The Longest Way Round for Character Trait Development Question Bank

The Longest Way Round for Character Trait Development Question Bank

For Coaches, Facilitators and Leaders

Supporting Meaningful Conversations About Character Traits and Authentic Professional Paths

"Character traits don't just tell us who we are - they reveal where our unique gifts can make their greatest impact.”

200+ Questions to Open, Deepen, and Guide The Longest Way Round Conversations

This question bank provides 200+ ready-to-use questions designed to help coaches, facilitators, and leaders open, deepen, and guide conversations with clients or colleagues discovering their authentic character traits, navigating professional setbacks, and finding where their natural qualities can create meaningful impact.

Nine Essential Conversation Frameworks:

1. Opening Character Conversations – Questions that help clients or colleagues explore their natural traits and authentic qualities
2. Recognising Natural Character Traits – Questions for identifying genuine strengths versus performed abilities
3. Navigating Professional Setbacks – Questions about using rejection or failure to discover authentic path
4. Learning From Great Storytellers – Questions inspired by literary and cinematic wisdom about character development
5. Redirecting Talents to New Contexts – Questions for applying existing strengths in different environments
6. Building Community Through Character – Questions about creating environments that honour authentic traits
7. Aligning Character With Professional Choices – Questions for making decisions based on natural qualities
8. Sustaining Character Alignment – Questions for maintaining authenticity over time
9. Supporting Others' Character Development – Questions for facilitating authentic trait recognition and holding space for character work

Throughout the question bank, questions are organised by professional development purpose, allowing you to quickly find language that fits your clients’ or colleague’s current moment. Each section includes questions that invite exploration, helping others discover their own clarity about how their authentic character traits can guide meaningful professional direction.

This resource stands alone as a practical tool for immediate use in professional development sessions, with deeper exploration of character development available in School of WorkLife's The Longest Way Round: A Journey of Character.

One-time purchase. Unlimited professional use in individual and group settings.