Resources

Strategic Alliances for Gen AI: How to Build Them and Make Them Work

Insights from Strategic Alliances for Gen AI: How to Build Them and Make Them Work by McKinsey & Company (May 2024)

All About Teams: A New Approach to Organizational Transformation

Insights from All About Teams: A New Approach to Organizational Transformation by McKinsey & Company (December 2024)

Captain’s Gam (January 2026)

Recording of the Captain’s Gam on January 22, 2026 (Topic: Helmwise Captains Read the State of the Sea).

The Path to AI ROI: Why a Secure, Scalable Platform is Critical

Insights from The Path to AI ROI: Why a Secure, Scalable Platform is Critical by Foundry Co. (November 2025)

How to Capture the Elusive Performance Edge in True Transformations

Insights from How to Capture the Elusive Performance Edge in True Transformations by McKinsey & Company (December 2025)

Captain’s Conclave (January 2026)

Recording of the Captain’s Conclave on January 8, 2026 (Topic: Energizing the Core Discipline).

Overcoming Two Issues That are Sinking Gen AI Programs

Insights from Overcoming Two Issues That are Sinking Gen AI Programs by McKinsey & Company (June 2025)

Captain’s Gam (December 2025)

Recording of the Captain’s Gam on December 23, 2025 (Topic: Why Wise Men Seek and Follow a Star).

When Failure is an Option: Fostering Organizational Innovation and Learning

Insights from When Failure is an Option: Fostering Organizational Innovation and Learning by McKinsey & Company (June 2024)

The Change Agent: Goals, Decisions, and Implications for CEOs in the Agentic Age

Insights from The Change Agent: Goals, Decisions, and Implications for CEOs in the Agentic Age by McKinsey Quarterly (October 2025)

Captain’s Conclave (December 2025)

Recording of the Captain’s Conclave on December 11, 2025 (Topic: The Need to Lead: A Topgun Instructor’s Lessons on How Leadership Solves Every Challenge).

The AI Trust Gap: Why Every Enterprise Needs Content Guardrails

Insights from The AI Trust Gap: Why Every Enterprise Needs Content Guardrails, by Markup AI (September 2025)

Captain’s Gam (November 2025)

Recording of the Captain’s Gam on November 25, 2025 (Topic: Grabbing Hold of the Golden Rope: Recollections from Helmwise Captains of Game-Changing Moments with their Crew and Other Captains).

A New Operating Model For a New World

Insights from A New Operating Model For a New World, by McKinsey & Company (June 2025)

Captain’s Conclave (November 2025)

Recording of the Captain’s Conclave on November 13, 2025 (Topic: The 4 Dimensions of Culture and the Leaders Who Shape Them).

Beyond Strategy: Competing in the Age of Autonomous Intelligence

Insights from Beyond Strategy: Competing in the Age of Autonomous Intelligence, by Boston Consulting Group (November 2025)

5 Critical Skills Leaders Need in the Age of AI

Insights from 5 Critical Skills Leaders Need in the Age of AI, by Harvard Business Review (October 2025)

Episode 22: Leading in the Age of AI: How Smart Leaders Turn Risk Into Opportunity

In episode 22, co-hosts Scott Medeiros, President of Helmwise, and Chandler Rose, CEO of the Rosewood Family of Companies, continue their two-part conversation on one of the most important topics in business today: artificial intelligence (AI).

Captain’s Gam (October 2025)

Recording of the Captain’s Conclave on October 30, 2025 (Topic: Why Unprecedented Things Seldom Are: How History’s Lessons Repeat for Us).

Why These Companies Insist On a 72-Hour Work Week

Insights from Why These Companies Insist On a 72-Hour Work Week, by The Washington Post (October 2025)

How Well Can Top AI Models Do These Jobs?

Insights from How Well Can Top AI Models Do These Jobs?, by Sherwood News (September 2025)

The Widening AI Value Gap

Insights from The Widening AI Value Gap, by Boston Consulting Group (September 2025)

Captain’s Conclave (October 2025)

Recording of the Captain’s Conclave on October 9, 2025 (Topic: Rules of Resilience).

