A UK-based insurance software firm serving major comparison platforms had reached a familiar but dangerous inflection point.
On paper, things looked reasonable:
- A growing product organisation in the UK
- A capable engineering organisation in Poland
- Five Product Owners and a senior product manager
- A clear market and steady demand
In reality, delivery was slowing, decisions were being second-guessed, and teams were frustrated on both sides.
UK product leaders were making decisions for a market their engineers could not see. Polish engineers were building solutions for customers they had never met, in a regulatory environment they did not understand. Context was leaking at every hand-off.
The leadership tension was subtle but corrosive:
- Decisions were centralised because leaders didn’t trust the system to make them well
- Teams wanted autonomy but lacked clarity
- “Agile” was spoken about, but leadership behaviour had not changed
The organisation wasn’t failing due to capability. It was failing due to misaligned leadership assumptions.
The Initial Request, and the Real Problem
The request sounded simple: “We need Product Owner training.”
From a senior leader’s perspective, this often translates to:
- “Our people aren’t doing what we expect.”
- “We need consistency.”
- “We need execution without chaos.”
The real issue was not skill gaps. It was that no one had explicitly redesigned how decisions, learning, and accountability should work in a distributed organisation.
Titles existed. Authority did not. Processes existed. Context did not. Good people existed. Alignment did not.
This was a system failure, not an individual one.
The Leadership Diagnosis
Early engagement focused on how work actually flowed, not on what leaders believed was happening.
Several constraints became immediately visible:
Product leadership without decision clarity Product Owners were expected to “own outcomes” but were still operating under implicit approval chains. This created hesitation, backlog churn, and passive behaviour.
Engineering operating without market context Engineers were implementing features accurately, but not insightfully. When context is missing, teams optimise for compliance rather than value.
Geographical separation amplifying weak leadership signals Ambiguity that might survive in a co-located team becomes lethal when teams are distributed. Every gap widens.
Agile language masking unchanged control structures Leaders wanted empowerment, but continued to intervene when discomfort appeared. Teams noticed. Trust eroded.
From a senior leadership lens, the risk was clear: the organisation was scaling cost faster than clarity.
The Intervention: Mentorship, Not Instruction
Instead of courses or workshops, the engagement was designed as embedded leadership mentorship.
The intent was not to “teach product management,” but to:
- Make leadership assumptions visible
- Shift decision ownership to where information actually existed
- Create fast feedback between intent and outcome
The work unfolded alongside real delivery, not outside it.
Key elements included:
- Weekly leadership-level conversations grounded in live work
- Direct inspection of decision paths, not artefacts
- Deliberate practice applied inside active backlogs and planning conversations
- Immediate feedback on behaviour, not theory
At one point, two sub-teams were given the same leadership challenge.
One declared it impossible. The other solved it within existing constraints.
That contrast did more to reset leadership thinking than any slide deck could have.
What Changed for Leadership
Within eight weeks, the shifts were unmistakable.
Product leaders stopped waiting for permission Decision ownership became explicit. Confidence followed clarity.
Engineering leaders gained business signal Engineers began making better trade-offs because they understood why the work mattered, not just what to build.
Cross-border conversations became about outcomes, not compliance Meetings shifted from status defence to problem-solving.
Escalations dropped as teams solved problems locally Leaders regained time and focus because the system no longer depended on them for every decision.
One executive captured it succinctly after a full day of intense work across time zones:
“They were still engaged, still thinking, still asking how to make this work. That’s when I knew this wasn’t just training.”
Why This Matters to Senior Leaders
This case illustrates a pattern many leaders face:
You cannot delegate outcomes if your system only supports obedience. You cannot scale decision-making without redesigning trust. You cannot fix leadership problems by sending people on courses.
What changed here was not capability, but operating conditions.
The Leadership Takeaway
This was not a product initiative. It was not an agile initiative. It was a leadership system redesign, executed inside real work.
For senior leaders, the lesson is direct:
Sustainable improvement does not come from better people. It comes from better conditions for people to lead.
Assess Whether Leadership Structure Is Constraining Your Distributed Organisation
If decisions are centralised, context is leaking across borders, or teams lack clarity despite having capable people, a diagnostic conversation can identify where leadership design needs to change.
No sales theatre. No obligation.