Start Here — What Brought You to This Conversation?

• What immediate trigger led you to evaluate a billing/platform change right now? Options: Vendor end-of-life (EOL), Failed product launch, Regulatory mandate, Performance/stability issues, Strategic modernization, Other
• What is your target timeline for a decision and an initial rollout? Options: <3 months, 3–6 months, 6–12 months, 12–24 months, No firm timeline
• Who is sponsoring this initiative, and which functions must be involved to get to a decision? Options: CIO/CTO, VP of IT/BSS, Head of Finance, Head of Commercial/Product, Head of Network/Operations, Other
• In one short sentence, what would a successful outcome look like for your team?
• What are the three biggest risks or fears that make you hesitant about migration?

Can Your Current Stack Launch the Next Big Product Without a Rewrite?

• How confident are you that your legacy BSS can support your next 5G/converged bundle without months of custom dev? Options: Very confident, Somewhat confident, Not confident, We haven't assessed this
• Give one concrete example of a product or bundle you tried to launch and where the billing or catalog limited you—what happened?
• How long did it take (or how long would you estimate) to implement that product change in your current stack? Options: Weeks, 1–3 months, 3–6 months, 6–12 months, Longer than 12 months
• Who in your org currently owns product configuration vs. who owns custom development for the billing engine? Options: Product team (config only), Dev/Engineering (custom code), Shared responsibility, Not clearly defined
• How does the delay or inability to launch new offers show up in commercial KPIs (e.g., churn, ARPU, missed revenue)? Give examples.

What Billing Scenario Would Keep You Up at Night?

• Which single billing scenario do you consider most likely to cause revenue leakage or customer harm if it fails? Options: Roaming settlements, Converged bundling across fixed/mobile, Partner/wholesale revenue share, Promotions and rebates, Interconnect/clearing house flows, Real-time rating/charging
• How often does that scenario occur, and what magnitude of revenue or customers does it touch? Options: Daily (high volume), Daily (low volume), Weekly, Monthly, Occasional/special cases
• Have you seen a concrete incident in the past 24 months where that scenario caused a material issue? Describe impact and remediation steps.
• What is your finance team's tolerance for billing error during cutover (e.g., allowed % variance in billed revenue for first billing cycle)? Options: <0.1%, 0.1–0.5%, 0.5–1%, 1–3%, >3%/Unacceptable
• Which stakeholders must be satisfied that revenue integrity is preserved before decommissioning the legacy flows? Options: Finance, Commercial/Revenue Ops, Billing Ops, Legal/Compliance, Executive Sponsor

The Truth About Your Data, History, and Mediation

• If we attempted a trial migration tomorrow, what volumes and types of historical data would we need to move/verify (e.g., subscriber records, CDRs, invoices)? Options: Subscriber master data, CDR/usage history, Invoices/statement history, Custom rating rules, Partner settlements, Other
• Estimate the size and complexity: how many subscribers, years of history, and distinct rating rules/customizations exist? Options: <1M subs / <1 year / <50 rules, 1–5M / 1–3 years / 50–200 rules, 5–20M / 3–7 years / 200–1000 rules, >20M / >7 years / >1000 rules
• Which mediation and legacy systems hold your canonical usage and billing artifacts today? Options: In-house mediation, Vendor mediation (name it), Legacy BSS (name), Data lake/warehouse, Multiple siloed systems
• What are the top three data quality or mapping issues you expect during migration (e.g., missing fields, inconsistent product codes, timezones)?
• Who owns the canonical data and who will be our go-to technical contact for resolving data exceptions?

Who Holds the Kill Switch — Decision, Governance, and Timelines

• When a cutover shows discrepancies, who has the final authority to pause or roll back—and what criteria do they use? Options: CIO/CTO, Head of Finance, Program Steering Committee, Joint decision (named roles), Other
• What governance cadence would give you confidence during migration (e.g., daily stand-ups, weekly steering, executive readouts)? Options: Daily, 3x/week, Weekly, Bi-weekly, Monthly
• How quickly do you need to reconcile billing and revenue numbers post-cutover to meet financial close or reporting needs? Options: Within 24 hours, 48–72 hours, One billing cycle, Up to 30 days, Longer than 30 days
• What escalation path or SLAs do you require for critical issues discovered during cutover?
• Are there external parties (regulators, large wholesale partners) who must be notified or sign off during the cutover? If so, who and what are their requirements?

