Cloud Readiness & Roadmap

The Problem: Migrating What You Have, Not What You Need

Most migrations start with an inventory and a target date. Every server on the list is assigned a destination, and the plan becomes “move everything, then optimize.” In practice, the optimization rarely happens.

As a result, the outcome is predictable. Unused servers keep running, but now they appear on a monthly invoice. Meanwhile, teams design identity, networking, and security under deadline pressure, one workload at a time. Over time, the landing zone grows the same way the old data center did.

The Cloud Readiness & Roadmap is a fixed-scope assessment conducted before any of that. First, I look at what you run today. Then I decide with you what each workload should become, design the Azure foundation it needs, and put the work in an order your team or a partner can execute.

Some of the answers will be “don’t move this.” For example, you may be better off retiring some workloads, replacing them with SaaS, or keeping them on-premises. If that is the honest conclusion, the roadmap will say so.

Who This Is For

A Good Fit If

  • You run workloads on VMware, Hyper-V or physical servers and are considering Azure, but you have no agreed plan.
  • A hardware refresh, data center contract or license renewal forces a decision within the next 6–18 months.
  • You already run some workloads in Azure, but nobody has assessed the rest of the estate, and the landing zone grew without a design.
  • Leadership wants a cost comparison and a realistic timeline before it approves a migration budget.
  • You need to know which workloads have data residency or regulatory constraints before anything moves.

Not a Good Fit If

  • You have already decided to move everything as-is and only need hands to do it. In that case, Azure Migrate and a migration partner are the faster route.
  • Everything already runs in Azure. Instead, the Architecture Integrity Review is the right package.
  • You only need to migrate one or two servers. In that case, the assessment would cost more than the decision it informs.

The Method: Decide, Then Design, Then Sequence

Azure Migrate tells you which servers can run in Azure and what a like-for-like VM would cost. I use it too. However, it cannot tell you whether a workload should move at all, what it depends on, or what foundation it needs to run safely.

That is why the roadmap follows three rules:

  1. Decide before you design. Every workload gets one of the Cloud Adoption Framework dispositions: retire, retain, rehost, replatform, refactor, rearchitect, rebuild or replace. Retiring and replacing come first, because the cheapest migration is the one you don’t do.
  2. Design before you build. I design the landing zone against all eight Azure landing zone design areas before the first workload moves, instead of assembling it one workload at a time.
  3. Sequence by dependency and risk, not by convenience. I build the waves from real dependencies and business constraints. Low-risk workloads go first, so your team learns on systems that can tolerate mistakes.

In addition, every recommendation cites its evidence: measured utilization, a dependency, a license term, a regulatory requirement, or an interview. If a decision rests on an assumption, the roadmap names it.

Assessment Scope

The assessment covers four things: what you run today, what each workload should become, the Azure foundation it requires, and the regulatory constraints that shape all three.

Current Estate

  • Server inventory, measured CPU, memory, disk and network utilization, and operating system support status.
  • Application dependencies, based on dependency analysis and interviews with application owners.
  • Licensing position: Windows Server and SQL Server with Software Assurance, and what that means for Azure Hybrid Benefit.
  • Migration blockers, such as unsupported operating systems, hardware dongles, latency-sensitive integrations and vendor support terms.

Workload Rationalization

Each workload receives a disposition (retire, retain, rehost, replatform, refactor, rearchitect, rebuild, or replace), along with the reason and the business owner who approved it.

Target Foundation: The Eight Landing Zone Design Areas

DESIGN AREAWHAT I DEFINE
Billing and Entra tenantAgreement type, tenant model, billing scopes
Identity and access managementHybrid identity with Entra ID, privileged access model, admin separation
Resource organizationManagement group hierarchy, subscription model, naming and tagging
Network topology and connectivityHub-spoke or Virtual WAN, hybrid connectivity (VPN or ExpressRoute), DNS, IP addressing
SecuritySecurity baseline, Defender for Cloud scope, key and secret management
ManagementMonitoring, backup, disaster recovery, patching
GovernanceAzure Policy baseline, cost management, compliance requirements
Platform automation and DevOpsInfrastructure as code approach and deployment pipelines for the platform

Data Residency and Regulation

Which workloads hold personal or regulated data, which Azure regions are acceptable, and what GDPR, NIS2, or sector rules require of the design. Where it matters, I also cover the EU Data Boundary and what it does and does not change.