Why You Need Systems Thinking Now

Insights from Why You Need Systems Thinking Now, by Harvard Business Review (September-October 2025)

Episode 21: AI at the Helm: Risks Leaders Can’t Ignore

In episode 21, co-hosts Scott Medeiros, President of Helmwise, and Chandler Rose, CEO of the Rosewood Family of Companies, reunite to discuss one of the most urgent topics in business today: artificial intelligence (AI).

The Learning Organization: How to Accelerate AI Adoption

Insights from The Learning Organization: How to Accelerate AI Adoption, by McKinsey & Company (July 2025)

Captain’s Gam (September 2025)

Recording of the Captain’s Conclave on September 25, 2025 (Topic: Stewardship 360°).

Stewardship Is How Businesses Can Build Value for Future Generations

Insights from Stewardship Is How Businesses Can Build Value for Future Generations, by World Economic Forum (September 2025)

Reward, Risk, and Regulation

Insights from Reward, Risk, and Regulations: American Attitudes Toward Artificial Intelligence, by Gallup (May 2025)

Why 95% of AI Projects Fail – and How to Break Out

Insights from Why 95% of AI Projects Fail – and How to Break Out, by Sabine VanderLinden (LinkedIn, 2025)

Captain’s Conclave (September 2025)

Recording of the Captain’s Conclave on September 11, 2025 (Topic: Conquering Crisis).

Your AI Strategy Needs More Than a Single Leader

Insights from Your AI Strategy Needs More Than a Single Leader, by Harvard Business Review (Aug. 2025).

Captain’s Gam (August 2025)

Recording of the Captain’s Gam on August 28, 2025 (Topic: How Much Capital is on Your Balance Sheet?).

15 Small Business Growth Strategies for 2025

Insights from 15 Small Business Growth Strategies for 2025, by U.S. Chamber of Commerce (Jan. 27, 2025).

Captain’s Conclave (August 2025)

Recording of the Captain’s Conclave on August 14, 2025 (Topic: The Wisdom of the Bullfrog).

McKinsey Technology Trends Outlook 2025

Insights from McKinsey Technology Trends Outlook 2025, by McKinsey & Company (July 2025).

The Organization of the Future: Enabled by Gen AI, Driven by People

Insights from The Organization of the Future: Enabled by Gen AI, Driven by People, by McKinsey & Company (September 2023).

Cohort Interstitial (July 2025)

Recording of the Helmwise Cohort™ Interstitial held on July 24, 2025, hosted by Jim Van Eerden (Topic: Finding & Following Your North Star).

Seizing the Agentic AI Advantage

Insights from Seizing the Agentic AI Advantage, by McKinsey & Company (June 2025).

The CEO’s Workout for Peak AI Performance

Insights from The CEO’s Workout for Peak AI Performance, by Julie Bedard and Nicolas de Bellefonds of Boston Consulting Group (March 2025).

Captain’s Conclave (July 2025)

Recording of the Captain’s Conclave on July 10, 2025 (Topic: The Outward Mindset: Seeing Beyond Ourselves).

Top Leadership Skills to Prioritize and Develop in 2025

Insights from Forbes’ article by Kara Dennison, Top Leadership Skills to Prioritize and Develop in 2025 (2024)

The Outward Mindset

Chapter-by-Chapter Review (with Page References) The Outward Mindset By The Arbinger Institute (2019). NOT FOR REDISTRIBUTION

Episode 20: Unlocking Sustainable Growth: Powerful Strategies for SMBs with Brian Chunglo

In episode 20, filling in for co-host Chandler Rose is Brian Chunglo, Chief Operating Officer of the Rosewood Family of Companies and Interim President of ProVantage Corporate Solutions. Brian joins co-host Scott Medeiros for a rich, experience-driven conversation that offers real-world lessons from the front lines of leadership.

How COOs Maximize Operational Impact from Gen AI and Agentic AI

Insights from McKinsey & Company’s report, How COOs Maximize Operational Impact from Gen AI and Agentic AI (2024).

