{"id":"3f671750-4335-4af9-ae6e-db6ed83825fd","shortId":"SXQpJr","kind":"skill","title":"due-diligence","tagline":"Conduct commercial, operational, financial, strategic, and technology due diligence for M&A, investment, partnership, or vendor decisions. Use when assessing acquisition targets, performing quality of earnings analysis, evaluating working capital, reviewing technology and IP, pla","description":"# Due Diligence\n\nAssess business opportunities through rigorous analytical frameworks. This covers commercial, operational, financial, strategic, and technology due diligence — from scoping the engagement through risk synthesis and investment recommendation.\n\n---\n\n## DD Types and When to Use Them\n\n| DD Type | Core Question | Focus Areas |\n|---------|---------------|-------------|\n| Commercial | Can we win? | Market position, customers, growth, competitive dynamics |\n| Operational | Can we run it? | Processes, systems, people, efficiency, scalability |\n| Financial | Is it real? | Revenue quality, working capital, cash flow, projections |\n| Strategic | Should we do it? | Strategic fit, synergies, integration, cultural compatibility |\n| Technology & IP | Is it viable? | Architecture, technical debt, IP ownership, security |\n| Legal & Regulatory | Is it clean? | Litigation, compliance, contracts, data privacy |\n\nMost transactions require at least commercial, operational, and financial DD. The mix depends on the deal.\n\n---\n\n## Phase 1: Scope Definition\n\nDefine the boundaries before doing any analysis. Unfocused DD wastes time and misses what matters.\n\n### Transaction Context\n\nEstablish:\n- **Transaction type**: Acquisition, PE investment, strategic partnership, vendor assessment, internal assessment\n- **Target**: Company name, industry, size\n- **Deal value**: Estimated range\n- **Timeline**: How much time for DD\n- **Access**: Data room contents, management availability, ability to speak with customers/suppliers\n- **Team**: Who's doing the work, what expertise is available\n\n### Focus Area Prioritization\n\n| Area | Priority | Key Questions | Data Available? |\n|------|----------|---------------|-----------------|\n| Market | High/Med/Low | What must we understand about the market? | Y/N |\n| Customers | High/Med/Low | What must we understand about the customer base? | Y/N |\n| Operations | High/Med/Low | What must we understand about how the business runs? | Y/N |\n| Financials | High/Med/Low | What must we validate about the numbers? | Y/N |\n| Technology | High/Med/Low | What must we understand about the tech stack? | Y/N |\n| Legal/Regulatory | High/Med/Low | What risks need legal review? | Y/N |\n\nPrioritize ruthlessly. Focus on what could kill the deal or materially change the price.\n\n---\n\n## Phase 2: Information Gathering\n\n### Information Request List\n\n**Corporate:**\n- Articles of incorporation\n- Board minutes (last 2 years)\n- Organizational charts\n- Shareholder agreements\n- Material contracts and amendments\n\n**Financial:**\n- Audited financials (3-5 years)\n- Monthly management accounts (last 24 months)\n- Revenue by segment, product, geography, customer\n- Cash flow statements\n- Debt schedules and covenant compliance\n- Budget vs. actual analysis (last 2 years)\n- Tax returns and outstanding tax positions\n\n**Commercial:**\n- Customer list with revenue by customer (last 3 years)\n- Contract templates and key customer contracts\n- Pricing history and discount schedules\n- Sales pipeline and win/loss data\n- Customer churn data and reasons\n- NPS or customer satisfaction data\n\n**Operational:**\n- Process documentation for key workflows\n- Technology systems inventory\n- Key vendor list with spend and contract terms\n- Headcount by function, level, tenure\n- Capacity utilization data\n- Quality metrics and incident history\n\n**Technology:**\n- Architecture diagrams\n- Technical debt assessment (if available)\n- Security audit results\n- IP portfolio (patents, trademarks, trade secrets)\n- Open-source dependency audit\n- Development team metrics (deploy frequency, incident response)\n\n**Legal:**\n- Pending or threatened litigation\n- Regulatory filings and compliance status\n- Material contract summary\n- Insurance policies\n- Data privacy compliance documentation\n\n---\n\n## Phase 3: Analysis\n\n### Commercial Due Diligence\n\n#### Market Assessment\n\n| Metric | Finding | Source | Confidence |\n|--------|---------|--------|------------|\n| Total addressable market (TAM) | $ | Industry reports, bottom-up analysis | H/M/L |\n| Target's market share | % | Company data vs. market estimates | H/M/L |\n| Market growth rate (CAGR) | % | Historical trend, analyst consensus | H/M/L |\n| Market position | #X of Y competitors | Competitive analysis | H/M/L |\n\nKey questions: Is the market growing or shrinking? Is growth structural or cyclical? What disruption risks exist? How defensible is the target's position?