Chapter 8: Discovery in Complex Accounts

Executive Summary

Discovery in complex B2B accounts differs fundamentally from consumer research. You're navigating regulated environments (finance, healthcare), multi-stakeholder dynamics (buyers ≠ users), long evaluation cycles (3–12 months), and operational constraints (legacy systems, compliance requirements, change-averse cultures). This chapter presents methods for conducting discovery in enterprise settings: contextual inquiry with field shadowing, stakeholder interviews across organizational silos, constrained prototyping within security boundaries, and evidence synthesis that drives both product roadmap and sales enablement. Effective discovery in complex accounts accelerates deals, reduces implementation risk, and surfaces insights that generic user research misses—ultimately leading to products that enterprise customers actually deploy, adopt, and renew.

Definitions & Scope

Discovery

The continuous practice of understanding customer problems, contexts, and needs before building solutions. Discovery answers: What jobs are customers trying to do? What's blocking them? What outcomes matter?

Complex Accounts

B2B customers with: (1) Multi-stakeholder buying committees (6+ influencers), (2) Regulated industries (finance, healthcare, government), (3) Long sales cycles (3–12 months), (4) Operational constraints (legacy systems, strict security/compliance), (5) High switching costs.

Discovery Methods for Enterprise

• Contextual Inquiry: Observe customers in their work environment.
• Stakeholder Interviews: 1:1 conversations with buyers, users, gatekeepers.
• Field Shadowing: Spend hours/days with field workers, admins, operators.
• Diary Studies: Customers log experiences over weeks (capture edge cases, seasonal patterns).
• Constrained Prototyping: Low-fi prototypes within security boundaries (no real data, on-prem demos).

Scope

This chapter applies to enterprise B2B IT services (SaaS, platform, infrastructure) with complex accounts. Relevant for Product, Design, Research, Sales, CS, and Solutions Engineering teams.

Customer Jobs & Pain Map

Framework / Model: The Enterprise Discovery Framework

Four-Phase Discovery Cycle

Phase 1: Pre-Discovery Planning (1–2 Weeks)

Objectives: Define discovery goals, recruit participants, prepare protocols.

Activities:

• Define research questions. Examples: "What blocks admins from provisioning users in <10 min?" "What compliance requirements affect our roadmap?"
• Map stakeholders (use Chapter 7 framework). Identify who to interview (Economic Buyer, Champion, End Users, Gatekeepers).
• Recruit 8–15 participants per account (mix of roles). Work with Sales/CS to gain access.
• Prepare interview guides, observation protocols, NDAs (for sensitive environments).

Deliverables: Research plan, participant list, interview guides.

Phase 2: Field Discovery (2–4 Weeks)

Objectives: Gather evidence via interviews, observations, shadowing.

Methods:

Contextual Inquiry (Observe + Interview)

• Spend 2–4 hours with users in their work environment.
• Watch them complete tasks (don't interrupt). Note workarounds, frustrations, tools used.
• Ask: "Why did you do that? What would happen if you couldn't? What's the consequence of errors?"

Stakeholder Interviews (1:1, 45–60 min)

• Economic Buyer: "What outcomes justify this investment? How do you measure success? What risks keep you up at night?"
• Champion: "What's the internal business case? What objections do you face? What would make you a hero?"
• Security/Compliance: "What are non-negotiables? (Data residency, audit trails, certifications.) What evidence do you need?"
• End Users: "Walk me through your last [task]. What went wrong? What workarounds do you use?"

Field Shadowing (Full-Day, 1–3 Days)

• Shadow field workers, admins, analysts for full day(s).
• Capture: Tools used, workflows, interruptions, collaboration patterns, offline needs, peak load times.
• Note: Physical environment (noisy warehouse, low connectivity, multi-tasking), constraints (wearing gloves, no mouse, small screen).

