AI isn't the problem. Your decisions are. | Why your AI strategy is making everything worse | The Best Leadership Podcast For VPs and Managers
  • October 6, 2026

122. AI isn’t the problem. Your decisions are. | Why your AI strategy is making everything worse

The Iceberg of Ignorance says senior leadership only knows 4% of a company’s problems. The frontline knows 100%. Yet senior leaders are the ones making the big strategic AI decisions right now.

That’s a problem. Specifically, it means most of you are building an AI strategy for problems you haven’t even defined.

AI has become the corporate version of the flashy red Mustang in a mid-life crisis. It feels innovative. It looks great in board decks. It scares competitors. But just because you’re dressed as a superhero doesn’t mean you can fly. And just because you have an AI strategy doesn’t mean you have a problem worth solving.

In this episode, I unpack the 5 predictable pitfalls of starting with the solution, what real business problems actually look like, the 70-person SaaS company that bet their AI strategy on a 6-week sprint and lost 3 clients, and the 3-question Leader’s Litmus Test to keep yourself honest.

🎧 Press play. Start with the problem.

In this episode:

â–¶ The Iceberg of Ignorance: why leaders know 4% of their company’s problems
â–¶ Tool-first thinking and the corporate mid-life crisis
â–¶ The 5 pitfalls of starting with the solution instead of the problem
â–¶ The 4 characteristics of a real problem: pain, cost, problem statement, improvement
â–¶ The 70-person SaaS company whose AI strategy lost them 3 clients in 6 weeks
â–¶ My web host that replaced its support team with AI (and became unusable)
â–¶ The 3-question Leader’s Litmus Test before any AI strategy decision

If your AI strategy started with “we should use AI” instead of “we have this specific problem,” this one’s for you.



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Referenced in this episode:



Show Notes

[00:00] Introduction
[00:35] Conversation About AI and Leaders
[02:05] Tool-First Thinking
[02:40] The Problem With Starting At The Solution
[03:16] What Real Problems Actually Look Like
[04:25] When AI Makes Bad Problems Worse
[06:04] The Leader’s Litmus Test
[06:37] Start With the Problem, End With the Tool
[08:00] The Future Isn’t About The Fastest


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