? (00:51) The Tetris analogy: when meetings feel like blocks falling (02:20) Step 1 — Calendar audit explained (04:06) Step 2 — Analyzing results: the two pies and two truths (07:53) Step 3 — Making changes and mindset shifts (09:04) Protecting your focus like it’s a meeting with the CEO (11:11) Setting boundaries and saying no with confidence (12:48) Closing thoughts — audit, analyze, shift Follow Keith Cowing: Follow on LinkedIn: https://linkedin.com/in/keithcowing   Join the Executives Unplugged community for free coaching via email: https://kc.coach Subscribe to the show: YouTube: https://www.youtube.com/playlist?list=PLU_rgycqchjl1jNqjOeJFepyr9yfcXWcM Spotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN Apple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263

    14 min
  2. From Silos to Studios: A New Playbook for Building Faster, Smarter Teams

    JUL 23

    From Silos to Studios: A New Playbook for Building Faster, Smarter Teams

    Your org chart is obsolete. It's time to move from silos to studios. The old model of large, hyper-specialized teams is now a liability. If you're looking to leverage AI to innovate faster than the competition, this episode offers a playbook.  Product leader Nate Gosselin introduces a new model inspired not by corporate frameworks, but by hip-hop producers. He breaks down the concept of the "Product Producer" and the shift from rigid, siloed teams to small, nimble "studios" powered by AI. This conversation provides a tactical guide for leaders to rethink their org design, tackle technical debt, and build the multidisciplinary teams needed for the future.  In this episode, you’ll learn:  (01:31) What is a "Product Producer"?  (05:12) The Skills to Hire For: AI Literacy and Multidisciplinary Talent  (11:09) Managing AI Like a Team of Highly Capable Interns  (13:30) Where to Start: Low-Risk, High-Impact AI Projects  (16:33) How to Use AI to Tackle Your Scariest Tech Debt  (20:49) The New Org Model: Shifting from Assembly Lines to Creative Studios (31:53) Your First Step: A Practical Guide to Implementing AI in Your Workflows (39:08) The Personal Transformation for Leaders: From Specialist to Builder Follow Keith Cowing:  LinkedIn: https://linkedin.com/in/keithcowing  Subscribe to free coaching via email: https://kc.coach Subscribe to the show:  YouTube: https://www.youtube.com/@kcowing  Spotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN  Apple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263 Follow Nate Gosselin:  LinkedIn: https://www.linkedin.com/in/nate-gosselin  Website: https://www.heynate.me/

    46 min
  3. Driving Rapid Change Without Breaking Your Team: Mastering the Art of Cadence and Commitment

    JUN 30

    Driving Rapid Change Without Breaking Your Team: Mastering the Art of Cadence and Commitment

    The pressure on leaders to deliver rapid, transformative change has never been higher. But how do you move fast without leaving your people behind? In this episode, host Keith Cowing sits down with Perry Steinberg, a seasoned Chief Product Officer with deep experience leading through high-stakes transitions at both public companies and fast-paced private equity-backed firms. Perry unpacks his core leadership philosophy for navigating this exact challenge, revealing how to maintain cohesion and drive results simultaneously. In this conversation, you will learn: The Art of Cadence and Commitment: The methods Perry uses to build trust and alignment, even when making difficult decisions.Leading the 'Mindset Shift': Discover techniques to guide an organization through a fundamental change in thinking and strategy.From Chaos to Cohesion: Hear how Perry unified disparate teams and roadmaps post-acquisition to create a single, focused vision.Staying Relevant in the AI Era: Understand why past playbooks are obsolete and what skills are critical for leadership in a world of constant technological disruption.This episode is for any leader tasked with steering their organization through uncertainty. --- Access free, email-based coaching for executives. Join the conversation at https://kc.coach.

    31 min
  4. Don't Leave Your Moral Compass at Home with Natasha Jaffe

    JUN 18

    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 SubstackIn 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.

