Quick Snapshot — Who Are We Talking About?

• What's your role and which team are you representing in this engagement? Options: Director of Platform Engineering, VP Infrastructure, Platform Engineer / Manager, Security/Compliance Lead, Developer Team Lead, SRE/Operations, Other
• How large is your platform team (headcount)? Options: 1-5, 6-10, 11-20, 21-50, 50+
• Roughly how many developer teams or squads does your platform team support? Options: 1-5, 6-20, 21-50, 51-100, 100+
• What internal use case do you want to pilot first? Options: Environment provisioning, Service onboarding, Secrets rotation, Kubernetes namespace setup, CI/CD pipeline provisioning, Other
• How many open infrastructure tickets are in your current queue right now (estimate)? Options: <50, 50-100, 101-200, 201-500, >500
• What is the single most urgent outcome you want from a pilot (one sentence)?

Who Really Decides — Not Just Who Signs the Contract

• If this project succeeds, who will benefit the most — and who has the most power to stop it?
• Which titles or roles must be involved in the decision to pilot and expand? Options: Director/VP Platform, Security/Chief Information Security Officer, Dev team lead, SRE/Operations lead, Cloud/Infrastructure lead, Procurement/Legal, Other
• Who are the primary influencers (not just approvers) and what are they most concerned about?
• Which stakeholder groups must sign off on security guardrails before any developer self-service is enabled? Options: Security/Compliance, Cloud Ops, Platform Engineering, Legal/Privacy, Central IT/Governance, Other
• Who will own the ongoing success metrics after the pilot (names/titles if possible)?

Where the Friction Actually Lives

• Tell us the one recurring incident or story that proves your current provisioning process is broken.
• How often do developers bypass the platform team and provision resources themselves? Options: Never, Rarely, Occasionally, Monthly, Weekly, Daily
• Which manual steps or handoffs create the largest time sink for platform engineers? Options: Manual cloud console changes, Custom Terraform edits, Ticket triage and follow-up, Manual approvals, Secrets/config propagation, Other
• What's a typical end-to-end provisioning lead time today for your standard environment? Options: <1 hour, 1-4 hours, 1 business day, 2-3 business days, >3 business days
• Have there been security incidents or near-misses caused by ad-hoc provisioning in the last 12 months? Describe briefly.

What Would ‘Good’ Feel Like for Each Team?

• If the platform team stopped being the bottleneck overnight, what would your developers say first?
• Which three metrics would you expect to change most noticeably after a successful pilot? Options: Open ticket count, Mean provisioning lead time, Developer satisfaction (NPS), Security incidents detected, Number of self-service provisions, Time platform engineers spend on tickets
• For platform, security, and developers separately, what numeric targets would feel like a clear win?
• How critical is it that security policies are enforced automatically by the solution rather than via manual checks? Options: Critical — must be automatic, Important — prefer automatic, Accept manual checks initially, Not important
• What developer experience must the portal deliver to achieve adoption (speed, templates, self-service, documentation, support)? Options: Fast provisioning, Pre-approved templates, Clear docs + examples, Minimal required inputs, Support/rollback path, Other

The Trade-offs You're Quietly Accepting

• What compromises have you allowed in operational practice to keep things moving that you'd hate to admit at a leadership review?
• Are you tolerating longer lead times to preserve control or customization? Options: Yes — we prioritize control/customization, No — we prioritize speed, Mixed approach, Undecided
• Which existing tools, workflows, or vendor relationships are off-limits for a pilot? Options: Jira, GitHub/GitLab, Terraform, Vault/Secrets manager, Kubernetes distro, Cloud provider tooling, Other
• What minimum level of customization will developer teams require from a golden path template? Options: None — one-size fits all, Minor parameters, Significant customization per team, Depends on team
• Which likely source of scope creep should we explicitly guard against?

