Transition Planning – Mutual Insurances
Sector: Insurance
Role: Technical Coach / Consultant
Engagement: Platform migration planning and team enablement
Type: Confidence-led strategy and coaching for high-stakes legacy transition
A UK mutual insurer needed to replace a critical legacy platform – undocumented, unsupported, and deeply entangled.
The tech was fragile. But the real blocker was confidence.
Engineers weren’t sure how to move. And stakeholders weren’t sure who could lead.
The Challenge
- A compiled “black box” system – no source code, no documentation
- Functionality bolted on through SSIS, SSRS, and stored procedures
- Tightly coupled systems with invisible dependencies
- Years of stalled efforts led to delivery fear and organisational hesitation
- Capable engineers operating in silos, hesitant to lead
- Leadership had appetite, but no clear path forward
The ask: How do we move forward without full certainty – and without outsourcing control?
What I Did
Planning Under Uncertainty
- Introduced structured planning methods to move without perfect clarity
- Wrote, and ruled out an in-house build option to unblock supplier discussions
- Supported RFI/RFP and decision-making with technical framing
Architecture & Migration Support
- Designed a high-level “to-be” architecture
- Helped shape a phased transition plan that fit delivery capacity and risk appetite
Coaching & Confidence Building
- Introduced lightweight decision-making and documentation standards (LADR, RFC)
- Facilitated workshops and team coaching – stepping back as confidence grew
- Helped bridge siloed functions through collaborative planning
What Changed
From Hesitation to Ownership
- The team led migration planning conversations with business leaders
- Co-created artefacts became living tools – not abandoned decks
From Consultant Dependency to Internal Momentum
- A supplier was selected with confidence
- Delivery planning progressed without external hand-holding
From Doubt to Trust
- The business stepped back from relying on external delivery
- Internal engineering became trusted owners of the transition
Reflections
The blocker wasn’t tech debt. It was confidence debt.
With structure, encouragement, and clarity, I helped a capable team reset – and start leading from the inside.
When teams believe they can move, they do.
Planning a high-stakes system transition?
Let’s rebuild confidence – and momentum that holds without dependency.
Book a 20-minute discovery call