Edition 1 · 17 June 2025
Deal-Maker, Not Checkbox
The purpose of Technical Due Diligence and using a risk register as a deal-making tool
Read editionTech Due Diligence Playbook
Notes and essays on technical due diligence, software governance, risk, and scale.
New here? Start with the guide: what technical due diligence is, when it is used, and a software-deal checklist.
Edition 2 · 25 June 2025
One Size Never Fits All
Right-sizing Technical Due Diligence scope by transaction type: minority stake, majority buyout, and carve-out
Read editionEdition 3 · 2 July 2025
The Metrics That Matter
Key deployment, incident, and cost signals that predict platform scalability
Read editionEdition 4 · 9 July 2025
Debt or Deal-Breaker?
Technical debt identification, classification, and its impact on deal valuation
Read editionEdition 5 · 16 July 2025
Scaling Without Bleeding Cash
Cloud cost analysis, FinOps practices, and spend optimisation as due diligence signals
Read editionEdition 6 · 23 July 2025
Incident Response and the Culture Behind the Numbers
Incident response maturity and engineering culture as due diligence signals
Read editionEdition 7 · 30 July 2025
Build vs. Buy: Innovation or Lock-In?
Evaluating build vs buy decisions: innovation potential versus vendor dependency risk
Read editionEdition 8 · 6 August 2025
Security & Compliance in the AI Act Era
Security posture and compliance readiness under the EU AI Act and related regulation
Read editionEdition 9 · 13 August 2025
Vendor Due Diligence & Third-Party Risk
Vendor and third-party dependency assessment and supply chain risk in Technical Due Diligence
Read editionEdition 10 · 20 August 2025
Data Governance & Sovereign-Data Readiness
Data governance frameworks, data sovereignty obligations, and regulatory compliance readiness
Read editionEdition 11 · 27 August 2025
The People Lens
Engineering team quality, leadership capacity, culture, and key-person risk in Technical Due Diligence
Read editionEdition 12 · 3 September 2025
API Strategy & Integration Readiness
API design quality, integration architecture, and partner ecosystem readiness
Read editionEdition 13 · 10 September 2025
Business-Continuity & Resilience Stress-Test
Business continuity planning, disaster recovery, and platform resilience under stress
Read editionEdition 14 · 17 September 2025
Cloud Strategy & Deployment Models
Cloud provider strategy, multi-cloud options, and deployment model evaluation
Read editionEdition 15 · 22 October 2025
Platform Architecture Assessment
Platform architecture review: modularity, coupling, extensibility, and scalability
Read editionEdition 16 · 5 November 2025
DevSecOps Maturity & Shift-Left Security
DevSecOps practices, shift-left security integration, and CI/CD pipeline security maturity
Read editionEdition 17 · 12 November 2025
Database Architecture & Data Strategy
Database architecture choices and data strategy for scalable, maintainable platforms
Read editionEdition 18 · 25 December 2025
Year-End Wrap-up for 2025
2025 year-end review of the Tech Due Diligence Playbook series
Read editionEdition 19 · 7 January 2026
Quality Assurance & Testing Maturity
QA processes, test coverage, and testing maturity as due diligence signals
Read editionEdition 20 · 21 January 2026
Product-Tech Fit
Alignment between product strategy and technical capability as an investment signal
Read editionEdition 21 · 11 February 2026
Infrastructure as Code & GitOps
Infrastructure-as-code practices and GitOps workflows as engineering maturity signals
Read editionEdition 22 · 25 February 2026
Tech Governance for Hypergrowth
Technology governance frameworks for rapidly scaling organisations
Read editionEdition 23 · 11 March 2026
Multi-Tenant Architecture Assessment
Multi-tenant architecture patterns, tenant isolation strategies, and scalability assessment
Read editionEdition 24 · 25 March 2026
Observability & Monitoring Excellence
Observability stack, monitoring practices, and operational alerting maturity
Read editionEdition 25 · 8 April 2026
Performance Engineering & Load Testing
Realistic load testing versus synthetic benchmarks, bottleneck discovery, and capacity modelling as scalability signals
Read editionEdition 26 · 13 May 2026
People Risk and Succession Planning
Critical-role mapping, vesting cliffs, succession depth, and executive ownership as people-risk signals in diligence
Read editionEdition 27 · 10 June 2026
The Post-Close 100-Day Tech-Value Plan
Turning diligence findings into a sequenced, owned 100-day plan that reduces priced-in risk and builds the value thesis
Read editionEdition 28 · 22 October 2026
Exit-Readiness & Integration Playbooks
Preparing for a buyer's integration questions before an exit: code ownership, tested migrations, change-of-control clauses and a one-page exit-readiness canvas
Read editionEdition 29 · 4 November 2026
Continuous Due Diligence
Watching a handful of agreed tech signals between two diligences: what to track, information rights, a quarterly one-page note and signs it is not working
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