    26 min
  5. From Ballet to Scalpel to CEO: Reinvention, Resilience & Hiring Unconventionally

    APR 30

    From Ballet to Scalpel to CEO: Reinvention, Resilience & Hiring Unconventionally

    Ready to ditch the resume buzzwords and hire for true potential? Struggling with your own career pivot or leading teams through change? Join Keith Cowing on Executives Unplugged with Dr. Susan Lovelle, a former professional ballet dancer turned plastic surgeon, now founder & CEO of Balanced Performance, and her long-time colleague Tonya Sook, a Certified Family Nurse Practitioner. Discover Dr. Lovelle's unconventional approach to hiring – prioritizing inner skills over years of experience – and how it built a thriving practice. Hear her incredible story of multiple reinventions, driven by passion and necessity, and learn how to navigate your own transformations. Tonya shares the ground-level view of building a culture of trust and excellence. Learn practical strategies for assessing talent beyond the resume, fostering team alignment, managing your energy to avoid burnout, and applying the "Listen, Let Go, Live" method for peak performance. Guests Dr. Susan Lovelle: Former professional ballet dancer (17 years), plastic surgeon, and now Founder/CEO of Balanced Performance, helping executives optimize their health and leadership. Learn more at Balanced Performance. Tonya Sook APRN-C: Certified Family Nurse Practitioner specializing in medical aesthetics, hormone therapy, dermatology, and functional medicine, dedicated to holistic patient well-being. View on your favorite platform Youtube: https://youtu.be/Stgj-ZwL45w Spotify: https://open.spotify.com/episode/6n4zRnSVJf1ZfRITtG1VK8?si=lO_8BZWoTXWL5WeT-ZhvQw Apple Podcasts: https://podcasts.apple.com/us/podcast/from-ballet-to-scalpel-to-ceo-reinvention-resilience/id1769131263?i=1000705573303 [00:00:00] Intro / From Dance to Medicine [00:00:19] Welcome & Guest Introductions [00:01:24] Hiring Philosophy: Skills Over Experience [00:02:47] The Group Interview & Testing for Inner Workings [00:04:10] Why Experience Can Be Overrated [00:04:41] Tonya Sook: Cultivating Culture & Trust [00:05:08] Enabling Teams to Be Themselves [00:06:09] Learning Leadership Through Delegation [00:07:36] Reinvention 1: Ballet to Medical School [00:09:39] Reinvention 2: Surgery to Lifestyle Coaching (The Wake-Up Call) [00:11:25] Finding Your Energy & Root Causes [00:12:55] The L3 Method: Listen, Let Go, Live [00:14:14] Tonya Sook: The Art of Nurse Practitioner Leadership (Gentle Firmness) [00:16:33] Learning You Can't Help Everyone [00:17:35] Discipline: The Common Thread from Ballet to Business [00:19:45] Performance: How You Show Up Matters [00:21:57] What's Next? Scaling Impact Through Corporate Wellness [00:22:49] Lessons Learned from Working Together [00:24:07] Why Dr. Susan Isn't a "Typical" Surgeon [00:26:20] Key Takeaways & Conclusion

    27 min
  6. From Big Company to AI Startup, a product, and revenue in 12 Months: How Fast Execution Beats Perfect Planning with Uday Chakravarthi

    FEB 27

    From Big Company to AI Startup, a product, and revenue in 12 Months: How Fast Execution Beats Perfect Planning with Uday Chakravarthi

