Lessons from the Front Line of D365 with Chris Lalley

What does it actually take to land a complex ERP or Dynamics 365 transformation without becoming another horror story?

In this episode of The Catch Up, host Phillip Blackmore sits down with seasoned programme leader Chris Lalley to unpack the realities of delivering large‑scale finance and D365 projects in the real world. They explore how careers evolve from operational finance into programme leadership, why variety and curiosity matter, and how personal quirks like “dishwasher‑level” OCD can be a genuine asset in delivery.

Throughout the conversation, Chris returns to a consistent theme: technology‑enabled transformation is fundamentally about people, not platforms. That message is timely. Recent research shows that while ERP capabilities have advanced, 55–75% of projects still fail to hit their original objectives, with average cost overruns near 189%, largely due to organisational, not technical, issues. Chris explains how he approaches new engagements, from establishing vision and sponsorship to assessing team capability and rescuing “programmes in jeopardy”. For leaders about to embark on a D365 or ERP journey, this episode offers grounded, experience‑led guidance on what success really demands.

Click Here to Watch the Video Episode.

• (00:00) - Welcome to The Catch Up Podcast
• (01:45) - From Big Five Accounting to Early Transformation Projects
• (03:40) - Finding the Bug for Large-Scale Change Programmes
• (05:00) - OCD, Attention Span and the Appeal of Programme Work
• (07:10) - The Dishwasher Story and Structured Thinking
• (09:13) - First Steps into Microsoft ERP and Dynamics 365
• (13:15) - Greenfield versus Mature Organisations in ERP Delivery
• (17:03) - Starting a New Programme: People, Vision and Strategy
• (20:06) - Recovering Programmes in Jeopardy and Rebuilding Confidence
• (26:43) - Learning from Mistakes and Getting Capability Right
• (33:32) - Fixed Price vs Time and Materials in ERP Contracts
• (39:50) - Defining Success and the Role of Executive Sponsors

Chris Lalley: Chris Lalley is an experienced ERP and finance transformation programme leader with a background that spans Big Five accounting, industry finance roles and large‑scale technology‑enabled change. Starting his career in operational finance at firms such as Arthur Andersen and Ernst & Young, he led major internal projects including a global PeopleSoft implementation and the establishment of an offshore shared service centre in Bangalore. That exposure to complex programmes sparked his move into full‑time project and programme leadership, where he has since delivered and recovered high‑stakes ERP and Dynamics 365 initiatives across multiple sectors. Drawing on years of hands‑on delivery, Chris is known for his focus on people, structure and sponsorship as the real levers of success in transformation.

Episode Insights:

• Successful Dynamics 365 and ERP programmes are driven more by people, clarity of vision and sponsorship than by the underlying technology stack.
• The first weeks on a programme should be spent meeting stakeholders, understanding their motivations and aligning ERP outcomes to business strategy, not rushing into Gantt charts.
• Change management is usually under‑invested, yet it affects not only employees but also customers when portals and digital channels are redesigned.
• Capability at the right time is non‑negotiable: under‑resourcing business analysts, architects or change leads early on slows delivery and magnifies risk later.
• Programme directors must be willing to say when “conditions for success don’t exist” and walk away, protecting both their own reputation and the client’s investment.

Action Points:

1. Define success in business terms before you start: Agree a clear vision, outcomes and measures of success with the C‑suite before mobilising your D365 or ERP programme. This includes how the transformation supports overall strategy, what benefits you expect and how you will track them over time. Without this foundation, scope, design and prioritisation quickly drift.
2. Invest properly in change management, not just technology: Treat change, communications and training as a core workstream with its own budget, leadership and methodology. Map who is impacted inside and outside the organisation, from finance teams to customers on portals, and design their journey through the change. Under‑investing here is one of the fastest routes to user resistance and poor adoption.
3. Build the right team and lock in key people: Identify the critical roles across business, partner and contractor resources, then secure the best people you can for a realistic duration. Use contracts and governance to minimise churn in key posts like solution architect, programme manager and lead BAs. Consistent faces and continuity of knowledge are vital for multi‑year ERP journeys.
4. Be honest about risk and willing to make compromises: Accept that large ERP programmes are hard, will involve setbacks and will require compromises on scope or design. Use structured risk management to surface issues early, and re‑baseline plans where necessary rather than pretending original timelines and budgets are still realistic. Adjusting course is a sign of control, not failure.
5. Protect your reputation by recognising “no‑win” conditions: If executive sponsorship is weak, decision rights are unclear, or one dominant leader overrides expert input on everything, recognise that the conditions for success may not exist. Have the courage to surface this clearly and, if necessary, withdraw. In a niche market, being associated only with realistic, well‑governed programmes is long‑term career insurance.

The Catch Up Podcast brings you candid conversations with industry leaders, consultants, and change-makers from the Microsoft Dynamics and tech ecosystem. Hosted by Phillip Blackmore, Sales Director at Catch Resource Management, each episode dives into the real stories behind business transformation, career pivots, and scaling success. Expect thoughtful interviews, practical insights, and honest reflections.

Brought to you by Catch Resource Management, a leading UK recruitment specialist for Microsoft Dynamics and ERP talent, this podcast is your inside track to the people shaping the future of enterprise technology. Tune in for new episodes and stay ahead of the curve.

The Catch Up Podcast is produced by Story Ninety-Four in Oxford, UK.