When Can AI Make Good Decisions? The Rise of AI Corporate Citizens

Insights from McKinsey & Company’s report, When Can AI Make Good Decisions? The Rise of AI Corporate Citizens (2024).

What is Responsible AI?

Insights from IBM’s report, What is Responsible AI? (February 2024).

Captain’s Conclave (June 2025)

Recording of the Captain’s Conclave on June 12, 2025 (Topic: Seasonality).

10 Professional Skills You Need to Stay Ahead of the AI Curve

Insights from Forbes’ report, 10 Professional Skills You Need To Stay Ahead Of The AI Curve (June 2025).

Top 5 Leadership Trends of 2025

Insights from Korn Ferry’s 2025 Report, Top 5 Leadership Trends of 2025 (April 2025).

Cohort Interstitial (May 2025)

Recording of the Helmwise Cohort™ Interstitial held on May 29, 2025, hosted by Jim Van Eerden (Topic: Changes in the Sea State).

The Unexpected Benefits of Being Humble

Insights from The Epoch Times’ 2025 Report, The Unexpected Benefits of Being Humble (May 2025).

The State of AI

Insights from McKinsey & Company’s 2025 Report, The State of AI (March 2025).

Assessing AI Risk

Insights from Harvard Business Review’s 2025 Report, Inside Adobe’s Approach to Assessing AI Risk (May 2025).

Captain’s Conclave (May 2025)

Recording of the Captain’s Conclave on May 13, 2025 (Topic: The AI-Driven Leader).

42 AI Prompts

This list of 42 AI Prompts will assist Captains in becoming stronger AI-driven leaders.

AI Prompt Tool

AI Prompt Tool Excel downloadable file is available at the link below.

The AI-Driven Leader

Chapter-by-chapter review (with page references) of The AI-Driven Leader
By Geoff Woods (2024). NOT FOR REDISTRIBUTION

Evolution and Revolution

1998 HBR article by Larry E. Greiner (first published in 1972) that was the genesis for Helmwise’s “white caps” principle.

Recommended Reading

List of Helmwise curated books recommended for business Captains and their crews to grow personally and professionally.

State of the Global Workplace

Insights from Gallup’s 2025 Report, State of the Global Workplace (May 2025).

Episode 19: Leadership & Belief: Integrating Faith in the Business World

In episode 19, we’re going off-script with our conversation this month as we dive into a topic not often discussed in boardrooms—but one that shapes our leadership deeply: religion and beliefs in business.

Rosewood Core Values Checklist

This Core Values Checklist from the Rosewood Family of Companies helps our team reflect weekly on how well they’re living out our values through self-assessment and accountability.

Rosewood’s Core Values: What They Mean

This document defines each Core Value of the Rosewood Family of Companies, explaining what each value means for every level of the organization. This document helps guide consistent behaviors, foster accountability, and strengthen a values-driven culture.

How People Are Really Using Gen AI in 2025

Insights from the Harvard Business Review article, How People Are Really Using Gen AI in 2025 (April 2025).

Cohort Interstitial (April 2025)

Recording of the Helmwise Cohort™ Interstitial held on April 17, 2025, hosted by Jim Van Eerden (Topic: Reading the Times by Jeffrey Bilbro.).

Real Results from Gen AI in Services

Insights from McKinsey & Company article, From Promising to Productive: Real Results from Gen AI in Services (August 2024).

Episode 18: Leading with Character: Timeless Traits of Impactful Leaders

In episode 18, we draw from the 14 leadership traits taught in Marine Corps officer training—memorized with the acronym “BUCKLE DID TIE JJ”—and reflect on the values that have shaped our approach to leadership for decades.

Cohort Interstitial (March 2025)

Recording of the Helmwise Cohort™ Interstitial held on March 27, 2025, hosted by Rick Hasty (Topic: When Love Leads).

The Art of 21st-Century Leadership

Insights from McKinsey & Company article, The Art of 21st-Century Leadership: From Succession Planning to Building a Leadership Factory (March 2024).

