Continuous Strategy Engineering—Beyond Waterfall Planning With Tom Gilb and Simon Holzapfel

"The professors of strategy have no clue as to what Evo is. They are locked in decades ago, waterfall mode."

Tom's analysis is stark: the people teaching strategy in business schools haven't undergone the same agile transformation that software development experienced. They still think in terms of 5-year plans that get tested at the end—a guaranteed recipe for discovering failure too late. The alternative? Decompose any large strategy into weekly value delivery steps. And if you think that's impossible, ask any AI to do it for you—it will produce 52 reasonable weekly increments in about a minute.

"If you're doing small-scale stuff that OKRs were designed for, like planning your personal work 14 days hence, OKRs are wonderful. If you're designing the air traffic control system for Europe, they're just too simple."

Tom distinguishes between tools appropriate for personal productivity and those needed for complex organizational strategy. OKRs force some thinking, which is good, but they weren't designed for—and have never been adapted to—large-scale systems engineering. His paper "What is Wrong with OKRs?" documents roughly 100 gaps between simple OKRs and what robust value requirements actually require.

Check out Tom Gilb's paper on what's wrong with OKR's and how to fix it.

"We have no mental model for most of leadership about how you actually align people around clear vision."

Simon introduces the concept of a Hoshin-Kanri "sprinkler" system—imagine strategic clarity flowing from the top and misting over everyone's desk as alignment. Most organizations lack anything resembling this. They have Moses descending from expensive consultant retreats with tablets, but no continuous two-way flow of strategic information. The result? Teams work hard on things that don't matter while critical values go unaddressed.

About Tom Gilb and Simon Holzapfel

Tom Gilb, born in the US, lived in London, and then moved to Norway in 1958. An independent teacher, consultant, and writer, he has worked in software engineering, corporate top management, and large-scale systems engineering. As the saying goes, Tom was writing about Agile before Agile was named. In 1976, Tom introduced the term "evolutionary" in his book Software Metrics, advocating for development in small, measurable steps. Today, we talk about Evo, the name Tom uses to describe his approach. Tom has worked with Dr. Deming and holds a certificate personally signed by him.

You can listen to Tom Gilb's previous episodes here.

You can link with Tom Gilb on LinkedIn

Simon Holzapfel is an educator, coach, and learning innovator who helps teams work with greater clarity, speed, and purpose. He specializes in separating strategy from tactics, enabling short-cycle decision-making and higher-value workflows. Simon has spent his career coaching individuals and teams to achieve performance with deeper meaning and joy. Simon is also the author of the Equonomist newsletter on Substack.

And you can listen to Simon's previous episodes on the podcast here.

You can link with Simon Holzapfel on LinkedIn.