Section 9: Tailor the Case for Timing and Context

Even the best business case can fail if it’s delivered at the wrong moment—or in the wrong format.

Timing is political. Context is everything.
Whether you're making a bold annual ask or submitting a fast-turnaround proposal during a crisis, how and when you deliver your business case matters as much as what's in it.

This section helps you adapt your message and approach for different decision environments—so your proposal doesn’t just sound good, it lands well.

🗓️ Match Your Case to the Budget Cadence

Start by mapping where your organization is in the planning cycle:

🧭 Annual Budget Planning

• Best time for strategic asks and multi-year initiatives

• Expect more formal structure: ROI modeling, benchmarking, execution timelines

• Align with enterprise planning goals and board-level metrics

Recommendation: Anchor in long-term value, risk reduction, and multi-phase outcomes.

🔁 Quarterly or Mid-Year Checkpoints

• Good for refinements, quick wins, or phase two of a longer plan

• Be nimble: show ROI acceleration, unblockers, or course correction value

• Emphasize speed, readiness, and measurable impact within the quarter

Recommendation: Use data from what’s already working to support next-phase asks.

🚨 Out-of-Cycle / Crisis-Based Requests

• Often reactive: breach response, audit findings, new compliance mandates

• Shorter timelines, higher scrutiny

• Must clearly show urgency and time-sensitive risk or exposure

Recommendation: Keep it concise. Emphasize “cost of delay” and non-negotiable minimums.

🎯 Align with Strategic Moments

Timing also means political timing:

• Is this adjacent to a transformation program, merger, new tech launch, or cost-cutting wave?

• Can you align your case to support what leadership already wants to do?

• Is there a stakeholder change (new CFO, new CIO, new board chair) that shifts your opportunity window?

When you attach your case to a strategic moment—it becomes part of the narrative.

📎 Format and Framing Based on Audience

Adapt how you present your case based on the decision-makers and forum:

• Board / C-Suite → Focus on impact, risk, and strategic relevance

• Finance Committee → Emphasize ROI, BCR, trade-offs, and fiscal discipline

• Transformation Office → Align with business readiness, change adoption, and cross-functional outcomes

• IT or GRC Steering Group → Emphasize technical feasibility and operational sustainability

One case. Multiple framings. Same core truth.

🧠 Strategic Inputs to Carry Forward

This section reminds you:

• The best time to pitch is when the organization is ready to act, not just when you’re ready to ask

• You gain momentum by aligning with moments of focus, transformation, or vulnerability

• You maintain credibility by tailoring the format to the forum

📝 Section 9 Planning Questions

1. What planning window or approval process is currently open (or about to open) that your case should align with?

2. What other strategic or political events could strengthen or distract from your proposal?

3. How can you adjust the framing or format of your case to fit the room you’re walking into?