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10 Steps For A Successful Windows 10 or Office 365 Migration Using A Service Integrator

Last week, we spoke about how to negotiate a successful Windows 10 or Office 365 migration deal with a service integrator. But what happens once the contracts are signed? Should you sit back and let them take the reigns completely or is there something you can do to ensure the success of this project?

Some enterprises assume that because they just hired an expert organization to take this project off their hands, they can simply drop the ball and let the integrator pick it up and run with it. But while your outsourcer brings a tremendous value to the table, it is completely unrealistic to expect that they will do the best job possible without associated input from your side.


That is why I want to walk you through some key considerations and things you can do to ensure your outsourcer delivered project is set up for success. Below you will find some of the high level activities that we advise to ensure you retain control of the budget and workload.

  1. Create A Dedicated Internal Team
  2. Formalize Roles, Responsibilities & Deliverables In A Service Level Agreement
  3. Decide On The Right Tooling (Single Version of Truth)
  4. Define KPIs & Metrics
  5. Understand The Project Scope & Capacity Limits
  6. Decide On Collaboration & Communication Guardrails
  7. Be Aware Of Any Interdependencies
  8. Remain In Control & Provide Support Where Needed
  9. Don't Forget About Project Wrap Up & End User Training
  10. Keep Future Update Management In The Back Of Your Mind

Let's have a look at each of those points in more detail:

1) Create A Dedicated Internal Team

The first thing you want to do is to create a dedicated team of skilled people who will collaborate with the outsourcer on this project. Depending on your project and your organizational structure, roles for this team might vary, but at a minimum you need business liaisons, project managers, and executive stakeholders to represent your side. 

Even in this first step, it pays off big time to sit down with the project or account management team from the SI side and map out all roles and responsibilities on a matrix. Include what your internal team will be doing versus what tasks and responsibilities will be handled by the external team, as well as how those two entities are going to interact.

2) Formalize Roles, Responsibilities & Deliverables In A Service Level Agreement

This is one of the most common pitfalls! Once the project is outsourced and the SI says, "I need X, Y and Z", the customer says something like: "Oh well, we’re too busy, so we can’t provide you with that right now." And just like that, the SI is operating with one hand tied behind its back from the onset of the project.

To prevent that from happening, you need to formally define responsibilities and deliverables in a Service Level Agreement (SLA). This often-ignored, but absolutely critical element of success is basically a contract between your internal and the outsourcer team that maps out the project engagement framework. This should include the timeframes in which you expect to operate for decisions and information exchange, and the escalation process for non-delivery on either side.

Keep in mind — whilst you have procured a service, you must still remain accountable for the delivery internally. Basically, you can’t expect an outsource provider to come in, not give them any information or help, and run this project efficiently. This has to be a partnership or it’s never successful.

3) Decide On The Right Tooling (Single Version of Truth)

The next step is to build a collaborative plan. No matter what you’ve outsourced, which pieces you are doing internally versus external, and how you’re going to prioritize, the key here is making the data transparent and being able to work in a common platform.

Using an IT Transformation Management Platform, such as Juriba Dashworks, as your tool to extract, consolidate, normalize, and rationalize all your relevant data as well as a central command and control center, all members of the team can be looking at the same sets of data. This way, there is no blame-shifting or finger-pointing should something go awry, and you can both agree a collaborative plan based on data.

If you don't already have tooling in place, make sure you’re asking your SI what tooling they’re bringing in as part of this project, and whether you can keep it afterwards. Since both Windows 10 and Office 365 will need continuous update management after the initial migration, you will want to consider that when choosing your tooling.

Alternatively, you can purchase your tooling before outsourcing and ask the SI to run with the platform that you’re using so you can keep more control of the project. If you are planning to purchase a migration management platform ahead of time, be sure to communicate that early on to your SI!

