Unlocked with Kristyn Drennen

Kristyn Drennen
  • 5.0 (8)
  • ENTREPRENEURSHIP

You didn’t build your business just to burn out in it. And you didn’t become a leader to feel stuck in the day-to-day. Welcome to Unlocked with Kristyn Drennen — where high-achieving founders, operators, and executives stop tolerating complexity and start building the businesses (and lives) they actually want. Kristyn Drennen is a powerhouse Fractional COO, Certified Exit Planning Advisor, and MetaPerformance™ Executive Coach for elite leaders who are scaling with purpose and preparing for high-value exits. She’s known for rolling up her sleeves inside multi-million-dollar companies to align leadership, drive operational clarity, and help owners regain their freedom — all while unlocking extraordinary growth. Each episode goes beyond theory. Expect straight talk, smart strategy, and transformational questions that cut through the noise. Whether you're leading a growing business or leading from the C-Suite, you’ll leave with real tools, new perspective, and the reminder that it's possible to love your business again.

  1. Are You Leading the Business - or Carrying It? with Charlie Rhea

    1D AGO

    Are You Leading the Business - or Carrying It? with Charlie Rhea

    Many founders start their businesses because they love building, creating, and solving big problems — but somewhere along the way, they become the bottleneck. In this episode of Unlocked, Kristyn Drennen is joined by EOS Implementer Charlie Rhea to break down the leadership structure that helps founders scale without burning out: the visionary–integrator partnership. Charlie explains the critical distinction between an EOS Implementer and an Integrator, why those roles are often confused, and how they work together to support healthy execution. Kristyn shares real-world examples from her work as a fractional integrator, including why asking a visionary to also lead, manage, and hold a leadership team accountable almost always backfires. Together, they dive deep into the visionary seat — what it is, what it is not, and why so many founders struggle to step fully into it. From protecting culture and casting vision to creating space for strategic thinking, this conversation gives founders a clear picture of what leadership looks like when it’s functioning well. This episode is especially timely for leaders heading into annual planning, navigating growth complexity, or feeling stuck between strategy and execution. If you want your business to grow beyond you — without losing control — this conversation will give you practical clarity on what needs to change next. KEY HIGHLIGHTS The difference between an EOS Implementer and an Integrator — and why confusing the two creates frictionWhy visionaries struggle when they try to lead, manage, and hold their teams accountableWhat the visionary seat actually owns when it’s working wellHow the visionary–integrator relationship drives leadership team effectivenessPractical ways to keep vision alive inside the business — not just on paperLINKS & RESOURCES Discover your Founder’s Freedom Score! Free tools, instant results: Founder's Freedom ScoreLearn more about EOS Worldwide: https://www.eosworldwide.comConnect with Charlie Rhea on LinkedInRecommended Books:Traction by Gino WickmanRocket Fuel by Gino WickmanLiving Forward by Michael Hyatt & Daniel HarkavyIf this episode resonates, share it with a fellow leader who needs to hear it. And if you’re ready to unlock your capacity and lead from your zone of genius, book a conversation with Kristyn and the TCXO team. 🎧  👉 Subscribe to Unlocked with Kristyn Drennen on Spotify, Apple, or YouTube — and share this episode with a visionary leader who needs to hear it. Learn more about TransformCXO: https://transformcxo.com Connect with Kristyn Drennen on LinkedIn: Kristyn’s LinkedIn  Follow Kristyn on Instagram: @kristyndrennencxo

    46 min
  2. Operating Systems, AI, and the Future of Leadership with John Kitchens

    JAN 28

    Operating Systems, AI, and the Future of Leadership with John Kitchens

    What actually makes a business operating system work — and why do so many fail to deliver the clarity leaders expect? In this episode of Unlocked, Kristyn Drennen is joined by John Kitchens, a seasoned business coach with deep experience in EOS, Scaling Up, and operational leadership. Together, they unpack what operating systems really are, when a business is ready for one, and why the “install and forget” mindset leads to disappointment. The conversation goes far beyond frameworks. John and Kristyn explore the intersection of operating systems, financial acumen, AI, and leadership development — including the growing divide between transactional businesses and those built on experience and long-term value. John also shares why mentorship and leadership pipelines matter more than ever as AI reshapes entry-level roles. This episode is a must-listen for founders, integrators, and leadership teams who want structure without rigidity — and growth without burning out. Key Highlights What a business operating system really is (without the jargon)How to know when your company is ready for EOS, Scaling Up, or another frameworkWhy financial ownership is critical in the integrator roleAI as a thought partner — not a crutchThe future of leadership, mentorship, and experience-driven businesses Links & Resources Connect with John: https://johnkitchens.coachJohn Kitchens Coach PodcastFollow John on LinkedIn & social platforms: @JohnKitchensCoachBook Recommendations from this episode Traction – Gino WickmanScaling Up – Verne HarnishThe AI-Driven Leader – Geoff WoodsUnreasonable Hospitality – Will GuidaraHug Your Customers – Jack MitchellRaving Fans – Ken Blanchard & Sheldon BowlesGiftology – John RuhlinIf this episode resonates, share it with a fellow leader who needs to hear it. And if you’re ready to unlock your capacity and lead from your zone of genius, book a conversation with Kristyn and the TCXO team. 🎧  👉 Subscribe to Unlocked with Kristyn Drennen on Spotify, Apple, or YouTube — and share this episode with a visionary leader who needs to hear it. Learn more about TransformCXO: https://transformcxo.com Connect with Kristyn Drennen on LinkedIn: Kristyn’s LinkedIn  Follow Kristyn on Instagram: @kristyndrennencxo

