IPM Day Speaker Spotlight: Darrel Popowich
Your AI tool works, but your AI initiative is still failing. That’s not a paradox. According to Darrel Popowich, Founder and CEO of Transformation Craft, it is the most predictable outcome in project leadership right now. Ahead of his presentation at IPM Day 2026, we ask him why organizations keep solving the wrong problem, and what leaders should do instead.
His answers aren’t about technology at all. They are about culture, trust, and the order in which you build them. Interview conducted by Lori Milhaven, EVP of IIL.
Lori: Why do most AI initiatives fail even when the technology works as intended?
Darrel: Most AI rollouts start at the wrong end of the sequence. Leaders jump straight to Trajectory, such as new dashboards, new KPIs, ‘AI-driven metrics’, without ever establishing Culture, Relationships, Acceptance underneath it. CRAFT calls this ‘skipping Culture,’ and it’s not optional to skip. When you measure AI adoption before you’ve built acceptance for it, you get gaming and compliance theater instead of real capability.
Lori: Why does moving faster on AI adoption often create more organizational problems than it solves?
Lori: What are the early warning signs that an AI project is about to stall inside an organization?
Darrel: Watch the language and behavior, not the usage stats. When people startmust ‘I use it because I have to’, instead of ‘I use it because it helps,’ that’s a sign they may be moving from Commitment back toward Compliance on the Letter of Acceptance.
You’ll also see quieter signals. Workarounds may start spreading peer-to-peer instead of through official channels. Questions that once surfaced in team meetings shifting to side conversations or direct messaging. People double-checking AI’s output more than they double-check their own. Login numbers may look healthy right up until the project stalls, because compliance can look like adoption for a while.
Lori: What is the difference between pushing AI adoption and creating pull for AI adoption within a team?
Darrel: Push relies on authority; pull relies on relationships and focus. If people trust the leader (Relationships) and the AI initiative is one of the few things the organization is prioritizing right now (Focus, not spread across twelve competing priorities), people pull it toward themselves because it’s obviously the thing that matters. Push says, ‘do this.’ Pull says, ‘this is worth doing,’ and lets the team arrive there.
Lori: What is one practical step a project leader can take to improve AI adoption in their organization?
Darrel: Run a 20-minute Culture Compass conversation with your team before you touch the tool again. Ask two questions: ‘What does success look like here today, without AI?‘ and ‘What would be true for you to trust a tool with part of that?‘ You’ll learn more about your real adoption barrier in 20 minutes than in a quarter of usage reports.
In closing, the takeaway is uncomfortable, but it matters: don’t measure adoption before you have built the conditions for it. Login numbers can tell you who is using the tool, but not what your team believes about the change. Sometimes, a 20-minute conversation can tell you far more.
Darrel goes deeper on CRAFT and the Ladder of Acceptance at IPM Day 2026 going live November 5, 2026, in his on-demand presentation, AI Is Moving Faster Than Your Organization Can Adapt: What Project Leaders Need to See First.
Darrel Popowich is a leadership coach, transformation consultant, keynote speaker, and former senior executive with over 25 years of experience leading enterprise transformations across industries. He is the Founder of Transformation Craft, a coaching and consulting practice that equips leaders and project professionals with practical tools to drive meaningful, people-centered change.
Known for blending emotional intelligence with strategic execution, Darrel helps organizations turn stalled initiatives into success stories. Previously, Darrel held several leadership positions at the Business Relationship Management Institute (BRM Institute), including Chief Visionary Officer, COO, Board Member, and Executive Council Member.
Executive Vice President at International Institute for Learning (IIL)
Our deepest purpose is to enable growth and success of individuals, teams and organizations with long-lasting, high quality learning in a technology-driven world. Lori is honored to have been with IIL over 30 years, and to make it her mission to focus on continuous improvement, client driven success and to go above and beyond to meet expectations.