Hard Dates, Non-negotiables, and Timeline Reality

• If leadership gave you an immovable deadline to show measurable improvement, what would break first?
• Is there a fixed date or compliance milestone driving this timeline? Options: Yes — regulatory/compliance, Yes — product launch, Yes — exec milestone/board review, No fixed date, Other
• What start date and pilot duration would you ideally target?
• How many engineering hours per week can your platform team commit to encoding templates, integrations, and testing during the pilot? Options: <5 hours/week, 5-10 hours/week, 10-20 hours/week, >20 hours/week
• Do security and platform workstreams need to run in parallel, or can one gate the other? Options: Parallel required, Prefer parallel, Sequential — security gates platform, Sequential — platform gates security, Unsure

How You'll Know We're Succeeding (or Not)

• If the pilot fails, what metric will your executives ask about first? Options: Ticket volume, Provisioning lead time, Security incidents, Developer adoption, Cost, Other
• Which primary success metrics must be reported at pilot close (select up to three)? Options: Ticket reduction (%), Provisioning lead time, Number of self-service completions, Security violations prevented, Developer satisfaction (survey), Time spent by platform team on tickets
• What are the current baseline values we should measure from (ticket count, avg lead time, etc.)? Please list values.
• How frequently do you want progress updates during the pilot? Options: Daily, Weekly, Bi-weekly, Monthly, Milestone-based only
• If targets aren't met at pilot close, which remediation options would be acceptable? Options: Extend pilot with more resources, Bring in vendor implementation support, Narrow scope and retry, Rollback changes, Other

Hidden Risks, Contractors, and Historical Band-Aids

• Which fragile scripts, one-off dashboards, or tribal processes are keeping your day-to-day running and would complicate a formal pilot?
• Are contractors, consultants, or third-party vendors currently performing provisioning tasks? Options: Yes — contractors, Yes — managed service, No external help, Unknown
• How much single-person tribal knowledge is required to complete standard provisioning today? Options: None — documented, Some — a couple engineers, Significant — one or two people, Widespread but inconsistent
• What previous attempts have you made to solve this and why did they stall or fail?
• Which partial compliance controls exist today that will need completion during the pilot? Options: IAM policies, Encryption at rest, Network segmentation, Audit logging, VPC/service boundaries, Other

Who Needs to Be in the Room

• If you could invite only five people to the kickoff who would guarantee progress—and who will actively block it if absent?
• Which roles must be present at the kickoff and who should be optional observers? Options: Platform engineering (must), Security/Compliance (must), Developer representative (must), Cloud ops (optional), SRE (optional), Procurement/Legal (as needed), Other
• Who currently manages cloud and Kubernetes credentials and will grant access for encoding/templates/testing? Options: Platform engineering, Central cloud team, Cloud provider admin, SRE, Dev team, Other
• Which communication channels and cadence do you prefer for cross-team updates during the pilot? Options: Slack, Email, Confluence/Jira, Weekly sync meetings, Ad-hoc calls, Other

Final Commitment — What's the Smallest Useful Pilot?

• What is the minimally scoped pilot (target use case, acceptance test, and boundaries) that would compel you to scale if successful?
• Which integrations and modules must be included in the minimal pilot to make it meaningful? Options: Git repo integration, CI/CD pipeline hookup, Terraform modules, Secrets manager integration, Developer portal UI, RBAC/Identity provider, Other
• What internal budget or headcount will be allocated to the pilot (if known)? Options: No budget allocated, < $10k or internal time only, $10k-$50k, $50k-$200k, > $200k, Unclear
• Who will be the day-to-day owner (single point of contact) for decisions and blockers during the pilot? Please provide name/title.
• Are you ready to schedule a 90-minute stakeholder alignment kickoff to finalize roles, timeline, and acceptance criteria? Options: Yes — schedule now, Need internal alignment first, Not ready yet

A Fast Map of Where You Are Now

• Which statement feels most true about your current provisioning situation? Options: We’re drowning in tickets and can’t keep up, We can handle volume but it’s costly and slow, We have pockets of pain but it’s manageable, We rarely get provisioning requests
• How many open infrastructure/provisioning tickets are in your queue right now? (give a number or best estimate)
• What is the typical end-to-end lead time for a standard environment request today? Options: <1 hour, 1–8 hours, 1–3 days, 3–7 days, >7 days
• How many engineers are on your platform team who regularly touch provisioning tickets? Options: 1–3, 4–7, 8–12, 13–20, 20+
• Roughly how many development teams rely on the platform for new environments or service onboarding? Options: 1–5, 6–20, 21–50, 51–100, 100+
• Which single provisioning use case would you most likely choose for an initial pilot? Options: Developer environment provisioning, Service onboarding (namespaces + CI), Secrets management rotation, Cloud account/project creation, Other

If We Stood Aside, What Would Burst Into Flames?

