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High-Stakes Escalation: Deal at Risk
Complex political scenario with CEO escalation and renewal risk. Demonstrates appropriate medium-confidence decision-making, information gathering before final call, and executive escalation path.
Input
What you provide to the skill
CRM refinement release (Feb). Goal: 40% admin task time reduction. Top customer escalates CEO request for custom reporting. Deal at risk.
Output
What the skill generates for you
Scope Analysis: Custom Reporting Request
Decision: OUT OF SCOPE (with conditional escalation path)
Confidence Level: Medium (pending deal validation)
Strategic Alignment Analysis
| Criteria | Assessment | Details |
|–––––|————|———||
| Supports Primary Goal | No | Primary goal is 40% admin task time reduction via UX improvements. Custom reporting is feature expansion, not efficiency optimization. |
| Required for Core Value | No | Core CRM refinement value (simplified workflows, bulk operations, automated processes) delivers without custom reporting. |
| Aligns with Success Metrics | No | Success metric is task time reduction. Custom reports don’t impact admin task efficiency—they’re a separate analytical capability. |
| Timeline Compatible | No | Custom reporting framework (query builder, export engine, permission layer, UI) is 6-8 weeks. February release is at risk. |
Resource Impact Assessment
Effort: Extra Large (6-8 weeks)
Components:
- Custom report builder UI/UX
- Query engine with permission filtering
- Export capabilities (PDF, CSV, Excel)
- Report scheduling/distribution system
- Performance optimization for large datasets
- Security review for data access patterns
- QA across permission levels and data volumes
Opportunity Cost: Would require removing or delaying core refinement features (bulk operations, automated onboarding, simplified navigation) or pushing release to late March/early April.
Timeline Impact:
- Best case: 2-3 week delay to late Feb
- Realistic: 4-6 week delay to mid-March
- Risk: Cascading delays if integration issues arise
Risk Factors
- Scope creep pattern: “Customer needs” expanding defined project scope mid-release
- Political pressure: CEO escalation creating urgency disconnect from strategic goals
- Revenue risk: “Deal at risk” framing may or may not reflect actual renewal conditions
- Feature bloat: Adding reporting undermines focus on task efficiency core value
- Technical debt: Rushed implementation of complex feature creates maintenance burden
Critical Questions Before Final Decision
Deal validation needed:
- Is the renewal truly blocked, or is custom reporting a strong preference?
- What is the actual renewal date and decision timeline?
- What specific reporting capabilities are required for compliance/operations?
- Can existing reporting + manual workarounds satisfy interim needs?
- Would phased delivery work (basic Q2, advanced Q3)?
- What’s the ARR value of this customer vs. timeline risk?
Decision Tree
If renewal imminently blocked AND no workarounds AND high ARR: Escalate to exec team for strategic decision (revenue vs. Q1 delivery timeline). Present full trade-offs.
If renewal timeline extends to March+: Commit to Q2 delivery (March-April), keep February CRM refinement focused on efficiency goals.
If basic reporting satisfies need: Build minimal viable reporting in scope (predefined reports only, no customization), defer advanced features to Q2.
If workarounds exist: Provide manual reporting support via customer success, add custom reporting to Q2 backlog.
Stakeholder Communication
Subject: Re: Custom Reporting Request - CRM Refinement Scope
Hi [Customer Success Lead],
Thank you for escalating the custom reporting request. I understand the urgency given the CEO-level escalation and renewal risk.
Decision: Before making the final call, I need to validate the deal context. Depending on answers, we have paths from interim workarounds to strategic escalation.
Why this isn’t straightforward: Our February release is scoped specifically to achieve 40% admin task time reduction through UX refinement. Custom reporting is a separate analytical capability that doesn’t serve that efficiency goal and would require 6-8 weeks of engineering effort—risking the February timeline entirely.
What I need from you by EOD Friday:
- Renewal specifics: Actual renewal date? Is custom reporting explicitly blocking the deal, or a strong preference?
- Reporting requirements: What specific reports/data do they need? For what use case (compliance, operations, analytics)?
- Workaround viability: Would predefined reports work temporarily? Can CS provide manual reporting interim?
- Business context: What’s the ARR value? Who’s the decision maker on their side?
Options depending on answers:
Option A - Interim Workaround (if timeline flexible):
- Provide manual reporting via CS team through March
- Commit to custom reporting in Q2 (March-May delivery)
- Position as “prioritized roadmap item” based on their feedback
- Keeps February refinement on track, satisfies customer medium-term
Option B - Minimal Scope Addition (if basic reporting satisfies):
- Add predefined reports to February scope (2-week effort)
- Defer custom query builder to Q2
- Trade-off: Remove one planned feature (e.g., automated onboarding)
- Gets them 80% of value, keeps most of timeline intact
Option C - Strategic Escalation (if truly blocking high-value renewal):
- Present to exec team: Revenue risk vs. timeline + scope goals
- Options: Delay February release, pull resources from other projects, or negotiate customer timeline
- Requires exec sign-off on trade-offs
- I’ll prepare full impact analysis for decision meeting
Next Steps:
Let’s schedule a call with the customer this week to understand the specific reporting needs and explore workarounds. Once I have answers to the questions above, we can make the call by Monday.
I’m committed to finding a path that works—just need to understand the constraints we’re operating under.
[Your name]
Trade-off Documentation
Preserved by keeping out of scope:
- February release date for CRM efficiency goals
- 40% admin task time reduction metric
- All committed refinement features (navigation, bulk ops, automation)
- Engineering focus on core value proposition
- Team capacity for post-release support/stabilization
Deferred:
- Custom reporting framework → Q2 (March-May)
- Advanced analytics capabilities → Q2+
- Report scheduling/distribution → Q2+
Potential trade-offs if added to scope:
- Timeline: 2-6 week delay to late Feb/mid-March
- Features: Remove 1-2 planned refinements (automation, bulk operations)
- Quality: Rushed reporting implementation creates technical debt
- Metrics: May not achieve 40% task time reduction goal
Conditions for reconsideration:
- Customer confirms renewal is blocked (not just preferred) by custom reporting
- Renewal date is before Q2 delivery timeline (March+)
- No viable workarounds (manual reporting, predefined reports, export assistance)
- ARR value justifies trade-offs (exec decision with full impact visibility)
- Customer accepts February delay in exchange for reporting inclusion
Internal Escalation Path
If this requires strategic decision:
To: [VP Product/Engineering, CEO]
Subject: Strategic Decision Required - Customer Reporting Request vs. CRM Timeline
Context: Top customer (escalated via CEO) requesting custom reporting for February CRM release. Request doesn’t align with scope but deal reportedly at risk.
The Trade-off:
- Add reporting: 6-8 week effort → February becomes late March/April, removes planned features, or requires additional resources
- Defer to Q2: Preserve February timeline and efficiency goals, risk customer renewal
What I need:
- Validate deal risk (is renewal truly blocked?)
- Strategic call: Revenue vs. timeline integrity
- If we proceed, which features do we cut or do we accept delay?
Recommendation pending deal validation: If renewal isn’t immediately blocked, commit to Q2 delivery with interim workarounds. If blocked, exec decision required on timeline vs. revenue.
Decision meeting: Monday 10am once we have customer context.
About This Skill
Analyze feature requests against project scope and strategic goals to prevent scope creep.
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