Start Here: The One Outcome That Changes Everything

• When this program is finished, what single outcome would make you feel like every challenge, stakeholder fight, and dollar spent was worth it?
• Which of the following outcome categories are highest priority for your leadership team right now? (pick up to three) Options: Clinical quality / safety, Operational efficiency (throughput, LOS), Financial performance (revenue, cost to operate), Interoperability / regulatory compliance, Clinician satisfaction / retention, Patient experience
• By when does executive leadership expect to see measurable progress on these priorities? Options: Within 3 months, 3–6 months, 6–12 months, 12–24 months, No firm timeline
• Who will be the most visible executive to celebrate or call out this program’s success (title and name if possible)?
• Tell us about a past initiative your executive team celebrated — what signal or metric made them stand up and say “that worked”?

If the Metrics Could Scream, Which Ones Would Tell You to Panic?

• Which metric(s) would you consider a show-stopper if they deteriorated after go-live? Options: Mortality / readmissions, Medication safety events, Patient throughput / ED boarding, Revenue cycle days/denials, System availability / downtime, Other
• What are the current baseline values for your top 3 metrics (please list metric and current value)?
• How long have those baselines been your status quo — are they trending, stable, or recently changed? Options: Short-term (<6 months), Medium (6–24 months), Long-term (>24 months), Volatile / fluctuates
• If a key metric slips during deployment, what is your preferred response cadence and escalation path? Options: Daily war room with execs, Weekly recovery team, Local service-level fixes then review, Pause/minor rollback, Other
• Who in your organization owns validation of these metrics post-live (title/function)?

Clinician Momentum: Will Your People Use What We Build?

• If clinicians could vote with their feet, what would they do when a new workflow feels slower or less intuitive? Options: Adapt begrudgingly, Find workarounds, Decline to use new tools, Escalate to leadership, Other
• Which clinician groups are mission-critical for adoption in the first 90 days (pick all that apply)? Options: Hospitalists, Emergency physicians, Nursing (inpatient), Operating room clinicians, Ambulatory physicians, Pharmacy/Medication safety, Allied health (PT/OT/Resp)
• Describe one workflow that cannot change without creating serious risk or operational chaos (what, why, and who will push back).
• What have clinicians said — in their own words — about previous EHR or workflow changes? Give a brief quote or paraphrase.
• Which of these approaches best reflects how you want to measure clinician adoption? Options: Direct observation / audits, System usage analytics (time, clicks), Clinical outcome correlation, Satisfaction surveys / NPS, Hybrid model
• How much variation across facilities or specialties should the initial design tolerate vs. standardize? Options: Standardize nearly all workflows, Standardize core, allow local tweaks, High variability allowed, Unsure — need recommendations

Where Will the Dollars Actually Appear — and When?

• What financial outcomes are non-negotiable (e.g., reduce agency spend, increase net patient revenue, cut transcription costs)?
• Which of the following financial time horizons is your finance team using for ROI expectations? Options: 12 months, 24 months, 36 months, 3–5 years, Longer than 5 years
• What is the minimum net financial improvement you need to justify this project to the board (percentage or dollar figure)?
• Which finance artifacts will you expect from us to validate ROI (pick all that apply)? Options: Detailed cost model, Sensitivity analysis, Post-live performance dashboard, Quarterly variance reports, Other
• Have you previously realized the kinds of savings you’re targeting on past IT projects? If yes, what enabled them; if not, what blocked them?

What Data Journey Must Be Perfect — and What Can Be Pragmatic?

• If a single dataset had to be 100% correct from day one, which would it be and why? Options: Medications, Allergies, Problem lists/diagnoses, Master patient index / identifiers, Orders/history, Other
• Which source systems hold that data today (EMR, ancillary systems, spreadsheets)? Please list systems and owners.
• What is your tolerance for manual reconciliation after migration (pick one)? Options: None — zero manual fixes, Minimal — small percentage, Moderate — acceptable for a short period, High — expect manual cleanup
• Which data types must remain continuously available during cutover (pick all that apply)? Options: Active meds, Allergies, Active orders, Lab results, Imaging history, Scheduling/appointments, Patient identity
• Do you have a preferred reconciliation or validation tool/process we should integrate with or adopt?
• Are there anticipated interoperability constraints (e.g., HIE, CCD/C-CDA requirements, external labs, third-party apps) we must honor from day one?

