"The Exit Comes Before the Onboarding" — Why Every Cloud Strategy Needs an Exit Plan!

Let me ask you something upfront.

When was the last time you bought a house, a car, signed a contract, or boarded a plane without at least some idea of what you’d do if things went sideways? Probably never. Tbh, I try to avoid thinking about this when boarding a plane, but for other, more obvious reasons. You have insurance, an emergency exit, a backup plan. And yet, when it comes to the cloud, this vast, sprawling, rapidly evolving digital ecosystem, most organizations dive in headfirst… and forget all about the exit.

Until it’s too late.

Today, we’re flipping the script.

We’re going to talk about something that doesn’t get enough attention in glossy cloud brochures or migration kickoffs: the cloud exit strategy.

The most mature cloud strategies start with the end in mind.

But Wait, Why Would You Want to Leave the Cloud?

Let’s get this straight: I’m not anti-cloud. I love the cloud. I teach the cloud. I help companies thrive in the cloud. But loving the cloud doesn’t mean ignoring the fine print.

Cloud isn’t always cheaper. It’s not always better. It’s not immune to outages, price increases, mergers, acquisitions, bankruptcies, regulatory overhauls, or even plain old buyer’s remorse.

Your provider might change the rules of the game overnight, introducing new licensing models, shifting service locations, or retiring that one API your business depends on. You might outgrow your provider’s capabilities. Or maybe the service quality tanks, support, for example. Maybe there’s a compliance shake-up. Maybe you're suddenly paying triple and can’t figure out why.

Enter: your exit strategy. Think of it as a fire escape plan for your cloud estate. You hope you’ll never use it. But you’ll be damn glad it’s there when the smoke starts pouring in.

What a Cloud Exit Strategy Really Means

This isn’t just about flipping a switch and moving everything “back on-prem” or to another cloud provider.

A real exit strategy is nuanced, layered, and strategic. It’s not about abandoning the cloud, it’s about maintaining autonomy. It’s about making sure you’re never cornered by your architecture, your contracts, or your lack of preparation. Or at least, a lot less.

Here’s what a solid exit strategy includes:

• A full inventory of data, applications, systems, and dependencies
• Defined exit triggers (when do we pull the plug?)
• Pre-selected alternative environments
• Tools and scripts ready for data export and migration
• Pre-approved SLA interpretations and compliance safeguards
• A clear execution timeline
• A test plan. It’s like a backup, it’s a 100% worthless if it’s not tested (and works).
• Communication plans, DR updates, post-exit reviews, and, yes once executes a new exit strategy for your next environment

In other words: It’s not a button you push. It’s a discipline, a process.

The Closer You Are to IaaS, the Easier You Can Bail

Not all cloud models are created equal when it comes to exits.

If you’re operating in an Infrastructure as a Service (IaaS) model, you have more control. You manage the OS, apps, and data. That means more portability. Sure, you can’t just drag an Azure VM into AWS and click "run," but migration tools and cross-platform strategies exist. You’ve got options. Investigate and test them.

In contrast, SaaS is a different beast. Ever tried exporting all your SharePoint data with full fidelity, metadata, workflows, permissions, and integration mappings? Good luck. With SaaS, you’re often at the mercy of whatever export functions your vendor provides. Microsoft 365 just being one example, of course. Everything is “exportable”, just figure out how to do it, how long it takes, and what (third party) tools there are available to make life easy. Also, keep an eye on the file formats of you destination platform.

And then there’s PaaS and serverless. These cloud-native favorites scale like magic, but they’re often so tightly coupled to one provider’s tech stack that migrating means rebuilding. Lock-in, anyone?

SLAs: The Devil is in the Details

Let’s talk about the least sexy, most misunderstood part of every cloud contract: the Service Level Agreement (SLA).

Here’s what most people miss:

• Scheduled maintenance doesn’t count as downtime
• Beta services aren’t covered at all
• Credits are capped at the monthly bill for that service
• You have to report violations yourself—and do it fast
• SLAs can change, sometimes without prior notice

That’s right. No lawyer, no lawsuit. Just a few dollars off your next bill and a mandatory  “Have a nice day.”

So when you build your exit strategy, build it with these realities in mind. Read the SLA like your business depends on it, because it might.

OK, So How Do You Start?

Here’s the rough structure I recommend, one I dive deep into in my book as well:

• Step 1: Assemble and Organize Build your team. Assign responsibilities. Create a central repository for all relevant documents, contracts, tools, and migration playbooks.
• Step 2: Map and Measure Document everything. Systems, apps, data, networks, roles, throughput, dependencies. The more detail, the better. Inventory is king.
• Step 3: High-Level Planning Identify potential exit triggers, rising costs, missed SLA targets, compliance issues. Define when and why you’d hit the eject button.
• Step 4: Build the Plan Create detailed exit paths for each major system and dataset. Include time, cost, and tools needed to execute.
• Step 5: Execute and Review Trigger your plan when needed. Communicate broadly. Secure your data. Verify deletion. Follow up. Document lessons learned. And yes—start crafting your next exit strategy.

Exit Strategies in the Real World

Take XYZ-Care Health Group, for example, a fictional healthcare organization I use in my book. They rely on Azure Virtual Desktop (AVD), an EHR system, and several cloud-hosted tools. Given the sensitivity of patient data and GDPR requirements, a cloud exit strategy isn’t optional, it’s essential.

Their plan outlines how to:

• Export and reimplement EHR data securely
• Maintain application functionality during a move
• Use encryption and safe protocols throughout migration
• Define scenarios that justify an exit (e.g., GDPR non-compliance, pricing hikes)
• Analyze Azure’s SLA nuances that may affect business continuity

It’s a proactive, controlled, and risk-aware approach. Which, if you’re dealing with patient data, is exactly what you need.

Important (key) Questions Worth Losing Sleep Over

1. Have you considered an exit strategy before going live in the cloud?
2. What cloud-specific dependencies are you secretly ignoring?
3. What role does compliance play in your organization, and how could an exit strategy help you respond quickly to changing laws and regulations?
4. Can you confidently migrate your mission-critical systems elsewhere, today?
5. How does your organization ensure that data and applications remain well-documented and portable, so a migration to another solution can go smoothly?
6. Are your current SLAs clear, fair, and enforceable—or just optimistic?
7. Is your team capable of executing a full cloud exit if disaster strikes?

If you can’t answer these clearly, it’s time to revisit your cloud strategy.

Final Thought: Cloud is Great. Lock-In is Not.

Here’s the deal: cloud-first doesn’t mean cloud-forever. It means flexibility. Agility. Optionality. Hybrid.

“Never get so busy with the cloud that you forget to make an exit plan.” – Dolly Parton (sort of)

Having an exit strategy doesn’t make you pessimistic. It makes you prepared. And in a world where cloud rules can shift overnight, that might just be your smartest move.

Make sure to get a copy of the Cloud Exit Strategy Cheat Sheet (PDF). Click on the image below to download your FREE PDF copy.