Last Updated: October 16, 2026
The Inspire Podcast — Practical Leadership for People Who Run Companies
Is Your Organization Really AI-Ready?
Many business owners have tried AI, hit a wall, and decided it isn’t for them. Others are waiting for the perfect policy before they turn it on. In this episode of The Inspire Podcast, Jason Diamond Arnold, Director of Leadership Solutions at Inspire Software, sits down with Chris Wollerman, CEO and co-founder of Inspire Software, and Bill Pappa, Director of Business Solutions at Inspire Software, to talk about why waiting to integrate AI into your organization intelligently is the riskiest move you can make, and what a smart first step looks like.
HOW DO YOU GET YOUR ORGANIZATION READY FOR AI?
- Connect AI to your core systems so it works from one central hub instead of in departmental silos.
- Get started now with a short, readable AI policy instead of waiting months for the perfect one. It also addresses how “shadow AI” (personal accounts fed with company data) may be undermining your and your clients’ private information.
- Audit your workflows before you automate. Bringing AI to an inefficient process tends to multiply the inefficiency.
- Start with simple, routine processes for quick wins, then go after the bigger projects.
- Lead the human side of the change: be clear that AI is there to remove tedious work, and use a change team to hear where people are struggling and where people are having real gains with AI in your organization.
QUESTIONS THIS EPISODE ANSWERS
- What do you say to a business owner who is resistant to AI?
- Why are some companies waiting, and what does that delay cost them?
- What is shadow AI, and how does a lightweight policy help?
- Why start with a workflow audit before you touch AI?
- What happens in a two-week AI audit?
- How do you lead the people side of an AI rollout?
- Why connect AI to one central hub instead of letting each department pick its own tools?
WHO THIS VIDEO IS FOR
Owners, CEOs, and executive teams at small and mid-sized businesses who have heard the AI pitch but have not yet changed how work gets done, plus the operations and people leaders who will carry the change.
CHAPTERS
- 0:00 Highlight: the human side of AI change
- 1:11 Welcome: Jason, Chris and Bill
- 2:54 What to tell a business owner who resists AI
- 5:30 Automation multiplies inefficiency
- 6:40 Why companies wait: compliance and shadow AI
- 9:11 Just get started with a lightweight AI policy
- 10:39 A cautionary tale, and why to audit first
- 15:01 Inside a two-week AI audit
- 19:06 Where to start after the audit
- 19:51 Start simple, and don’t skip the human side
- 22:30 Leading the change: culture and a change team
- 26:26 Why AI needs one central hub
- 28:23 Why a partner, and why data is everything
- 31:10 Creating better data, not just more
- 32:11 Wrap-up and how to reach us
ABOUT INSPIRE SOFTWARE
Inspire is the unified platform connecting strategy to the OKRs, performance, recognition, leadership development, planning, and task management that carry it out, in one platform, with coaching from the Inspire team. Ask us about an AI readiness audit for your organization.
CAN WE HELP YOU LEAD YOUR ORGANIZATION IN THE 21st CENTURY?
Want to Have a Conversation with Us?: https://inspiresoftware.com/about-us/contact/?utm_source=youtube&utm_medium=inspire-podcast&utm_campaign=org-ai-ready
Talk to our team about an AI audit: https://meetings-na2.hubspot.com/bill-pappa?utm_source=youtube&utm_medium=inspire-podcast&utm_campaign=org-ai-ready
What leaders say on G2: https://www.g2.com/products/inspire-software-inspire/reviews
Subscribe to The Inspire Podcast and tell us in the comments what you want Chris and Bill to cover next: https://www.youtube.com/@inspiresoftware
Related Resources
For More on How AI Can Help Executive Leaders Create a Strategy Execution Engine through Continuous Performance Management, read this Inspire article: https://inspiresoftware.com/the-execution-engine/
For More Insights on how to Turn Strategy into Action Through OKRs, read this Inspire article: https://inspiresoftware.com/ai-for-planning-toward-okrs-helps-organizations-turn-strategy-into-action/
Download the free eBook — The Six Steps to a Winning Strategy: https://inspiresoftware.com/resources/ebook-the-6-steps-to-a-winning-strategy/
Get the State of Strategy Execution in 2025 report: https://inspiresoftware.com/resources/the-state-of-strategy-execution-in-2025/
Featured Co-host: Chris Wollerman — CEO and Co-Founder, Inspire Software. Chris has spent his career helping organizations connect strategy, goals, performance, and leadership into a single execution system. About Inspire Software Inspire helps companies align strategy with performance to drive effective execution and employee engagement through meaningful, measurable results. The platform connects strategy, OKRs, continuous performance management, leadership development, and recognition to turn intent into action.
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