Regulatory, Reporting, and That 2 a.m. Wake-Up Call

• What regulatory report or compliance requirement would cause the most damage if it failed in the first 6 months post-live? Options: Meaningful Use / Promoting Interoperability, CMS quality measures, State reporting, Medication error reporting, HIE notifications, Other
• Which reporting owners are accountable for those requirements (title/team)?
• Have you had any recent audits or penalties tied to data/reporting accuracy? If so, what were the root causes? Options: Yes — vendor/system issues, Yes — internal process gaps, No, Not sure
• How important is a vendor-provided audit trail and attestation capability for your compliance team? Options: Critical, Very important, Nice to have, Not important
• How would a regulatory miss feel to your team — reputationally and operationally? Describe the likely internal reaction.

Multi-Facility Reality: Which Domino Falls First?

• If the rollout had to fail in one facility first, which one is most likely and why?
• Which of these describes your preferred deployment approach? Options: Big bang across all facilities, Phased by region/facility, Phased by service line (e.g., inpatient then ambulatory), Hybrid / pilot then scale
• What local variations across sites (policies, integrations, third-party devices) must be accommodated rather than forced to conform?
• What are your blackout windows or peak periods when changes cannot occur (seasonal, fiscal, clinical)?
• Which local leaders do we need buy-in from before scheduling a go-live at a facility (roles/names)?
• How many full-time equivalents (FTEs) can each facility realistically allocate to build and go-live support? Options: <5, 5–10, 11–25, 26–50, >50

Acceptance: How Will We Know We’ve Truly Succeeded?

• What does a successful acceptance look like in concrete terms for the first 90 days post-live?
• Which of the following acceptance criteria will you require before signing off on deployment completion? (select all that apply) Options: Data reconciliation complete, Clinician workflow validation, Performance benchmarks met, No critical defects, Training completion rates, Regulatory reporting validated
• Who will formally sign off on acceptance at each stage (build, UAT, go-live, stabilization)? Please list roles.
• If early metrics are below target, how long should we wait before calling the phase unsuccessful? Options: 2 weeks, 1 month, 3 months, 6 months, Depends on metric
• What ongoing governance rhythm do you want for post-live optimization reviews? Options: Weekly, Bi-weekly, Monthly, Quarterly, Ad-hoc as needed
• What incentives or penalties (if any) does your organization expect to attach to meeting or missing acceptance targets? Options: Financial incentives, Escalation to executives, Contractual remedies, No formal incentives/penalties, Other

Risks, Emotions, and the Stories You’re Telling the Board

• What story are you prepared to tell the board if the first quarter post-live shows mixed results?
• Which internal or external critics are most likely to amplify negative outcomes (physician groups, unions, media, regulators)? Options: Physician leadership, Nursing leadership, Finance team, Patient advocacy groups, Local media, Other
• What do you fear most will be blamed on the vendor versus internal change management?
• Which mitigation actions would make you feel more confident against those risks (e.g., extra training, shadowing, staged cutover)? Options: Additional super-user staffing, Longer stabilization window, Pilot sites before scaling, Stronger rollback plans, More executive engagement
• How will we know when it’s time to shift from firefighting to optimization emotionally and operationally?

Next Steps: Small Bets That Build Confidence

• What is one small, low-risk pilot we could run in 30–60 days that would prove momentum toward your top outcome?
• Which stakeholders must be part of that pilot’s steering committee (titles/names)?
• What data or artifact would you need from us to brief leadership after that pilot (pick all that apply)? Options: Pilot dashboard & metrics, User feedback summary, Cost/benefit snapshot, Risk register & mitigations, Roadmap to scale
• Realistically, what decision or commitment would you expect from your leadership after a successful pilot? Options: Greenlight to scale, Additional funding, More time for planning, Reevaluate approach, No decision expected
• Finally, what’s the best way for our team to keep this conversation honest and useful—weekly check-ins, a shared dashboard, or something else? Options: Weekly check-ins, Shared real-time dashboard, Bi-weekly steering meetings, On-demand updates, Other