4) Define KPIs & Metrics

Having a great set of project data is one thing, but using it to effectively prioritize and manage your different workstreams is quite another, especially when you need to track the efforts of your outsource partner. That is why you will need to define and agree your shared metrics and key performance indicators (KPIs). This could be the number of application packages coming through the factory, total readied users by business unit, weekly deployment progress, and much more. For a complete list, please check out our ultimate list of migration KPIs.

Remember to set up your KPIs and metrics collaboratively with your outsourcing provider and as early as possible so that you know whether you are succeeding or failing and whether you’re on track or not. This also gives you a common platform from which to measure delivery on both sides of the fence.

5) Understand The Project Scope & Capacity Limits

Now that we understand the framework, roles and responsibilities, and we have our KPIs in place, we are ready to think about the delivery mode. Here is where you scope out your project and categorize your hardware, software or mailboxes based on your previously defined criteria.

Since you will be using a data warehouse driven IT Project Management Platform, you and your SI can set up overarching program rules on the data to define the work that needs to happen. Work with your Service Integrator to understand their capacity, e.g., how many users, devices or mailboxes can they manage per night?

6) Decide On Collaboration & Communication Guardrails

Something a lot of teams will take for granted (and, as a result, later run into massive problems) is how EXACTLY you will be communicating and collaborating with each other. For example, will there be real/near-time updates from everyone in the same tooling? Will you own the tooling but the outsourcer inputs data via CSVs? Or the opposite of that?

7) Be Aware Of Any Interdependencies

Understanding how the collaboration is going to work from a tooling perspective is important — but you also have to know when to expect that key dependencies are going to be met.

For example, if you have to upgrade your Config Manager in every site, understanding when that’s going to happen is obviously going to have a key impact on when you can deploy. Similarly, if you’re creating a new Golden Windows 10 Image, you need to know when that image needs to be completed by. Once those key milestones are in place, you can start building your plan off the back of that. Again, which pieces are in scope for which party, and the ability to track that activity centrally will be critical to any scheduling plans you may have.

8) Remain In Control & Provide Support Where Needed

Now that your project is setup, your guardrails and metrics are defined, and both parties know when to expect what from whom, it’s all about efficient management and control. It is your responsibility to stay on top of your outsourcer to ensure that they are getting through the number of applications and deployments they need to, and that there’s enough support internally to make that happen.

9) Don't Forget About Project Wrap Up & End User Training

Something that is often an after-thought but greatly contributes to the perceived success of the entire mission is your project wrap-up, end-user handover and training. While it is exciting to think about how to get big numbers on the board, we also need to think a step ahead. Who will handle each of these tasks? Who will interact with the end users and how? How will the communication be handled and can it be automated? Who is responsible to close out the project? Asking those and other questions now will avoid being rushed later. 

10) Keep Future Update Management In The Back Of Your Mind

Both Windows 10 and Office 365 are Software-as-a-Service products, which means they will receive updates twice a year that need to be rolled out similarly to this initial migration project. Since the process is almost exactly the same and you will need the same tooling and similar, even if fewer, resources, you should keep that in mind as you are going through this project.

If you’ve worked well together and you’ve gotten the right platform in place, you could consider addressing this with your service provider. Otherwise you’re going to have to reinvent the wheel.


Outsourcing your Windows 10 or Office 365 migration to a service provider can be tricky as you are handing over a lot of control to a third-party. Your team will have to work with an external team they might not yet know, possibly introduce new tooling, and different project management methods. There are hundreds of things that could go wrong if this relationship is not managed appropriately.

While you won't be able to prepare for all eventualities, you should prepare for those that are the most common pitfalls and have the highest impact in terms of business disruption. Large IT migration projects are notorious for going over budget or taking much longer than initially anticipated, so how you plan for managing the initiative can have huge benefits. The devil is in the details and only strategic planning, a methodical approach, and a centralized command and control center providing everyone with a single version of the truth will allow you to stay on top and in control. 

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