    50 min
  3. Business as a Ministry: Building Sound Businesses, Steady Leaders, and Strong Families with Paulina Walters

    JAN 7

    Business as a Ministry: Building Sound Businesses, Steady Leaders, and Strong Families with Paulina Walters

    In this deeply personal and practical conversation, Kristyn Drennen sits down with TransformCXO co-founder Paulina Walters to unpack what it truly means to operate a business as a ministry—without sacrificing performance, profitability, or accountability. Drawing from Paulina’s journey through C12 and her evolution as a leader, the conversation explores how faith, stewardship, and intentional leadership practices shape healthier organizations. Together, they discuss how leaders often operate from depletion rather than purpose, and how shifting that posture can radically transform culture, retention, and results. Kristyn and Paulina also share the framework that anchors TransformCXO’s mission: Sound Businesses. Steady Leaders. Strong Families. The episode highlights why leadership steadiness creates organizational calm, how people-first cultures outperform over time, and why profit and purpose are not competing priorities—but reinforcing ones. This episode is for business owners and leaders who feel stretched thin, are questioning how they show up at work and at home, and want to build something meaningful without doing it alone. Key Highlights What “business as a ministry” actually means in practiceWhy leading from depletion undermines both people and performanceHow people-first leadership improves retention and long-term profitabilityThe role of peer advisory groups like C12 in leadership formationThe ripple effect from steady leaders to families and communitiesLinks & Resources Connect with Paulina Walters on LinkedInExplore TransformCXO: https://transformcxo.comGet your Founder’s Freedom Score: https://transformcxo.comIf this episode resonates, share it with a fellow leader who needs to hear it. And if you’re ready to unlock your capacity and lead from your zone of genius, book a conversation with Kristyn and the TCXO team. 🎧  👉 Subscribe to Unlocked with Kristyn Drennen on Spotify, Apple, or YouTube — and share this episode with a visionary leader who needs to hear it. Learn more about TransformCXO: https://transformcxo.com Connect with Kristyn Drennen on LinkedIn: Kristyn’s LinkedIn  Follow Kristyn on Instagram: @kristyndrennencxo

    42 min
  4. Designing a People-First Organization: What Makes a Merger Actually Work with Sara Hoffman

    12/17/2025

    Designing a People-First Organization: What Makes a Merger Actually Work with Sara Hoffman

    Mergers test everything: leadership, communication, trust, and culture. Many organizations focus on systems, contracts, and integration plans, but overlook the human experience inside the transition. In this episode of Unlocked, Kristyn is joined by Sara Hoffman, Managing Partner at Conexus Insurance Partners, for a candid conversation about designing a people-first organization in the midst of growth and change. Sara shares how Conexus approached their merger with intention, using clear leadership rhythms, consistent communication, and shared accountability to keep people aligned. Rather than relying on slogans or values statements alone, the leadership team focused on building structures that reinforced trust and clarity week after week. You’ll hear how separating ownership conversations from leadership execution created psychological safety, why predictable communication rhythms reduced uncertainty, and how peer-to-peer recognition helped bring core values to life in a tangible way. This episode is especially relevant for leaders navigating mergers, acquisitions, partnerships, or rapid growth who want to protect culture while still driving execution. What You’ll Learn Why most mergers struggle with culture, even when the strategy is soundHow leadership rhythms and meeting structure shape the employee experienceThe importance of separating ownership dynamics from leadership executionHow peer recognition reinforces values more effectively than top-down messagingWhat it really means to design a people-first organization, not just talk about oneAbout the Guest Sara Hoffman is a Managing Partner at Conexus Insurance Partners, where she helps lead a growing, people-centered organization built on clarity, trust, and intentional leadership. Sara brings a grounded, practical perspective on culture, communication, and what it takes to lead well through change. Links & Resources Learn more about Conexus Insurance PartnersConnect with Sara Hoffman on LinkedInExplore TransformCXO and fractional Integrator/COO support

    46 min
  5. Managing Change: Are You Creating Clarity or Adding Chaos?