Diary Studies (1–2 Weeks)

• Customers log experiences via survey/app (daily or when specific event occurs).
• Use for: Seasonal patterns (month-end reporting crunch), intermittent issues (sync failures), emotional highs/lows.

Deliverables: Field notes, interview recordings, photos/videos (with consent), diary entries.

Phase 3: Synthesis & Insights (1 Week)

Objectives: Analyze data, identify patterns, generate insights.

Activities:

• Affinity Diagramming: Cluster observations into themes (e.g., "provisioning pain points," "compliance blockers," "offline needs").
• Journey Mapping: Map current-state journeys for key personas (Chapter 12). Identify pain points, workarounds, opportunities.
• Jobs/Pains/Gains Mapping: Consolidate from interviews (Chapter 2 format).
• Opportunity Scoring: Rank insights by frequency, severity, and business impact.

Synthesis Workshop (4–8 Hours, Cross-Functional)

• Participants: PM, Design, Eng, Sales, CS (8–12 people).
• Activities: Review themes, debate priorities, align on top insights.
• Output: Top 5–10 discovery insights with evidence (quotes, observations).

Deliverables: Affinity diagram, journey maps, jobs/pains/gains table, prioritized insights list.

Phase 4: Action & Validation (Ongoing)

Objectives: Translate insights into roadmap, validate with prototypes/pilots.

Activities:

• Roadmap Alignment: Map insights to roadmap themes (OKRs, initiatives). Example: Insight "Admins struggle with bulk provisioning" → Initiative "Build SCIM auto-sync + role templates."
• Constrained Prototyping: Build low-fi prototypes that respect security constraints. Example: Clickable wireframes (no real data), on-prem demo environment.
• Validation Sessions: Show prototypes to customers (5–8 participants). Measure: Task success, comprehension, willingness to adopt.
• Pilots: For high-risk features, run pilots (10–20 customers, 30–90 days). Measure outcomes (time savings, error reduction, adoption).

Deliverables: Roadmap updates, prototypes, validation reports, pilot results.

Diagram description: Visualize as a cycle: Planning → Discovery → Synthesis → Action → (Loop back to Discovery for next iteration). Continuous, not waterfall. Discovery informs roadmap, roadmap drives discovery focus.

Implementation Playbook

0–30 Days: Launch First Discovery Initiative

Week 1: Define Scope & Recruit

• Pick 1 complex account (ideally current customer, open to collaboration).
• Define research questions (3–5 questions). Example: "What blocks fast user provisioning?" "What compliance needs affect our product?"
• Map stakeholders (Economic Buyer, Champion, Admin, End Users, Security). Recruit 8–12 participants.
• Prepare: Interview guides, observation protocols, NDAs (if needed).

Week 2–3: Conduct Discovery

• Schedule sessions: 5 stakeholder interviews (1:1, 60 min), 3 contextual inquiries (2–4 hours each), 1 field shadowing (full day).
• Run sessions. Take detailed notes, record (with consent).
• Example Schedule:
  • Day 1–2: Stakeholder interviews (Economic Buyer, Champion, Security).
  • Day 3–5: Contextual inquiry (watch Admins provision users, Analysts generate reports).
  • Day 6: Field shadowing (shadow field worker for full day).

Week 4: Synthesize & Share

• Transcribe sessions (Otter.ai, Rev, or manual).
• Affinity diagram: Cluster observations into themes.
• Create 1-page summary: Top 3 insights, supporting quotes, recommended actions.
• Share with stakeholders (PM, Design, Eng, Sales, CS). Present in team meeting.

Artifacts: Research plan, session notes/recordings, affinity diagram, 1-page insights summary.

30–90 Days: Scale Discovery & Integrate into Workflow

Month 2: Expand to 3 Accounts

• Repeat discovery with 2 more accounts (different segments: SMB vs Enterprise, different industries).
• Compare insights across accounts. Identify universal pains vs segment-specific.

