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I Have Some Questions...
Most people know the headline of a leader’s story. Few know the path it took to get there. This podcast goes beyond titles, book launches and business wins, to explore the lived journey behind the thought leader.
Through deep, unhurried conversations, we uncover the moments that shaped them—the doubts, pivots, convictions, and quiet breakthroughs that built their body of work.
Each episode features authors, coaches, executives, and bold thinkers who have forged their own path. Instead of rehearsed talking points, they’re invited into a space where thoughtful questions unlock something more human. The result is a layered conversation that reveals not just what they preach, but how they became the kind of person who can teach it.
Because we believe the best stories aren’t always told—they’re revealed. And when brilliant people are given the right questions and the room to answer them fully, what emerges is insight you can feel, frameworks you can apply, and a deeper understanding of what it truly takes to lead, create, and contribute at a meaningful level.
I Have Some Questions...
156: "Delegation Without Scaffolding Can Break Your People" ft. Alli Murphy
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In this co-hosted episode, Erik and Alli break down how great leaders actually delegate, develop people, and engineer growth opportunities.
They explore why most stretch projects fail, how to build “scaffolding” around new responsibilities, and why understanding someone’s failure patterns matters more than most leaders realize.
Instead of treating delegation like a simple handoff, they argue that leadership development should feel much more like apprenticeship—intentional, structured, and reflective.
🧭 Conversation Highlights
Scaffolding Creates Better Delegation
Alli shares how she asks team members to define the support they need before taking on a stretch project:
- Dedicated check-ins
- Milestones
- Training resources
- Recap systems
- Coaching conversations
The goal isn’t removing responsibility—it’s creating safe access to growth. Most Leaders Delegate Poorly. Erik explains that many leaders communicate the outcome they want… then disappear.
Without structure, prioritization, or accountability, stretch opportunities often become frustrating instead of developmental.
Understanding Failure Modalities. A standout concept from the episode is “failure modalities”—the predictable ways people struggle under pressure.
💡 Key Takeaways
- Delegation should be engineered—not improvised.
- Ownership increases when people help design their own support systems.
- Milestones create clarity and momentum.
- Stretch projects work best when failure is survivable.
- Leadership development looks more like apprenticeship than traditional corporate training.
- Reflection after the project is where much of the learning happens.
❓ Questions That Mattered
- How do you know when someone is ready for more responsibility?
- What support helps someone grow without removing ownership?
- Are you delegating intentionally—or just hoping they figure it out?
- What’s the most likely way this person could fail?
- What capability do you want them to build over the next six months?
🗣️ Notable Quotes
“I’ve started thinking about it more as engineering opportunity.”
“What scaffolding do you need to make sure this goes well?”
“The scaffold doesn’t do the work for you—it gives you safe access to the work.”
“We’ve lost the art of apprenticeship.”
“Don’t let fear have the driver’s seat.”
🔗 Links & Resources