Transition Planning - Mutual Insurances
Sector: Insurance
Role: Technical Coach / Consultant
Engagement Type: Platform Migration Planning & Team Enablement
From stalled platform plans and siloed teams to confident ownership and a credible migration path - through strategic planning and confidence coaching.
The Challenge
A UK-based mutual insurer was preparing to replace its legacy insurance platform, a critical system with no vendor support, no source code, and deep entanglement with the wider business. While the organisation had capable engineers, years of stalled or failed initiatives had led to low confidence across the board - engineers unsure how to move forward, and stakeholders unsure who to trust.
They needed a credible migration plan - and a team confident enough to own and deliver it.
The Starting Point
- The legacy system was a compiled “black box” with no source code or documentation
- Development had been reduced to bolting functionality directly onto the database layer (SSIS, SSRS, stored procedures)
- The system was tightly coupled to many others, and few understood its actual dependencies
- Previous modernisation efforts had stalled, creating a culture of caution and organisational hesitation
- Teams operated in functional silos (Dev, Ops, Data) without a shared sense of ownership or delivery rhythm
What I Did
Planning Under Uncertainty
- Introduced structured planning techniques that allowed the team to move forward without complete certainty
- Authored a credible in-house build option to eliminate it from consideration during supplier selection
- Supported the RFI/RFP and supplier selection process with technical input and decision-framing
Architecture & Migration Support
- Designed and documented the high-level “to-be” architecture
- Helped the team structure a phased transition plan that respected risk appetite and delivery constraints
Coaching & Confidence Building
- Introduced decision-making and documentation formats (LADR, RFC) that became team standards
- Facilitated workshops and 1:1 coaching, gradually stepping back as confidence and competence grew
- Encouraged collaborative planning across historically siloed teams
What Changed
Team Ownership
- The internal team shifted from hesitation to leadership
- They led planning discussions with the business and continued evolving the artefacts we’d co-created
Planning Maturity
- A supplier was confidently selected
- Delivery planning moved forward, no longer dependent on external consultants for momentum
Organisational Trust
- The organisation scaled back its planned reliance on external delivery support
- The business began to see the internal team as credible owners of the migration
Reflections
The real blocker wasn’t tech debt - it was confidence debt. This work showed how structure, clarity, and encouragement can reboot a stalled team. When people feel safe to plan and empowered to lead, delivery starts to move again - without hand-holding.
If you’re planning a major system transition or need to rebuild delivery confidence in-house - I can help.
Book a 20-minute discovery call