\n\n#### Customer Analysis\n\n| Metric | Finding | Risk Level | Trend |\n|--------|---------|------------|-------|\n| Top 10 customer concentration | % of revenue | H/M/L | Improving/Stable/Worsening |\n| Average contract value | $ | | Direction |\n| Net revenue retention (NRR) | % | Above/Below 100% | Direction |\n| Gross churn rate | % | vs. industry benchmark | Direction |\n| Logo churn rate | % | Segment comparison | Direction |\n| Average contract duration | months | vs. industry | Direction |\n\nCustomer concentration above 20% in top 3 customers is a yellow flag. Above 40% is a red flag. NRR below 100% means the installed base is shrinking — the business must sell faster than it leaks.\n\n#### Revenue Quality\n\n| Metric | Finding | Assessment |\n|--------|---------|------------|\n| Recurring vs. one-time revenue | % recurring | Strong (>80%) / Moderate (50-80%) / Weak (<50%) |\n| Revenue recognition risks | Assessment | H/M/L |\n| Backlog / committed revenue | $ | Coverage ratio vs. plan |\n| Pricing power | Assessment | Expanding / Stable / Eroding |\n| Cross-sell / upsell as % of new ACV | % | Growing or declining |\n\n#### Competitive Position\n\n| Factor | Target | Comp A | Comp B | Assessment |\n|--------|--------|--------|--------|------------|\n| Market share | % | % | % | Position and trajectory |\n| Pricing | $ | $ | $ | Premium / Par / Discount |\n| Differentiation | Claim | Claim | Claim | Sustainable? |\n| Win rate vs. competitors | % | — | — | Strong / Weak |\n\n### Operational Due Diligence\n\n#### Process and Efficiency\n\n| Area | Finding | Risk | Improvement Potential |\n|------|---------|------|---------------------|\n| Capacity utilization | % | H/M/L | Assessment |\n| Key process bottlenecks | Findings | H/M/L | Assessment |\n| Automation level | % | H/M/L | Assessment |\n| Quality metrics | Findings | H/M/L | Assessment |\n\n#### Technology Assessment\n\n| Area | Finding | Risk | Detail |\n|------|---------|------|--------|\n| Architecture scalability | Assessment | H/M/L | Can it support 3-5x growth? |\n| Technical debt | Quantified estimate | H/M/L | Remediation cost and timeline |\n| IP ownership and protection | Status | H/M/L | Patents, trade secrets, licenses |\n| Security posture | Assessment | H/M/L | Last audit, certifications, incidents |\n| Data architecture | Findings | H/M/L | Quality, governance, portability |\n| Open-source dependencies | Audit status | H/M/L | License compliance, security |\n| Development velocity | Metrics | H/M/L | Deploy frequency, lead time, MTTR |\n| Cloud infrastructure | Status | H/M/L | Provider, costs, lock-in risk |\n\n#### Management and Team\n\n| Dimension | Finding | Risk | Detail |\n|-----------|---------|------|--------|\n| Leadership depth | Assessment | H/M/L | Bench strength below C-suite |\n| Key person dependencies | Names/roles | H/M/L | Single points of failure |\n| Succession planning | Status | H/M/L | Documented plans, readiness |\n| Track record | Performance history | H/M/L | Delivery on past commitments |\n| Cultural assessment | Findings | H/M/L | Values, decision-making, adaptability |\n| Retention risk | Assessment | H/M/L | Turnover trends, engagement, comp benchmarking |\n| Organizational structure | Assessment | H/M/L | Efficiency, spans of control, layers |\n\nManagement assessment often predicts post-deal success better than financial analysis. A mediocre business with a strong team outperforms a strong business with a mediocre team.\n\n### Financial Due Diligence\n\n#### Quality of Earnings\n\n| Item | Reported | Adjusted | Adjustment Reason |\n|------|---------|---------|-------------------|\n| Revenue | $ | $ | Non-recurring items, timing differences |\n| EBITDA | $ | $ | One-time costs, owner compensation, related-party transactions |\n| Net income | $ | $ | Normalizing adjustments |\n\nThe gap between reported and adjusted EBITDA tells you how much the seller is dressing up the numbers. Adjustments exceeding 20% of reported EBITDA warrant extra scrutiny.