Executives Unplugged

Keith Cowing
  • 5.0 (7)
  • ENTREPRENEURSHIP
  • UPDATED BIWEEKLY

Top CEOs have coaches behind the scenes. Executives Unplugged takes you into those rooms for candid conversations with leaders about how they find clarity in the chaos. We distill the systems and mindsets required to navigate high-stakes decisions and build world-class companies.

  1. Why 50% of Startup Executive Hires Fail (and How to Fix It)

    3D AGO

    Why 50% of Startup Executive Hires Fail (and How to Fix It)

    Over half of startup executive hires fail in the first 18 months and many in the first 30 days. Executive hiring is a high-stakes gamble. One bad fit doesn't just cost money; it can derail your entire momentum and kill team morale. Yet, most companies are still playing a game of mutual selling that incentivizes flaunting and filtering over honesty and results. Meghan Oliver decided to stop playing that game. After stepping off the corporate hamster wheel to build her own business, she found a way to bypass the interview dance entirely. She joined a Series A healthcare company as a fractional product leader. No elongated interview process, just real problems to solve on day one. What started as a 90-day experiment ended with Meghan rewriting the company’s product and operations playbook and stepping in as full-time COO. In this episode, Meghan reveals her framework for how to wildly reduce the risk of a mis-hire and either close your next great executive or land your next great gig. Chapter Markers: 00:00 — Why traditional executive hiring often fails 01:00 — Meghan’s path: burnout, sabbatical, and discovering fractional 03:20 — Starting fractional at RightMove Health as CPO 04:20 — Finding clarity in context, not just function 07:20 — What makes a fractional executive role actually work 10:50 — Evolving from fractional CPO to full-time COO 13:20 — Why combining product and ops cuts coordination tax 15:00 — The power of a 90-day “try before you buy” 15:40 — Navigating health insurance and benefits as fractional 18:40 — How the role shift felt seamless for the team 20:40 — Building conviction and quieting self-doubt 22:40 — Advice for CEOs and executives on fractional hires 26:20 — What’s happening at RightMove Health (and open roles)Follow Meghan Oliver: https://www.linkedin.com/in/meghan-oliver/ Shoutouts RightMove Health: https://rightmovehealth.com Follow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowing Join the Executives Unplugged Inner Circle: https://execs.tv Subscribe to the show YouTube: https://www.youtube.com/@execsunplugged Spotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN Apple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263

    28 min
  2. 250 Board Meetings Later: This CEO’s playbook will change your board meetings forever

    NOV 26

    250 Board Meetings Later: This CEO’s playbook will change your board meetings forever

    Matt Blumberg reveals why he bans slides, forces independent directors to audition for a seat, and uses AI to simulate Steve Jobs in the boardroom. For many founders, the board meeting is a dreaded time sink full of status updates and glazed eyes. In this episode Matt Blumberg, the CEO of Markup AI and author of Startup Boards, breaks down how to turn your board meetings into your ultimate strategy session. Matt shares the story of a "perfect" board candidate who failed a live audition, the "Rule of Ones" that will lead to an effective board composition, and why he strictly forbids slides during meetings. He also reveals a new experiment: using AI agents to simulate a "Fantasy Board" meeting with personalities like Steve Jobs and Warren Buffett to stress-test decisions before the real directors show up. Executives will come away with a playbook to stop reporting and start using their board to build the business. Chapters00:00 — The No Slides Rule 02:04 — Turning the eye roll into strategy 03:20 — The Audition: Making directors do the work 06:58 — How to reference check your VCs 08:59 — The "Rule of Ones" for board composition 13:25 — Stop writing 50-page board decks 17:24 — Specific rules for better conversations 20:58 — Inside the Markup AI pivot 23:05 — The "Fantasy Board": Simulating Steve Jobs with AI 26:19 — How to fire a board member 28:17 — Why every CEO should sit on another board Follow Matt on LinkedIn: https://www.linkedin.com/in/mattblumberg/ Shoutouts Startup Boards: https://www.amazon.com/Startup-Boards-Building-Effective-Directors/dp/111985928X Markup AI: https://markup.ai Fred Wilson: https://avc.xyz Mike Collins: https://www.linkedin.com/in/mike-collins-362100/ Follow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowing Join the Executives Unplugged inner circle: 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

    30 min
  3. Mastering executive offsites

    NOV 4

    Mastering executive offsites

    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 tone05:00 — The value of “having a sleep” between days07:40 — The CEO’s role: set vision, not the agenda10:50 — Creating meeting agreements that drive honesty16:20 — The facilitator’s job: manage time and truth18:50 — Handling conflict when the “fight” breaks out22:30 — Tools for structure: parking lots, sticky notes, and timers25:40 — Decision-making without consensus traps28:20 — The “Fist to Five” tool for real alignment30:20 — Ensuring follow-through and lasting impact33:30 — 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.coListen to Kelly’s Podcast: https://www.lifefromwithin.com/ Follow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowingSubscribe to Keith’s free coaching via email: https://kc.coach/ Subscribe to the show:YouTube: https://www.youtube.com/@kcowingSpotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKNApple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263

    35 min
  4. How to bring startup speed to big organizations

    OCT 21

    How to bring startup speed to big organizations

    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. 00:00 — Moving fast meets resistance04:00 — “Learn the business”: slowing down to speed up09:00 — The big swing that fell flat — and the lesson in humility17:00 — Piloting change and earning trust one team at a time22:00 — Turning internal wins into customer-facing AI26:00 — Balancing empathy, momentum, and trust31:00 — Reducing fear, sparking excitement: leading through change36:00 — What’s next: voice tech, connection, and being more human 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

    39 min
  5. From Trade Shows to Target’s Shelves: Growing 500% in a Year with Recoup Co-founder Siwat Siengsanaoh

    OCT 9

    From Trade Shows to Target’s Shelves: Growing 500% in a Year with Recoup Co-founder Siwat Siengsanaoh

    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

    33 min

  6. SEP 15

    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
  7. 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
  8. 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
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Ratings & Reviews

5
out of 5
7 Ratings

About

Top CEOs have coaches behind the scenes. Executives Unplugged takes you into those rooms for candid conversations with leaders about how they find clarity in the chaos. We distill the systems and mindsets required to navigate high-stakes decisions and build world-class companies.

Information

  • Creator
    Keith Cowing
  • Years Active
    2024 - 2025
  • Episodes
    16
  • Rating
    Clean
  • Copyright
    © 2025 Keith Cowing
  • Show Website
    Executives Unplugged