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The biggest gap between AI success in startups vs. enterprises isn’t the technology. It’s permission. The biggest gap between AI success in startups vs. enterprises isn’t the technology. It’s permission. This image captures the real reason AI succeeds in startups and stalls in enterprises: the permission gap. Startups vs. Enterprises: The Permission Gap Startups pass… Continue reading The biggest gap between AI success in startups vs. enterprises isn’t the technology…
Last Saturday, I wrote about what work should never be handed to an AI agent — even if the tech can do it. Last Saturday, I wrote about what work should never be handed to an AI agent — even if the tech can do it. This week, let’s talk about what actually goes wrong… Continue reading Last Saturday, I wrote about what work should never be handed to an AI agent…
Stop Writing Blank Checks for “AI”: A Project Manager’s Guide to Real Budgeting Stop Writing Blank Checks for “AI”: A Project Manager’s Guide to Real Budgeting I see it every day one of my feeds: A CEO announces a “transformative AI initiative,” a top-tier consultancy hands over a seven-figure bill, and six months later, the… Continue reading Stop Writing Blank Checks for “AI”: A Project Manager’s Guide to Real Budgeting
Where Do I Start With AI? (Hint: It’s Not a Vendor Demo) Where Do I Start With AI? (Hint: It’s Not a Vendor Demo) “Where do I start?” It’s the question haunting every boardroom and project kickoff in 2026. Usually, the response is a flurry of expensive activity: a department head signs up for a… Continue reading Where Do I Start With AI? (Hint: It’s Not a Vendor Demo)
Why Most AI Initiatives Fail Before They Start And Why “Phase Zero” Is the Step Everyone Skips Why Most AI Initiatives Fail Before They Start And Why “Phase Zero” Is the Step Everyone Skips Most AI initiatives don’t fail because the model was bad. They fail because the organization wasn’t ready. I see this pattern… Continue reading Why Most AI Initiatives Fail Before They Start And Why “Phase Zero” Is the Step Everyone Skips
Prevent AI Waste — Before You Start Prevent AI Waste — Before You Start It’s a new year, and I just published a short video on something I see far too often: organizations rushing into AI and wasting time, money, and credibility before they ever get value. Two quick notes to set expectations: I’m not… Continue reading Prevent AI Waste — Before You Start It’s a new year…
AI Without Phase Zero Is Putting the Cart Before the Horse AI Without Phase Zero Is Putting the Cart Before the Horse Most AI initiatives fail because organizations rush to what before agreeing on why. If you’ve ever seen a team rush into AI tools, pilots, or use cases without alignment, you’ve already seen the… Continue reading AI Without Phase Zero Is Putting the Cart Before the Horse
AI Agents in the Real World: What Breaks First AI Agents in the Real World: What Breaks First Last Saturday, I wrote about AI agents in Phase Zero — before tools, vendors, or pilots. This week, let’s talk about what actually goes wrong when you try to implement AI agents too early. These are not… Continue reading AI Agents in the Real World: What Breaks First
As the new year approaches, a lot of leaders are being asked one uncomfortable question: What’s our AI plan—and how confident are we in it? As the new year approaches, a lot of leaders are being asked one uncomfortable question: What’s our AI plan—and how confident are we in it? Most AI initiatives fail not… Continue reading As the new year approaches, a lot of leaders are being asked one uncomfortable question…
Most AI initiatives don’t fail because of the technology. Most AI initiatives don’t fail because of the technology. They fail because leaders are forced to make high-stakes decisions without a clear starting point. If you’re accountable for strategy, operations, or innovation in a mid-market organization, this probably feels familiar: Too much AI hype Too many… Continue reading Most AI initiatives don’t fail because of the technology. They fail because leaders are forced to make high-stakes decisions without a clear starting point…
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