Episode Overview
In this roundtable edition of Mastering Agility/Scaling with Agility Gang, hosts Yuval Yeret, Rich Visotcky, and Jim Sammons unpack the role of courage and conviction in agile leadership. They share real-world stories—from reorganising an Israeli cyber-security scale-up to confronting “invisible electric fences” in large enterprises—and demonstrate how small, repeatable acts of bravery compound into systemic change. Practical frameworks, such as the Hypothesis Prioritisation Canvas, Appreciative Inquiry, and Critical Uncertainties, illustrate how leaders can replace process theatre with principled, context-driven experiments.
Highlight Quotes / Concepts
“Sometimes the bravest move is simply admitting you don’t know—and turning that into a testable hypothesis.” — Yuval
“You can spot a timid leader by the number of fences they’re sitting on; have an opinion and move the needle.” — Jim
“Policies you wrote to solve yesterday’s problems shouldn’t shackle tomorrow’s possibilities.” — Rich
Invisible guardrails vs. true regulatory constraints
Choosing not to decide is still a decision—make it explicit
Portfolio thinking beyond IT: treating the organisation itself as a product
Chapters
(00:28) Exploring Leadership and Courage
What does it look like to be a leader beyond a job title? The hosts define everyday acts of courage.
(02:09) Empowered Teams and Small Acts of Courage
Yuval shares a story about using simple transparency—a common board—to build conviction and confidence.
(05:57) Transparency and Decision Making
How making work visible can be a courageous first step.
(07:04) Balancing Courage and Conviction
Jim and Rich explore why conviction sometimes lags behind courage and how to handle it.
(09:40) Practical Leadership Tips
Advice for leaders: be someone people want to follow, and don't be afraid to take a stand.
(15:04) Decision Making Frameworks
Yuval introduces the Hypothesis Prioritization Canvas to de-risk big decisions.
(18:31) Testing and Validating Decisions
How to think in experiments—large and small—to build conviction over time.
(28:22) The Importance of Choice in Leadership
Leaders must learn to say no and avoid defaulting to consensus or inertia.
(29:00) Learning from Target’s Data Breach
Rich shares a story illustrating why proactive decisions (even without clear ROI) are sometimes essential.
(30:38) Testing Ideas in Smaller Timeframes
How to shrink experiments to learn faster and reduce risk.
(32:02) Encouraging Boldness in Decision Making
Making bold choices doesn’t always mean taking big risks—it often means just starting.
(32:08) Real-World Examples of Courage in Leadership
Jim recounts coaching moments when simply talking to customers was the bold move.
(38:07) Overcoming Invisible Barriers
Invisible fences—self-imposed constraints—often hold leaders back more than actual policies.
(48:41) Practical Techniques for Leadership Development
The group shares activities like critical uncertainties, appreciative interviews, and empathy maps to help leaders grow.
(50:33) Final Thoughts on Leadership and Agility
A reminder that yesterday’s policies were made to solve yesterday’s problems—and leaders have the power to change them.
Notable Quotes
“We had courage but no conviction—so we shrank the change until it felt safe enough to try.” — Yuval
“I’ve never faulted a leader for the wrong call if I could see how they got there.” — Jim
“Choice is how we play the hand we’re dealt; pretending we have none is still a choice.” — Rich
“If your Definition-of-Done lives on a faded fax sheet, you’re cheating the company out of your salary.” — Yuval
Guest Links & Resources
Appreciative Inquiry – Cooperrider & Srivastva
Liberating Structures (Critical Uncertainties, Ecocycle, Appreciative Interviews) – liberatingstructures.com
Experiment invitation: This week, pick one “invisible fence” in your organisation—something you assume you can’t do—and design a one-week safe-to-fail test to probe whether the fence is real. Share your plan (or results) and learning e.g. on Linkedin (Tag us if you’d like!)
Get started on your nuanced scaling journey in Yuval’s free Scaling w/ Agility Crash Course
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