Four Work Samples and a Debrief Form

The Work-Sample Library

Companion to The CTO You Actually Need · Updated 2026-09-29

Each work sample gives the candidate a brief, a task, and three changes to the constraints. Score the evidence with the debrief form at the end, and submit the form before discussion.

A Startup Weighs a Large Contract Against Runway

Candidate brief. A 16-person B2B startup has nine months of runway, six engineers, three pilot customers, and a product that requires manual support. One pilot will pay a meaningful annual contract if the company adds custom identity, reporting, and a security review. The CEO wants the full request in eight weeks. The engineers believe the core data model must change first. An investor expects a convincing growth story in ten weeks.

Task. Prepare for a 60-minute executive discussion. State what you would learn, what you would decide now, what you would defer, how you would protect runway and customer learning, and what you would tell the CEO, customer, engineers, and investor.

Constraint changes.

  1. The customer says the identity requirement is mandatory but reporting can wait.
  2. A data-rights issue appears in the proposed reporting feature.
  3. The strongest engineer announces plans to leave.

Evidence to score. Learning priority, technical contact, customer and runway tradeoff, candor, sequencing, and team judgment.

A Scale Company Splits Capacity Four Ways

Candidate brief. A 1,200-person SaaS company missed a quarter. Product leaders want all capacity on enterprise features. A recent outage exposed weak service ownership. Cloud cost per customer is rising. A platform team seeks 20 percent of product capacity for identity and observability migration. Sales has promised two customer-specific exceptions.

Task. Propose a 90-day decision process and capacity position. Identify what evidence you need, which decisions belong to whom, and how you prevent a platform program from becoming entitlement.

Constraint changes.

  1. The CFO requires a 10 percent technology-cost reduction.
  2. The CISO says one exception creates material exposure.
  3. The largest customer threatens to leave if the roadmap slips.

Evidence to score. Integrated business judgment, capacity, risk, platform economics, executive influence, and reversible choices.

An SME Depends on One Managed Provider

Candidate brief. A 450-person distributor runs ERP, CRM, warehouse, e-commerce, and reporting through several vendors. One managed provider holds most architecture knowledge. Cyber insurance identified recovery gaps. The CEO wants AI forecasting. Business teams maintain critical spreadsheets and oppose another transformation.

Task. Define the first 90 days and the first three investment decisions. State what should not begin yet.

Constraint changes.

  1. The managed provider contract renews in 60 days.
  2. A recovery test fails.
  3. The sales leader has already promised AI forecasting to the board.

Evidence to score. Control, vendor judgment, practical risk, business adoption, focus, and executive truth.

A Business Unit Collides With an Enterprise Platform

Candidate brief. A business unit needs a new customer platform in nine months. Enterprise architecture mandates a shared identity and data platform whose delivery date is uncertain. The unit can buy a specialist product now. The CISO prefers the enterprise path. The unit president owns the revenue commitment. Finance wants to avoid duplicate cost.

Task. Design the decision and exception process. Do not simply choose a platform. Show authority, evidence, funding, time, precedent, and exit.

Constraint changes.

  1. The enterprise platform slips by one quarter.
  2. The specialist product has a three-year minimum contract.
  3. Another unit requests the same exception.

Evidence to score. Federal judgment, capital, risk, local accountability, precedent, and escalation.

Record Each Work Sample on One Debrief Form

CriterionCandidate evidenceInterviewer observationChanged-constraint responseUnknown or follow-up
Framing
Questions and evidence
Business and technical tradeoffs
Decision rights
Candor and uncertainty
Communication
Learning and update

Submit the form before discussion. Do not include a personality judgment.