Operational due diligence checklist
Twenty-four questions, and where each answer lives.
The checklist a deal team actually works from, organized by dimension. Each line names the question, the system that answers it, and whether the answer is a document request or a metadata read.

Delivery & Execution
6 questions- Is deploy frequency keeping pace with engineering headcount?
- What is cycle time, and has it drifted over four quarters?
- What proportion of work is reopened after review?
- Is there a documented release process, and is it followed?document
- How much work-in-progress is older than 90 days?
- What is the current known-defect backlog?document
Culture & People
6 questions- Which functions have stopped communicating, and when?
- What is response latency between engineering and product?
- What is voluntary attrition by function over eight quarters?document
- How concentrated is the meeting load on the leadership group?
- Is there a single point of failure in any critical system?
- What is the current org chart, dated?document
Go-to-Market
6 questions- What share of ARR is closed by the top rep?
- How has pipeline velocity moved across four quarters?
- What is the stage-transition timing distribution?
- What are the top-ten customer contracts and their terms?document
- Is win rate moving, and against whom?
- What is the renewal calendar for the next twelve months?
Financial Vitality & Risk
6 questions- How many days after period end do the books close?
- How are receivables aging, and is it drifting?
- What share of revenue sits with the top three accounts?
- Which systems have a single administrator?
- What are the outstanding contingent liabilities?document
- What insurance is in force, and at what limits?document