{ "name": "Roadmap Backcast Evaluator", "description": "Evaluates backcasting roadmaps for target clarity, milestone sequencing, dependency mapping, critical path identification, and feasibility assessment", "criteria": [ { "name": "Target Outcome Specificity", "weight": 1.4, "scale": { "1": "Vague target ('launch product', 'improve system') with no date or success criteria", "2": "Target has date but outcome unclear or unmeasurable ('product better', 'customers happy')", "3": "Target somewhat specific with date (e.g., 'launch by Q1') but missing quantifiable success criteria", "4": "Specific measurable target with fixed date (e.g., '1000 customers by Jan 31, 2025') and clear criteria", "5": "Exemplary: Precise measurable outcome with fixed date, quantified success criteria (conversion rates, NPS, revenue), constraints documented (budget, scope, quality), strategic importance articulated" } }, { "name": "Milestone Quality and Sequencing", "weight": 1.5, "scale": { "1": "No milestones or milestones are activities ('working on X') not deliverables", "2": "Milestones listed but not sequenced, vague deliverables, missing key checkpoints", "3": "5-10 milestones identified working backward, deliverables stated but some vague, basic sequencing", "4": "Clear milestones with specific deliverables, logically sequenced backward from target, owners assigned, durations estimated", "5": "Exemplary: 5-10 milestones with verifiable deliverables (not activities), precise backward sequencing using 'what must be true before' logic, each with owner/duration/prerequisites, milestones align to natural project phases, no missing critical checkpoints" } }, { "name": "Dependency Mapping Completeness", "weight": 1.4, "scale": { "1": "No dependencies identified or implicit assumptions only", "2": "Some dependencies noted but incomplete, no distinction between sequential/parallel", "3": "Major dependencies mapped, sequential vs parallel identified, some gaps in upstream/downstream links", "4": "Comprehensive dependency mapping, clear prerequisites and enabled tasks for each milestone, parallel workstreams identified", "5": "Exemplary: All dependencies explicitly mapped (sequential, parallel, converging, diverging), dependency graph or table provided, handoff requirements specified, coordination points identified, external dependencies flagged with extra buffer" } }, { "name": "Critical Path Identification", "weight": 1.5, "scale": { "1": "No critical path identified or not understood", "2": "Critical path mentioned but incorrectly identified or not validated", "3": "Critical path identified (longest dependent chain) but slack on non-critical tasks not calculated", "4": "Critical path correctly identified with duration, non-critical paths have slack calculated", "5": "Exemplary: Critical path precisely identified using CPM (forward/backward pass), slack calculated for all milestones, critical vs non-critical clearly distinguished, management strategy for critical path defined (monitoring, buffer allocation, acceleration options)" } }, { "name": "Buffer and Risk Management", "weight": 1.3, "scale": { "1": "No buffers included, optimistic estimates only", "2": "Generic buffer mentioned ('add some extra time') but not quantified or placed", "3": "Buffers added (e.g., 20%) but uniform across all tasks regardless of uncertainty", "4": "Risk-appropriate buffers (20-30% for moderate, 40%+ for high uncertainty), placed on critical path", "5": "Exemplary: Buffers calibrated by uncertainty (10-50% range), PERT or 3-point estimates used, project buffer vs feeding buffers distinguished (CCPM), risk register with mitigation/contingency plans, triggers for re-planning defined, buffer consumption monitoring plan" } }, { "name": "Feasibility Assessment Rigor", "weight": 1.4, "scale": { "1": "No feasibility check, assumed possible without analysis", "2": "Basic comparison (target date vs today) but no buffer, resource constraints, or risk consideration", "3": "Feasibility assessed (available time vs required time) with buffer, but resource/scope constraints not addressed", "4": "Rigorous feasibility: time + buffer + resource constraints + scope, verdict (feasible/tight/infeasible) with clear reasoning", "5": "Exemplary: Comprehensive feasibility assessment including time/buffer/resources/scope/risks, Monte Carlo or probability analysis (P50/P80/P95), if infeasible clear options provided (extend deadline X weeks, reduce scope Y features, add resources $Z cost), trade-off analysis for options, honest assessment not wishful thinking" } }, { "name": "Resource and Capacity Planning", "weight": 1.2, "scale": { "1": "No resource consideration, assumes unlimited capacity", "2": "Resources mentioned but not quantified (team size, budget, constraints)", "3": "Resource requirements estimated but not compared to available capacity, gaps not identified", "4": "Resource requirements vs available capacity analyzed, gaps identified with mitigation (hiring, contractors)", "5": "Exemplary: Resource loading chart showing demand over time, peak capacity vs available, over-allocation identified and resolved (resource leveling/smoothing), hiring/onboarding timeline factored into plan, budget allocated to milestones, resource constraints drive sequencing decisions" } }, { "name": "Actionability and Communication", "weight": 1.1, "scale": { "1": "Theoretical roadmap with no execution plan, stakeholders unclear, no ownership", "2": "Some execution details but vague, ownership not