Jeff Winter 12/29/25 Jeff Winter 12/29/25

The Hardest Part of AI Isn’t Intelligence. It’s Letting Go.

Most AI initiatives fail not because the technology isn’t smart enough, but because organizations never decide which decisions they’re willing to let go of.

Jeff Winter 12/28/25 Jeff Winter 12/28/25

The Crooked House Problem: When Stability Stops Progress

A crooked 17th-century building becomes a metaphor for why stabilizing misaligned systems can preserve the past but quietly block progress when the goal is growth.

Jeff Winter 12/27/25 Jeff Winter 12/27/25

Think Big. Start Small. Go Fast.

We love tidy slogans because they sound actionable and safe.
This article unpacks how a familiar transformation mantra was born, why it still shows up everywhere today, and where organizations consistently get tripped up when turning good intentions into real progress.

Jeff Winter 11/24/25 Jeff Winter 11/24/25

The Magazine Cover You Really Do Not Want To Be On

A look at the real reasons digital and AI transformations collapse and what leaders must change to stay off the cover of any technology-failure magazine.

Jeff Winter 11/18/25 Jeff Winter 11/18/25

Has Anyone Seen My ROI?

ROI is a superhero when used in the right places, a black hole when used in the wrong ones, and a discipline, not a deliverable, if you actually want it to work.

Jeff Winter 11/10/25 Jeff Winter 11/10/25

If Your Tech Disappeared Tomorrow, Would Anything Change?

Most companies call their efforts “digital transformation,” but if the operating model would function the same without the technology, then nothing transformative has happened, and this article explains why lasting change only occurs when the business itself evolves, not just the tools around it.

Jeff Winter 11/2/25 Jeff Winter 11/2/25

Forget Prediction. Build Readiness

A practical guide for manufacturers on how to strengthen their digital transformation readiness, move faster with confidence, and turn uncertainty into advantage.