Start: Tell Us Where You Stand

• Give us a one-paragraph snapshot of your current clinical systems footprint (EHR(s), ancillary systems, number of hospitals/clinics covered).
• Which primary inpatient/outpatient EHR vendor(s) are you using today? Options: Epic, Cerner/Oracle, Meditech, Allscripts, Athenahealth, Home-grown, Multiple vendors, Other
• How many distinct inpatient and ambulatory platforms (separate databases) are actively used across your enterprise right now? Options: 1, 2, 3–5, 6–10, More than 10, Unsure
• Who on your team will be our primary day-to-day partner for discovery and system mapping? Options: CIO, CMIO, CNIO/Chief Nursing Informatics, VP/Director of IT, Director of Clinical Applications, Other
• How would you describe the overall sentiment about the current systems among frontline clinicians? Options: Highly frustrated, Frustrated but tolerant, Neutral, Generally satisfied, Enthusiastic

If Your Current Systems Could Speak, What Would They Confess?

• What is the single most consequential thing the current environment fails to deliver (clinical, operational, or financial)?
• Which recurring failures or workarounds do you see clinicians using because the system won’t support the right workflow?
• How often do these failures lead to measurable harm, near-misses, billing impact, or lost productivity? Options: Daily, Weekly, Monthly, Quarterly, Rarely, Unsure
• Tell us a specific story where a system limitation caused a patient safety, compliance, or major operational issue—what happened and who had to step in?
• How long have these pain points been tolerated, and what efforts have been tried previously to fix them? Options: <6 months, 6–12 months, 1–3 years, 3–5 years, Over 5 years

Which Workflows Are Sacred (and Which Are Negotiable)?

• Which clinician workflows must remain unchanged to preserve safety, regulatory compliance, or clinician trust? Options: Medication administration (BCMA), ICU documentation, Order sets for critical care, Surgical/procedural documentation, Nursing handoffs, Specialty clinic templates, Other
• Who are the clinical champions or groups that will push back hardest if their workflow changes? Please name roles and departments.
• Where have you seen workflow redesign succeed in the past—what conditions or tactics made it work?
• How much variation across facilities or specialties do you need to preserve (e.g., identical templates vs. regional customizations)? Options: Standardized across enterprise, Minor local tweaks allowed, Significant local customization, Fully independent workflows per site, Unsure
• If we proposed changing a high-impact workflow, what evidence or outcomes would convince stakeholders to adopt it?

Where Does Your Data Live—and Where Is It Breaking Down?

• Which of these data sources are part of your active clinical landscape today? Options: Lab LIS, Radiology PACS, Pharmacy system, ADT/ADT feed, Device telemetry/monitoring, HIE/external CCDs, Revenue cycle system, Other
• How would you rate the maturity of your interface estate (discoverability, documentation, monitoring, ownership)? Options: Very mature, Mature but brittle, Fragmented, Immature/mostly manual, Non-existent
• What percent of critical clinical data exchanges are currently automated vs. manual (e.g., fax, PDF, human re-entry)? Options: 90–100% automated, 70–89%, 50–69%, 25–49%, <25% automated, Unknown
• Where do you see the biggest interoperability gaps—data that never reliably arrives, arrives late, or arrives in unusable form? Options: External lab interfaces, Image/results availability, Medication history from community pharmacies, Device/monitoring feeds, Referrals and transitions of care, Other
• Can you share a recent example where missing or poor-quality data changed clinician behavior or delayed care?

If We Move Your Data, What Has To Be Perfect?