• Tell us about a recent time when manual provisioning or a developer bypass caused a security, cost, or reliability incident—what happened and who noticed it first?
• How frequently do developers bypass platform processes and self-provision cloud resources or namespaces? Options: Never, Rarely, Occasionally, Often, Almost always
• Which safeguards currently require manual checks or approvals before resources are allowed (select all that apply)? Options: IAM/roles changes, Network/NACL or firewall changes, Billing/cost center assignment, Security scanning/compliance sign-off, Secrets access, Other
• What scripts, internal portals, or ticket automation do you have today that people use to provision resources? Please list names, owners, and the single biggest limitation for each.
• How do you currently discover policy violations caused by ad-hoc provisioning (automated alerts, periodic audits, user reports, not at all)? Options: Automated monitoring/alerts, Periodic manual audit, Reported by developers/ops, We don’t detect these reliably

The Quiet Toil: Who’s Doing the Heavy Lifting?

• How many hours per week does the average platform engineer spend on tickets, one-offs, or emergency provisioning? Options: <5 hours, 5–10 hours, 11–20 hours, 21–40 hours, >40 hours
• For a representative ticket, list each manual step performed (e.g., run terraform script, create IAM role, update DNS) and the approximate time each step takes.
• What percentage of your provisioning tickets are repeatable (same steps) versus bespoke requests? Options: Mostly repeatable (>75%), About half/half, Mostly bespoke (>75%), Don’t know
• Which ticket types consume the most platform cycles? Select the top three. Options: New developer environments, Service onboarding (namespace + CI), Access/IAM requests, Secrets rotation, Infrastructure changes (network, storage), Billing/account setup, Other
• How does this reactive work impact your ability to deliver roadmap items or improve the platform (concrete examples or recent trade-offs)?

Why Past Automation Efforts Didn’t Stick

• Which automation or portal projects have you built or tried (internal PaaS, Backstage, Terraform modules, scripts) and why did they not reduce tickets as expected?
• Which integration points were the hardest to maintain or caused the most breakage (select all that apply)? Options: Cloud account management, IAM/roles integration, Kubernetes onboarding, CI/CD hooks, Ticketing/Jira automation, Cost reporting/billing tags, Secrets managers
• Who is currently responsible for creating and approving golden-path templates (platform team, security, each dev team, external consultants)? Options: Platform team, Security/compliance team, Individual dev teams, Cross-functional committee, No clear owner
• On average, how long does it take your team to encode a new organizational standard into a reusable template today? Options: <1 day, 1–3 days, 1–2 weeks, 2–6 weeks, Longer than 6 weeks
• What governance, policy, or cultural barriers have repeatedly stalled attempts to automate provisioning?

What Metrics Will Make You Sleep Better?

• If ticket volume dropped by 50% and provisioning lead time fell under 1 hour, what would that change for your stakeholders (safety, budget, headcount, developer velocity)?
• Which of the following metrics do you currently track or care about for provisioning success? (select all that apply) Options: Open ticket count, Average provisioning lead time, MTTR for outages, Number of security violations, Developer satisfaction/CSAT, Cost per environment, Template adoption rate
• How do you currently measure provisioning lead time—what timestamps or systems are used (request creation, approval, resources available)? Options: Request created → resources available, Approval time only, Work logs / manual measurement, We don’t have a clear measurement
• What acceptance criteria would make a pilot successful for you? Please include numeric targets, measurement method, and who must sign off.
• Which tradeoffs are acceptable if they help you reach faster provisioning (select all that apply)? Options: Stricter templates with fewer options, Additional automated guardrails in place of manual review, Periodic audit instead of pre-approval, No tradeoffs—must match current controls

Where Do Requests Actually Stall?

• In your current workflow, which single step creates the most frequent delays—approval, manual scripting, environment validation, secrets/config, or infra readiness? Options: Approval/manager sign-off, Manual script execution, Validation/testing failures, Secrets or credential provisioning, Cloud infra/account readiness
• Please map approximate lead time per step for a typical provisioning flow (e.g., approvals: X hrs, scripting: Y hrs, validation: Z hrs). Paste a short list or table.
• How often do requests come back for rework due to missing information or failed tests? Options: Never, Rarely, Occasionally, Often, Almost always
• Which request fields or data points are most frequently incomplete or incorrect (select top three)? Options: Account/billing info, Environment type/purpose, Network/subnet details, IAM roles required, CI/CD pipeline details, Owner/contact information
• Which team or role is the most common escalation point when provisioning stalls (platform, security, network, dev team leads, SRE)? Options: Platform team, Security/compliance, Network/infra, Dev team lead, SRE/operations

A Minimal Pilot: Can We Agree on One Small Win?

