14 Must-Include Items For Your Windows 10 Servicing RFP

May I ask you a personal question? What is the hardest part about Windows 10 Servicing for you?

Based on talking to many of our clients and partners, I would venture to say your answer would focus on the scary "Unknown". It isn't the actual process of rolling each update out, because once you have an efficient, repeatable, and industrialized process, it will almost run itself. It also isn't the initial testing and evaluating as each new version becomes available in the Insider Preview.

Instead, for most IT managers and executives that I have talked to, the hardest part is the massive shift away from those massive one-off big-bang migration projects every two to three years and entrusting your entire IT estate to a still to-be defined Business-as-Usual (BAU) workflow using sophisticated automation and management tooling when you might not know what it looks like yet.

[This post is part of the "Definitive Guide To Windows 10 Servicing" blog series.]

It's scary because it is unknown. Here is the good news, though: You are not alone. Many organizations (large and small) are struggling to define how they intend to manage Windows-as-a-Service (WaaS) moving forwards. They must determine whether they will manage it within their Business-as-Usual team, run it as a specific project function, or set it up as part of an existing / new supplier arrangement.

No matter which path you choose, you will want to know exactly what you are searching for and what questions to ask when you get there. Today, I will walk you through how I would write a "Request for Proposal" (RFP) when looking for my future WaaS tooling based on dozens of RFPs I have seen over the last two years as well as my extensive experience in enabling enterprises to accelerate IT transformation. 

There are some key considerations you will want to make sure are built into the tooling and services, or specified at RFP:

1) Ability To Gather Inventory Correctly

In order to be able to know what is in scope, understand your readiness, and to kick off your process, you must first gather your inventory of users, devices, and applications accurately. You will want to look for an IT Transformation tool that can hook into your existing in-house infrastructure and technology (e.g., Microsoft Active Directory (AD), Microsoft System Center Configuration Manager (SCCM), Windows Upgrade Readiness and others).

In addition, be sure to get a tool that is scalable. We have seen it more than once that one business unit goes ahead and procures tooling that fits their current needs but isn't scalable for the entire organization — leading to multiple tools and increased licensing and maintenance costs.

2) Live & Actionable View Of Your Environment

Once you have gathered your inventory, it is mission-critical that your IT Transformation management tool keeps you in sync with your live environment. It won't be feasible to export your inventory data into an Excel spreadsheet or hand-cranked database!

You will absolutely need tooling that will allow you to add and remove assets as well as reflect other changes as you will need to make changes on the fly. This sync should happen real- or near-time on an ad hoc or (in larger organizations) on a scheduled basis (e.g., overnight).

3) Solve The Application Compatibility Conundrum

One of the biggest roadblocks enterprises encounter with managing their Windows 10 updates is application compatibility. Although downplayed by Microsoft as a non-problem, I know of no larger organization who would be comfortable to only test the recommended 1% of applications and just run with it. 

So, you need to look out for tooling that is able to support application compatibility feeds and/or integrates with third-party tools that will:

• Run your apps through a quick application certification workflow to determine which need further manual intervention and
• Provide you with automated application packaging and testing capabilities. 

After you have determined upgrade compatibility and possible upgrade paths (e.g., free/paid upgrade available), you will need to be able to use these as triggers. For example, if an application is compatible with the new Windows 10 version, its status should automatically set to "Green", which then in turn will move the dependent devices into a ready state.

4) Support Local Hierarchies

Another less obvious dependency that your tooling needs to support are department and location hierarchies. As you will manage your Windows-as-a-Service rollout with the help of deployment rings, you will have to ensure that you can spread or aggregate your scheduling risk as required into the appropriate deployment rings. This will also allow you to regulate capacity management. 

5) Allow Multiple, Simultaneous Projects

In contrast to big-bang migrations, your WaaS management process won't be beginning and ending at a set time. This means you will have to manage multiple BAU streams at the same time. For example, in addition to running three to four Windows 10 Servicing initiatives at once, organizations will also need to manage Office 365 updates twice a year, refresh their hardware based on the individual's device lifecycle, roll out new applications, and much more.

