The Meeting That Should Scare You
CIO: "We're migrating to Azure. How much will it cost?"
Consultant: "$800K, 18 months."
Reality: $2.3M, 28 months, half the apps still on-prem.
Why Migrations Fail
Not technical problems. Organizational problems:
- Nobody knows what applications exist
- Teams can't find installation media
- License compliance is "figure it out later"
- Dependencies discovered in month 14
The 55 Questions
Before touching Azure Migrate, answer these for EVERY application:
Application Basics
- What does this app do? (If nobody knows, retire it)
- Who owns it? (Name + phone number)
- Where's the installation media?
- What's the license model?
Dependencies
- What databases does it connect to?
- What APIs does it call?
- What calls it?
- What shared services does it use?
Current State
- How many VMs?
- What OS versions?
- What's the network topology?
- What's using public IPs?
Business Context
- What's the business impact if it's down?
- When can we migrate it? (Maintenance windows)
- Who approves changes?
The Problem
Teams skip this. They:
- Deploy Azure landing zones
- Start Azure Migrate
- Discover in month 6 nobody knows what they own
Then:
- Budget doubles
- Timeline extends
- Political pressure builds
- Consultants suggest "hybrid strategy" (translation: we failed)
What Actually Works
Phase 1: Discovery (Before Azure)
- Application inventory
- Dependency mapping
- License audit
- Owner identification
Timeline: 2-3 months
Cost: $50K-$150K
Value: Prevents $2M+ overruns
Phase 2: Rationalization
- Retire 20-30% of apps (nobody uses them)
- Rehost 40-50% (lift-and-shift)
- Refactor 20-30% (modernize)
- Retain 10% on-prem (compliance, cost)
Phase 3: Azure Deployment
Now you can actually use Azure Migrate successfully.
Download the Framework
Complete 55-question assessment with:
- Application questionnaire
- Dependency mapping template
- License compliance checklist
- Week-by-week migration timeline
👉 [Download Migration Assessment Framewor
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