• If you had to pick a single low-risk pilot that could demonstrate measurable improvement in 4–8 weeks, what is it and why is it the right bet?
• Which development team (name or profile) would be the ideal pilot participant—who is motivated, has repeatable needs, and low risk for production impact?
• What access and permissions will we need to run a pilot (select all that apply)? Options: Cloud account/project access, Kubernetes cluster admin or namespace access, CI/CD pipeline credentials, Secrets manager read/write, Ticketing/Jira integration, Billing tagging permissions, Other
• Who are the stakeholders that must be engaged and available during the pilot (roles or names for sign-off and troubleshooting)?
• What would prevent you from greenlighting a pilot in the next 30 days (select all that apply)? Options: Budget not approved, Security sign-off pending, Key staff unavailable, Competing priorities, Technical debt blocking work, None—we’re ready

Tell Us About Your Team's Daily Reality

• How many engineers are on your platform team today? Options: 1-5, 6-10, 11-20, 21-50, 51+
• Which of these responsibilities does your team currently own? Options: Environment provisioning, Secrets management, Kubernetes cluster ops, Service onboarding, Developer portal/UX, Cost management, Security & compliance
• Which internal groups rely on your team most frequently? Options: Product engineering, Data teams, Security/InfoSec, SRE/Operations, QA/Platform testing, Other
• What is the single most important outcome your Director of Platform wants this year?
• How do you currently measure platform team effectiveness? Options: Open ticket count, Mean time to provision, Developer satisfaction (NPS), Policy compliance rate, Cost per environment, Other

Are We Letting Tickets Run the Platform?

• When you scan the backlog, does the platform feel driven by reactive tickets instead of proactive design? Options: Yes — tickets dominate our roadmap, Somewhat — a mix of reactive and planned, No — we mostly deliver proactively, Not sure
• How many open infrastructure/provisioning tickets do you have right now (approx)? Options: <50, 50-199, 200-499, 500-999, 1000+
• What's the typical lead time an engineer waits for a new environment today? Options: <1 hour, 1-4 hours, Same day, 1-3 days, 3+ days
• Which request categories occupy most of the queue right now? Options: New environments, Secrets/key rotation, Kubernetes namespaces, Service onboarding, Networking/VPC changes, Other
• Tell us a recent story where a ticket backlog directly impacted delivery or morale.

Where Does Time Vanish?

• Which single manual step consistently consumes the most platform engineer time? Options: Request triage & context gathering, Environment provisioning steps, Manual IAM/permissions changes, Custom scripting per team, Security exceptions
• On average, how many hours does a manual provisioning flow take from request to usable environment? Options: <1 hour, 1-4 hours, 4-8 hours, 8-24 hours, 24+ hours
• Which internal scripts, portals, or runbooks are currently part of the provisioning path? Options: Terraform modules, Helm/Kustomize charts, Custom web portal, Backstage plugins, Ad-hoc scripts (bash/python), No formal tooling
• How often do developers bypass the platform and provision outside your controls because it's faster? Options: Regularly, Sometimes, Rarely, Never, Unsure
• What steps have you tried to automate or simplify already, and what stopped them from fully succeeding?

Who Holds the Keys — and How Tight?

• Are your access controls and security guardrails automated, or do they require manual review and exceptions? Options: Mostly manual with exceptions, Mixed automated and manual, Mostly automated/policy-as-code, Don't know
• Which policy-as-code or enforcement tools are in use (if any)? Options: Open Policy Agent / Rego, HashiCorp Sentinel, AWS Config / Guardrails, Custom checks, None / ad-hoc
• Which compliance or policy requirements must templates enforce from day one? Options: Least privilege/IAM, Network segmentation, Encryption at rest/in transit, Audit logging, Data residency, Other
• Have you experienced a security incident or near-miss due to ad-hoc provisioning in the last 12 months? Options: Yes — incident, Yes — near miss, No, Prefer not to say
• Describe your current model for Kubernetes/cloud access (e.g., service accounts, RBAC patterns, SSO integration).