Month 2–3: Build Discovery Muscle

• Train PM, Design, Sales, CS on discovery methods (workshop: 4 hours, hands-on).
• Create discovery toolkit: Interview guides, observation templates, synthesis playbooks.
• Assign discovery owners: PM leads stakeholder interviews, Designer leads contextual inquiry, Solutions Eng leads technical discovery.

Month 3: Validate Insights

• Build prototypes for top 3 insights. Example: Insight "Admins need bulk provisioning" → Prototype: SCIM wizard.
• Run validation sessions (5–8 customers). Measure task success, feedback.
• Update roadmap based on validation (build, iterate, or kill ideas).

Checkpoints: Discovery completed for 3 accounts, cross-functional team trained, prototypes validated, roadmap updated.

Design & Engineering Guidance

Design Patterns for Enterprise Discovery

Constrained Prototyping

• In regulated environments, can't use real customer data. Use synthetic data, anonymized examples, or isolated demo environments.
• Example: For healthcare, create demo with fake patient data (HIPAA-compliant). For finance, use sample transactions (no real PII).

Contextual Design Artifacts

• Create journey maps with photos from field (with consent). Shows real environment (warehouse, hospital, trading floor).
• WCAG 2.1: If discovery reveals low-vision users, ensure prototypes tested with screen readers, high contrast.

Edge Case Documentation

• Discovery often surfaces edge cases (offline, peak load, errors). Document in user stories.
• Example: "As a field worker with no connectivity, I need to complete inspections offline so I don't lose data."

Engineering Patterns for Technical Discovery

Integration Discovery

• Ask: "What systems must we integrate with? (CRM, ERP, SSO, data warehouse.) What data formats? (REST, SOAP, CSV, SFTP.)"
• Document: Integration requirements, APIs, auth methods, data schemas.
• Build: Reference architecture diagrams, integration POCs.

Performance Discovery

• Ask: "What's your data volume? (Users, records, transactions.) Peak load times? Acceptable latency?"
• Measure: If possible, instrument pilot to capture real performance data.
• Set: Performance budgets based on discovery (e.g., "Support 10K concurrent users, <2s response time").

Compliance Discovery

• Ask: "What regulations apply? (GDPR, HIPAA, SOC2, PCI.) What audit trails needed? Data residency requirements?"
• Document: Compliance checklist per account/segment.
• Build: Compliance-ready features (audit logs, data residency, encryption).

Accessibility, Security, Privacy in Discovery

• Accessibility: During shadowing, note assistive tech used (screen readers, voice input). Test prototypes with these tools.
• Security: For Security stakeholder interviews, ask about threat model, acceptable risk, pen-test requirements. Build threat modeling into design phase.
• Privacy: For Legal/Compliance interviews, ask about data retention, consent, export/delete. Embed privacy controls in product.

Back-Office & Ops Integration

Sales Discovery Playbooks

Pre-Sales Discovery Checklist

• First call: Map stakeholders (Chapter 7). Identify Economic Buyer, Champion, Gatekeepers.
• Second call: Stakeholder interviews (jobs, pains, success criteria).
• Third call: Technical discovery (integrations, compliance, performance).
• Fourth call: Demo based on discovery (show solutions to discovered pains).

Discovery-Driven Proposals

• Structure proposal around discovered jobs/pains. Example: "You said provisioning takes 2 hours. Our SCIM auto-sync reduces it to 10 minutes."
• Include evidence from discovery (anonymized quotes, workflow diagrams).

CS Discovery During Onboarding

Implementation Kickoff Discovery

• First CS meeting: Re-validate assumptions from Sales discovery. Ask: "What's changed since the sale? Any new stakeholders? Updated priorities?"
• Technical discovery: "What's your SSO provider? Data sources? Existing workflows?"
• Create implementation blueprint: Map discovered needs → onboarding tasks → success criteria.

Adoption Discovery (Post-Launch)

• 30/60/90-day check-ins: "Which features are you using? Which are hard to use? What's blocking you?"
• Use insights to refine onboarding, create help content, flag product gaps.

