Background

When SaaS firm Passenger engaged me, they were dealing with a challenge that’s common in fast-growing product companies, but difficult to articulate clearly.

They had scaled quickly; new customers, new capabilities, and increasing product complexity had driven real success. But as the organisation grew, the way teams understood the system hadn’t kept pace with the system itself. What had once been relatively clear had become harder to reason about:

• Teams were attending stand-ups simply to stay informed

• Communication channels became overloaded

• Responsibilities were increasingly blurred

• Changes in one area created unexpected impacts elsewhere

Passenger had reached a point where the organisation had scaled, but its shared understanding hadn’t. Capabilities had expanded, dependencies had multiplied and team responsibilities had evolved organically, but there was no longer a clear, shared picture of how it all fit together.

There was a lack of clarity about:

• how value flowed

• where boundaries should exist

• and how teams needed to collaborate to deliver effectively

The brief

Passenger wanted to make sense of what was happening before deciding what to change.

The goal was to reconnect three things that had drifted apart:

• user needs

• team responsibilities

• technical and capability boundaries

By doing that, the organisation could:

• reduce unnecessary coordination

• lower cognitive load on teams

• and create the conditions for faster, more focused delivery

The engagement

Rather than running a single workshop, we created a steady cadence of sense-making.

• Weekly 1-hour sessions over 12 weeks with key stakeholders

• Collaborative mapping of users, needs, and capabilities

• Exploration of how teams interacted to deliver value

• Space between sessions for reflection and validation

This format allowed insights to emerge gradually, grounded in real work rather than hypothetical redesigns.

What became visible

As we mapped how value actually flowed through the organisation, several patterns became clear, not as abstract problems—but as concrete, observable friction.

• Capabilities were split across teams, creating hidden dependencies

• Teams were involved in too many areas, increasing cognitive load

• Ownership boundaries were blurred, leading to hesitation and rework

• Planning complexity reflected structural complexity, not just process issues

Seeing these problems in context, connected to user needs and value delivery, changed how they were understood. Instead of debating solutions in isolation, the team now had a shared view of:

• How value flowed (and where it didn’t)

• Where coordination was essential vs accidental

• Which problems were worth solving first

Outcomes

This created the foundation for more confident decision-making. By the end of the engagement, Passenger had:

• A clearer picture of how their organisation actually operated

• A shared language for discussing flow and team boundaries

• Identified specific areas where small structural changes could improve delivery

• Greater confidence in making incremental, evidence-based improvements

They were able to move forward through targeted changes grounded in real insight.

Feedback

“Working with Rich gave us the space to step back and properly understand what was going on in our organisation. We’d been feeling the effects of growth but hadn’t been able to clearly articulate it. This work helped us connect the dots between what we were trying to deliver, the flow of value, and how teams were interacting. What stood out was the focus on understanding before acting. We built a shared view of where the friction was and why it existed, and that gave us much more confidence in the changes we were making.” Tom Quay, CEO, Passenger

Could this help your organisation?

This engagement is typical of teams who aren’t in crisis—but know something isn’t quite working. It’s particularly useful:

• Before committing to structural change

• When planning repeatedly exposes the same constraints

• When teams feel overloaded but the cause isn’t clear

The goal isn’t to prescribe change, it’s to make the system visible enough that better decisions become obvious. I’m always happy to explore what you’re seeing and whether this kind of focused discovery could help.