Cohort Interstitial PDF (March 2025)

PDF file of Rick Hasty’s “When Love Leads” presentation for the March Cohort Interstitial, held on March 27, 2025.

Captain’s Conclave (March 2025)

Recording of the Captain’s Conclave on March 13, 2025 (Topic: Better Good Profit).

Good Profit

Chapter-by-chapter review (with page references) of Good Profit
By Charles G. Koch (2015). NOT FOR REDISTRIBUTION

Episode 17: Steering the Ship: How Harmony Keeps You on Course

In episode 17, we explore a concept that challenges the traditional notion of work-life balance. Fresh from a recent Helmwise Cohort, we share insights from a session that resonated deeply with us—why true success isn’t about balance but rather harmony.

Good Leadership is About Asking Good Questions

Insights from Harvard Business Review article, Good Leadership is About Asking Good Questions, written by John Hagel III (Jan 2021).

Captain’s Conclave (February 2025)

Recording of the Captain’s Conclave on February 11, 2025 (Topic: Better Decisions, Fewer Regrets).

Better Decisions Fewer Regrets

Chapter-by-chapter review (with page references) of Better Decisions, Fewer Regrets by Andy Stanley (2020). NOT FOR REDISTRIBUTION

Episode 16: Full Speed Ahead: Aligning Your Business for the Upcoming Year

In episode 16, we’re charting a course for success in the year ahead! Just as a skilled captain sets a clear course before setting sail, organizations must align their teams and strategies to navigate the challenges and opportunities of a new year.

Cohort Interstitial (January 2025)

Recording of the Helmwise Cohort™ Interstitial held on January 28, 2025, hosted by Helmwise Captains John Stahl-Wert and Mark Peterson (Topic: Build on Strength—One of the Five Serving Leader Principles).

Captain’s Conclave (January 2025)

Recording of the Captain’s Conclave on January 14, 2025 (Topic: Revenge of the Tipping Point).

Revenge of the Tipping Point

Chapter-by-chapter review (with page references) of Revenge of the Tipping Point by Malcolm Gladwell (2024). NOT FOR REDISTRIBUTION

Episode 15: Leadership Alignment: Finding the Right Fit for Business Success

In episode 15, we draw inspiration from a fascinating moment during our latest Helmwise Cohort. Leaders often face pivotal questions as they navigate their journey, and one question stood out: Is the captain and the ship truly a match for the journey ahead?

Captain’s Conclave (December 2024)

Recording of the Captain’s Conclave on December 10, 2024 (Topic: The Messy Middle).

2023 COO Forum Insights

Insights from McKinsey’s COO Forum into current trends impacting operations executives based on their 2023 survey.

The State of Leadership 2021

Insights from John Hagel III highlight the evolving role of leaders who embrace vulnerability by asking powerful questions, especially during times of crisis and uncertainty.

The Messy Middle

Chapter-by-chapter review (with page references) of The Messy Middle. By Scott Belsky (2018). NOT FOR REDISTRIBUTION

Admiral William H. McRaven – University of Texas at Austin 2014 Commencement Address

Remarks by Naval Adm. William H. McRaven, BJ ’77, ninth commander of U.S. Special Operations Command, Texas Exes Life Member, and Distinguished Alumnus. University-Wide Commencement at The University of Texas at Austin, May 17, 2014.

Cohort Interstitial (November 2024)

Recording of the Helmwise Cohort™ Interstitial held on November 26, 2024, hosted by Brad and Drew Formsma (Topic: Gratitude as a Captain).

Captain’s Conclave (November 2024)

Recording of the Captain’s Conclave on November 12, 2024 (Topic: Beyond Measure: The Big Impact of Small Changes).

Beyond Measure

Chapter-by-chapter review (with page references) of Beyond Measure: The Big Impact of Small Changes by Margaret Heffernan. NOT FOR REDISTRIBUTION

Episode 14: The Steady Ship: Leading with Consistency and Credibility

In episode 14, we dive into the power of consistency in leadership and how it affects performance throughout your entire enterprise. Just as a captain leads their crew and ship with steady direction, building a culture rooted in core values is essential to ensuring consistency across every level of the organization.