\n\n#### Working Capital\n\n| Component | Current | Trend | Seasonal Pattern | Cash Impact |\n|-----------|---------|-------|-----------------|-------------|\n| Accounts receivable | $ (X days) | Direction | Pattern | $ |\n| Accounts payable | $ (X days) | Direction | Pattern | $ |\n| Inventory | $ (X days) | Direction | Pattern | $ |\n| Net working capital | $ | Direction | Pattern | Funding need |\n\nWorking capital is where deals get renegotiated. Establish a normalized working capital figure and tie the purchase price to it. Seasonal businesses require month-by-month analysis.\n\n#### Capital Expenditure\n\n| Category | Historical (3-year avg) | Forecast | Maintenance vs. Growth |\n|----------|------------------------|----------|----------------------|\n| Category 1 | $/yr | $/yr | Split |\n| Category 2 | $/yr | $/yr | Split |\n\nDistinguish maintenance capex (required to keep the business running) from growth capex (investment in expansion). Underinvestment in maintenance capex flatters short-term earnings but creates a liability.\n\n#### Cash Flow\n\n| Metric | Year -2 | Year -1 | Current | Trend |\n|--------|---------|---------|---------|-------|\n| Operating cash flow | $ | $ | $ | Direction |\n| Free cash flow | $ | $ | $ | Direction |\n| Cash conversion (FCF/EBITDA) | % | % | % | Direction |\n\nCash conversion below 70% needs explanation. Common culprits: growing working capital, high capex, or earnings quality issues.\n\n---\n\n## Phase 4: Risk Assessment\n\n### Risk Categorization\n\n**Critical risks (deal killers)** — Issues that could make the deal unviable:\n\n| Risk | Likelihood | Impact | Mitigation |\n|------|------------|--------|------------|\n| Risk description | H/M/L | H/M/L | What can be done |\n\nExamples: undisclosed litigation, regulatory non-compliance, fraud indicators, irreplaceable key person with no retention plan, market in structural decline.\n\n**Major risks (deal adjustments)** — Issues that materially affect valuation or deal terms:\n\n| Risk | Likelihood | Impact | Mitigation |\n|------|------------|--------|------------|\n| Risk description | H/M/L | H/M/L | What can be done |\n\nExamples: customer concentration, technical debt requiring significant remediation, management gaps, integration complexity.\n\n**Minor risks (price adjustments)** — Issues that affect value but are manageable:\n\n| Risk | Likelihood | Impact | Mitigation |\n|------|------------|--------|------------|\n| Risk description | H/M/L | H/M/L | What can be done |\n\nExamples: operational inefficiencies (often upside opportunities), minor compliance gaps, below-market compensation structures.\n\n### Red Flag Indicators\n\nWatch for these — any one of them warrants deeper investigation:\n\n- Revenue acceleration in the run-up to sale (pulling revenue forward)\n- Unusual changes in accounting policies or estimates\n- Customer concentration increasing while being presented as \"diversified\"\n- Key employees departing in the months before the transaction\n- Capital expenditure declining while revenue grows (underinvestment)\n- Working capital trends diverging from revenue trends\n- Related-party transactions at non-market terms\n- Gaps or inconsistencies between management presentations and data room documents\n- Reluctance to provide access to customers or key employees\n\nRed flags are not necessarily deal killers. They're signals to investigate further. Sometimes the explanation is benign. Sometimes it changes the deal.