If Success Was a Metric, What Would It Feel Like?

• If we reduced tickets by half and brought provisioning under an hour, what's the first real-world change you'd notice?
• Which KPIs will your leadership use to declare the pilot a success? Options: Open ticket count, Average provisioning lead time, Developer satisfaction (survey), Policy compliance rate, Onboarded teams count, Cost per environment
• What minimum improvement threshold would make you comfortable recommending expansion? (pick best fit) Options: ≥50% ticket reduction & <1 hour provisioning, 30–49% reduction & <4 hours, 10–29% reduction & <24 hours, Other
• Who must sign off on pilot results for you to move to a broader rollout? Options: Director of Platform, VP/Head of Infrastructure, Security lead/CISO, Engineering manager for pilot team, Finance/Cost owner, Other
• How will you collect evidence for these KPIs (tools, dashboards, ticketing filters)?

What Would Break If We Changed This?

• What is the single worst outcome that would cause you to halt a self-service rollout? Options: Security compliance failures, Developer backlash / disruption, Operational instability, Unexpected cost growth, Loss of control/traceability
• Which teams or stakeholders are most likely to resist centralizing templates and why?
• Do you have any irrevocable constraints (audits, vendor contracts, regulatory controls) that would prevent certain automations? Options: Yes — major constraints, Some constraints but manageable, No hard constraints, Unsure
• How much internal engineering capacity can you realistically commit to encode standards into templates during the pilot? Options: None — we need help, 0.5 FTE, 1 FTE, 2 FTE, 3+ FTE
• If something unexpectedly fails in production during the pilot, what emergency process must we follow?

Let’s Design a Pilot They Can't Say No To

• If you could choose only one focused use case to prove value quickly, what would it be? Options: Dev environment provisioning, Service onboarding (new microservice), Kubernetes namespace creation, Secrets & credential rotation, Other
• Which specific development team or product area would participate in the pilot?
• What integrations must the pilot include to be meaningful (e.g., Jira, GitHub Actions, CI system, identity provider)? Options: Jira, GitHub/GitLab, CI/CD (Circle/GHA/Jenkins), Identity provider (Okta/AzureAD), Cloud provider APIs, Other
• What non-functional constraints must the pilot obey (cost cap, regions, data residency, maintenance windows)?
• Who will be the day-to-day owner inside your organization for the pilot? Options: Platform engineer(s), Engineering manager of pilot team, Security engineer, Program manager, Other

Signals We'll Use to Celebrate — and To Course-Correct

• Which early warning signal should cause us to pause and remediate the pilot immediately? Options: Policy violations detected, No measurable ticket reduction, Provisioning times not improving, Production instability, High user complaints
• What is the minimum ticket-reduction percentage that would make you say the pilot is promising? Options: ≥50%, 30–49%, 10–29%, <10%, Undecided
• How would you prefer guardrail validation to run: automated policy tests, scheduled manual audits, or a hybrid? Options: Automated policy tests, Scheduled manual audits, Hybrid automated + manual, Undecided
• How frequently would you like a status report during the pilot (and what format works best)? Options: Daily (brief), Twice-weekly, Weekly, Bi-weekly, Monthly
• Who should receive escalation alerts if a critical guardrail fails or a blocker appears? Options: Platform lead, Security lead, Pilot engineering manager, SRE on-call, Program manager, Other

Practical Access & Constraints (Don't Make Us Guess)

• If we can’t get cloud or Kubernetes access within the first week, what approval or dependency is likely blocking it? Options: Security approval, Change control board, Cloud ops SLA, Credential provisioning, Budget/chargeback, Other
• Which cloud providers and runtimes must the pilot support? Options: AWS, Azure, Google Cloud, On-premises Kubernetes, Managed Kubernetes (EKS/GKE/AKS), Other
• Do you have representative test data and synthetic workloads available for the pilot? Options: Yes — ready, Partially — needs preparation, No — we need help creating them
• Are there network, VPC, or firewall restrictions that will affect provisioning flows? Options: Yes — significant restrictions, Some restrictions, No meaningful restrictions, Unsure
• Is there a preferred sandbox or staging account we should use for initial work? Provide details or contact if available.