Captain’s Conclave (October 2024)

Recording of the Captain’s Conclave on October 15, 2024 (Topic: Turn the Ship Around!).

Cohort Interstitial (September 2024)

Recording of the Helmwise Cohort™ Interstitial held on September 24, 2024, hosted by Jim Van Eerden and Michael Meredith (Topic: The Fourth Turning Is Here: What the Seasons of History Tell Us about How and When This Crisis Will End, by Neil Howe).

Turn the Ship Around!

Chapter-by-chapter review (with page references) of Turn the Ship Around!: A True Story of Turning Followers into Leaders by L. David Marquet. NOT FOR REDISTRIBUTION

Optimism Test

Take Psychology Today’s insightful Optimism Test to help quickly gauge your outlook on life.

Episode 13: Accountability and Leadership Standards as a Captain

In episode 13, we dive deep into a crucial topic: accountability and leadership standards. As a leader and a captain, holding yourself and your crew accountable is vital, as it fosters trust, ensures high performance, and creates a culture of integrity within the team.

Captain’s Conclave (September 2024)

Recording of the Captain’s Conclave on September 17, 2024 (Topic: Dichotomy of Leadership).

Dichotomy of Leadership

Chapter-by-chapter review (with page references) of Dichotomy of Leadership By Jocko Willink & Leif Babin (2018). NOT FOR REDISTRIBUTION

Episode 12: Empowering Leaders: Intentional Growth and Leadership Insights

In episode 12, we explore the importance of intentional growth in leadership, discussing the critical need for personal and professional development. Join us as we highlight the importance of stepping out of our comfort zones and learning from diverse perspectives.

Cohort Interstitial (August 2024)

Recording of the Helmwise Cohort™ Interstitial held on August 27, 2024, hosted by Professor Michael Meredith (Topic: SPIN Selling by Neil Rackham).

Captain’s Conclave (August 2024)

Recording of the Captain’s Conclave on May 14, 2024 (Topic: Who Not How).

Who Not How

Chapter-by-chapter review (with page references) of Who Not How by Dan Sullivan. NOT FOR REDISTRIBUTION

Celebrating One Year of The Powerhouse Perspective

In recognition of our first year as a podcast, we’ve compiled our best clips into a highlight reel filled with powerful insights and inspiring moments.

Cohort Interstitial (July 2024)

Recording of the Helmwise Cohort™ Interstitial held on July 30, 2024, hosted by Dr. John Stahl-Wert (Topic: How Serving Leadership Drives Measurably Superior Performance).

July’s Interstitial – CSL Model

Provided is a PDF copy of the CSL Model from our July 2024 Interstitial, hosted by Dr. John Stahl-Wert.

Captain’s Conclave (July 2024)

Recording of the Captain’s Conclave held on July 9, 2024 (Topic: Essentialism).

Essentialism

Chapter-by-chapter review (with page references) of Essentialism by Greg McKeown. NOT FOR REDISTRIBUTION

Episode 10: A Captain’s Guide: Keeping Your Crew Informed and Focused

In episode 10, we explore effective communication on board your ship. Learn how the Captain can convey their vision to the crew, ensuring everyone stays aligned and focused as they face upcoming challenges.

Captain’s Conclave (June 2024)

Recording of the Captain’s Conclave held on June 11, 2024 (Topic: Chasing Failure).

Chasing Failure

Chapter-by-chapter review (with page references) of Chasing Failure by Ryan Leak. NOT FOR REDISTRIBUTION

Episode 9: Leading Your Crew to Success: Strategies for Effective Team Leadership

In episode 9, we delve into how to effectively lead your crew once you have the right people in the right roles.

Episode 8: Charting Your Crew: Choosing the Right Team for Your Business Voyage

In episode 8, we continue our journey by diving deep into the crew. What capabilities do they need? How does a captain select the right crew? How do we look at their capabilities and skills to ensure they are suitable for the journey ahead?

