Realistic Planning Through Pathway Conversations​

A Smarter Way to Plan in Uncertain Times​

Traditional planning often falls short—high in risk, cost, and failure rates. But what if planning could be realistic, low-risk, and truly effective?

Realistic Planning Through Pathway Conversations teaches you how to transform any kind of planning—strategic, scenario, project, or community—using a framework built around four powerful, collaborative conversations. Co-developed by Jack Ricchiuto and Jane Rogan, this approach helps teams stay aligned, focused on what truly matters, and ready to act in the face of uncertainty.

This hands-on, three-part online course (90 minutes per session) helps you minimise risk, optimise success, and navigate complexity with ease. Join Jack Ricchiuto and discover a smarter way to plan.

Starts July 15, 2025​

Course dates: July 15 22 & 29
Time: 10:00 am – 11:30 am EDT

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Three takeaways from the course!

Minimise risk and planning fatigue

Use strategic questioning to bring clarity, focus, and efficiency to your planning process—no more guesswork, just actionable insights.

Engage teams around shared purpose

Discover how the right questions can spark deeper conversations, engage everyone in the room, and drive better results.

Apply a simple, proven model to complex contexts

Learn how to ask the right questions at the right time to navigate challenges and make smarter decisions.

What you'll get

Three online lessons

Engage in interactive online sessions with full access to course materials, anytime, anywhere.

Personalised Guidance

Get a one-on-one session with your instructor to apply Strategic Doing to your own projects with expert support.

Free E-Book

Receive a complimentary PDF copy of Flawless Planning (2024, Nuance Works) by Jack Ricchiuto to deepen your learning.

Who is your guide?

Jack Ricchiuto

Jack Ricchiuto is a strategist, author, and facilitator who helps individuals and organisations shape a future distinct from the past. With experience spanning multinational corporations, startups, nonprofits, and civic groups, he specialises in guiding teams through complexity with clarity and purpose. Known for the Flawless Planning Model, Jack focuses on asking the right questions to drive innovation and collaboration. His expertise in leadership development and systems change has been shared at institutions like Harvard and UC Berkeley, helping leaders rethink strategy and decision-making.

What other say about the course

"I would like to say thank you for this opportunity and privilege to do something totally new in my culture where people like to take order without questioning them. Questioning is a very important action. There is a lot you need to know before you go into the right framing of a question. There are many changes I have to do but I am willing to try when I get the chance."
DANNIE YUNG
Consulting Officer
"This was incredibly helpful and inspiring. As a member of climate advocacy groups, I've struggled with how to empower communities around climate change. This provided fresh perspectives and tools, revitalising my approach with new energy. My background in organisational change management made me realise we've been solving the same problem repeatedly, but this has offered new, practical approaches to engage people."
CATHERINE SHINNERS
Change Management
"I appreciate this new perspective and context. This whole notion that trying to answer questions through discussion leads us to a knowledge bank that we already have whereas what we're trying to do is develop a new knowledge bank. I think this was a huge revelation and I am looking forward to finding opportunities to spring that on an audience to try to get them to think differently."
JOHN HARRISON
Sales and Enablement Leader

Whether you’re working in an organisation, community, or cross-sector network, this course offers a practical and powerful way to make planning truly work. Realistic Planning Through Pathway Conversations™ equips you with tools to move from assumptions to shared clarity, from complexity to coordinated action. Join us to shift how planning happens—from something people endure to something they believe in.

Course structure: 

  • Session 1: July 15 – Framework overview
  • Session 2: July 22 – Organisational applications
  • Session 3: July 29 – Community applications

Contact info: 

If you need more info or are interested in enrolling your team, send us a message at communications@tiao.world.

Starts July 15, 2025​

Course dates: July 15 22 & 29
Time: 10:00 am – 11:30 am EDT

Price: US$ 450

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Hours
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SIGN UP NOW!