Episode Summary
Ron and Deb welcome Jason Tanaka for a conversation about AI, leadership, and the difference between real strategy and what Jason calls “AI theater.” Jason brings a background in software, technology, financial services, and AI advisory work, helping leaders make consequential technology decisions and turn them into reality.
Jason compares an AI playbook to a football playbook. You do not run every play in order. You choose the right play based on the situation, the people, the goal, and what is happening on the field. In the same way, every company needs an AI strategy that fits its business, culture, risks, and desired outcomes.
This is where leadership development becomes essential. AI adoption is not just about buying tools or handing out licenses. It is about helping leaders understand what they are really trying to accomplish, where AI can create value, and where it may create risk. Without that clarity, organizations can spend a lot of time and money on tools that never produce a meaningful return.
Company Culture Shapes AI Adoption
The human element of AI matters just as much as the technology. Some people inside an organization will experiment quickly. Others will barely use the tools. Some may build workflows or applications without clear oversight, creating what Jason calls “shadow AI.”
That is why company culture and communication matter so much. If leaders do not explain the purpose of AI adoption, employees may hear fear instead of opportunity. They may wonder whether AI is here to help them, replace them, or make their work less valuable. Strong leadership communication helps people understand the intention behind the change and how they can participate in shaping it.
Communication Problems Can Kill AI ROI
Ron, Deb, and Jason also explore why many companies struggle to get a return on AI investment. The issue is often not the tool itself. It is the gap between strategy and the people doing the work.
Jason points out that line-level managers and process experts often understand the real breakdowns better than anyone else. They know where customers get frustrated, where systems fail, and where work slows down. If those people are included in the AI conversation, organizations have a much better chance of using AI to solve real problems.
But if AI decisions stay at the top, or if employees are left to figure it out alone, communication problems can quickly turn into wasted effort, shadow systems, and missed opportunities.
Leadership Training in the Era of AI Adoption in Businesses
The question then becomes, “what happens to human value when AI can complete more tasks?”
Ron notes that many people draw their sense of worth from getting things done. When AI starts doing those tasks faster, people may begin to wonder what they are worth now. Jason offers a helpful distinction: AI is not necessarily replacing jobs. It is replacing tasks. And when tasks change, jobs change.
That means leaders need to help people reconnect with the human advantage: creativity, judgment, context, relationships, and the ability to decide what matters. AI can outthink people in many ways, but it still needs humans to guide the intention behind the work.
The companies that succeed with AI will not be the ones chasing the most impressive demos. They will be the ones that create thoughtful playbooks, include the people closest to the work, communicate clearly, and build a company culture where people can experiment without losing sight of real business outcomes.
If you’re navigating AI adoption, leadership challenges, communication problems, or cultural shifts inside your organization, we’d love to hear your story.
Reach out to Ron at ron@macklinconnection.com or Deb at deb@macklinconnection.com to learn more about joining a community designed to support your personal and professional growth.
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