• Which specific data domains must be migrated with near-perfect fidelity (e.g., medication lists, problem lists, allergies, discrete flowsheets)? Options: Medications, Allergies, Problems/diagnoses, Orders history, Labs/results, Imaging reports, Discrete nursing documentation, Other
• How many years of historical clinical data must remain fully accessible in the new system? Options: All history (no limit), Last 10+ years, Last 5–10 years, Last 1–5 years, Only last year, Clinical summaries only
• What level of transformation during migration is acceptable—full record conversion, summarized historical views, or archive-only access? Options: Full conversion of discrete data, Conversion + summarized notes, Summaries in new system + archive access, Archive only
• What are your tolerances for data reconciliation errors during go-live (e.g., percent of records requiring manual reconciliation)? Options: <0.1%, 0.1–0.5%, 0.5–1%, 1–5%, >5%, Unsure
• Describe any regulatory, legal, or accreditation requirements that affect how we must handle or retain migrated data.

Who Else Needs to Be Able to Talk to Your System (Today and Tomorrow)?

• Which external partners must remain integrated at go-live (labs, state HIEs, ambulatory partners, payers, imaging centers)? Options: Reference labs (Quest/GenPath), Local labs, State HIE, Long-term care EMRs, Home health vendors, Payers/claims partners, Imaging centers, Other
• What interface standards and protocols do your partners require (HL7 v2, CCD/CCDA, FHIR, DICOM, X12, APIs)? Options: HL7 v2, HL7 v3/CCDA, FHIR APIs, DICOM, X12/EDI, Custom APIs, Other
• Who owns each major interface today (internal team, vendor, third-party integrator)? Options: Internal IT/Integration team, Vendor, Third-party integrator, Clinical engineering, No clear owner
• What monitoring and incident response exists for mission‑critical interfaces (automated alerts, runbooks, 24/7 support)? Options: 24/7 monitoring & on-call, Business hours monitoring + escalation, Ad hoc/manual monitoring, None
• Is there any partner or system that will not permit a cutover or change without formal legal/commercial negotiation? Options: Yes — list partners below, No, Unsure

People, Capacity, and the Timeline That Will Actually Happen

• If the board asked you to summarize the realistic timeline for a phased enterprise migration, what would you say—and why might that be optimistic?
• Which internal teams are available to support design, build, and testing (and what percent of their time can be dedicated)? Options: IT/integration (FTE %), Clinical informatics (FTE %), Nursing leads (FTE %), Physician champions (FTE %), Training/education (FTE %)
• How much formal project management and governance do you currently have for EHR initiatives? Options: Mature PMO + governance, PMO exists but limited, Ad hoc project leads, No formal PMO
• What is your preferred cutover model for facilities—big bang, phased per hospital, parallel run, or hybrid—and why? Options: Big bang, Phased by facility, Phased by service line, Parallel run, Hybrid (please describe)
• What internal constraints (seasonality, accreditation, executive reviews) create windows where cutovers are impossible?

Risks, Workarounds, and The Things That Keep You Awake

• Which three failure scenarios would be unacceptable during or immediately after go-live?
• What contingency playbooks do you currently have (rollback, dual documentation, surge staffing), and when have they been used? Options: Rollback plan exists, Dual documentation plan, Surge staffing contract, No contingency plan, Other
• How tolerant is your executive leadership of short-term disruption in exchange for long-term improvement? Options: Very tolerant, Somewhat tolerant, Low tolerance, Zero tolerance, Depends on metrics
• Are there union, medical staff, or regulatory constraints that limit overtime, surge staffing, or process changes during go-live? Options: Yes — unions/agreements, Yes — medical staff bylaws, No major constraints, Unsure
• What early-warning signs should we put in place that would trigger a rapid-escalation protocol?

Acceptance: What Must Be True for You to Sign Off?

• What concrete acceptance criteria will you require at facility and enterprise level (data integrity checks, clinician sign-off, throughput metrics)?
• What performance targets must the system meet on day one (e.g., chart open times, order latency, medication administration throughput)?
• What clinician satisfaction or adoption metrics will you use to judge success in the first 90 days? Options: SUS/UX scores, Net Promoter Score among clinicians, Order completion rates, Chart completion rates, Adoption vs. baseline metrics, Other
• Who has final sign-off authority for go/no-go at the facility and enterprise levels? Options: CIO, CMIO, CNIO, Hospital CEO, Joint clinical/operational committee, Other
• After go-live, what does a successful stabilization period look like at 30, 90, and 180 days? Please provide measurable targets where possible.

Quick Orientation — Where are we starting from?