The assessment does not include a penetration test, an application code review, or a detailed design of individual application architectures. Instead, those follow later for the workloads that need them.

How the Engagement Runs

  1. Briefing Call. First, we agree the scope, the decisions you need to make, and who should take part. You then get a fixed-fee quote.
  2. Discovery starts. Your team deploys the Azure Migrate appliance (or provides an equivalent export), and I confirm data is arriving. Performance data needs time to collect, because sizing and cost estimates are only as good as the period they cover.
  3. Interviews and dependency mapping. Meanwhile, I work with application owners on what each system does, who depends on it, and what constraints it carries.
  4. Rationalization workshop. Next, we agree a disposition for each workload together. These are your decisions; I bring the recommendation and the evidence behind it.
  5. Foundation design and roadmap. After that, I design the target landing zone and build the migration waves.
  6. Readout. Finally, I walk your technical team and decision-makers through the roadmap, with time for questions.

Elapsed time depends mainly on the discovery period and on how quickly application owners are available. The tier table below gives typical durations, and we agree the exact schedule in the Briefing Call.

Deliverables

DELIVERABLEWHAT IT CONTAINS
Readiness reportEstate summary, migration blockers, licensing position, and the data residency and regulatory constraints that affect the design
Workload disposition registerEvery workload with its disposition, the reason, its dependencies and the owner who agreed it
Target landing zone designHigh-level design across the eight design areas, with the key decisions and the reasons for them
Migration roadmapWaves in sequence, with the workloads, dependencies, prerequisites and main risks for each
Cost estimateProjected monthly Azure cost per wave and at steady state, with the assumptions (reservations, savings plans, Azure Hybrid Benefit) and an accuracy range
Readout sessionWalkthrough and Q&A with your team

The cost estimate is an estimate, not a quote. For that reason, it states its data sources, how long I measured performance, and what would change it.

Scope and Pricing

TIERTYPICAL ESTATETYPICAL DURATIONFIXED FREE FROM
FocusedUp to 50 servers, one site, up to 15 applications4 weeks€4,500
StandardUp to 200 servers, up to two sites, up to 40 applications6 weeks€8,500
ExtendedLarger estates, multiple sites or regulated workloadsAgreed in briefingOn request

What Moves the Price

  • Number of servers and applications in scope.
  • Number of sites and the hybrid connectivity they require.
  • Number of application owners to interview.
  • Regulated or personal data that needs a residency and compliance assessment.
  • Whether part of the estate already runs in Azure, so the design must integrate it.

We fix the final fee after the Briefing Call. After that, it only changes if the scope does.

What I Need from You

You don’t need an existing inventory. In fact, building it is part of the work.

Access

  • A read-only account for vCenter or Hyper-V, so the Azure Migrate appliance can discover servers and collect performance data. If you can’t deploy the appliance, an RVTools or equivalent export also works, but sizing will be less accurate.
  • Credentials for software inventory and dependency analysis on the servers in scope, if you want application-level detail.
  • Read access to Active Directory and, if you have one, your existing Entra ID tenant.
  • An Azure subscription for the Azure Migrate project. Discovery and assessment carry no Azure Migrate charge.

Time

  • An infrastructure contact who can deploy the appliance and answer technical questions.
  • One to two hours with each application owner.
  • A decision-maker at the rationalisation workshop and the readout.

In practice, the availability of application owners is what most often delays an assessment. For that reason, we agree names and dates in the Briefing Call.

Access and Confidentiality

  • All access is read-only, so I make no changes to your servers, network or tenant.
  • The Azure Migrate project runs in your own subscription, in a region you choose. As a result, discovery data stays there.
  • I store working files in the EU and delete them [X] days after final delivery, unless you ask me to keep them.
  • I sign your NDA, or provide mine, before you grant any access.

After the Roadmap

I write the roadmap so your own team, or any partner you choose, can execute it. In other words, you don’t depend on me for the next step.

However, if you want help, I can:

  • Build the landing zone as infrastructure as code, with the Azure Policy baseline from the design.
  • Support the first migration wave, so your team runs the later ones.
  • Review the environment after migration with the Architecture Integrity Review.

Start with a Briefing Call. A 45-minute call about your estate and the decision you need to make. You leave with a clear scope and a fixed-fee quote, whether or not you go ahead.

Both options go directly to me. No sales funnel, no account managers.