What Exact Signals Will Let You Call This a Win?

• Which measurable acceptance criteria must be met before the migration is labeled successful? Options: Billing accuracy %, Revenue reconciliation tolerance, Number of critical defects, End-user complaint rate, Performance SLAs
• What minimum billing accuracy percentage would you require for the first three billing cycles post-cutover? Options: 99.99%+, 99.9%–99.99%, 99%–99.9%, 95%–99%, <95%
• How will you verify acceptance—do you want automated reconciliation reports, manual spot checks, or third-party validation? Options: Automated reconciliation, Manual spot checks, Third-party audit, Hybrid approach
• What rollback conditions would force you to restore the legacy system (examples: >X% revenue variance, inability to invoice top N accounts)?
• Who signs the final acceptance and what documentation or evidence will they require?

If We Could Build the Migration Path Together, What Would It Look Like?

• Which migration approach do you prefer to reduce risk: phased by product, phased by customer segment, parallel run then cutover, or big-bang? Options: Phased by product, Phased by customer segment, Parallel runs then cutover, Big-bang cutover, Hybrid
• What internal capabilities must change to support that approach (e.g., new runbooks, automation, training, dedicated reconciliation team)?
• How many parallel environments and test fixtures can you provide for staging, and what level of access will our engineers have? Options: Full access to staging and test data, Limited access with anonymized data, Only API access, No dedicated environments available
• What would be a realistic pilot scope (number of subscribers, product types, or geographies) to validate migration before scaling? Options: Small sample (<1K subs), Medium (1K–50K), Large (50K–1M), Full region/offer
• What internal metrics should we track during the pilot to decide to scale (list top 3)?

Ready for the First Step — What Would Make Us Start?

• What evidence do you need from a short proof-of-concept to be comfortable advancing (e.g., end-to-end invoice parity, zero critical defects, performance benchmark)? Options: Invoice parity, No critical defects, Performance benchmarks, Successful partner settlements, Customer-facing billing proof
• Who needs to be involved in the POC and who will be the day-to-day decision-maker during that work?
• What budget or commercial constraints should we know about before proposing a pilot scope? Options: Pre-approved pilot budget, Requires procurement approval, Needs exec authorization, No budget yet
• If we can demonstrate your top-risk scenario working end-to-end in a POC, when would you be prepared to schedule the next review? Options: Immediately after POC, Within 2 weeks, 1 month, Depends on exec calendar
• What worries or objections should we address now so the POC and next steps feel achievable to your stakeholders?

Tell Us About Your Billing Ecosystem (quick orientation)

• Which billing, mediation, and rating systems are currently in production for your core services? Options: Oracle BRM, Amdocs, Netcracker, Ericsson Billing, In-house/custom, Other
• How many active subscribers are on the system(s) you just listed? Options: <100k, 100k–1M, 1M–5M, 5M–20M, >20M, Unsure
• Which environments do we need to be aware of (prod, pre-prod, legacy sandbox, billing archive), and who controls access? Options: Production, Pre-production/Test, Legacy sandbox, Archived environment, Third-party managed, Other
• Roughly what portion of your monthly revenue flows through these systems today? Options: <25%, 25–50%, 50–75%, 75–99%, 100%, Unsure
• Who are the day-to-day owners across IT, finance, and commercial we should engage during discovery (names + roles)?

What Legacy Secrets Are Costing You (reframe the 'we just live with it' story)

• If we stop saying 'it's always been this way' — what single legacy behavior do you believe most erodes margin, time, or customer trust?
• How often do billing errors, disputes, or credit notes occur—daily, weekly, monthly—and which product lines are most affected? Options: Daily, Weekly, Monthly, Quarterly, Rarely, Unsure
• When billing errors happen, what is the typical downstream impact (revenue leakage, customer churn, regulatory fines, operational cost)? Options: Revenue leakage, Increased churn, Operational overhead, Regulatory exposure, Brand/customer trust damage, Other
• Tell us about a recent billing incident that forced manual intervention—what happened, who responded, and how long to resolve?
• Which legacy customizations or undocumented hacks do teams rely on to keep launches or promotions running?