• How would you describe your team's overall readiness for pre-deployment right now? Options: Very ready, Reasonably ready, Some gaps but manageable, Significant gaps, Unsure
• Who is the single point-of-contact we should coordinate with for day-to-day pre-deployment decisions (name, title, best contact method)?
• Which facilities and care settings are in scope for this deployment wave? Options: Main acute hospital, Community hospitals, Ambulatory clinics, Emergency departments, Surgical centers, Long-term/post-acute, Other
• What is the committed go-live window and any immovable dates we must honor (regulatory, board, fiscal-year, union constraints)?
• Who on your executive team has final sign-off authority for deployment readiness? Options: CIO, CMIO, CNO/Chief Nursing Informatics Officer, COO, Chief Legal/Compliance, Other
• What recent wins or proof points make you confident about this launch?

If This Goes Sideways, Who Feels the Pain First?

• Imagine an unexpected full-day outage on day one—who within your organization would escalate first and why?
• Which outcomes would be most damaging if the deployment caused disruption: patient safety, revenue, regulatory reporting, staffing burnout, or reputation? Options: Patient safety, Revenue cycle, Regulatory reporting, Clinician burnout, Public reputation, Other
• Tell us about a past deployment or IT incident that didn’t go as planned—what happened, and what still worries you about repeating it?
• How fast do you need detection and remediation when critical issues appear (minutes, hours, same day, next day)? Options: Minutes, Within an hour, Same day, By end of day, Within 48 hours
• Who owns incident communications to clinicians, patients, and regulators during an outage? Options: IT Incident Manager, CMIO, CNO, Communications/PR, Legal/Compliance, Other
• How would you describe the emotional state of frontline clinicians about this change—excited, wary, exhausted, hopeful, or something else? Options: Excited, Wary, Exhausted, Hopeful, Resigned, Other

What’s Hidden in Your Data — Where the Surprises Live

• If you had to name the single riskiest data source in migration, which is it and why?
• Which systems hold structured patient data we must migrate? Options: Legacy EHR/Clinical system, LIS (lab), RIS/PACS (imaging), Pharmacy system, Scheduling/ADT, Revenue/ERP, Other
• Which unstructured or semi-structured repositories will need special treatment (scanned records, PDFs, dictation, HIE archives)? Options: Scanned charts, PDF reports, Dictation/transcription, HIE/Health Information Exchange, Legacy tapes/backups, Other
• Estimate the scale: number of patient records, discrete orders, and archived notes to be migrated (ballpark is fine).
• Describe the top three data quality issues you expect (duplication, missing timestamps, inconsistent codes, legacy IDs, others).
• Who are the named data owners and SMEs we can engage for mapping and validation?
• Are there any active legal holds, research datasets, or consent restrictions that limit data migration or test data use? Options: Yes — legal holds, Yes — research/consent restrictions, No, Unsure

Can Systems Talk When It Counts? — Interfaces & Interoperability

• If a key interface fails on cutover, which downstream service would suffer the most and why?
• Please select the interface standards you currently use or require: Options: HL7 v2, HL7 v3/CDA, FHIR (R4), DICOM, X12/EDI (claims), Proprietary APIs, Other
• Which external partners require live interfaces at go-live (labs, radiology centers, state immunization registry, HIEs, third‑party labs)?
• Do you have test endpoints and sandbox credentials available for all inbound/outbound integrations today? Options: All available, Most available, Some available, None available, Unsure
• Which integrations must be real-time vs acceptable as batch/hourly during early cutover? Options: Real-time required, Near real-time acceptable, Hourly batch acceptable, Daily batch acceptable
• Who is responsible for build and troubleshooting of interfaces on your side (internal team, third-party integrator, vendor), and are SLAs in place? Options: Internal integration team, Third-party integrator, Vendor-managed, Combination, No clear owner
• What latency or throughput thresholds will you use to judge interface performance during validation?

People & Roles — Who's Owning Launch vs. Running Care?