Therefore, your tooling must support multiple, simultaneous projects. But beware — you will want to find a tool that gives you efficiency savings by managing all initiatives together in one tool rather than simply allowing parallel projects that don't interact!

6) Utilizes An Industrialized, Repeatable Project Framework

We have mentioned above that it is absolutely essential to the success of your project to create an industrialized and repeatable process framework — otherwise you will not be able to keep up with the high project/process velocity of change this requires, resulting in business users on unsupported devices!

You will need a tool that allows you to quickly define the basic rules (such as specific deployment ring enrollment criteria, capacity restraints, and milestones/tollgates) upfront and refine them with each iteration. Here is where you will also set up any automated project email communication and self-service capabilities. 

7) Default Asset Grouping 

Managing your Windows 10 Servicing process by using deployment rings will enable you to manage staggered and parallel trenches and work streams, saving you time and resources. But in order to be able to manage your estate efficiently in deployment rings, you will first need a tool that allows you to onboard and manage default grouping of assets.

8) Support Application Rationalization 

One of your main goals should be to increase efficiency and find potential for rationalization with each iteration. Therefore, your tooling should be able to support application rationalization per project (i.e. keep a version for Windows 10 1709 but upgrade it to a new version for 1803). This will help you keep your application inventory count as minimal as possible while ensuring that all applications are up-to-date, supported and properly licensed. 

9) Ability To Manage Asset Readiness

Knowing when your asset is ready is key in running a smooth and efficient WaaS process. Your IT Transformation management tool therefore must be able to manage your asset readiness, including applications, computers, users and technical tasks, within an automated workflow and be able to be triggered by external and internal objects or milestones reached. 

10) Capacity-Restrained Scheduling

Given the velocity required for this type of activity, it is important not to overload either the network, the service desk, or your scheduling team with too many deployments in a small time frame. On the flip side, you also don't want to pay for under-utilized resources! To make this process as streamlined and smooth as possible, look for a tool that supports capacity-restrained scheduling. This way, you can define capacity rules based on your unique project situation as well as adjust your scheduling depending on suddenly open capacity slots to get to the finish line even faster. 

11) Automated Email

To run such an intensive process successfully, you will not only need your users' buy-in but also their active participation. The best ways to do that are to increase transparency with clear and timely communication and communicate individual responsibilities and set expectations as they occur,

However, a project of this size can easily require a handful to a dozen emails each cycle, resulting in tens or even hundreds of thousands of emails. So, be sure your tooling provides an automated email communications engine for end users (possibly in multi-language) where you can schedule emails that get automatically triggered based on a T-minus schedule. 

12) Self-Service Capabilities

In addition to automated email communication, you can boost user engagement by providing them with sophisticated, yet adaptable and intuitive, self-service capabilities. This way, your end users can volunteer for an earlier migration slot, select a device from a pre-selected list, validate data, and much more. 

13) Real-Time Reporting

To wrap it up, one of the most important features your management platform can provide you with is real-time status dashboards. While your team can all have access to the same detailed project data on the scope and past vs. current vs. projected progress (one version of the truth), your business unit managers, executive management, and other stakeholders can get real-time insights at a click of a button — something that used to take hours or even days!

14) Ability To Clearly Scope Your Service Requirements

If you are planning to outsource your Windows 10 Servicing to a third-party supplier or service integrator, you will need a way to clearly scope your requirements. In other words, you will need to know which components you want the partner to manage:

• Build/image certification/creation,
• Application compatibility,
• Application rationalization,
• Application testing,
• User Acceptance Testing,
• Scheduling / deployment ring management,
• Business communications and/or user communications,
• Update deployment, as well as
• Reporting and PMO.

Without this data, you will almost buy a big black box and be at the mercy of the service provider. While a lot of service integrators have helped many other enterprises set up and manage this process before and aren't "out to get you", every situation is different and it is advisable for both sides to know what the facts are to make precisely informed decisions.

You could simply make it a requirement for the project to utilize the IT Transformation Management tool of your choice as part of the project. The benefits here are that you will have absolute transparency into the project at all times, you own the data and the process, and you can choose to bring as little or as much of the process in-house as you like!