Gary A. Bolles is a globally respected thought leader on the future of work, technology, and organizational transformation. He is the Chair for the Future of Work at Singularity University, where he advises leaders, organizations, and governments on navigating disruption and building adaptable, inclusive systems of work.

Gary is the author of The Next Rules of Work, a widely acclaimed guidebook for leaders facing uncertainty in a fast-changing world. His work focuses on the intersection of human potential and exponential change—helping individuals and institutions unlock opportunity through mindset, skillset, and toolset transformation.

As a global keynote speaker and educator, Gary has reached over 1.6 million learners on LinkedIn Learning. He is also a partner at Charrette LLC, co-founder of Next CoLabs, and co-founder of eParachute.com—a platform designed to support career changers and job seekers in LIFEwork transitions.

His consulting and strategic design work has impacted clients including Google, Deloitte, London Business School, and the World Bank. Gary’s expertise stems from decades of innovation in workforce strategy, event facilitation, and future-forward thinking.

Through his writing, speaking, and advising, Gary helps organizations not just respond to change—but become architects of it.

Ross and Gary talk about transformation, playbooks, resetting, building systems to adapt, skills, work roles, problem solving, adapting, focusing on tasks, skills manifestos, simple visions, business values, human skills, living documents, refreshing to continually adapt, iceberg diagrams, helping individuals knowing their own skills, future value, workshops, generative AI, self inventory, encouraging people,  job titles, enterprise, taxonomy, constantly adapting and the Book - The Skills Powered Organisation. The pair also discuss stepping back, hiring managers, team guides, changing mindsets, compensation, incentives, skill to alternative routes, development, rethinking governance, going to the edge, changing organisations core, Book - Culture Transformation, relationships with the world of work, reskill index, collection problem solving, teams, skill building networks, constant assessment, becoming irrelevant, the consequences of inaction, leveraging tool, curiosity, testing your own AQ, expanding skill sets and changing environments.

Timecodes:

• 00:21 Intro to Gary
• 02:35 Inspiration for Gary's book (The Next Rules of Work)
• 06:20 Works tasks and human skills
• 08:20 Starting the transformation
• 10:59 Great things from skills manifestos and mistakes to avoid
• 13:51 Key assets
• 17:37 Tasks being bigger than expected
• 22:53 Ontology, framework and common language
• 28:02 Resources to co-elevate and redo work
• 29:54 Skills to problem solve
• 32:29 Skills governance
• 37:43 Barriers and tips for legacy organisations to gain freedom
• 41:26 Talent Cycle & Skills Venturing
• 46:53 Lifelong learning
• 49:20 The consequences of inaction
• 51:37 What is Gary excited about
• 53:52 The last time Gary did something for the first time

Connect with Gary:

• Website
• LinkedIn

Connect with Ross:

• Website
• LinkedIn
• Moonshot Innovation