    In this episode of Executives Unplugged, Keith Cowing sits down with Uday Chakravarthi, former head of product at Atlassian and current CEO of Clinch AGI, an agentic AI company revolutionizing how companies sell and grow. Uday shares his journey from idea to his first $100K in revenue in just 12 months, revealing the strategies that fueled his success: ruthless prioritization, weekly sprints, and a customer-first mindset. From managing a costly API glitch in the middle of the night to leveraging advisors for go-to-market mastery, Uday’s story is packed with actionable insights for CEOs, founders, or anyone looking to accelerate team performance and growth. Key topics include: The zero-to-one journey: How Uday refined his idea, assembled a core team, and got first customers quickly.Time-zone challenges: Strategies for async communication, “bat phone” emergencies, and using Loom/WhatsApp for round-the-clock collaboration.Surrounding yourself with expertise: Building advisory boards, the difference between “cheerleader” advisors and hands-on experts, and how to get real-time coaching on your sales calls.Fast execution: Why shipping weekly sprints and labeling “deal-breaker” features help close deals and energize the team.Real-world examples: How a coding error led to thousands of dollars in AI API charges—and why having rapid response processes in place was critical.Show Notes: [0:00] Intro: Uday’s runaway API call costing thousands overnight.[1:25] Uday’s Journey: From Atlassian to founding Clinch AGI in the agentic AI space.[3:39] Speed Secrets: Building a core team, async communication, and customer collaboration.[8:14] Advisory Boards: How Uday strategically filled skill gaps with experts.[17:48] Actionable Advice: Validate problems early, invest in relationships, and prioritize ruthlessly.[19:31] Execution Hacks: Weekly sprints, AI-driven prioritization, and “deal breaker” focus.Where to Find Uday: Connect with Uday Chakravarthi on LinkedIn: https://www.linkedin.com/in/abhyuday/Learn more about Clinch AGI: clinchit.ioWhere to Find Keith: Visit Keith Cowing’s coaching site for CEOs and product leaders: kc.coachFollow Keith on LinkedIn for leadership insights: linkedin.com/in/keithcowing References from the Show: Executive Product Leadership Program: Unlock AI’s potential for your team with this two-day in-person workshop at Cornell Tech in September. Details at kc.coach/cornellIf you loved this episode, share it with a fellow leader or leave a five-star review to help others discover Executives Unplugged. Subscribe for more real talk from top executives.

    23 min
  7. From the Mat to the Boardroom: Iron Mike Steadman on Grit, Branding & the Power of Action

    FEB 6

    From the Mat to the Boardroom: Iron Mike Steadman on Grit, Branding & the Power of Action

    What does it take to get back up when life knocks you down? In this episode of Executives Unplugged, Iron Mike Steadman - collegiate boxing champion, veteran, entrepreneur, and business coach - shares his journey from the boxing ring to the boardroom, revealing hard-earned lessons on resilience, branding, and the power of action. Mike takes us inside one of his toughest leadership moments: running a nonprofit boxing gym in Newark, NJ, when COVID shut everything down overnight. With his back against the ropes, he found a way to pivot, reinvent, and build something even stronger. Now, as a sought-after business coach for veteran entrepreneurs, he helps others define their brand, find their market, and take decisive action in the face of uncertainty. 🔹 Key Takeaways: •How to turn adversity into momentum—even when you feel stuck •Why action builds confidence •The power of niching down and owning your brand identity •How to battle imposter syndrome and step into leadership with clarity •What it really takes to sell yourself and your business with conviction Whether you’re an entrepreneur, leader, or someone looking for the mindset to push through tough times, this episode delivers practical lessons and real-world insights that will get you off the mat and back in the fight. 🎧 Listen now and take your leadership to the next level! YouTube Spotify Apple Podcasts Mike Steadman: ironmikesteadman.com Black Veteran Entrepreneur: Validate your business model, build your brand, and step into greatness Keith Cowing (host): kc.coach References: The Four AgreementsThe Confident MindHow Champions ThinkPlay Bigger