Where Does Subscriber History Live — and How Much Can You Trust It?

• Imagine a regulator or finance audit asking for 24 months of charge history—how confident are you that the data is complete and auditable? Options: Very confident, Somewhat confident, Not confident, Unsure
• Where is subscriber and charging history stored today (billing DB, data warehouse, tape/archive, vendor black box)? Options: Billing database, Data warehouse/EDW, Flat files/tape/archive, Vendor black box, Third-party backup, Other
• Are there known gaps, format mismatches, or timezone/timestamp inconsistencies in your historical records? Options: No known gaps, Some gaps documented, Significant gaps, Format mismatches, Timezone/timestamp issues, Unsure
• How do you currently reconcile historical revenue or usage differences between systems—automated jobs, manual spreadsheets, or ad-hoc scripts? Options: Automated reconciliation, Manual spreadsheets, Ad-hoc scripts, Vendor reports, No reconciliation process, Other
• If we asked for a 1,000-account sample with 12 months of billing events for validation, what obstacles would we hit—from legal, privacy, or technical perspectives?

Rating, Rules, and Exceptions — The Devil in the Details

• Which three rating rules or exceptions, if mis-implemented, would cause the largest revenue or customer-impacting failures?
• How are rating rules currently authored, versioned, and approved—business UI, config files, custom code, or a mix? Options: Business UI, Config files, Custom code/scripts, Database-driven rules, Mixed approach, Unsure
• Do you have rate cards, discount trees, and partner settlements documented in machine-readable form, or are they primarily tribal knowledge? Options: Fully documented/machine-readable, Partially documented, Primarily tribal knowledge, Locked in vendor docs, Unsure
• How often do product managers request ad-hoc rating exceptions (e.g., manual promos, one-off credits), and how are those handled? Options: Daily, Weekly, Monthly, Rarely, Never
• Are there any business rules that depend on external/partner inputs that are high-latency or unreliable? Options: Yes—multiple, Yes—one or two, No, Unsure

Mediation, Integrations, and Real-Time Gaps (where data gets lost or slowed)

• Which integration or mediation touchpoint do you blame most when launches miss their targets?
• Which protocols and message types move billing-relevant events in your stack? Options: Proprietary binary, REST API, SOAP/XML, Diameter, FTP/SFTP files, SMPP, Other
• What is your real-time vs batch split for charging decisions today (percentage or qualitative)? Options: Mostly real-time (>75%), Mixed (25–75%), Mostly batch (>75%), All batch, Unsure
• List the top three external systems we must integrate with for a migration (e.g., CRM, OSS, mediation, partners):
• What typical message volumes/peak TPS and average latency SLAs should we design for during parallel runs and cutover?

Migration Constraints and Risk Hotspots (what could stop the project)

• What single constraint—technical, operational, legal, or political—would stop leadership from approving cutover?
• Do you have regulatory or data residency constraints that narrow where and how subscriber data can be migrated? Options: Yes—strong constraints, Yes—some constraints, No, Unsure
• What is your preferred coexistence strategy during migration: full parallel, phased by product, customer cohort, or cutover by region? Options: Full parallel, Phased by product, Cohort-based, Region-by-region, Other
• How long can you realistically run legacy and new billing stacks in parallel without incurring unacceptable cost or complexity? Options: <1 month, 1–3 months, 3–6 months, 6–12 months, >12 months, Unsure
• What rollback criteria would you require during cutover to stop and revert (billing inaccuracy thresholds, revenue variance, critical customer impact)?