Commitments & Next Steps — What Can We Agree On Today?

• What would make you comfortable saying 'start the pilot now' at the end of this discovery?
• What is your target timeline from kickoff to first measurable result? Options: 2 weeks, 1 month, 2 months, 3+ months, Undecided
• Who are the essential stakeholders we should include in kickoff and weekly reviews? Options: Director/Head of Platform, Security lead/CISO, Pilot team engineering manager, Cloud/Kubernetes ops, Finance/Cost owner, Other
• What internal blockers should we escalate now so the pilot doesn't stall?
• What communication cadence and channels do you prefer during the pilot (standups, Slack channel, weekly demo, executive summary)? Options: Daily standup + Slack, Twice-weekly touchpoint, Weekly demo + summary, Bi-weekly executive update, Ad-hoc as issues arise

Quick Check — Where We Begin

• In one sentence, why are you exploring a platform self-service solution right now?
• How many open infrastructure or provisioning requests are typically in your queue? Options: <50, 50–99, 100–199, 200–499, 500+
• What is the average end-to-end provisioning lead time developers experience today? Options: <1 hour, 1–8 hours, 1–3 days, 3–7 days, >1 week
• Which single use case do you want to solve first to prove value? Options: Environment provisioning (dev/test), Service onboarding, Kubernetes namespace provisioning, Secrets & credentials rotation, Other
• Who on your team is the primary champion for this initiative? Options: Director / VP Platform, Head of Infrastructure / SRE, Engineering Manager, CTO, Other

Are You Still Hand-Provisioning?

• How many times this week does your platform team manually run scripts, copy credentials, or touch cloud consoles to fulfill requests? Options: 0, 1–5, 6–15, 16–50, 50+
• Which ticket types repeatedly require manual intervention? Options: New environment creation, Service onboarding, Secrets provisioning, Network/security changes, Access requests, Other
• Can you describe a recent ticket that took longer than expected and what manual steps were involved?
• Do you currently have any internal portals, scripts, or Terraform modules that teams use to self-serve? If so, list the main ones and who owns them.
• Roughly how many distinct home-grown modules, scripts, or playbooks are floating around your org right now? Options: None, 1–5, 6–15, 16–30, 30+

What's Really Breaking Your Day?

• Which recurring problem causes the most operational pain for your platform team? Options: Ticket backlog growth, Long provisioning lead times, Security workarounds by developers, Inconsistent environments, Escalation churn, Other
• How many engineering hours per week does your team spend triaging or fulfilling these requests (estimate)? Options: <10 hrs, 10–25 hrs, 26–50 hrs, 51–100 hrs, 100+ hrs
• Tell us about the last security or compliance gap that happened because of ad-hoc provisioning or bypassing the platform team.
• When these issues hit, how does it affect developer velocity and product deadlines (examples welcome)?
• How worried are you about developer teams creating shadow infrastructure if waits continue? Options: Very worried, Somewhat worried, Occasionally concerned, Not worried

Who's On The Hook When Things Go Sideways?

• If a provisioning error causes an outage or security exposure, who is held accountable? Options: Platform Director/VP, SRE Lead, Service Owner / Team Lead, CTO, Depends on incident
• Which stakeholders must sign off on a pilot (platform, security, developers, compliance, finance)? Select all that apply. Options: Platform Engineering, Security / InfoSec, Developer Team Leads, Compliance / Legal, Finance / Procurement, Product / Business
• What does your current escalation path look like when a provisioning request is blocked or fails?
• Do you have a budget and headcount allocated for a pilot/POC, or would approval be required? Options: Budget & headcount already allocated, Budget allocated, headcount TBD, Need both approvals, Unsure
• What's the political or cultural friction we should know about when working with the teams involved?

If This Worked Perfectly — What Changes?

• Imagine developers rarely file this ticket—what does your team do differently with that time?
• Which measurable outcomes would convince you the pilot succeeded? Select all that matter. Options: ≥50% ticket reduction, Provisioning <1 hour, No manual security reviews, Developer satisfaction increase, Reduced cost per environment, Fewer escalations
• Which single metric is the non-negotiable gate for expanding beyond the pilot? Options: Ticket reduction %, Provisioning lead time, Security/compliance passes, Developer adoption rate, ROI / cost reduction
• What target thresholds would you set for ticket reduction and lead time to feel confident scaling?
• How soon after a successful pilot do you want to start onboarding a second use case? Options: Immediately (0–1 month), Short runway (1–3 months), Medium (3–6 months), Later (6+ months)

What's Stopping You From Getting There?

