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Dr. Henry Cloud is a bestselling author, psychologist, and leadership expert whose work on boundaries, relationships, and emotional health has shaped leaders around the world. If you are familiar with Henry, you know that he doesn’t just diagnose problems—he helps leaders understand what growth actually looks like, and how we can take responsibility for it in real life. Our President and CEO, David Ashcraft, recently sat down with Dr. Cloud for a conversation about his upcoming book Your Desired Future. This book is basically a masterclass in how to lead—yourself and other people and is exactly what we’ve come to expect from Henry: deep psychological insight with super practical application. Whether you are just getting started in your leadership journey, or you’ve been at it for a while now, this conversation is an absolute game-changer, and we are so glad we can bring it to you today.
INTHIS EPISODE
0:00 Intro
03:40 Dr. Cloud’s history with the Global Leadership Network.
04:15 Why does he keep coming back to the Global Leadership Summit year after year?
06:45 Why did he write the book Your Desired Future, and who did he have in mind as the audience?
15:20 Getting started with the model.
26:50 How do you deal with low performers in a smaller organization?
31:10 The challenge of dealing with personnel issues in a church.
33:40 Among the five leadership steps, is there one that tends to derail leaders or organizations more than the others?
36:45 How much do personality and wiring affect a leader’s ability to succeed in these five areas?
39:50 What should leaders do if they are the only person in the organization and don’t have the resources to fill all fiveleadership roles?
41:30 When someone seeks help from experienced leaders, should they ask for advice, resources, or financial support?
43:30 If someone follows these five leadership principles, what kind of outcome should they realistically expect?
37:45 Outro
LISTEN
Apple Podcasts | Spotify | YouTube
STANDOUTSAND TAKEAWAYS
- Great leaders get better when they step outside their bubble and learn from voices and perspectives they normally wouldn’t encounter.
- The work writes the books—They grow out of the patterns of high-performing leaders as they solve real problems.
- There is a one-to-one match between how the human body does anything and how great leadership is supposed to function.
- Leadership is simply moving something from where it is now to a better future that doesn’t yet exist.
- Humans uniquely have the ability to imagine a future reality that isn’t here yet—and leadership begins when you decide that future should exist.
- Once you see the future, leadership is about recruiting and aligning the rightpeople who can actually make it happen.
- Strategy answers the question: “How will we win?”—and great strategy requires saying no to many good ideas so the best one can succeed.
- Organizations fail not because they lack vision, but because they avoid measuring performance and holding people accountable.
- Grace should lead to growth and fruitfulness—not a culture where poor performance is ignored.
- Healthy leadership first tries to restore and develop struggling people before removing them.
- Leaders should hire and structure teams based on the future they are building, not just on who is currently available.
- Every leader is naturally strong in some leadership functions and weak in others, so great leaders ensure the system covers all five even if they personally cannot.
- You don’t need money to build leadership capacity—you need the humility and initiative to ask others for help and wisdom.
- Progress begins the moment you move—even a mustard seed of action can unlock the people and resources you need.
- These leadership principles don’t guarantee success, but without them you’ll never know whether your idea failed—or was simply never executed well.
- The five leadership functions mirror how the human body works—because that’s exactly how God designed systems to move from intention to action.
- Great leaders accept uncertainty and simultaneously work to increase certainty. Develop intentional systems to get better, regardless of what you’re doing. You can be content and hungry at the same time.
LINKSMENTIONED
- Website: Dr. Henry Cloud
- Book: Your Desired Future: The Five EssentialSteps That Take You Where You Want to Go (Pre-Order on Amazon)
- Website: Team365
- Website: Global Leadership Summit 2025
- Website: Global Leadership Network
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Leadership That Lasts
Team365 isn’t just a platform. It’s a commitment to grow, lead and live with purpose — every single day. Whether you’re here for content, community or clarity, you’re in the right place. Your leadership matters. Let’s keep going.