Captain’s Conclave (May 2024)

Recording of the Captain’s Conclave on May 14, 2024 (Topic: High Road Leadership).

High Road Leadership

Chapter-by-chapter review (with page references) of High Road Leadership by John C. Maxwell. NOT FOR REDISTRIBUTION

The State of Operations 2023

Insights from the COO Forum into the current trends affecting operations executives based on their 2023 survey.

The State of Organizations 2023

McKinsey’s 2023 report of the ten shifts that are transforming organizations.

Self-deception

McKinsey/NPR interview (May 2021) with Skankar Vedantam, author of Useful Delusions, that examines the power and paradox of the self-deceiving brain.

Institutional Super Powers

McKinsey article on how companies can build institutional capability (Mar 2023)

CEO Excellence

McKinsey CEO Excellence Assessment Tool – Where CEOs are confident and vulnerable (Feb 2024).

Continuous Employee Listening

McKinsey article (May 2023) on how leaders can use people analytics to identify critical needs, make decisions, and stengthen employee value.

Pieces of Eight

The eight critical questions used to validate that the Captain, Ship, and Crew are ready to embark towards its next Waypoint.

Traction

Chapter-by-chapter takeaways (with page references) of Traction by Gino Wickman. NOT FOR REDISTRIBUTION

Actions to Amplify

Leadership Actions to Amplify Your Organizations Impact by Franklin Covey.

Inflation Metrics

2022 Business Guide from Oracle NetSuite on the four inflation metrics to watch.

Cues Summary

One-page graphical depiction of the core elements presented in the book Cues by Vanessa Van Edwards.

Willink 101

List of concept and takeaways from Jocko Willink’s books Extreme Ownership and The Dichotomy of Leadership.

Sinek 101

Key takeaways from Simon Sinek’s books Start With Why, Leaders Eat Last, and Infinite Game.

Lencioni 101

A list summary of the principles or concepts published in 8 of Patrick Lencioni’s 11 books on organizational health.

Collins 101

Summary of the principles published in the books Built to Last, Good to Great, Great By Choice, and How the Mighty Fall by Jim Collins.

Helmwise Glossary

Glossary of the acronyms and terms used by Helmwise in its thought leadership and Cohort experiences.

Episode 7: Sailing Through the Seas of Decision-Making: Unveiling Your WHY

In episode 7, we discuss the art of decision-making as we chart our course toward realizing our noble “WHY” alongside our trusty crew and ship.

Episode 6: Neurochemistry and the Captain’s Mind: Navigating Your Ship

In episode 6, we discuss the science of neurochemistry, neurochemistry, uncovering how our brain intricately shapes our thoughts, perceptions, and decision-making processes, empowering us to become more effective Captains of our Ship.

Episode 5: The Captain’s Compass: Charting Your Business Course to Success

In episode 5, we emphasize the critical significance of comprehending your current position as a captain and the trajectory of your business, prompting the pivotal question: “Where do I chart it to?”

Episode 4: Mastering the Helm: Essential Skills for Captains of Business

In episode 4, we unravel the steps captains need to take in order to enhance their self-awareness and effectively steer the course of the business they lead, delving into the essential skills and qualities they must embody to keep their new ship afloat.

Episode 3: Navigating Uncharted Waters: Unforeseen Challenges, Accountability & Selfless Leadership

In episode 3, we explore the parallels between skilled captains navigating unpredictable waters and leaders preparing for unforeseen challenges, while also discussing the importance of servant leadership, accountability, and self-reflection in fostering growth for both leaders and their teams.

Episode 2: Charting Your Leadership Course – Navigating the Seas of Business

In episode 2, we explore the origins of the Helmwise name, rooted in Scott’s marine background and Chandler’s passion for boating, while delving into the sea metaphor that sets the tone for future episodes, guiding you on why navigating your business like a skilled captain is essential.

Episode 1:  Unveiling Your Purpose – Discovering the “Why” Behind Your Business

In our introductory episode, co-hosts Scott Medeiros and Chandler Rose have an engaging discussion all about uncovering the essence of your company’s purpose — the all-important “why.”