\n\n---\n\n## Phase 5: Synthesis and Recommendation\n\n### Investment Thesis\n\nFrame the deal in terms of:\n1. **What makes this attractive** — the strategic rationale and value creation opportunity\n2. **What could go wrong** — the key risks and their mitigations\n3. **What the deal is worth** — implied valuation given the findings\n\n### Recommendation Format\n\n```\n## Due Diligence Summary: [Target]\n\n### Investment Thesis\n[One paragraph: why this deal makes sense or doesn't]\n\n### Key Strengths\n1. [Strength with evidence]\n2. [Strength with evidence]\n\n### Key Concerns\n1. [Concern with evidence and mitigation]\n2. [Concern with evidence and mitigation]\n\n### Risk Assessment\n| Category | Risk Level | Key Risks |\n|----------|------------|-----------|\n| Commercial | H/M/L | [Risks] |\n| Operational | H/M/L | [Risks] |\n| Financial | H/M/L | [Risks] |\n| Strategic | H/M/L | [Risks] |\n| Technology | H/M/L | [Risks] |\n\n### Valuation Implications\n| Factor | Adjustment |\n|--------|------------|\n| Revenue quality adjustments | +/-$ or % |\n| Customer risk discount | -$ or % |\n| Operational improvement upside | +$ or % |\n| Integration costs | -$ |\n| Net adjustment | $ or % |\n\n### Recommendation\n[PROCEED / PROCEED WITH CONDITIONS / DO NOT PROCEED]\n\n### Conditions Precedent (if proceeding)\n1. [Condition — rationale]\n2. [Condition — rationale]\n\n### Next Steps\n1. [Action — owner — timeline]\n2. [Action — owner — timeline]\n```\n\n---\n\n## Integration Assessment (M&A Context)\n\nWhen DD is for an acquisition, integration planning starts during DD, not after close.\n\n### Integration Complexity\n\n| Area | Complexity | Timeline | Key Dependencies | Cost Estimate |\n|------|-----------|----------|-----------------|---------------|\n| Systems integration | H/M/L | Months | Dependencies | $ |\n| Organization integration | H/M/L | Months | Dependencies | $ |\n| Customer migration | H/M/L | Months | Dependencies | $ |\n| Process harmonization | H/M/L | Months | Dependencies | $ |\n| Culture integration | H/M/L | Months | Dependencies | $ |\n\n### Synergy Quantification\n\n| Synergy | Type | Year 1 | Year 2 | Year 3 | Confidence | Risk |\n|---------|------|--------|--------|--------|------------|------|\n| Revenue synergy | Revenue | $ | $ | $ | H/M/L | Timing risk |\n| Cost synergy 1 | Cost | $ | $ | $ | H/M/L | Execution risk |\n| Cost synergy 2 | Cost | $ | $ | $ | H/M/L | Execution risk |\n\nCost synergies are generally more reliable than revenue synergies. Revenue synergies take longer to materialize and depend on customer behavior you can't fully control. Discount revenue synergies by 50% in your base case.\n\n### Day 1 Readiness\n\n- Communication plan for employees, customers, vendors\n- Interim operating model defined\n- Key talent retention packages in place\n- Regulatory approvals obtained\n- IT systems access and continuity plan\n- Customer-facing team briefed and scripted\n\n---\n\n## Context Adaptation\n\nAdapt the DD approach based on the deal context:\n\n| Context | Emphasis |\n|---------|----------|\n| **M&A** | Synergy assessment, integration complexity, valuation adjustments, Day 1 readiness |\n| **PE Investment** | Value creation levers, exit scenarios, management incentive alignment, 100-day plan |\n| **Strategic Partnership** | Capability complementarity, cultural fit, governance model, IP sharing terms |\n| **Vendor Assessment** | Operational reliability, financial stability, contractual protections, business continuity |\n| **Internal Assessment** | Capability gaps, improvement priorities, investment needs (drop M&A terminology) |\n\n---\n\n## Working Principles\n\n- **Focus on materiality.** Prioritize issues that could kill the deal or change the price by more than 5%. Don't spend equal time on everything.\n- **Triangulate everything.** Management tells one story. The data room tells another. Customers and suppliers tell a third. The truth is somewhere in the overlap.\n- **Red flags are negotiation tools, not always walk-away signals.** A customer concentration risk discovered in DD becomes a price adjustment or an earn-out structure.\n- **Document all assumptions and limitations.** What you couldn't verify is as important as what you confirmed. Future you (or the lawyer) will need to know.\n- **Connect findings to valuation.** Every DD finding should translate to \"and that means the deal is worth more/less/the same because...\"\n- **Start integration planning during DD.** The information you gather during DD is the foundation for the integration plan. Don't throw it over the wall and start fresh.\n- **Operational DD reveals upside.** Financial DD finds problems. Operational DD often finds improvement opportunities — inefficiencies the acquirer can fix, capabilities the acquirer can scale.\n- **Talk to customers and suppliers when possible.** Management representations are necessary but insufficient. 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