Technical due diligence
On this page 9 topics
Overview
Topics
- Assessing architecture
- risk
- team capabilities
- modernization needs
Learn first
3.5 h of practice (estimate)
Learning outcomes
- Assess an unfamiliar organization's architecture, code health, operations, security, and team capability quickly.
- Separate deal-breaking risks from fixable debt and estimate remediation cost.
- Produce a due-diligence report for acquisitions, vendor selection, or internal modernization.
- Recommend a modernization plan sized to the findings.
Lessons
- 01When due diligence is needed
- 02Assessing architecture and code health
- 03Assessing operations and security
- 04Assessing team capability and key-person risk
- 05Risk severity and remediation cost
- 06Writing the report
- 07Demo: a two-week due diligence of an acquisition target
- 08Demo: presenting findings to a deal team
Lab and exercises
Lab
STF-010-LAB1 · Acquisition review
Outcomes: 1–4 · Time: ~2.5 h
- Review the payments start-up's architecture docs, repository sample, incident history, and team interview notes (case materials).
- Assess architecture, code health, operations, security, and team capability with a common checklist.
- Build a risk register separating deal-breakers from fixable debt with costed remediation.
- Write the report with a go/no-go recommendation and conditions, plus a modernization outline sized to the findings.
- Present to a role-played deal team and answer challenges.
Acceptance: top risks costed; recommendation stated with conditions.
Exercises (case-based; six exercises)
| ID | Outcome | Task |
|---|---|---|
| STF-010-EX01 | 1 | Given a one-page description of a target, list the ten questions and evidence requests you would send in day one. |
| STF-010-EX02 | 1 | Review a sample repository summary (no tests, two-year-old dependencies, one deployer) and rate each area. |
| STF-010-EX03 | 2 | Classify six findings as deal-breaker or fixable debt and estimate cost ranges with confidence. |
| STF-010-EX04 | 2 | A colleague criticizes the target's code style. Redirect the review to risk with three better findings to look for. |
| STF-010-EX05 | 3 | Write the summary page of a due-diligence report with recommendation, conditions, and unknowns. |
| STF-010-EX06 | 4 | For a target with a fragile monolith and strong team, outline a modernization plan sized to the findings. |
Show solutions
- EX01 Examples: last three incidents, backup restore test, access list, vulnerability scan, payment-compliance evidence, architecture diagram, deployment process, team structure, key-person map, customer concentration.
- EX02 Test gaps are high risk for change; old dependencies medium to high (security); single deployer is key-person risk; give ratings and fixes.
- EX03 Deal-breakers: unlicensed core code, no way to meet required scale. Fixable: missing tests, dependency upgrades. Costs in engineer-months with ranges.
- EX04 Style rarely drives risk; check change failure history, data protection, recovery capability.
- EX05 Lead with go with conditions or no-go; top three risks with costs; unknowns and extra access needed.
- EX06 Stabilize with tests and monitoring, then strangle the riskiest modules behind interfaces; retain the team; stage the investment.
Outcome coverage: all four outcomes are covered by exercises and lab.
Workplace evidence: an assessment you produced that informed an acquisition, vendor, or modernization decision.
Quiz
Outcomes: O1 rapid assessment · O2 deal-breakers versus fixable debt · O3 the report · O4 modernization plan.
A self-check for you: nothing is graded, saved or sent anywhere. Choose an answer, then check it. You can try again as often as you like.
Practical part
Six case exercises STF-010-EX01 to EX06 plus the lab, with the report presented to a role-played deal team. Pass: at least five of six exercises correct, quiz at least 8/10, and a report whose top risks are costed and whose recommendation states conditions.
Common mistakes
Judging style instead of risk; missing people risks; findings without cost estimates.
Assessment
Report and presentation to role-played deal team.
Workplace evidence
An assessment you produced that informed an acquisition, vendor, or modernization decision.
Career relevance
Vendor evaluation (ARC-040) and legacy modernization (ARC-010).