Unboxing the Office | Episode 17: Leading Through AI Transformation with Harry Osle

AI implementation is not just a technology decision. It is a leadership, culture, and people decision.

In Episode 17 of Unboxing the Office, Bernie Youngblood sits down with Harry Osle, Principal and Chief Human Resources Officer at The Hackett Group, to unpack what it actually takes for organizations to succeed in the AI era.

Harry shares why too many leaders invest in AI platforms without investing in the people expected to use them, how small wins create momentum for enterprise change, and why the most successful organizations will combine the will to transform with the skills to make it happen.

From AI readiness and benchmarking to workforce capability, HR’s evolving role, and building a culture that can absorb change, this conversation is a practical look at how leaders can move beyond the AI hype and create real, lasting impact.

✅ In this episode, they explore:

— Why leadership determines whether AI transformation succeeds
— The mistake of investing in AI without reskilling people
— How AI can increase capacity, efficiency, and engagement
— Why organizations should start small and build momentum
— Benchmarking as a roadmap for organizational change
— How The Hackett Group uses AI to accelerate insight and execution
— Culture as an outcome of leadership and daily operations
— Why HR must shift from supporting HR to driving business impact
— AI skills, storytelling, and the future workforce capability gap
— The importance of “will and skill” in leading through change

📚 Chapters

00:00 Welcome to Harry Osle and the AI conversation
01:50 Why AI is finally “game time”
03:10 What separates organizations that adapt from those that struggle
07:43 Where leaders get AI implementation wrong
09:54 AI investment must include investment in people
11:12 The Ferrari analogy: technology without the skills to use it
13:57 Why great leaders do not start with a blank sheet of paper
15:14 What The Hackett Group does and how benchmarking works
18:20 Benchmarking as an organizational health check
22:19 The potential of AI-powered benchmarking data
24:24 How Hackett AI XPLR maps AI opportunities and ROI
27:35 Why AI transformation should start with small wins
29:05 How to bring employees along through AI change
33:43 Culture is an outcome of leadership
38:20 Strong cultures have more capacity for change
41:38 Adaptability, disruption, and the next generation of workers
43:35 AI as a platform for positive change
45:06 The future of HR in the AI era
47:39 Building organizational absorptive capacity
49:23 The Workforce AI Capability Index
52:27 The formula for success: will and skill

👉 Like, comment, and subscribe for more conversations about workplace culture, leadership, and the human side of business.

🔗 Connect with Harry Osle:
Email: hosle@thehackettgroup.com
LinkedIn: https://www.linkedin.com/in/harry-osle/

🔗 Learn more about The Hackett Group:
AI readiness with Hackett AI XPLR™: https://www.thehackettgroup.com/ai-xplr/
Gen AI in HR: https://www.thehackettgroup.com/gen-ai-in-hr/
The AI capability gap in HR: https://www.thehackettgroup.com/insights/ai-world-class-human-resources-2606/

🔗 Connect with Bernie Youngblood:
https://www.linkedin.com/in/bernieyoungblood/

🔗 Learn more about HOTLOGIC®, the AI Oven:
https://hotlogicappliances.com/

#UnboxingTheOffice #ArtificialIntelligence #AITransformation #Leadership #FutureOfWork #HumanResources #HotLogic