People, Processes, and Hidden Workarounds (who keeps the lights on)

• Who are the 2–4 subject-matter experts we must partner with to understand the undocumented workarounds and why they exist?
• Which teams maintain manual compensating controls (spreadsheets, scripts, manual credits) and how frequently are they used? Options: Billing operations, Finance, Commercial/Products, Customer Care, Partner ops, Other
• How mature are your runbooks, incident playbooks, and cutover decision gates—are they tested and up to date? Options: Fully mature and tested, Partially mature, Minimal/runbooks exist, No runbooks, Unsure
• If the person who knows the 'how to fix X' leaves tomorrow, what would it take to rebuild that knowledge?
• What training or governance will stakeholders insist on before sign-off for migration activities? Options: Formal training sessions, Shadowing runbooks, Certification for owners, Executive sign-off only, Other

If the Migration Could Be Perfect — What Would Nice Look Like?

• If technical constraints vanished, what three customer-facing improvements would you expect immediately after cutover?
• What accuracy and reconciliation targets would make you comfortable decommissioning the legacy stack (error rate, revenue variance, dispute rate)? Options: <0.1% error, <0.5% error, <1% error, <2% error, Other
• How much faster should product launches be after migration—days, weeks, or months? Options: Days, Weeks, Months, No change expected, Unsure
• What visibility and audit trails are non-negotiable for finance and compliance post-cutover? Options: Detailed charge lineage, Immutable audit logs, Automated reconciliation reports, Role-based access logs, Other
• Which KPIs or dashboards would you expect to see within 30 days of cutover to feel confident the migration succeeded?

Small Tests, Big Answers — What Sample Could Prove This Works?

• What is the smallest meaningful subscriber cohort or data slice we can extract now that would validate migration feasibility? Options: Top 1,000 revenue accounts, Representative 10k subscribers, Single product family, Partner-settled accounts, Geographic cohort, Other
• Which datasets should we prioritise for an initial extract: subscriptions, CDR/usage, invoices, payment history, or interconnect settlements? Options: Subscriptions, Usage/CDRs, Invoices, Payments, Interconnect/settlements, All of the above
• What legal, privacy, or anonymization steps would we need to run that sample through your security and legal teams?
• Do you have a sandbox or non-production copy of historical data that we can use for mapping and validation, or will we need to pull production extracts? Options: Sandbox exists, Partial anonymized copy, Only production extracts available, Unsure
• What timeline would you expect for an initial extraction, mapping, and validation run for that sample? Options: <2 weeks, 2–4 weeks, 1–2 months, 2–3 months, Unsure

Next Steps — Practical Access and Early Decisions

• What credentials, API endpoints, or SFTP locations can you provision for a discovery proof-of-data in the next 7–14 days?
• Which stakeholders should be in an initial technical walk-through to unblock data access and who is the single approver for scope changes?
• Given what we’ve discussed, what would be an acceptable minimal scope for a six-week discovery sprint? Options: Data mapping + reconciliation, Sample migration + reconciliation, End-to-end rating validation, Integration smoke tests, All of the above, Other
• What are the non-negotiable dates or blackout windows we must avoid for discovery work (billing cycles, regulatory reporting, product launches)?
• Finally, what would success look like for you at the end of this Current State Inventory stage (deliverables, level of confidence, sign-offs)?

Who’s Leading This Change?

• Who are the core decision-makers and approvers for this billing migration? (Select titles; add names/contacts in the next question) Options: CIO/CTO, VP of IT, Head of Digital Transformation, CFO/Head of Finance, Head of Billing/Revenue, Head of Commercial/Product, Head of Customer Care, Program/PMO Lead, Other
• Please provide names, titles, and contact emails for the 3–5 people we should engage immediately.
• What is the target window for cutover to the new billing platform? Options: Within 0–3 months, 3–6 months, 6–12 months, 12–24 months, No set timeline
• Which teams must be actively involved during discovery and cutover (IT, Finance, Commercial, Network, Legal, etc.)? Select all that apply. Options: IT/Platform, Finance/Revenue Assurance, Commercial/Product, Network/Provisioning, Customer Care/Support, Legal/Compliance, Data/Analytics, Partner/Interconnect
• Which single role or team will ultimately produce the go/no-go recommendation for cutover, and why?

Are You Comfortable With The Risk You’re Living With?

