The marketplace is full of AI noise, but what does it actually mean for how organizations innovate and learn? Dave and Peter revisit the classic pioneers-settlers-town planners model and discover something unexpected: AI has reversed the flow.

Where organizations once looked up the chain for scaling lessons, now large enterprises are watching small explorers to understand disruption, while entrepreneurs stitch together emerging technologies to solve real problems today. The old playbook doesn't quite work anymore.

We explore what this means for different types of organizations, why pretending to be a pioneer when you're not is a waste of time, and how to actually learn from what's happening in the marketplace instead of just making noise about it.

Key Takeaways:

1. The three-cohort model has flipped. In the AI era, large organizations are looking at what smaller explorers and entrepreneurs are doing, not the other way around. If you're not monitoring the marketplace to understand how others are solving problems with these technologies, start now.
2. Different organizations need different things from the AI landscape. Town planners should watch entrepreneurs for practical accelerators and explorers for early warnings about disruption. Entrepreneurs are stitching together emerging tech with real business problems to create immediate value.
3. Most established organizations aren't pioneering, and that's okay. If you have an HR department and multiple locations, you're not in the explorer space. Innovation labs aren't the same as true exploration. Understand which cohort you're actually in and learn accordingly.

You know that expensive software system your company bought that everyone... stopped using? Deborah Kaminetzky sees this pattern constantly. Projects delivered on time and on budget that still fail because nobody wants to touch them.

Deb brings a unique lens to technology implementation. She's a former attorney turned project management consultant who specializes in what she calls the "messy middle" – the space between buying software and actually getting value from it. Her secret? Translation. Not just between tech teams and business teams, but between what's being sold and what people actually need to do their jobs.

In this episode, we dig into why user involvement isn't just a nice-to-have (spoiler: shadow IT is alive and well), the difference between being heard and influencing outcomes, and why your C-suite needs to stop treating technology teams like the organizational stepchild.

This Week's Takeaways:

1. Solve the problem before you buy the solution – Understanding what you're actually trying to fix has to come before you start shopping for software. This seems obvious, but most organizations skip this step entirely.
2. Mediation matters more than metrics – When users are involved in gathering information and partially in decision-making, adoption happens. When they're just told what to do, they find workarounds. The question is: how much of that involvement is just making people feel heard versus actually changing what gets built?
3. Outcomes over outputs – On-time, on-budget means nothing if the software gathers dust. Find ways to measure whether you're getting the value you expected, not just whether you hit the deadline.

Want to reach out? Email us at feedback@definitelymaybeagile.com or visit definitelymaybeagile.com.

What happens when you need to ship software in environments where failure isn't just expensive, it's catastrophic? Ivan Gekht, CEO of Gehtsoft, joins Peter and Dave to challenge how we think about agile delivery in high-stakes, regulated systems.

Forget the innovation lab. Ivan argues that real innovation happens 10 minutes at a time, every day, at your desk. He shares why learning without outcomes is just an expensive distraction, why retrospectives reveal more than sprint planning ever will, and how the biggest transformation killer isn't resistance, it's apathy.

Plus, the dinner party analogy that will change how you negotiate scope vs. time, and why organizations that obsess over features are asking the wrong questions entirely.

Key Topics:

• Why "nobody cares" is the hardest transformation problem to solve
• The reversed iron triangle: hitting dates by flexing scope
• Theory of Inventive Problem Solving (TRIZ) and structured innovation
• Goals vs. features: reframing conversations with leadership
• Why agile fails when it becomes anarchy

This Week's Takeaways:

• Language and framing matter more than we think. Finding the right words and the right way to present ideas can genuinely shift how change happens in an organization.
• The Theory of Inventive Problem Solving deserves a deeper look. Innovation isn't the big thing happening in the cool kids area; it's the thing that happens every day at your desk.
• The dinner party analogy is going straight into my next executive presentation. When sales want locked dates and fixed scope, this framework shows why that's wishful thinking, and what actually works instead.

We love to hear feedback! If you have questions, would like to propose a topic, or even join us for a conversation, contact us here: feedback@definitelymaybeagile.com