    11/19/2025

    Managing Change: Are You Creating Clarity or Adding Chaos?

    In this episode of Unlocked, Kristyn sits down with organizational transformation expert Noel Andrews-Sotta to explore why change management is far more relevant and human than leaders realize. Noel introduces her Change Compass, a simple framework that helps teams navigate uncertainty with clarity, confidence, and stability. Most leaders think change management is only necessary in the “big” moments: acquisitions, restructures, major system rollouts. But the truth is, the micro-changes happening inside your business every day have a far greater impact on performance, culture, and emotional bandwidth. In this deeply practical episode, Kristyn and Noel unpack the subtle ways change shows up in an organization and how leaders can guide their teams through it with more empathy, steadiness, and strategic clarity. Noel shares her signature framework, The Change Compass, built around four simple but powerful questions that reveal what’s truly shifting, what’s stable, what’s known, and what still needs clarity. This tool has helped executive teams calm chaos, align messaging, resolve issues faster, and rebuild trust in moments of uncertainty. Listeners will learn how to apply this method during weekly leadership meetings, one-on-ones, process updates, team changes, and any moment where overwhelm or ambiguity begins to impact performance. Whether you're scaling quickly, restructuring, adding new roles, or simply navigating everyday disruptions, this episode gives you a clear and human-centered way to lead people through change, big or small. Key Highlights Why change management is underutilized in small, everyday momentsThe psychology behind why teams resist changeHow leaders unintentionally create more instabilityHow to facilitate Noel’s Change Compass with your teamThe differences between “what is changing” vs. “what feels like change”How to rebuild trust when you don’t have all the answersWhy the change curve matters and how to normalize itHow to shift teams from a victim mindset to a hero mindsetLinks & Resources Connect with Noel on LinkedIn Learn more about TransformCXO: https://transformcxo.com Change Curve Toolkit (recommended resource): Link Stay Connected If this episode resonates, share it with a fellow leader who needs to hear it. And if you’re ready to unlock your capacity and lead from your zone of genius, book a conversation with Kristyn and the TCXO team. 🎧  👉 Subscribe to Unlocked with Kristyn Drennen on Spotify, Apple, or YouTube — and share this episode with a visionary leader who needs to hear it. Learn more about TransformCXO: https://transformcxo.com Connect with Kristyn Drennen on LinkedIn: Kristyn’s LinkedIn  Follow Kristyn on Instagram: @kristyndrennencxo

    37 min
  6. Beyond High Performance: The Hidden Stuckness of High Achievers with David Shrum

    11/18/2025

    Beyond High Performance: The Hidden Stuckness of High Achievers with David Shrum

    What if your biggest obstacle isn’t lack of drive, but the very habits that made you successful? In this candid and practical episode, host Kristyn Drennen talks with executive coach David Shrum about what happens when high achievers plateau and how Meta Performance™ Coaching helps leaders break through the invisible ceilings that keep them stuck. David shares insights from his own leadership journey and explains how the shift from high performance to meta performance changes everything — from how you set goals to how you lead your team. Together, Kristyn and David unpack: The subtle “stuckness” that hides behind success.How curiosity, not advice, is the engine of great coaching.The athlete’s mindset — why growth requires getting back in the gym.The difference between performance at work and transformation through work.What to look for when hiring a truly great executive coach.Whether you’re an executive, entrepreneur, or lifelong learner, this conversation will challenge your assumptions about growth and inspire you to pursue the version of yourself you haven’t yet met. Key Highlights The “high performer problem” — and why doing more isn’t always the answer.How Meta Performance Coaching shifts focus from being the best to becoming limitless.Lessons from Amazon and Jeff Bezos on vision beyond success.The power of curiosity over advice in true coaching relationships.The connection between personal and professional transformation.Links & Resources Learn more about TransformCXO Executive Coaching: https://transformcxo.com/coachingConnect with David Shrum on LinkedIn: https://www.linkedin.com/in/david-shrumBook Recommendation: Beyond High Performance by Jason JaggardExplore more episodes at TransformCXO.com/Unlocked

