Tech Due Diligence Interview Questions - Medium

calendarDec 13, 2025 · 3 min read · due-diligence interview medium deep-assessment  ·
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Medium-level technical due diligence interview questions covering deeper assessment methodologies.

Q1: How do you conduct a comprehensive architecture review?

Answer:

Multi-Layer Assessment

Key Questions:

  • Is the architecture documented?
  • Are concerns properly separated?
  • How are services communicating?
  • What are the failure points?
  • How does data flow through the system?

Architecture Patterns Assessment

Q2: How do you assess data architecture and management?

Answer:

Data Flow Analysis

Assessment Areas:

Red Flags:

  • No data governance
  • Inconsistent schemas
  • No backup strategy
  • PII not encrypted
  • No data retention policy

Q3: How do you evaluate API design and integration quality?

Answer:

API Design Assessment

Integration Complexity

Questions:

  • How many external dependencies?
  • What happens if one fails?
  • Are there rate limits?
  • How is authentication handled?
  • What's the API versioning strategy?

Q4: How do you assess testing strategy and quality assurance?

Answer:

Test Pyramid Assessment

Ideal distribution: Many unit tests, fewer integration, minimal E2E

Coverage Analysis

But: Coverage % alone insufficient - check test quality!

Assessment Questions:

  • What's the test coverage?
  • How long do tests take to run?
  • Are tests run in CI/CD?
  • When was last test suite review?
  • Are critical paths tested?

Q5: How do you evaluate deployment and release processes?

Answer:

Deployment Maturity Model

Release Strategy

Key Metrics:

  • Deployment frequency (daily? weekly?)
  • Lead time (commit to production)
  • Mean time to recovery (MTTR)
  • Change failure rate

Q6: How do you assess observability and monitoring?

Answer:

Three Pillars Assessment

Assessment Questions:

  • What monitoring tools are used?
  • What metrics are tracked?
  • Are logs centralized?
  • Is distributed tracing implemented?
  • What's the alerting strategy?
  • How long to detect issues?

Alert Quality

Red Flags:

  • Alert fatigue (too many alerts)
  • No runbooks
  • Alerts without context
  • No SLOs/SLIs defined

Q7: How do you evaluate intellectual property and licensing?

Answer:

License Risk Assessment

Key Questions:

  • Are all dependencies documented?
  • Any GPL/AGPL dependencies?
  • Are licenses compatible?
  • Is there a license compliance process?
  • Who owns the code? (employees? contractors?)
  • Are IP assignments signed?

Dependency Audit

Q8: How do you assess technical scalability limits?

Answer:

Capacity Planning

Bottleneck Identification

Assessment Approach:

  1. Profile current performance
  2. Identify bottlenecks
  3. Project growth
  4. Calculate when limits hit
  5. Estimate cost to scale

Red Flags:

  • Already at capacity
  • No horizontal scaling path
  • Database can't shard
  • Monolithic architecture at scale
  • Exponential cost growth

Q9: How do you evaluate disaster recovery and business continuity?

Answer:

Key Metrics

Disaster Scenarios

Assessment Questions:

  • What's the backup frequency?
  • Where are backups stored?
  • How long to restore?
  • When was last DR test?
  • Is there geographic redundancy?
  • What's the failover process?

Q10: How do you assess technical team processes and culture?

Answer:

Development Workflow Maturity

Code Review Quality

Assessment Areas:

  • Sprint planning effectiveness
  • Estimation accuracy
  • Velocity trends
  • Bug escape rate
  • Time to resolution
  • Knowledge silos
  • Documentation culture
  • On-call rotation

Red Flags:

  • No code review
  • Cowboy coding
  • Knowledge in one person
  • No post-mortems
  • Blame culture
  • No process documentation

Summary

Medium tech due diligence topics:

  • Architecture Review: Multi-layer assessment, patterns
  • Data Architecture: Models, pipelines, quality
  • API Quality: Design, documentation, integrations
  • Testing Strategy: Pyramid, coverage, automation
  • Deployment: Maturity model, release strategy
  • Observability: Metrics, logs, traces, alerts
  • IP & Licensing: Ownership, dependencies, compliance
  • Scalability Limits: Capacity planning, bottlenecks
  • Disaster Recovery: RPO/RTO, redundancy, testing
  • Team Processes: Workflow, reviews, culture

These deeper assessments reveal technical maturity and risks.

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