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:
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.
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:
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.
Too many offsites miss the powerful opportunity to align a leadership team. Here’s how to make yours the exception.
In this episode, Kelly Dwyer, executive coach and facilitator, breaks down what separates transformational offsites from frustrating ones. She’s helped leadership teams at venture and PE-backed companies turn tense conversations into breakthroughs and knows exactly how to keep the “elephant in the room” from derailing trust.
Kelly and host Keith Cowing unpack a tactical playbook: how to prep the right way, design the space for honesty, navigate conflict, and make sure the alignment lasts.
Leaders will walk away knowing how to run an offsite that doesn’t just check a box, but changes how their team thinks, decides, and leads.
00:00 — Why offsites fail (and how to fix them)
02:10 — How prep work sets the tone
05:00 — The value of “having a sleep” between days
07:40 — The CEO’s role: set vision, not the agenda
10:50 — Creating meeting agreements that drive honesty
16:20 — The facilitator’s job: manage time and truth
18:50 — Handling conflict when the “fight” breaks out
22:30 — Tools for structure: parking lots, sticky notes, and timers
25:40 — Decision-making without consensus traps
28:20 — The “Fist to Five” tool for real alignment
30:20 — Ensuring follow-through and lasting impact
33:30 — Why offsites are the most powerful (and risky) meetings you’ll ever run
Follow Kelly Dwyer on LinkedIn: https://www.linkedin.com/in/kellydwyer/
Visit Kelly’s Website: https://kellydwyer.co
Listen to Kelly’s Podcast: https://www.lifefromwithin.com/
Follow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowing
Subscribe to Keith’s 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
A startup founder joins a 10,000-person company to build AI from scratch and learns how to move fast without losing trust.
Moving fast inside a big company can feel impossible. You’re hired to shake things up - but if you move too quickly, you lose people. This episode dives into that tension. Atlassian’s Head of AI, Nisha Iyer, shares what happens when a startup founder joins a 10,000-person company and tries to build new AI products from the inside. She unpacks learning to slow down, earning trust, and building momentum the right way - without giving up the spark that made you effective in the first place.
Executives and operators will relate to the tension between urgency and patience - and take away ideas for leading change without burning out your team or losing trust.
Shoutouts:
The First 90 Days — https://www.amazon.com/First-90-Days-Strategies-Expanded/dp/1422188612
Atlassian — https://www.atlassian.com
Rovo — https://www.atlassian.com/software/rovo
Follow Nisha Iyer: https://www.linkedin.com/in/nisha-ranjani-iyer/
Follow Keith Cowing: https://linkedin.com/in/keithcowing
Subscribe to Keith’s 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
If you want 5x growth, you need more than a great product. In this episode, Recoup co-founder Siwat Siengsanaoh breaks down how trade shows, advisory boards, and fast feedback loops turned ginger-forward beverages into a national Target launch. You’ll learn how to build an advisory bench, get massive distribution, expand margins, and use polarizing positioning to earn raving fans.
(00:00) Intro — From trade shows to Target shelves
(03:20) Lean teams, volunteers, and winning Pitch Slam
(06:48) Building an advisory board that moves margins
(13:16) Polarization as a brand strategy: the ginger edge
(16:33) Customer feedback and fast iteration
(25:45) Rethinking risk: small bets, tight feedback loops
Drink recoup: https://www.recoupwellness.com/
Follow Siwat Siengsanaoh on LinkedIn: https://www.linkedin.com/in/siwatsiengsanaoh/
Follow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowing
Join the Executives Unplugged Community and get free office hours: https://kc.coach/executives-unplugged
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
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
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/
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:
This episode is for any leader tasked with steering their organization through uncertainty.
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Access free, email-based coaching for executives. Join the conversation at https://kc.coach.
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:
In this episode, we discuss:
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
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:
Show Notes:
Where to Find Uday:
Where to Find Keith:
References from the Show:
If 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.
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!
Mike Steadman: ironmikesteadman.com
Black Veteran Entrepreneur: Validate your business model, build your brand, and step into greatness
Keith Cowing (host): kc.coach
References:
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!
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.
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
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