• If we put the entire deployment on a whiteboard, which critical roles are missing from your roster today?
• Which of the following dedicated roles do you already have staffed for this wave? Options: Project Manager, Technical Lead/Architect, Data Migration Lead, Clinical Lead (CMIO/CNO SME), Training Lead, Go-live Ops/Command Center Lead, Interface Engineer
• How many full-time equivalent (FTE) internal staff can be allocated to the build and hypercare windows? Options: 0–2, 3–5, 6–10, 11–20, 20+
• Describe your clinician superuser model: number of superusers per department, release time from clinical duties, and escalation path.
• Where do you anticipate the most resistance—physicians, nursing, allied health, scheduling/revenue teams—and why? Options: Physicians, Nursing, Allied health (PT/OT/etc.), Scheduling/Front desk, Revenue cycle, Other
• What is your capacity for hands-on training in the 30 days before go-live (number of seats, simulation labs, protected time)?
• What is the escalation path and decision cadence during the first 14 days post‑go‑live?

Access, Environments & Security — Is the House Open?

• If we need production-level access for migration or testing, how quickly can you grant it and what approvals are required? Options: Same day with approvals, 1–3 business days, 3–7 business days, Longer than 7 days, Depends on data
• Which environments do you have available and how many instances of each (dev, test, pre‑prod, production)?
• What network or security constraints should we plan for (VPN, IP allowlist, firewall windows, proxy, FIPS requirements)?
• Do you require privileged access controls, background checks, or specific onboarding for vendor staff working with PHI? Options: Yes — privileged access & checks, Yes — limited onboarding, No special requirements, Unsure
• Are there policies around using production PHI in test environments or must data be synthetically or de‑identified? Options: Production allowed with controls, De-identified only, Synthetic data required, Varies by dataset
• Who manages SSO/identity providers and can create service accounts for integration testing? Options: Internal IAM team, Third-party identity provider, Vendor-managed, No single owner
• Are penetration testing, security attestations, or HITRUST/ISO reports needed before we can access environments? Options: Yes — required, Optional but preferred, Not required, Unsure

If We Have to Back Out, What’s the Plan?

• If you had to revert to the legacy system in the first 72 hours, what would be the single biggest obstacle to doing so?
• Do you have a documented rollback plan that includes data reconciliation, communication, and cutover reversal steps? Options: Yes — fully documented, Partial plan exists, No plan, Plan in development
• What are your tolerances for rollback triggers (e.g., safety event, unrecoverable interface failure, unacceptable performance metrics)?
• Who would lead the rollback decision and which stakeholders must sign off?
• What communication channels and cadence would you use to notify clinicians, patients, and partners if a rollback happens?
• Describe any technical or contractual constraints that would make rollback impractical or impossible.

Measurement & Acceptance — How Will We Know It's Good?

• What are the top 3 acceptance criteria that must be met before you sign formal go-live acceptance?
• Which migration validation methods do you require: record-level reconciliation, sampling, automated checks, clinician sign-off, or other? Options: Record-level reconciliation, Sampling/spot checks, Automated validation scripts, Clinician verification sign-off, Other
• What performance targets must the system meet (transaction latency, page load times, concurrent users, order entry throughput)?
• How will clinician workflow validation be documented and signed off—simulation runs, observed sessions, or training competency checks? Options: Simulation runs, Observed clinical sessions, Training competency checklists, Clinician acceptance surveys, Other
• What absolute thresholds would force a pause or rollback (e.g., >X% failed migrations, >Y minute average response time, critical safety defects)?
• How long of a hypercare period do you require and what metrics will define success at 30, 60, and 90 days?
• Who signs the final acceptance certificate and how is warranty/defect remediation governed?

Timeline, Constraints & Political Landmines — What’s Non-Negotiable?