Data & SLOs for Discovery

Discovery Coverage SLO

• Define: "100% of Enterprise deals ($50K+ ACV) have formal discovery (≥5 stakeholder interviews, ≥1 contextual inquiry) before proposal."
• Track: In CRM, add "Discovery Completed" field. Report on coverage.

Discovery Impact Metrics

• Win rate: Discovery-informed deals vs non-discovery.
• Time-to-close: Discovery deals should close faster (clearer fit, fewer objections).
• Implementation time: Discovery-informed implementations should be smoother (fewer surprises).

Metrics That Matter

Instrumentation:

• CRM: Track discovery activities (interviews, shadowing) per opportunity.
• Product: Tag roadmap items with originating discovery insights.
• CS: Track implementation smoothness (on-time, surprises, rework).

AI Considerations

Where AI Helps

Interview Transcription & Synthesis

• AI transcribes interviews (Otter.ai, Fireflies). Summarizes key themes.
• Example: "Top themes from 10 interviews: (1) Provisioning pain (8 mentions), (2) Compliance gaps (5 mentions), (3) Offline needs (3 mentions)."

Stakeholder Sentiment Analysis

• AI analyzes interview transcripts for sentiment (positive, negative, frustrated).
• Alert: "Security stakeholder sentiment negative—address compliance gaps before proposal."

Discovery Insights Repository

• AI tags and indexes discovery insights (searchable by job, pain, persona, account).
• Use case: PM searches "provisioning pains, financial services" → surfaces relevant insights from past discovery.

Guardrails

Consent for AI Processing

• Inform interview participants: "We'll use AI to transcribe and analyze. Opt out if preferred."
• For regulated industries (healthcare, finance), verify AI vendor compliance (HIPAA, GDPR).

Human Review of AI Insights

• AI may misinterpret context (e.g., sarcasm, domain jargon). Always have human review AI-generated summaries.

Privacy & Anonymization

• When sharing discovery insights across teams, anonymize customer names, sensitive details.
• AI tools: Ensure no PII leakage (e.g., customer data used to train models).

Risk & Anti-Patterns

Top 5 Pitfalls

1. Sales Theater Discovery: Checking Boxes, Not Learning

   • Sales asks scripted questions, doesn't listen. Discovery report filed, never used.
   • Avoid: Train on active listening. Ask "why" 5 times. Use insights in proposal and demo.

2. End User Only Discovery: Ignoring Gatekeepers

   • Interview only End Users, miss Security/Legal needs. Deal blocked late by gatekeepers.
   • Avoid: Map all stakeholders (Chapter 7). Interview Economic Buyer, Champion, Gatekeepers, End Users.

3. Office-Only Discovery: Missing Real Context

   • Interview users in conference room. Miss real environment (noisy warehouse, offline field, peak load).
   • Avoid: Contextual inquiry, field shadowing. Observe in situ.

4. Discovery-to-Roadmap Gap: Insights Don't Drive Action

   • Beautiful discovery reports, no roadmap impact. Insights forgotten.
   • Avoid: Synthesis workshop with PM, Design, Eng. Map insights to OKRs/roadmap. Track insight-to-roadmap ratio.

5. One-and-Done Discovery: No Continuous Learning

   • Discovery done once during sale, never again. Post-sale, CS doesn't rediscover as needs evolve.
   • Avoid: Continuous discovery. CS does discovery at onboarding, 30/60/90 days. Product does discovery quarterly with key accounts.

Case Snapshot

Company: B2B SaaS platform (field service management) Challenge: Low win rate (22%), long sales cycles (150 days), high implementation failures (40% of projects delayed >60 days, 15% cancelled). Sales demos were generic, missed customer-specific needs. Post-sale, surprises emerged (unknown integrations, workflows, compliance needs).

