Most advisory engagements start with a pitch deck and end with a deliverable nobody reads. Structural diagnosis works differently. Every engagement follows the same method — Observe, Hypothesise, Test, Revise — but the depth, timeline, and output change depending on what you need. There are three engagement models, each designed for a different moment in the investment lifecycle. All three share the same diagnostic discipline. None involve motivational workshops, personality assessments, or slide decks that tell you what you already know.
Organizational Due Diligence
Timeline: 2 weeks. Trigger: Pre-investment.
This is the assessment you run before you write the check. Standard DD evaluates the market, the technology, and the team. Organizational DD evaluates the operating structure that has to deliver on the thesis — the part your current process doesn’t look at.
The engagement includes founder interviews, team mapping, and a decision architecture audit. I assess how decisions actually get made (not how the org chart says they should), where authority sits, where information flows, and where throughput is structurally capped. I evaluate scaling readiness — whether the current operating model can support the growth your investment thesis requires without a fundamental redesign.
Deliverable: A structural assessment with a risk profile. Not a judgment of the team. A map of the system they’re operating in, the specific structural risks to the thesis, and the organizational interventions that would mitigate them. The assessment either confirms the structural capacity to execute or identifies exactly what needs to change post-close.
The most expensive organizational DD is the one you didn’t do. Eighteen months of board advice and executive reshuffles addressing symptoms while the structural cause compounds — that’s what skipping this assessment costs.
Portfolio Diagnosis
Timeline: 3-4 weeks. Trigger: Post-investment.
This is the deeper engagement. Something isn’t working — missed milestones, executive turnover, friction the board can see but can’t explain. The portfolio company has been through coaching, management reshuffles, maybe a COO hire. The problem persists because nobody has diagnosed the structural cause.
Portfolio diagnosis goes beyond the founder. I conduct interviews across the organization, map the actual operating model against the stated one, and identify the specific structural mechanisms producing the dysfunction. This means examining how teams are organized relative to the business model, where mandates conflict, where coordination costs are invisible, and where the organizational design actively prevents the outcomes everyone is working toward.
Deliverable: A diagnostic report with a structural map of the organization and specific redesign recommendations. Not generic advice. Specific interventions tied to specific mechanisms — the decision that needs to move, the mandate that needs to change, the coordination layer that’s missing or redundant.
Post-Investment Advisory
Timeline: 3-6 months, ongoing. Trigger: After diagnosis.
This is not a report. This is organizational change.
After the structural diagnosis — whether from a pre-investment assessment or a portfolio diagnosis — I work directly with the founder and leadership team to implement the redesign. Decision architecture gets restructured. Authority gets redistributed. Operating model gets realigned to the business model. The same people start producing different outcomes because the system they’re operating in has changed.
This is where most advisory engagements never go. Identifying the problem is the easy part. Redesigning the system while it’s running, without losing the people or the momentum — that’s the work. It requires sustained engagement, real-time hypothesis testing, and the willingness to revise when the intervention produces unexpected data. It’s not a project plan. It’s an iterative structural redesign with a feedback loop.
What all three share
Same method. Different depth. Different timeline.
Every engagement follows the Observe/Hypothesise/Test/Revise cycle. In a two-week pre-investment assessment, the cycle is compressed — faster observation, sharper hypothesis, rapid testing against available data. In a six-month advisory engagement, the cycle runs multiple times as interventions produce new information and the diagnosis gets refined.
All three produce actionable outputs. No engagement ends with “you have a culture problem” or “you need better communication.” Every output identifies specific structural mechanisms and specific interventions. The assessment tells you what’s broken and where. The diagnosis tells you why. The advisory engagement fixes it.
The difference between structural diagnosis and management consulting is that I don’t arrive with the answer. I arrive with a method that finds it.
If you want to understand what an engagement would look like for your portfolio or your next investment, let’s talk.