• What external dates or events make this go-live immovable (regulatory change, accreditation survey, fiscal year, mergers)?
• Are there blackout periods where we cannot change systems (holidays, peak season, residency onboarding, state reporting windows)? Options: Yes — list available, Some known blackout dates, No blackout dates, Unsure
• What budget or procurement constraints could affect staffing or third‑party work during deployment?
• Are there competing internal initiatives (other IT projects, construction, staffing reorganizations) that might reduce available resources? Options: Yes — multiple competing initiatives, A few competing initiatives, No competing initiatives, Unsure
• Who are the internal political stakeholders we should be aware of—advocates and likely detractors?
• Is there anything happening externally (state/federal audits, litigation, union negotiations) that could alter timelines or risk tolerance? Options: Yes, No, Unsure

Final Readiness Check — Tell Us the Truth

• If you had to give a blunt readiness verdict right now, would you: green (go), yellow (mitigate before go), or red (delay)? Options: Green — ready to go, Yellow — some mitigations needed, Red — delay recommended, Unsure

Quick Introductions: Who's in the Room?

• Which role(s) are you representing in this conversation? Options: CIO, CMIO, Chief Nursing Informatics Officer, Chief Medical Officer, Chief Nursing Officer, IT Director, Clinical Director, Other
• What single outcome would make this EHR program feel like a success to you in year one?
• What's your target timeline for first major milestone (e.g., single-hospital go-live, scope decision)? Options: <6 months, 6–12 months, 12–18 months, 18–36 months, Undetermined
• Which of these constraints most shapes your choices today? Options: Budget, Executive attention/priority, Workforce capacity, Regulatory deadlines, Interoperability obligations, Acquisition/consolidation timeline, Other
• If you could add one sentence that would help us understand your urgency, what would it say?

If We Keep Doing What We're Doing, What Breaks First?

• What tangible problems become worse if the current EHR strategy remains unchanged? Options: Clinician burnout, Patient safety incidents, Revenue loss / billing delays, Regulatory non-compliance, Data fragmentation, Delayed mergers/integrations, Other
• How often do those problems occur today? Options: Daily, Weekly, Monthly, Occasionally, Rarely, Unknown
• Tell us about a recent incident or pattern that illustrates this risk (a short story helps us prioritize).
• Who on your team feels the pain most acutely—what do they say about it? Options: Frontline physicians, Nursing leadership, IT/Integration teams, Revenue cycle, Quality & safety, Executive leadership, Other
• How long have you been tolerating these issues before deciding to act? Options: <6 months, 6–12 months, 1–3 years, 3–5 years, Longer than 5 years

What’s Costing You More Than You Think?

• Which hidden costs do you suspect are largest but least quantified today? Options: Clinician overtime and turnover, Duplicate testing and inefficiency, Delayed revenue recognition, Fines or regulatory risk, Data remediation and reconciliation, Opportunity costs for innovation, Other
• Do you have any current estimates (time, $ or FTEs) tied to these hidden costs? If yes, please summarize.
• Which of these outcomes would you prioritize to free up value within 12 months? Options: Reduce documentation time, Decrease order-sets errors, Improve revenue cycle speed, Reduce duplicate imaging/labs, Improve staffing efficiency, Improve interoperability with key partners, Other
• When leaders talk about 'value' for this program, where do they disagree? Options: Clinical quality focus, Financial ROI focus, Speed of deployment, Minimize disruption, Vendor risk appetite, Other
• How would you describe the emotional climate around these costs—frustration, resignation, urgency, or something else? Options: Urgent, Frustrated but hopeful, Resigned, Skeptical, Optimistic

Who Decides — and Who Keeps Getting Overlooked?

• If decision-making stayed as it is today, what kinds of decisions would be delayed or reversed? Options: Scope trade-offs, Budget approvals, Clinical design sign-offs, Interface priorities, Go-live dates, Governance changes, Other
• Who is the formal executive sponsor—and who has the informal influence that actually moves projects forward?
• Which stakeholder groups are least engaged but most critical to adoption (e.g., OR, ED, subspecialties)? Options: ED, OR/surgical services, ICU/critical care, Primary care clinics, Behavioral health, Revenue cycle, Other
• Have you mapped decision rights and escalation paths for major trade-offs (scope, timeline, clinical compromises)? Options: Yes, documented, Informally understood, Partial mapping, No
• Where have governance breakdowns cost you time or credibility before—what happened and how did you recover?