• If a migration caused a billing error that reduced monthly revenue by 0.5%, how would that play out operationally and politically in 30, 90, and 365 days?
• Which failure modes worry you most during migration? Select all that apply. Options: Subscriber billing errors, Unbilled revenue, Partner settlement mismatches, Chargeback disputes, Invoice delivery failures, Regulatory non-compliance, Customer experience degradation, Other
• Tell us about a recent incident or near-miss where billing or mediation caused revenue or customer-impacting problems—what happened and who had to intervene?
• How tolerant are your stakeholders of manual reconciliation or remediation work after cutover? Options: Zero tolerance — must be flawless, Minimal tolerance — short, defined window, Moderate tolerance — expect some cleanup, High tolerance — prolonged remediation acceptable
• Do you have an explicit maximum acceptable revenue leakage threshold for cutover? If yes, pick the closest. Options: No threshold defined, <0.1%, 0.1–0.5%, 0.5–1%, >1%, Custom (explain below)
• If you selected 'Custom', please specify the numeric threshold and how it was determined.

What’s Buried in Your Billing DNA?

• How many years of subscriber history, billing records, and mediation/CDR data must be migrated and remain accessible? Options: 0–1 years, 1–3 years, 3–7 years, 7–15 years, >15 years
• Map the systems that touch billing today (mediation, rating engine, CRM, billing, collections, data warehouse, interconnect) and flag which contain business-critical logic.
• Which billing rules or customizations are non-negotiable for the business (select examples that apply)? Options: Custom rating families, Promotional carry-forwards, Partner revenue share rules, Legacy rounding/tax rules, Customer-specific exceptions, Interconnect settlement logic, Other
• For the items you flagged as non-negotiable, how well are they documented and how long would validation take? Options: Well-documented — validation in days, Partially documented — validation weeks, Poorly documented — validation months, Undocumented — requires reverse engineering
• Are critical exceptions or one-off cases captured in systems, or do they live in spreadsheets and tribal knowledge? Options: Mostly in systems, Mixed — some spreadsheets, Mostly spreadsheets/tribal knowledge, Unsure

What Breaks First When Things Go Wrong?

• Which single operational process would you name as the highest-risk single point during cutover? Options: Data migration mapping, Real-time rating accuracy, Invoice generation and delivery, Payment reconciliation, Partner settlement, Customer care processes, Other
• Describe a previous billing outage or reconciliation mismatch that escalated—how quickly was it detected and what were the remediation steps?
• How mature are your rollback and incident response procedures for billing failures? Options: Formal, documented runbooks and rehearsed, Documented but untested, Informal/ad-hoc, No rollback plan
• What monitoring and alerting exist today for revenue-impacting anomalies (e.g., sudden ARPU drops, spike in rejections)? Options: Real-time dashboards & alerts, Near-real-time reports, Periodic manual reports, None
• How quickly can Finance and Product authorize emergency corrective measures (hours, days, weeks)? Options: Hours, 1–2 days, 3–7 days, >1 week

If Everything Went Right, What Would Change?

• If the migration finished with zero revenue leakage and no customer incidents, what immediate business actions would you take?
• Which KPIs would you prioritize improving in the first 6–12 months post-migration? (Select up to five) Options: Time-to-market for new bundles, Billing accuracy (%), Days Sales Outstanding (DSO), ARPU, Churn rate, Operational cost per invoice, Time to resolve billing disputes, Regulatory SLA compliance, Other
• Which teams or leaders would view a successful cutover as their biggest win, and why?
• What reconciliations, reports, or artifacts would finance require to sign off on success?
• How would you prefer cutover success to be measured during the first 30, 90, and 180 days (e.g., exception rate, revenue parity, user-impact incidents)? Options: Quantitative metrics only, Quantitative + qualitative sign-offs, Executive summary + exception reports, Custom — explain below
• If you chose 'Custom', please outline the combination of measures you would require.

What Would You Require to Say 'Go' on Cutover?