Discovery Intervention:

• Implemented enterprise discovery framework. Trained Sales, Solutions Eng, CS on contextual inquiry, stakeholder interviews.
• Pre-sale: Sales required to complete discovery for all Enterprise deals (>$50K ACV): ≥5 stakeholder interviews, ≥1 field shadowing.
• Discovery playbook: Week 1: Map stakeholders. Week 2–3: Interviews + shadowing. Week 4: Synthesis + demo customization.
• CS discovery at onboarding: Technical discovery (integrations, data sources), workflow validation.

6-Month Results:

• Sales: Win rate: 22% → 37% (68% increase). Time-to-close: 150 days → 95 days (37% reduction). Discovery-informed proposals resonated (customer quote: "You actually understand our business").
• Implementation: On-time rate: 60% → 88%. Surprises/rework: 40% → 12%. Discovery uncovered integrations, compliance needs early.
• Product: 18 discovery insights became roadmap items. Example: Offline mode for field workers (discovered via shadowing) → 35% adoption, 25% time savings.
• Customer Satisfaction: Post-implementation NPS: 18 → 42. Customers felt "heard" and "understood."

Checklist & Templates

Enterprise Discovery Checklist

• Define research questions (3–5 questions).
• Map stakeholders (Economic Buyer, Champion, End Users, Gatekeepers). Use Chapter 7.
• Recruit 8–15 participants per account (mix of roles).
• Prepare interview guides, observation protocols, NDAs.
• Schedule discovery sessions (interviews, contextual inquiry, shadowing).
• Conduct stakeholder interviews (1:1, 45–60 min). Focus on jobs, pains, success criteria.
• Conduct contextual inquiry (2–4 hours, observe users in their environment).
• Conduct field shadowing (full day, 1–3 days with field workers/admins).
• (Optional) Run diary study (1–2 weeks, capture seasonal/intermittent patterns).
• Transcribe and organize field notes/recordings.
• Affinity diagram: Cluster observations into themes.
• Create journey maps (current state, pain points, opportunities).
• Map jobs, pains, gains per persona.
• Synthesis workshop (cross-functional, 4–8 hours). Align on top insights.
• Prioritize insights (frequency × severity × business impact).
• Map insights to roadmap (OKRs, initiatives).
• Build constrained prototypes (respect security/compliance).
• Validate prototypes (5–8 customers, measure task success).
• Update roadmap, proposals, demos based on insights.
• Track discovery metrics (coverage, win rate, implementation success).

Templates

• Discovery Research Plan: [Link to Appendix B]
• Stakeholder Interview Guide: [Link to Appendix B]
• Contextual Inquiry Protocol: [Link to Appendix B]
• Field Shadowing Template: [Link to Appendix B]
• Affinity Diagram Canvas: [Link to Appendix B]
• Discovery Insights Summary (1-pager): [Link to Appendix B]

Call to Action (Next Week)

3 Actions for the Next Five Working Days:

1. Pick One Complex Account & Define Research Questions (Day 1): Choose 1 current customer or in-progress deal (Enterprise, >$50K ACV). Write 3 research questions. Example: "What blocks fast user provisioning?" "What compliance needs must we address?" "What workflows do admins use daily?"

2. Recruit & Schedule 5 Discovery Sessions (Day 2–3): Identify 5 stakeholders (Economic Buyer, Champion, Admin, End User, Security). Reach out via CS or Sales. Schedule: 3 interviews (60 min each), 1 contextual inquiry (2–4 hours), 1 field shadowing (if feasible, half-day).

3. Conduct First 2 Sessions & Synthesize (Day 4–5): Run 2 sessions (1 interview, 1 contextual inquiry). Take detailed notes. After sessions, spend 1 hour: List top 3 observations, 2 pain points, 1 opportunity. Share with PM, Design, or Sales. Discuss: How does this change our proposal/roadmap/demo?

Next Chapter: Chapter 9 — Quant + Qual Fusion