Meeting/Event Information
Your Tech Transformation Is in Trouble and AI Can’t Save It

July 16, 2026
8:00 AM - 9:30 AM
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Marsh McLennon Agency
20 North Martingale Rd
Schaumburg, IL 60173
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Session Summary:
Many digital transformations, AI initiatives, and complex software projects fail. Often the warning signs are there, but we have to act while there is still time to save the transformation. In this fast-paced, candid talk, Bob walks through what happens inside high-stakes transformation initiatives. Drawing on real-world experience, he shows how leadership decisions, people dynamics, and small breakdowns add up to stalled or failing execution. If you've been in a status update meeting thinking "this is not going to go well," welcome back to the movie you’ve seen before; let’s write a new ending to this one.
Audience
Leaders in Finance, HR, Operations, and IT who have a cross-functional view and can see these risks coming but are navigating when and how to raise them. Program managers, ERP project managers, or anyone else who is expected to deliver results without full control over the underlying issues.
Learning Objectives:
· Common problems and warning signs related to people, process, data, and technology.
· Dynamics that keep teams from speaking up even when they know something is wrong.
- Practical ways to address to these issues and keep your transformation on track.
Meet Our Speaker:

Bob Wallis works with leadership teams on high-stakes transformation efforts where the cost of getting it wrong is measured in real money, time, and credibility. He is brought in to pressure-test major initiatives before they begin or to stabilize and recover projects that have drifted off course. Bob has significant technology experience, but his work centers on the human and operational factors that ultimately determine success.
Reviews about Previous Talks
“In five minutes, Bob covers every common-sense question and thought you've ever had during a software implementation but couldn't voice out loud because, ‘politics.’ The next time a project like that is on the horizon, have Bob present to your leadership team beforehand. It'll save your entire organization a lot of grief and unnecessary expense.”
“Bob delivered a practical, insightful reminder that organizations don’t need bigger, flashier systems to succeed, they need alignment, readiness, and the courage to ask better questions before investing. His humor, honesty, and real-world experience made the session both refreshing and energizing. It left me feeling more confident about guiding teams toward solutions that actually work.”
*A light breakfast and coffee will be available.