Where Your Data Lives (And Why It’s Messier Than You Assume)

• Which legacy systems and data repositories must be migrated or integrated for this program to succeed? Options: Ancillary systems (Labs/Radiology), Old EHR/EMR instances, Financial/RCM systems, HIEs / Regional registries, Device data repositories, Homegrown databases, Other
• Describe the most fragile or opaque data flow you rely on today (where does data get lost or mistranslated?).
• What is your preferred data migration approach? Options: Big-bang cutover, Incremental phased migration, Dual-write with reconciliation, Hybrid/segmented by service line, Undecided
• Who currently owns data quality and reconciliation during transitions? Options: IT/data team, Clinical informatics, Vendor/implementation partner, Third-party data services, Not assigned
• What regulatory or retention rules (state/federal) complicate moving parts of your record? Options: Behavioral health, PHI retention laws, State-specific retention, Cancer registry reporting, Medicare/Medicaid rules, Other

What Would Clinicians Notice on Day One?

• If clinicians reacted honestly on day one, what would they praise—and what would they complain about?
• Which clinician workflows cannot change without compromising safety or throughput? Options: Medication administration, Order entry for critical care, ED triage workflows, Surgery scheduling and documentation, Transfusion documentation, Other
• How would you measure clinician acceptance in the first 90 days? Options: Satisfaction surveys, Click/time metrics, Order entry error rates, Escalations to clinical informatics, Training completion and competency, Other
• What training model has historically worked best here (e.g., super-users, classroom, just-in-time), and why? Options: Super-user model, Role-based classroom, E-learning + simulation, On-floor support (train-the-trainer), Hybrid
• Which three clinician roles must be onboard and confident by go-live to avoid clinical risk?

What Would Success Look Like — In Living Color?

• If you could show the board three metrics 12 months after go-live that prove success, which metrics would they be? Options: Reduced documentation time, Improved patient throughput, Revenue uplift / days in A/R, Lower safety incident rate, Interoperability transactions completed, User satisfaction
• What is the minimum acceptable improvement for each chosen metric (e.g., 10% reduction in documentation time)? Please list metrics and targets.
• Which quick wins could we realistically achieve during initial deployment to build confidence? Options: Standardized order sets, Resolved high-volume interfaces, Core documentation templates, Reduced login/time-to-order, Billing code harmonization, Other
• How will you balance the need for early wins with long-term platform optimization? Options: Phased scope with quick wins first, Parallel optimization program, Dedicated post-live team, Defer non-critical features, Undecided
• Who needs to sign off that success has been achieved—what governance artifacts or acceptance criteria are required?

What's the Real Stop Sign?

• If this project stalls or fails, what's the most likely root cause you foresee? Options: Budget constraints, Insufficient staffing, Clinical resistance, Data migration failure, Unclear governance, Legal/commercial impasse, Other
• Have you experienced a near-fail in a prior IT/clinical program? What specifically brought it to the brink?
• Which contractual or commercial terms are non-negotiable for your leadership to move forward? Options: Liability limits, Service levels / uptime, Acceptance criteria & remediation, Penalty or incentive structures, Support/optimization commitments, Other
• What contingency resources (budget, temp staff, third-party integrators) could you deploy if migration issues appear? Options: Contingency budget, Contracted integrators, Internal surge staff, Vendor-delivered experts, Not available
• What would a credible de-risking plan need to show to get you comfortable proceeding?

How We Move Forward Together

• What's the ideal governance cadence you want from us (meetings, steering, reports)? Options: Weekly tactical, Biweekly leadership, Monthly steering, Quarterly exec reviews, Combination
• Which pilot or earliest-phase scope would you prefer to validate assumptions quickly? Options: Single hospital inpatient, One specialty service line, Ambulatory clinics first, Interoperability with key partner, Data migration pilot only, Other
• What artifacts or deliverables would make you feel ready to approve a commercial commitment? Options: Detailed scope & acceptance criteria, Agreed timeline & milestones, Risk register and mitigation, Sample training and go-live plan, Price and payment schedule, Other
• Who should we bring into the next working session to accelerate alignment (names/roles)?
• How would you like us to summarize this discovery back to your team—what format and level of detail would be most useful? Options: Executive one-pager, Detailed discovery report, Roadmap with milestones, Risk and mitigation summary, Workshop to validate findings