• What is the single toughest technical assumption our solution would have to overturn in your environment?
• Which platform constraints could block encoding your standards into templates? Options: Proprietary tooling, Legacy networking restrictions, Limited cloud/K8s permissions, Policy engine incompatibility, No constraints
• What compliance or security controls must be automated vs. reviewed manually (e.g., IAM policies, resource tagging, network controls)?
• Have you tried a DIY portal or another vendor before? If so, what stopped it from delivering the expected results?
• On a scale from 1–5, how much resistance do you expect from developer teams to using a centralized self-service portal? Options: 1 — No resistance, 2 — Small, 3 — Moderate, 4 — Significant, 5 — Very high

Pilot — Small Win, Big Proof

• Which single development team would create the clearest, fastest proof if we focused the pilot there? Options: Frontend/product team, Core services/backend team, Platform-internal team, Data team, Other
• Name the exact target workflow for the pilot (e.g., create dev environment with DB, secrets, and network policy) and any non-negotiable steps.
• Which integrations are required for the pilot to be meaningful? (Select all that apply) Options: Jira / ticketing, Terraform Cloud / State, Kubernetes API, Cloud provider console (AWS/Azure/GCP), Secrets manager, CI/CD pipeline
• What access can you commit to providing within the pilot window (cloud admin, kubecluster admin, test data, service accounts)? Options: Cloud admin, Kubernetes admin, Limited IAM roles, Only read access, Will need to request approvals
• Who will be the day-to-day owner and ultimate approver for the pilot on your side? Please provide names and roles.

Can We Trust The Numbers?

• How confident are you in the ticket counts and lead-time measurements that will form the pilot baseline? Options: High — auditable, Moderate — some manual checks, Low — conversational estimates, Unsure
• Where will we pull baseline and pilot metrics from? (Select all relevant sources) Options: Jira (project/filter), ServiceNow, Internal spreadsheets, CI/CD logs, Cloud provisioning logs, Other
• Do you have automated logs or telemetry that show provisioning durations today, or will we need to instrument that? Options: Yes — telemetry exists, Partial — some logs, No — needs instrumentation, Unsure
• What time window should we use to calculate the baseline (e.g., last 30/60/90 days)? Options: 30 days, 60 days, 90 days, Custom — please specify
• If data gaps exist, how should we handle them for the pilot (estimate, conservative assumptions, extend baseline collection)? Options: Estimate with conservative buffer, Extend baseline collection, Instrument and pause pilot start, Other

Risks, Remediation, and Plan B

• If the pilot misses the success thresholds (e.g., <50% ticket reduction or provisioning >1h), how willing are you to allocate time for rapid remediation? Options: Very willing — iterate quickly, Somewhat willing — limited effort, Prefer to stop and reassess, Unsure
• What remediation window would be acceptable before deciding to stop (days/weeks)? Options: 3–5 business days, 1–2 weeks, 3–4 weeks, Longer / open
• Which roles must approve remediation changes (security, platform lead, product owner)? Options: Security lead, Platform engineering lead, Service owner / team lead, Compliance, Other
• What would be a deal-breaker that would make you walk away from the approach entirely?
• If the pilot succeeds, what is your rough plan for scaling — internal teams first, or horizontal across org? Options: Scale to similar teams first, Roll out horizontally by region, Prioritize critical services, Undecided

Commitment & Next Steps — What We Need From You

• What would make you comfortable committing to a pilot kickoff within the next 30 days?
• What is your preferred pilot kickoff window? Options: ASAP (this week), Next 1–2 weeks, Next 3–4 weeks, 1–2 months
• Which documents or artifacts can you share before kickoff to speed encoding (network diagrams, policy matrix, Terraform modules, runbooks)? Select all that apply. Options: Network diagrams, Security policy matrix, Existing Terraform modules, Runbooks / runbooks, No artifacts available
• What cadence of checkpoints would you prefer during the pilot? Options: Daily standup, Bi-weekly sync, Weekly review, Ad-hoc as needed
• Please list the names, roles, and preferred contacts of the core team who will participate in the pilot.