assigned, communication plan missing", "3": "Milestones have owners, basic communication plan (updates), but escalation path and decision gates unclear", "4": "Actionable: owners assigned, communication cadence defined (weekly updates, milestone reviews), escalation path for delays", "5": "Exemplary: Complete execution plan with named owners for each milestone, stakeholder communication plan (who/what/when), Go/No-Go decision gates at key milestones, escalation paths (3-level), status dashboard defined, next steps to initiate roadmap clear (approvals, kickoff, resource allocation)" } } ], "guidance": { "by_roadmap_type": { "product_launch": { "typical_milestones": "Requirements locked → Design finalized → MVP built → Feature complete → QA passed → Beta testing → GA launch", "critical_path_focus": "Design → Engineering → Testing (usually 60-70% of timeline)", "buffer_recommendation": "20-30% on engineering (unknowns), 20% on testing (bugs), 10-20% on beta (user feedback)", "red_flags": ["No feature freeze milestone", "Testing squeezed at end", "No beta period", "Scope creep not controlled"] }, "compliance_deadline": { "typical_milestones": "Gap analysis → Remediation plan → Controls implemented → Policies updated → Internal audit → External audit passed", "critical_path_focus": "Gap analysis → Remediation → Audit validation", "buffer_recommendation": "40%+ (cannot miss regulatory deadline, audit findings may require rework)", "red_flags": ["<30% buffer (high risk of missing)", "No internal audit before external", "Remediation not sequenced by dependency"] }, "strategic_transformation": { "typical_milestones": "Strategy approved → Pilot complete → Learnings applied → Phase 1 rollout → Phase 2 rollout → Full migration", "critical_path_focus": "Pilot and learning (foundation for scale)", "buffer_recommendation": "30%+ per phase (unknowns compound over time)", "red_flags": ["No pilot/learning phase", "Trying to scale without validation", "Organizational change management missing"] }, "event_planning": { "typical_milestones": "Date announced → Venue booked → Speakers confirmed → Content ready → Rehearsal → Event day", "critical_path_focus": "Venue booking (long lead time), speaker coordination", "buffer_recommendation": "10-20% (hard deadline, less flexible)", "red_flags": ["Venue not secured early", "No rehearsal milestone", "Content creation squeezed at end"] } } }, "common_failure_modes": { "optimistic_sequencing": { "symptom": "Assumes perfect handoffs, no rework, no blockers; 0% buffer", "root_cause": "Wishful thinking, pressure to say 'yes' to deadline, Hofstadter's Law ignored", "fix": "Add 20-30% buffer to estimates, use PERT 3-point estimates (optimistic/likely/pessimistic), review against historical data" }, "missing_dependencies": { "symptom": "Tasks planned in parallel that actually require sequential completion, integration surprises", "root_cause": "Didn't ask 'what must be true before this starts?', assumed work is independent", "fix": "Explicit dependency mapping (prerequisite/enables table), review with technical leads, identify converging/diverging points" }, "wrong_critical_path": { "symptom": "Managing wrong tasks as critical, actual delays surprise team", "root_cause": "Intuition-based not calculation-based, didn't account for all dependencies", "fix": "Use CPM forward/backward pass, calculate slack, validate with project management tool" }, "scope_creep_invalidates_plan": { "symptom": "Milestones slip because scope expanded mid-project", "root_cause": "No requirements freeze, stakeholder says 'just one more feature', change control missing", "fix": "Requirements freeze milestone, change control process (cost/timeline impact analysis before approving), stakeholder alignment on must-haves vs nice-to-haves" }, "ignoring_resource_constraints": { "symptom": "Plan shows 10 engineers needed, only have 5, tasks over-allocated", "root_cause": "Assumed can parallelize everything, didn't check capacity", "fix": "Resource leveling (delay non-critical tasks), resource smoothing (steady demand), hire/contract to fill gaps" }, "no_feasibility_check": { "symptom": "Backcast reaches before today, team commits anyway, fails predictably", "root_cause": "Sunk cost fallacy, pressure to commit, hope over reality", "fix": "Honest feasibility assessment, if infeasible present options (extend date, reduce scope, add resources), escalate to leadership for decision" } }, "excellence_indicators": [ "Target outcome is specific, measurable, with fixed date and quantified success criteria", "5-10 milestones working backward from target, each with clear deliverable", "Milestones sequenced using 'what must be true before' logic", "Dependencies explicitly mapped (sequential, parallel, converging, diverging)", "Critical path identified using CPM or visual dependency graph", "Slack calculated for non-critical milestones", "Buffers calibrated by uncertainty (20-50% range based on risk)", "Feasibility rigorously assessed: required time (with buffer) ≤ available time", "Resource constraints analyzed (team capacity vs requirements)", "If infeasible, clear options provided with trade-offs (extend deadline, reduce scope, add resources)", "Risk register for timeline threats with mitigation/contingency", "Owners assigned to each milestone", "Communication plan defined (weekly updates, milestone reviews, escalation path)", "Assumptions and constraints explicitly documented", "Honest assessment not wishful thinking (acknowledges tight timelines, risks)" ] }