Technical Due Diligence Checklist
A 96-item checklist for evaluating technology assets before investment or acquisition. The same framework used by professional investors and acquirers.
Get the Free ChecklistTechnical Due Diligence
Get objective technical assessment for acquisition, investment, or partnership decisions. I evaluate architecture quality, technical debt, team capability, and delivery risk, providing the validation you need to make confident decisions.
Fractional CTO services, technology development, and strategic guidance
Signs you need technical due diligence
Technical due diligence is right for you when:
- You're evaluating an acquisition and need independent technical validation
- You're preparing for investment and want to identify risks before they surface
- You need to understand whether a technology team can deliver their roadmap
- You're assessing technical debt and need to understand remediation costs
- You need a jargon-free report that boards and investors can actually understand
- You want faster, more thorough assessment using AI-augmented analysis tools
SoftWeb Development
How we can help
You're evaluating an acquisition, investment, or strategic partnership. You need to understand the technical reality behind the pitch deck. Is the architecture sound? Is the technical debt manageable? Can the team actually deliver what they're promising?
Technical due diligence provides independent assessment of technology assets, team capability, and delivery risk. I work across three distinct contexts:
- M&A due diligence for acquirers and PE firms evaluating integration complexity, deal-breakers, and valuation adjustments
- Investor due diligence for VCs and angels assessing growth potential, team capability, and competitive moat
- Technical health checks for CTOs and boards wanting proactive assessment and improvement roadmaps
Each context has different priorities, but all require the same thing: objective, expert analysis that translates technical findings into business decisions.
You get a clear, jargon-free report that answers the questions investors and boards actually care about: What are the technical risks? What will it cost to fix the problems? Can this team execute their roadmap?
Technical due diligence engagements are typically scoped based on deal complexity and timeline:
Architecture & Code Quality Assessment
Comprehensive review of system architecture, code structure, and technical decisions with impact assessment and remediation cost estimates.
Team Capability Evaluation
Assess the technical team's capability to execute their roadmap including team structure, skill distribution, and delivery velocity.
Technology Stack Review
Evaluate technology choices for sustainability and risk including vendor lock-in, licensing risk, and scalability.
Security & Compliance Assessment
Review security practices, authentication/authorisation design, data protection measures, and compliance posture.
Delivery Risk Analysis
Assess the organisation's ability to deliver their roadmap including velocity trends and technical debt trajectory.
Integration Complexity Review
For acquisitions, evaluate technical integration complexity and cost with timeline and cost estimates.
Our commitment
Why choose us
I've assessed technical organisations from the inside as a CTO and architect. I know the difference between technical debt that's manageable and architectural decisions that will require expensive rewrites.
My assessments follow a structured methodology covering seven core domains: technology stack and architecture, security and compliance, scalability, technical debt, development practices, team capability, and intellectual property.
I use AI-augmented analysis tools to assess large codebases quickly. The same approach I used to analyse 390+ repositories for documentation coverage and identify architectural patterns.
All engagements are conducted under strict confidentiality. You get a structured report prioritising technical risks by business impact, with specific recommendations and cost estimates for remediation.
Technical Due Diligence in action
See how we've applied this service to help clients achieve their goals
What our clients say
Working with Michael was an absolute pleasure. He was the border between the developers and the business and always managed to handle both sides' expectations and took the stress of the business on to himself to give the developers enough room to do amazing work. A great developer as well. Always a laugh, great personality, light hearted and I would definitely work with him again at a moment's notice.
Michael doesn't just tackle challenges; he approaches them with a no-nonsense attitude, cutting through complexities with a level of precision that's truly impressive. His ability to break down intricate problems and come up with elegant solutions is not only commendable but also a testament to his exceptional problem-solving skills.
Technical Due Diligence FAQs
What is technical due diligence and when is it needed?
Technical due diligence is an independent assessment of a technology platform, codebase, or technical team, typically performed before investment, acquisition, or major partnership decisions. You need it when evaluating a potential acquisition target, assessing technical risk before investment, validating vendor claims, or planning technology transitions. It provides objective analysis of technical quality, scalability, security, and risk to inform business decisions.
How do you assess codebases and technical platforms?
I use a combination of AI-augmented analysis tools and hands-on expert review. Automated tools scan for code quality issues, security vulnerabilities, and architectural patterns across the entire codebase (I've analysed 390+ repositories in a single engagement). Senior review then focuses on architectural decisions, scalability concerns, technical debt severity, and team capability assessment. Reports are jargon-free and prioritised by business impact, not just technical severity.
What does a technical due diligence report include?
Reports include an executive summary with risk rating, codebase quality assessment, technology stack evaluation, scalability and performance analysis, technical debt quantification, team capability assessment, and prioritised recommendations. Reports are written for business decision-makers, translating technical findings into commercial risk and opportunity language.
How long does technical due diligence take?
Typical engagements range from 3-5 days for focused assessments to 10-15 days for comprehensive reviews, depending on the size of the ecosystem. AI-augmented analysis significantly accelerates codebase review. Most clients need results quickly for transaction timelines, so I structure engagements to deliver initial findings within the first week.
What makes your approach to technical due diligence different?
I combine CTO-level strategic perspective with hands-on architect experience and AI-augmented analysis tools. This means faster, deeper assessment than traditional manual reviews, business-impact prioritisation rather than just technical checklists, and jargon-free reporting for non-technical stakeholders.
What's the difference between M&A due diligence and investor due diligence?
M&A due diligence focuses on integration: Can we merge these systems? What will it cost? Are there deal-breakers that affect valuation? Investor due diligence focuses on growth potential: Can this technology scale 10x? Is there a defensible competitive moat? Can this team execute?
When should I request a technical health check instead of transaction due diligence?
Technical health checks are for proactive assessment outside of transaction pressure. Common triggers include new CTO onboarding, pre-fundraising preparation, annual governance reviews, post-incident improvement planning, or technology roadmap validation. Health checks emphasise improvement roadmaps and ongoing advisory rather than go/no-go recommendations.
What are common red flags you look for in technical due diligence?
Critical red flags include undisclosed security breaches or unpatched vulnerabilities, massive technical debt requiring complete rewrites, key person dependencies, IP ownership issues, compliance violations, and unrealistic roadmaps. I distinguish between deal-breakers and yellow flags that are manageable with proper planning.
Ready to get started with Technical Due Diligence?
Let's discuss how we can help your business.