Five Questions Every CFO Should Ask Their D365 System Integrator

The most successful Microsoft finance transformations share a common characteristic: CFOs who maintain active, informed oversight throughout delivery. Not micromanagement—strategic engagement supported by the right questions at the right moments.

Your system integrator brings valuable technical delivery capability. But without informed CFO-level challenge, programmes drift from business objectives, accumulate risk, and deliver systems rather than value. The difference between transformation success and expensive disappointment often comes down to whether the CFO asked five critical questions.

1. How Does This Design Decision Impact My Finance Operating Model?

D365 implementations involve hundreds of configuration choices. Chart of accounts structure. Period-end process design. Reporting architecture. Each technical decision has direct implications for how your finance function operates post-go-live.

Strong system integrators welcome this question—it forces alignment between technical delivery and business reality. Weaker partners resist it because answering properly requires deep finance expertise, not just D365 technical knowledge.

What good looks like: Your SI should explain each major design decision in finance operating model terms—impact on month-end cycle time, reporting flexibility, control framework, and team capacity requirements. If explanations remain purely technical, you're at risk of receiving a compliant system that doesn't improve finance performance.

2. What Evidence Supports Your Assessment That We're On Track?

"The programme is green" means nothing without supporting evidence. CFOs deserve objective validation of programme health—not status reports coloured by commercial interest in avoiding difficult conversations.

This question isn't about distrusting your SI. It's about establishing an evidence-based partnership where progress claims are supported by demonstrable facts: requirements signed off, testing completion rates, user adoption metrics, business process performance data.

What good looks like: Your SI provides concrete evidence at each stage gate—documented user acceptance, measured process improvements, validated data migration accuracy. Process mining analysis showing actual process performance. Success by Design checkpoint completions. If evidence feels thin or anecdotal, independent validation becomes essential.

3. What Risks Are You Most Concerned About Right Now?

The best delivery partners surface risk early and honestly. They know that CFO-level visibility into genuine concerns enables faster decision-making, better resource allocation, and course correction before issues become critical.

This question creates space for honest conversation. It signals that you expect transparency, value early warning, and understand that complex transformations encounter challenges. SIs who respond with "everything's fine" either lack programme insight or fear honest dialogue—both are dangerous.

What good looks like: Your SI identifies specific risks—resource constraints, requirements ambiguity, integration complexity, change resistance—and presents mitigation strategies requiring your input or approval. Regular risk dialogue becomes a partnership strength, not a source of tension.

4. How Will We Validate That Promised Benefits Are Actually Materialising?

Business cases promise specific outcomes: faster month-end close, reduced manual effort, improved cash visibility, automated controls. Technical go-live doesn't equal benefit realisation. Without structured validation, promised returns quietly evaporate into "the system works, but we're not seeing the value we expected."

Strong SIs build benefit tracking into delivery from day one. They baseline current performance, define measurable targets, and validate improvements throughout implementation. This protects both parties—you get demonstrable value, they get recognised success.

What good looks like: Your SI presents a benefits realisation framework tracking specific finance KPIs—days to close, FTE effort on manual processes, report generation time, exception volumes. Regular reviews compare actual versus promised improvements with plans to address shortfalls.

5. Where Do You Recommend I Consider Independent Validation?

Paradoxically, the strongest system integrators actively recommend independent validation at high-risk decision points. They understand that objective third-party review strengthens programme credibility, accelerates decision-making, and protects both client and delivery partner when complexity is high.

This question tests whether your SI views independent oversight as threat or asset. Mature delivery partners welcome independent validation of design decisions, stage gate readiness, and benefit realisation—they know it reduces risk and builds client confidence.

What good looks like: Your SI identifies specific milestones where independent review adds value—major design decisions, go-live readiness, post-implementation benefit validation. They view independent expertise as complementary to delivery rather than competitive with it.

Why These Questions Matter

None of these questions implies distrust of your system integrator. They establish the foundation for an evidence-based partnership where technical delivery aligns to business value, risk is surfaced early, and programme success is measured in operational improvement rather than just technical completion.

The CFOs who ask these questions consistently—and insist on substantive answers—create the conditions for transformation success. They maintain strategic oversight without micromanaging delivery. They validate progress without undermining their delivery partner. They ensure investment translates into value.

When Independent Expertise Strengthens Your Position

If asking these questions reveals gaps—vague answers, resistance to evidence-based validation, reluctance to discuss risk—independent client-side expertise becomes essential. Not to replace your SI, but to strengthen your position with objective validation, evidence-based challenge, and dedicated capability representing your interests.

The most successful transformations combine strong delivery partnerships with independent client-side oversight. Your system integrator focuses on technical delivery. Independent specialists ensure that delivery translates into measurable business value.

That's not conflict. That's the governance model that protects complex, high-stakes Microsoft finance transformation investment.