• List your non-negotiable acceptance criteria that must be satisfied before permitting cutover.
• Which of these acceptance elements are already defined in your organization? Select all that apply. Options: Data parity & reconciliation rules, End-to-end acceptance test scripts, Performance/load benchmarks, Security & compliance sign-off, Operational runbook & staffed war-room, Rollback & contingency plan
• Who must sign final acceptance, and what artifacts (reports, reconciliations) do they require?
• Which cutover style aligns with your risk appetite? Options: Big-bang single cutover, Staged by customer segment, Staged by product line, Hybrid (mix of above), Undecided
• What contingency window (days) do you require before decommissioning legacy flows? Options: 0–7 days, 8–30 days, 31–90 days, >90 days

What’s Blocking Progress Inside Your Walls?

• What internal politics, processes, or resource constraints are most likely to delay this migration?
• Which stakeholders are most likely to resist a configuration-driven, faster-to-market billing model and why? Select all that apply. Options: Billing/Revenue Ops, Finance, Commercial/Product, Network/Provisioning, Legal/Compliance, Customer Care, Other
• How many full-time equivalents (FTEs) can you commit to migration support, and across which teams?
• Have past migrations experienced scope creep? If yes, what were the main drivers (select all that apply)? Options: Undocumented customizations, Late business requirements, Data quality surprises, Insufficient testing, Vendor-driven changes, Other
• What are your top three internal red lines (e.g., cannot stop issuing invoices, must preserve historical invoices, regulatory dependencies)?

Are Your Data & Environments Actually Ready?

• Do you have sanitized test datasets that reflect peak, edge, and partner-volume scenarios? Options: Comprehensive sanitized datasets available, Partial — some scenarios covered, Only synthetic or limited data available, No sanitized test data
• List the environments we can access for integration and cutover testing (dev, test, UAT, pre-prod, prod) and their current access status.
• Which feeds/connectors/APIs will require credentials or firewall exceptions for testing? Select all that apply. Options: Mediation/CDR feeds, CRM/Subscriber API, Payment gateway, Partner settlement API, Data warehouse/ETL, OSS provisioning API, Other
• Do you have SLAs for upstream data delivery and transformation, and are those SLAs currently met? Options: Yes — consistently met, Yes — frequently missed, No SLAs defined, Unsure
• How confident are you that data quality issues can be detected before cutover through automated checks? Options: High confidence — robust automation, Partial confidence — some automation, Low confidence — mostly manual, No confidence

Can We Operate Together — Governance & Escalation?

• What governance cadence do you expect during migration (committees, steering, war-room), and which roles must be present? Options: Weekly steering + daily war-room during cutover, Bi-weekly steering + daily war-room, Ad-hoc as needed, Monthly steering only
• What escalation path must be followed for revenue-impacting incidents during cutover (who, expected response SLA)?
• Are there legal, procurement, or commercial constraints that will affect liability, indemnity, or operational terms during cutover? Options: Yes — specific constraints, No constraints, Unsure — need to check
• Would you accept a time-boxed operational acceptance period governed jointly before decommissioning legacy systems? Options: Yes, Maybe — with conditions, No
• Who should be included in the post-cutover retrospective and what reporting cadence do you expect after cutover?

Ready to Commit to the Next Step?

• If we guaranteed no revenue loss and a tested rollback within 48 hours, what would still stop you from committing to a cutover date today?
• What specific deliverables or artifacts do you need from us to finalize an SOW and project plan? Select all that apply. Options: Detailed migration plan & timeline, Data migration runbooks, Acceptance test scripts & fixtures, Pilot/PoC with your scenarios, Commercial terms & liability clauses, Security & compliance artifacts, Other
• Who will sign the SOW and who will be the operational owners on your side once we start?
• Preferred communication channel and cadence during pre-deployment and cutover? Options: Dedicated Slack/MS Teams channel + daily standups, Email + weekly calls, Platform portal updates + weekly exec summary, Other
• When would you like us to schedule a joint readiness review workshop to confirm data, access, test fixtures, and risk controls? Options: Within 2 weeks, 2–4 weeks, 1–2 months, Later — specify

Getting Oriented: Who’s in the Room and Why?

