What 20+ Years of Agile Coaching Taught Me About Change That Actually Sticks

Agile coaching has evolved. Today, it’s less about “doing Agile” and more about designing the operating system that turns strategy into shipped outcomes—clear priorities, fast decisions, healthy rhythms, and teams who can learn and deliver in complexity.

When I started in Agile, the goal was pretty straightforward: help teams ship working software more often. Over time, the work evolved because the problems evolved.

Today, most organizations don’t struggle because they “don’t know Agile.” They struggle because strategy, priorities, funding, decision-making, and dependencies are messy. Teams are asked to move fast inside systems that weren’t designed for speed. That’s where modern Agile coaching lives now: in the space between leadership intent and delivery reality.

Here are the lessons I keep coming back to, especially when the stakes are high, the org is complex, and everyone is tired of “another transformation.”

1) Coaching isn’t about ceremonies anymore—it’s about the operating system

Teams don’t need more meetings. They need fewer collisions.

The biggest unlock is almost always an operating system that answers:

• What outcomes matter most right now?

• Who decides—and how fast?

• How do we see progress and risk early?

• How do we coordinate across a matrix without creating bureaucracy?

  
  

When those are clear, teams don’t need to be “motivated” into agility. They can simply do the work.

2) The bottleneck is often decision latency, not velocity

A lot of organizations think they need teams to “go faster.”

But the real slowdown is usually upstream:

• unclear tradeoffs

• competing priorities

• dependencies nobody owns

• decisions waiting on the same three leaders

One of the most valuable things I do is help leaders build decision forums and decision clarity, so teams aren’t stuck holding half-finished work while they wait for direction.

3) Metrics are only useful if they change decisions

I’m a big believer in flow and delivery metrics—cycle time, throughput, WIP, release cadence, quality signals. But metrics don’t matter if they’re used to judge people instead of improve systems.

The healthiest pattern I’ve seen looks like this:

• metrics create shared reality

• shared reality enables better tradeoffs

• better tradeoffs reduce thrash

• less thrash improves delivery and team health

When metrics become a weapon, they stop reflecting reality—and leaders lose the signal they actually need.

4) Real agility requires portfolio courage

This is the part nobody wants to hear: you can’t get predictability and speed while trying to do everything.

In every organization I’ve worked with, meaningful improvement required some version of:

• fewer priorities

• clearer sequencing

• tighter WIP limits at the portfolio level

• more explicit investment tradeoffs

If you want teams to move, the portfolio has to stop thrashing them.

5) Culture change isn’t a poster—it's practiced behaviors

Culture is what happens when pressure hits.

T

he changes that “stick” aren’t values statements. They’re behaviors embedded into the operating rhythm:

• leaders show up to reviews and make decisions

• teams surface risks early without punishment

• retros result in real changes (not therapy without action)

• learning is treated as part of delivery, not a distraction from it

This is why I focus so much on rhythms: they’re where culture becomes real.

6) Play is not a gimmick. It’s a shortcut to learning.

I use games and experiential activities because they compress time.

A well-designed exercise can surface:

• hidden communication patterns

• missing stakeholders

• how decisions really get made

• where work actually gets stuck

It’s not “fun for fun’s sake.” It’s a method for building shared understanding quickly—especially in cross-functional systems where talking about the problem hasn’t moved anything for months.

What I do now (and why it works)

Modern Agile coaching, for me, looks like a blend of:

• Operating cadence design (planning, reviews, decision forums)

• Portfolio clarity (priorities, tradeoffs, capacity)

• Visibility that leaders can use (dashboards, narratives, early risk signals)

• Human-centered change design (adoption, behavior change, safety to learn)

• Facilitation that builds real alignment (not consensus theater)

The goal isn’t to “implement Agile.” It’s to build a system where strategy reliably becomes shipped outcomes—and where people can do great work without constant thrash.

If you’re in the middle of hard change

If your teams are capable but stuck, it’s rarely a motivation problem. It’s a system problem.

And the good news is: systems can be redesigned—often with a few targeted changes that unlock momentum fast.

If you’re working through a shift in operating rhythm, portfolio prioritization, delivery excellence, or cross-functional alignment, I’d love to connect.