    35 min
  8. Incentives, Truth and Selling the Right Way with Wayne Morris

    12/19/2024

    Incentives, Truth and Selling the Right Way with Wayne Morris

    In this episode of Executives Unplugged, Keith sits down with Wayne Morris, founder of RVNU and seasoned Chief Revenue Officer for multiple Silicon Valley startups. Wayne shares his transformative insights on go-to-market strategies, building sustainable sales teams, and the critical role of truth in creating long-term success. 💡 Key Topics Covered:  • How to diagnose product-market fit and go-to-market fit.  • The truth-driven approach to selling and why it builds trust and success.  • Structuring sales team incentives for long-term growth and customer success.  • Leadership lessons from Silicon Valley and beyond.  • Wayne’s wild journey from London to Silicon Valley. Whether you’re a founder, sales leader, or just curious about what it takes to thrive in high-growth startups, this episode is packed with practical advice and compelling stories. 📍 Take Wayne’s Free Go-to-Market Assessment: RVNU.co You can find his Go-To-Market framework one pager highlighted on this post: https://rvnu.substack.com/p/rvnu-017-exposing-if-a-startup-will Direct link to the one page image: https://substackcdn.com/image/fetch/f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fadf1d891-263a-4bd1-ba16-9d96e0a4f152_2378x1326.png 📧 Connect with Host Keith Cowing: kc.coach Share your thoughts and feedback—Keith responds to every listener! If you enjoyed this episode, please like, subscribe, and share it with someone who might find it valuable. Don’t forget to leave a review to help others discover Executives Unplugged!

    48 min
  9. How to Lead From Growth Stage to IPO with Nayya President and COO Sarah Liebel

    10/21/2024

    How to Lead From Growth Stage to IPO with Nayya President and COO Sarah Liebel

    Join us for a candid conversation with Sarah Liebel, President and COO of Nayya, who shares her invaluable insights on maintaining a founder's mindset while empowering teams.  Learn about the art of empathetic yet decisive leadership and how to build trust with founders, making swift decisions with limited data in high-stakes environments. Tune in for a treasure trove of practical advice and strategies that provide a roadmap for navigating the complexities of high-growth environments.

    37 min
  10. From Self-Taught Developer to CTO and Inspiring Leader with Danielle Leong

    09/19/2024

    From Self-Taught Developer to CTO and Inspiring Leader with Danielle Leong

    Join us as Danielle Leong shares her inspiring journey from marketing to becoming Twilio's first female engineer and on to senior leadership roles at companies such as Github and FireHydrant. Danielle opens up about her experiences managing former peers, building self awareness and confidence, communicating transparently and holding people accountable. Danielle also shares some of her management templates and playbooks that she has open-sourced to the world in the form of a GitHub repository. Tune in to gain a wealth of insights on effective leadership, communication strategies, and continuous learning from one of the industry's most dynamic leaders. You can find Danielle's open-source management playbooks here: https://github.com/dmleong

    38 min
  11. From Open-Heart Surgery and Mom's Ginger Teas to Beverage Entrepreneur with Siwat Siengsanaoh

    09/18/2024

    From Open-Heart Surgery and Mom's Ginger Teas to Beverage Entrepreneur with Siwat Siengsanaoh

    From open heart surgery and Mom's ginger teas, to selling ginger-based beverages in grocery stores across the country, Siwat's story is one of passion and resilience. The episode delves into pivotal moments that shaped Siwat’s leadership style, from teamwork in a hospital, to launching a series of businesses, to inspiration from great coaches such as Carlo Ancelotti and Phil Jackson. This episode is packed with insights on resilience, developing a brand, and leading with purpose. Visit Recoup at: https://recoupwellness.com https://instagram.com/recoupwellness https://www.amazon.com/stores/recoup/page/B58DA3B7-E2E4-49F5-AE28-C8B982FABE17 Book recommendations from Siwat: Quiet Leadership by Carlo Ancelotti https://www.amazon.com/Quiet-Leadership-Winning-Hearts-Matches/dp/0241244935 11 Rings by Phil Jackson https://www.amazon.com/Eleven-Rings-audiobook/dp/B00CTE0YTC/ Tribal Leadership https://www.amazon.com/Tribal-Leadership-audiobook/dp/B07NF1R92F

    28 min
  • 11 Episodes

Ratings & Reviews

5
out of 5
6 Ratings

About

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.

Information

  • Creator
    Keith Cowing
  • Years Active
    2024 - 2025
  • Episodes
    11
  • Rating
    Clean
  • Copyright
    © 2025 Executives Unplugged
  • Show Website
    Executives Unplugged