• Which person or team initiated the search for a new billing platform today? Options: CIO/CTO, Head of BSS/OSS, VP Finance, Head of Commercial/Product, Regulatory/Compliance, Other
• What specific event or pressure made this project a priority right now? Options: Vendor EOL announcement, Failed product launch, New regulatory requirement, Revenue leakage detected, Cloud / modernization initiative, Other
• How urgent is a decision and cutover timeline from your leadership’s perspective? Options: Immediate (3 months), Near term (3–6 months), Planned (6–12 months), Longer runway (>12 months), Unsure
• Who will ultimately sign off the program commercially and who will sign off on cutover acceptance?
• What are the top three metrics leadership will use to declare this project a success?
• Who else needs to be kept informed during discovery (IT, Finance, Commercial, Network, Regulatory, Partners)? Please name teams and a single point of contact where possible.

If Your Billing Could Tell the Truth, What Would It Confess?

• How often in the last 12 months have billing errors materially affected revenue recognition or customer disputes? Options: Multiple times per month, Monthly, Quarterly, Rarely (once or twice), Never confirmed
• Can you share an example of a billing error that had a visible customer or financial impact and how it was resolved?
• Where do you most distrust the numbers today—rating accuracy, invoice formatting, partner settlements, or revenue reconciliation? Options: Rating accuracy, Invoice presentation, Partner settlements, Revenue reconciliation, Other
• How long does it typically take your team to detect and fix a significant billing discrepancy? Options: Same day, A few days, Weeks, Months, Not sure
• When billing mistakes happen, who bears the reputational cost (customer service, finance, commercial teams)? Options: Customer Service, Finance, Commercial/Products, Legal/Compliance, All of the above, Other
• What would be the one thing you’d change immediately about how billing issues surface and get resolved?

Hidden Complexity: What’s Really Running Under the Hood?

• How many distinct systems currently participate in creating a single customer invoice (mediation, rating, billing, adjustments, tax, CRM, payment)? Options: 1–2, 3–4, 5–7, 8 or more, Unknown
• Please identify the names or types of the legacy components we’ll need to integrate with or replace (list all that apply).
• How much subscriber and usage history must be preserved and migrated (examples: 1 month, 1 year, lifetime)? Options: 1 month, 3 months, 1 year, 3+ years, Full lifetime/history
• Where do you have the most undocumented or highly-customized logic—rating rules, interconnect settlements, promotional stacks, or adjustments? Options: Rating rules, Interconnect settlements, Promotions/discounts, Adjustments/credit logic, Other
• Which legacy vendor or in-house modules are considered untouchable or high-risk to change in the short term?
• What internal teams or external partners are responsible for maintaining those customizations today?

What’s the Real Cost If Migration Doesn’t Go as Planned?

• If cutover produced a material revenue reconciliation gap for one billing cycle, what would that mean for the business? Options: Minor operational headache, Material revenue impact, Regulatory reporting risk, Customer churn spike, Board escalation
• Has the operator experienced a migration or product launch failure in the past five years—what happened and what were the root causes?
• What tolerance do you have for post-cutover defects measured in dollars, percentage of invoices, and customer complaints?
• What legal, regulatory, or contractual obligations constrain how you manage billing corrections post-cutover?
• What would be the minimum set of controls or proof points that would convince Finance to proceed with legacy decommissioning?

Imagine Launch Day That Doesn’t Break Anything — What Does That Look Like?

• What are the non-negotiable acceptance criteria for cutover from Finance, IT, and Commercial?
• Which measurable signals will you use in the first 30, 90, and 180 days to confirm success (e.g., zero reconciliation gaps, X% fewer billing incidents)?
• What does a safe rollback look like—how much historical data and state would you need to preserve to return to legacy flows?
• How quickly do you expect to fully decommission legacy billing after a successful cutover? Options: Immediately (single cutover), Phased over months, Phased over years, We will maintain both long-term, Undecided
• If you could guarantee one outcome from cutover what would it be (choose one): revenue integrity, zero customer-impact, faster product launches, or lower operating cost? Options: Revenue integrity, Zero customer-impact, Faster product launches, Lower operating cost, Other