    41 min
  7. Who Deserves a Seat at Your Table? with Brandon Kinsey

    10/27/2025

    Who Deserves a Seat at Your Table? with Brandon Kinsey

    The Data and Humanity Behind Great People Decisions with Brandon Kinsey, Co-Founder of Kinsey Management When financial pressure rises, even the best leaders can fall into the “layoff trap”—cutting too quickly, hiring too emotionally, or keeping the wrong person in the right seat. In this powerful conversation, Kristyn Drennen and Brandon Kinsey challenge how founders make people decisions when it matters most. They explore how behavioral strategy and data-driven insight can help leaders move from reaction to reflection—pairing heart with hard truth. Brandon shares how Predictive Index helps identify alignment, resilience, and pressure-handling styles within teams, while Kristyn brings an operational and leadership lens to show how structure and data work together to create clarity. Listeners will learn how to: Avoid emotional bias when restructuring or hiringDiagnose leadership health and team fitUse behavioral data to strengthen decision-makingBalance courage, clarity, and compassion in moments of pressureCreate alignment around vision, communication, and credibilityIf you’ve ever wrestled with a tough leadership call, this episode will help you see people decisions through a more courageous, strategic lens—one grounded in both data and humanity. Key Highlights The hidden cost of the “layoff trap” and how founders can avoid itWhy gut-based decisions often create long-term culture damageFive alignment anchors every healthy team needsThe right time to use behavioral assessments in hiring or restructuringHow to combine emotional intelligence with objective dataWhy courageous clarity is the ultimate leadership multiplierLinks & Resources Learn more about Kinsey Management: https://kinseymgmt.comConnect with Brandon Kinsey on LinkedInExplore leadership transformation with TransformCXO: https://transformcxo.comStay Connected If this episode resonates, share it with a fellow leader who needs to hear it. And if you’re ready to unlock your capacity and lead from your zone of genius, book a conversation with Kristyn and the TCXO team. 🎧  👉 Subscribe to Unlocked with Kristyn Drennen on Spotify, Apple, or YouTube — and share this episode with a visionary leader who needs to hear it. Learn more about TransformCXO: https://transformcxo.com Connect with Kristyn Drennen on LinkedIn: Kristyn’s LinkedIn  Follow Kristyn on Instagram: @kristyndrennencxo

    56 min
  8. Is Your Business a Wealth Engine for Retirement? with Tiffany Charles

    10/15/2025

    Is Your Business a Wealth Engine for Retirement? with Tiffany Charles

    Entrepreneurs pour everything into their business — but when it comes to their personal wealth, even the most successful leaders often find themselves disorganized or exposed. In this episode of Unlocked, host Kristyn Drennen sits down with Tiffany Charles, Chief Growth Officer at Destiny Capital, to explore why every entrepreneur needs a Personal Wealth Operating System™ — and how aligning your personal and business goals creates true financial freedom. Together they unpack: Why your business should be your wealth engine, not your retirement planHow to bridge the gap between business success and personal financial clarityThe emotional side of money and why vulnerability is a leadership strengthWhat to do when your personal wealth feels messy, scattered, or reactiveSimple ways to start building structure and intentionality into your financial lifeResources Mentioned: Song: “Regulate” by Warren G & Nate Dogg — Tiffany’s ultimate walk-up anthemSphere Rocket Virtual Assistant Company – Kristyn’s go-to recommendation for virtual assistant supportLearn more about Destiny Capital: www.destinycapital.comConnect with Tiffany Charles on LinkedIn: linkedin.com/in/tiffanycharlesEmail: tiffany.charles@destinycapital.comStay Connected If this episode resonates, share it with a fellow leader who needs to hear it. And if you’re ready to unlock your capacity and lead from your zone of genius, book a conversation with Kristyn and the TCXO team. 🎧  👉 Subscribe to Unlocked with Kristyn Drennen on Spotify, Apple, or YouTube — and share this episode with a visionary leader who needs to hear it. Learn more about TransformCXO: https://transformcxo.com Connect with Kristyn Drennen on LinkedIn: Kristyn’s LinkedIn  Follow Kristyn on Instagram: @kristyndrennencxo

    52 min
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Ratings & Reviews

5
out of 5
8 Ratings

About

You didn’t build your business just to burn out in it. And you didn’t become a leader to feel stuck in the day-to-day. Welcome to Unlocked with Kristyn Drennen — where high-achieving founders, operators, and executives stop tolerating complexity and start building the businesses (and lives) they actually want. Kristyn Drennen is a powerhouse Fractional COO, Certified Exit Planning Advisor, and MetaPerformance™ Executive Coach for elite leaders who are scaling with purpose and preparing for high-value exits. She’s known for rolling up her sleeves inside multi-million-dollar companies to align leadership, drive operational clarity, and help owners regain their freedom — all while unlocking extraordinary growth. Each episode goes beyond theory. Expect straight talk, smart strategy, and transformational questions that cut through the noise. Whether you're leading a growing business or leading from the C-Suite, you’ll leave with real tools, new perspective, and the reminder that it's possible to love your business again.

Information

  • Creator
    Kristyn Drennen
  • Years Active
    2025 - 2026
  • Episodes
    13
  • Rating
    Clean
  • Copyright
    © 2026 Unlocked with Kristyn Drennen
  • Show Website
    Unlocked with Kristyn Drennen