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.

Episodes

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

    4D AGO

    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
  2. 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
  3. 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
  4. 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
  5. 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
  6. 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

  7. 10/08/2025

    Unlocking Your Zone of Genius with Delegate & Elevate

    Are you spending your best energy on the right things—or are you buried in tasks that drain you? In this solo episode, Kristyn Drennen breaks down the Delegate & Elevate strategy, a simple yet transformative exercise that helps leaders reclaim their time, focus on their zone of genius, and unlock capacity for what truly matters. Kristyn walks through the five steps of the framework: Find your 100% — define the hours you’re willing to work and still feel balancedList everything you do — get it all out of your head and onto paperList everything you should do — surface the strategic work that keeps getting pushed asideEvaluate your list — use the four quadrants to see where your time really belongsDelegate and elevate — free yourself from tasks that don’t serve your geniusYou’ll learn how to spot what belongs on your plate, what your team can take on, and how to elevate yourself back into the leadership role your business truly needs. Why it matters: When leaders make these shifts, they don’t just lighten their workload—they rediscover their energy, strengthen their teams, and fall back in love with their business. Resources & Links Download the Delegate & Elevate WorksheetLearn more about how TransformCXO helps leaders elevate at transformcxo.comSchedule a Discovery Call with Kristyn's preferred VA Company: SphereRocketStay 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

    15 min
  8. What If Better Rest Is the Key to Greater Results? with David Shrum

    10/01/2025

    What If Better Rest Is the Key to Greater Results? with David Shrum

    High performers love to push, grind, and go — but what if the missing link to greater results isn’t more effort, but better rest? In this episode of Unlocked, host Kristyn Drennen sits down with David Shrum, a Meta Performance™ Executive Coach and former EMS Director, to unpack why rest is not a luxury, but a critical discipline for leaders. Together they explore: The difference between passive breaks and active restHow to uncover and rewrite the limiting stories leaders carry about restWhat to do when you feel overwhelmed by vision — or starved for itWhy protecting your “furnace” of energy fuels better leadership, better families, and better resultsResources Mentioned: Rest: Why You Get More Done When You Work Less by Alex PangSleeping At Last’s Enneagram Album (especially songs 6 & 8)Connect with David Shrum on LinkedIn or via email.Reference Correction: Using furnace as a description for our energy reserves and the necessity to protect it comes from Jason Jaggard in his book Beyond High Performance. 🎧  👉 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

    43 min
  9. “I Can’t Fire Them” – Evolving Leadership Teams with Tina Caul

    09/24/2025

    “I Can’t Fire Them” – Evolving Leadership Teams with Tina Caul

    Summary: What happens when loyalty clashes with leadership? In this episode of Unlocked, host Kristyn Drennen sits down with powerhouse real estate leader Tina Caul to explore the messy middle of growing a business: wrong seats, tough calls, team misalignment, and the freedom that comes from making the hard decisions faster. Listeners will hear: ●      How to navigate wrong person/right seat dilemmas ●      The politics of titles, silos, and fragile egos ●      The turning point that forced Tina to change course ●      How finding her perfect integrator unlocked freedom and growth ●      Tina’s “Extra 10%”: the one soul-check question every visionary should ask Call to Action: Follow Tina on Instagram @tina_caul and on Facebook at Tina Caul.  👉 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

    45 min

  10. 09/12/2025

    Introducing Unlocked: Finding Joy, Growth, and Clarity in Business with Kristyn Drennen

    Welcome to the debut of Unlocked with Kristyn Drennen—a podcast for visionary leaders ready to discover what’s next. In this opening conversation, producer Jon Ekstrom interviews Kristyn to set the stage for the episodes ahead. Kristyn shares her story of building TransformCXO, where she and her team of fractional executives help business owners prepare for scale and high-value exits. She reflects on her philosophy of combining horsepower and joy in business—a fresh alternative to hustle culture—and why aligning values with execution is the key to lasting success. You’ll also hear: The personal story behind Kristyn’s drive to help owners prepare for business transitions.A candid look at why 90% of business owners regret selling their companies—and how to avoid it.The importance of intangible capital (people, processes, customers, culture) in building real enterprise value.A powerful framework for shifting from working in the business to working on the business.Kristyn’s commitment to leaving every listener with something tactical and actionable.This episode also features the first Unfiltered segment—a fun look at Kristyn’s walk-up song, guilty pleasures, and the experiences that humanize her beyond the boardroom. Key Highlights Why Kristyn launched Unlocked and what listeners can expect.The difference between transactional leadership and relational impact.Case studies of two mergers—and why one thrived while the other failed.The “Delegate & Elevate” mindset shift every leader needs.Kristyn’s belief that better businesses create stronger families and communities.Links & Resources Learn more about TransformCXO: https://transformcxo.comConnect with Kristyn Drennen on LinkedIn: Kristyn’s LinkedIn Follow Kristyn on Instagram: @kristyndrennencxo If you enjoyed this episode, please follow Unlocked with Kristyn Drennen on Apple Podcasts or Spotify and don't forget to rate, review and subscribe.  For more tools and insights, visit TransformCXO.com

    45 min
  11. “I don’t have time for that!” Finding Your Highest Sustainable Pace with Andrew Hartman of Time Boss

    09/12/2025

    “I don’t have time for that!” Finding Your Highest Sustainable Pace with Andrew Hartman of Time Boss

    High performers often pride themselves on their ability to grind—but at what cost? Andrew Hartman knows this story firsthand. As a scaling COO, he pushed himself to the breaking point, sacrificing his health, relationships, and sense of presence until burnout forced a change. That journey led Andrew and his wife, Kelly, to create Time Boss, a system designed to help leaders and teams run at their highest sustainable pace. In this conversation with host Kristyn Drennen, Andrew shares: His personal story of stress-induced health struggles and how burnout reshaped his career.Why “time is cash, not credit” and how leaders should budget it wisely.The simple weekly practices that unlock clarity, focus, and productivity.Why personal commitments like workouts, date nights, and family time must be non-negotiable.How companies can set healthy communication norms to reduce chaos and increase deep work.Kristyn and Andrew also dive into practical takeaways—how to stop letting your inbox run your day, how to reframe your calendar as a reflection of your values, and why leaders must move beyond tolerating life to choosing the life they want. Whether you’re a visionary business owner, an overwhelmed executive, or simply someone who wants to reclaim their time, this episode will leave you with tools and encouragement to step into a new way of working and living. Key Highlights Andrew’s raw story of burnout and recovery.The danger of “sprinting a marathon” in leadership.Why personal commitments should be treated like fixed costs.The Time Boss system: backlog, calendar, and daily list.Practical tips to reset, recover, and lead with clarity.Links & Resources Learn more about Time Boss: https://timeboss.usConnect with Andrew Hartman on LinkedIn: Andrew Hartman LinkedInWatch the free Time Boss Masterclass: https://timeboss.us/masterclassIf you enjoyed this episode, please follow Unlocked with Kristyn Drennen on Apple Podcasts or Spotify and don't forget to rate, review and subscribe.  Explore Kristyn’s work with TransformCXO: https://transformcxo.com

    51 min
  • 11 Episodes

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
    11
  • Rating
    Clean
  • Copyright
    © 2026 Unlocked with Kristyn Drennen
  • Show Website
    Unlocked with Kristyn Drennen