Who Needs to Own This — Because ‘We’ll Figure It Out’ Won’t Work

• Who will be the single accountable owner for migration decisions and sign-off on acceptance tests? Options: CIO, VP Finance, Head of BSS/OSS, Program Manager, Other
• Which teams must be embedded in the day-to-day cutover runbook (IT integration, billing ops, finance reconciliation, customer care)? Options: IT Integration, Billing Operations, Finance/Reconciliation, Customer Care/Support, Network/Provisioning, Legal/Compliance
• What cadence of governance and reporting do you require during discovery, build, and cutover (weekly, bi-weekly, monthly)? Options: Weekly, Bi-weekly, Monthly, Ad-hoc on milestones, Other
• Who will be responsible for testing and certifying acceptance tests from each stakeholder group?
• Are there existing change control or procurement rules that will lengthen decision cycles we should know about? Options: Yes—significant impact, Yes—moderate impact, No—minimal impact, Unsure

Where Will the Real Work Live — Data, Rules, or Change Management?

• Which of the following areas do you anticipate requiring the most effort during migration? Options: Data mapping and cleansing, Rating/rule translation, Partner settlement logic, Performance tuning, Process & org change, Testing and reconciliation
• How complete and clean is the mapping documentation between legacy fields and your target data model today? Options: Complete and validated, Partial, Poor/mostly undocumented, Nonexistent
• Do you have canonical test datasets and examples that represent your hardest billing scenarios? Options: Yes—comprehensive, Some test cases, No—need to create, Unsure
• How do you currently version or track rating rule changes and promotions (manual spreadsheets, CMDB, source control)? Options: Source control/CI, Configuration DB/CMDB, Spreadsheets, Ad hoc/manual, Other
• What internal change management work will be required to shift owners and processes to the new platform (training, org design, SLA changes)?

Small Bets That Build Trust — What Would You Let Us Prove First?

• Which scope for a proof-of-concept would most reduce your perceived risk: sample data migration, full converged billing scenario, partner settlement simulation, or end-to-end rating validation? Options: Sample data migration, Converged billing scenario, Partner settlement simulation, End-to-end rating validation, Other
• For that POC scope, what success criteria would you require to greenlight moving into a full project?
• How long of a parallel run would you feel comfortable with before turning off legacy flows? Options: One billing cycle, Two cycles, Three or more cycles, Depends on reconciliation results, Undecided
• Who from your team must validate POC results, and which artifacts do they need (reconciliations, test logs, discrepancy reports)?
• What access and data extracts will we need to run an effective POC (example: mediation records, raw CDRs, billing ledgers, customer master)?

Commercial and Operational Red Lines: What Would Stop This Deal?

• Which commercial terms are absolute deal-breakers for you (price, SLAs on revenue accuracy, indemnities, rollback liabilities)? Options: Price, SLAs on revenue accuracy, Indemnities, Rollback liabilities, Other
• What SLA metrics and penalties around billing accuracy and timeliness would be acceptable to Finance?
• Are there third-party partners (payment processors, tax engines, roaming partners) whose cooperation is required and might block go-live? Options: Yes—critical, Yes—manageable, No, Unsure
• Do you anticipate procurement or legal reviews that could extend contracting beyond your desired timeline? Options: Yes—significant delay, Yes—some delay, No
• What would you need to see in a commercial proposal to feel comfortable moving to an executive decision?

Today’s Commitment: What Would Make This Discovery Session Count?

• After this discovery, what specific deliverable would you like from us (data migration plan, cutover runbook, commercial term sheet, POC proposal)? Options: Data migration plan, Cutover runbook, Commercial term sheet, POC proposal, Risk register, Other
• How soon can your team provide the artifacts we asked for (access credentials, sample data, schema documentation)? Options: Immediately, Within 1–2 weeks, Within a month, Longer than a month, Unknown
• Who should we schedule as the next meeting with to validate findings and agree scope (names and roles)?
• What single risk should we prioritize in our follow-up plan so we address the thing that keeps you up at night?
• Is there anything about your org culture or past projects we should know to avoid the same mistakes?