Ironically, as I sit in a hospital emergency room—a setting where reliable IT infrastructure is literally a matter of life and death—I decided to complete a project that I had been working on: a comprehensive Windows 11 migration discovery checklist for healthcare organizations. This task is especially close to me because of my extensive experience in healthcare IT environments, where I’ve seen firsthand how critical systems must operate flawlessly to support patient care, compliance, and operational efficiency.
Healthcare IT isn’t just about keeping systems running; it’s about ensuring that clinicians have the tools they need to make life-saving decisions, that sensitive patient data remains secure and compliant with regulations, and that IT upgrades—like the transition to Windows 11—are planned and executed without disrupting these vital processes.
This checklist is the culmination of my years spent working in healthcare IT, where I’ve faced the unique challenges of balancing compliance, security, and usability in environments that demand 24/7 uptime. It’s designed to guide IT leaders through the migration process in a structured way, ensuring no critical step is overlooked.
If your organization is planning its Windows 11 upgrade and you need guidance or support to ensure a seamless, compliant migration, feel free to reach out to me directly here on LinkedIn. I’d be happy to assist with your project and share insights tailored to your specific needs.
This discovery document is designed to assess your organization's readiness for a Windows 11 migration. By starting with BANT (Budget, Authority, Need, and Timeline) questions, we ensure alignment with your organization's priorities and determine the scope of the migration. The subsequent sections delve deeper into technical, operational, and compliance aspects of the transition.
- “Do you have an allocated budget for IT modernization, specifically for the Windows 11 migration?”
- “What are your priorities for IT spending—hardware upgrades, software compatibility, compliance, or training?”
- “Are there any financial constraints or budget approvals that could delay the migration?”
- “Would you like assistance with building a cost analysis or ROI for this migration to present to stakeholders?”
- “Who are the key decision-makers for this migration project?”
- “Is there a designated project sponsor or executive champion for IT initiatives?”
- “Who needs to approve the budget and project scope for the migration?”
- “Will other departments, such as compliance or operations, need to sign off on the migration plan?”
- “Why is upgrading to Windows 11 important to your organization now?”
- “What challenges are you currently facing with your Windows 10 systems (e.g., compliance, cybersecurity, performance)?”
- “Are there specific risks associated with delaying this migration (e.g., HIPAA non-compliance, unsupported applications)?”
- “What improvements do you expect from moving to Windows 11 (e.g., better security, improved performance, streamlined IT management)?”
- “Are you aware that Windows 10 reaches end-of-life in October 2025?”
- “Do you have an internal timeline for completing the migration?”
- “Are there critical deadlines, such as audits or upcoming IT initiatives, that affect your migration timeline?”
- “Would you like assistance in creating a phased migration plan that aligns with your operational needs?”
3. Detailed Discovery Questions
3.1 Device Inventory and Compatibility
- “How many devices in your organization are currently running Windows 10?”
- “What types of devices are deployed across your organization (e.g., desktops, laptops, tablets, medical devices)?”
- “Do you have a centralized inventory system that includes device specifications (e.g., processor, RAM, storage, TPM 2.0 compliance)?”
- “Have you conducted a hardware compatibility assessment for Windows 11 requirements?”
- “How many devices will require hardware upgrades or replacements?”
- “Are there specific departments (e.g., ER, radiology, administration) with unique device needs?”
?3.2 Software Analysis and Application Compatibility
- “What are the main applications used by your organization (e.g., EHR, PACS, scheduling systems, billing software)?”
- “Have these applications been tested on Windows 11 for compatibility?”
- “Do you have vendor documentation confirming Windows 11 support for critical applications?”
- “Are there any legacy or proprietary applications that may require special configurations or updates?”
- “Do you use any custom scripts or integrations that need validation on Windows 11?”
- “What is your plan for remediating incompatible software (e.g., updates, replacements)?”
- “Are your antivirus and endpoint protection solutions tested and supported on Windows 11?”
- “How is user data currently stored (e.g., local devices, centralized servers, cloud storage)?”
- “What is your backup strategy for user data before migration?”
- “Do you have policies for backing up profiles and user-specific configurations?”
- “Are there users with exceptionally large amounts of data or unique storage needs (e.g., research, imaging)?”
- “Would you like assistance in planning and executing data migrations for specific departments or user groups?”
3.4 Compliance and Security
- “Are your current systems compliant with HIPAA and other healthcare regulations?”
- “Do you have a cybersecurity framework in place (e.g., NIST, ISO 27001)?”
- “Have you assessed how Windows 11’s security features align with your compliance needs?”
- “Are you using encryption for PHI and other sensitive data?”
- “What incident response or disaster recovery plans are in place for potential breaches during migration?”
- “Are there specific security configurations (e.g., multi-factor authentication, endpoint detection) that need to be reviewed or updated for Windows 11?”
3.5 Deployment Strategies and Tools
- “What deployment tools are currently in use (e.g., SCCM, Intune, Windows Autopilot)?”
- “Are you planning to deploy custom images across the network? If so, what imaging tools are used?”
- “Do you have a hybrid deployment model (e.g., some devices native, others VDI)?”
- “Are virtual desktop infrastructure (VDI) tools like Citrix, VMware, or Azure Virtual Desktop part of your strategy?”
- “How do you currently manage software updates and configurations (e.g., group policies, Intune)?”
- “Would you like guidance on optimizing your deployment process for efficiency and speed?”
3.6 Network Infrastructure
- “What is the current state of your network infrastructure (e.g., bandwidth, routers, switches)?”
- “Do you foresee any bottlenecks during deployment due to large-scale updates?”
- “How many remote or hybrid employees need to be accounted for in your migration plan?”
- “Are your VPNs, firewalls, and other network configurations compatible with Windows 11?”
- “Do you have adequate bandwidth to handle simultaneous OS updates, especially for larger organizations?”
3.7 Pilot Testing and Rollout Plans
- “Have you conducted pilot tests for other system upgrades or deployments in the past?”
- “Which departments or teams will be included in the pilot testing phase for Windows 11?”
- “What success criteria will you use to evaluate the pilot (e.g., application performance, user feedback)?”
- “What is your timeline for completing the pilot phase and proceeding to the full rollout?”
- “How do you plan to gather and incorporate feedback from pilot users into the broader migration strategy?”
?3.8 Training and Change Management
- “What training resources do you currently provide to staff for IT updates?”
- “Who is responsible for coordinating staff training during system upgrades?”
- “Do you anticipate a significant learning curve for staff adapting to Windows 11?”
- “Would you like assistance in creating training materials tailored to your organization’s needs?”
- “Have you identified staff roles or departments that may require more extensive training?”
3.9 Secure Asset Disposition
- “What is your current process for decommissioning outdated devices?”
- “Do you work with a certified IT asset disposition (ITAD) provider to ensure secure disposal?”
- “How do you handle data destruction on decommissioned devices (e.g., disk wiping, shredding)?”
- “Do you need documentation or certifications for audit purposes related to device disposition?”
- “Are there devices with sensitive data requiring special handling before disposal?”
3.10 Post-Migration Support and Optimization
- “What post-migration support do you anticipate needing (e.g., troubleshooting, user support)?”
- “Do you plan to monitor system performance and security after the migration?”
- “Would you like ongoing support to ensure compliance and system optimization?”
- “Do you require documentation or reporting to demonstrate migration success and compliance?”
- “How will you handle any lingering application compatibility issues post-migration?”
