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Let me ask you a question: Are you planning to go it alone on your Windows 10 enterprise upgrade? 

If you are like most people in the early planning phase that we have talked to in the past 12 months, you're probably thinking it will be easier than Windows 7, but you are not sure exactly how much work it will take. But is it really as simple as this for your organization? Should you head down a DIY route alone because it is all going to be such a non-event?

Microsoft is touting the ease of migration everywhere! Maybe you read the success story about Microsoft's IT team rolling out in-place upgrades to 96,000 people in less than ten weeks. Or perhaps you looked into the Microsoft FastTrack marketing materials that describe a transition to the new operating system as a simple switch with very little to no application compatibility issues or hardware restrictions. But should you believe this easy-upgrade-hype? 

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Well, the reality is that your organization probably can't achieve the same sort of velocity that Microsoft did.  Rolling out Windows 10 across tens or even hundreds of thousands of end users in your organization within a matter of weeks may be completely unrealistic — for many reasons:

  • Application Compatibility. The average enterprise Windows 10 rollout touches about 1,500 applications — of which only 25% are compatible out-of-the-box. 18% are incompatible, 44% are end-of-life, leaving 13% as unknown (no information available because they are in-house built or vendor no longer exists or has provided any compatibility statement).
  • Lack of Internal Resources. Over 20% of enterprise IT migration teams struggle with internal resource constraints. Since OS migrations have traditionally been big bang projects, the availability of in-house skills and manpower for managing this transition fluctuates. 
  • Budget Concerns. The average migration cost per device greatly depends on your migration methodology and tooling, but can lay anywhere between $493 to $693 per machine. About 15% of IT professionals see that as their biggest roadblock.
  • Project Length. Equally important to the budget constraints is the time it takes for this project to finish, as this can take an average 10,000 seat enterprise anywhere between 44 and 124 man weeks.
  • Lack of Internal Skills. Hiring the right IT migration skill sets off the street can be a lengthy and involved process, and some organizations will look to system integrators to fill that void. 
  • Executive Buy-In. The least-named, but nevertheless critical roadblock is a lack of executive buy-in. Without the top down support of your executives, it is hard to bring your business colleagues along on the journey.

(For further details on Windows 10 migration roadblocks and how to avoid them, check out this article.)

DIY Approach To Windows 10 Migration?

Recently, we have had a lot of customers mention that they are considering a Do-It-Yourself approach to this Windows 10 upgrade, largely because Microsoft marketing is claiming this to be the easiest rollout in the history of their operating system. Despite the issues you have seen many times before, and no matter how you managed OS upgrades in the past, they believe this time will be significantly easier.

But how do you avoid those DIY disasters that so often occur? Is it really easy enough for you to consider the DIY route? Having helped enterprises around the globe ready more than five million devices for successful migration, we have seen prospective customers attempt to go it alone dozens of times. Unfortunately, when we get involved, a program is often in recovery mode because DIY simply has not worked.

So, why is DIY so often a path to failure? Let's think about how you would decide whether you would complete your own home improvement. Going it alone is kind of like remodeling your kitchen or renovating your bathroom by yourself. It is a big job, but if you have the necessary experience, manpower, tools, time and knowhow to do so, you will probably be just fine.

However, as with most complex DIY projects, you will likely hit snags along the way. Maybe you find a rotten subfloor as you pry off your old one. Maybe there is mold, or you find carpenter ants, or even electrical or structural issues that have not previously been obvious. But you never know until you start. By the time you have understood the real scope of the work, you could have already spent a fortune on rectifying the basics, which practically guarantees that your project is already behind schedule and over budget.

To ensure that your DIY project doesn't turn into something worth turning into an episode of the BBC TV show "DIY SOS", we would like to take you through the major pitfalls to look out for, so you can be sure that you have covered all these concerns before setting out on your own. Ask yourself these questions:

  • Can I do it myself — do I have the skills?
  • If I can do it myself, do I have the right tools, resource availability and time to do it?
  • If I am doing it myself, how do I know that I am doing it correctly, or in the best way, and not leaving further work for later down the line?
  • Once I have done it myself, how can I ensure that I am positioned for simpler transitions next time?

Click here to download the Windows 10 Project Plan Template

If you are happy that you can tick off all of these items, here are some things you can do to avoid a DIY disaster.

5 All-Too-Common DIY IT Migration Pitfalls To Look Out For

While there are other roadblocks you might encounter when tackling your unique Windows 10 rollout, I want to focus on the five most common pitfalls that large organizations encounter when approaching a migration project in DIY mode:

1) Lack Of Internal Skills To Successfully Manage IT Migration

If you read the Microsoft marketing material around the planning, discovery, packaging, and scheduling of your planned migration, you could question whether you even need a proper migration project team, business liaisons or indeed any project methodology. They pulled off their own migration within nine weeks as an "in-place upgrade that maintained productivity and offered a consistent user experience" — so why can't you, right?

However, we have to remember that the Microsoft deployment probably doesn't reflect how you would roll out Windows 10 to your enterprise. Their methodology is essentially to make the OS available to their workforce and leave them to upgrade themselves. This requires no project management skills, or any of the rigor that you would usually associate with an enterprise level IT migration. Each user is effectively on his or her own.

But you will likely want a much higher level of control on your scheduling and user experience. You may not want to deliver an in-place upgrade because you want to switch on some of the more secure features, decrypt your laptops, or find that your PCs cannot support this method at all. So before you decide on going solo, ask yourself: Do I have the information I need to help my users upgrade? Do I have the internal skills to build and execute an IT migration that spans all of my business departments? Do I know how to best approach and deliver this upgrade experience?

If you were starting your home improvement, you would make sure that you knew what you were doing, or could at least call in the necessary skills. If your job requires some plumbing, you need to have plumbing skills or call in a plumber! It's the same for IT migration — you need a team of skilled resources to achieve project delivery. Read up on what's required, and then decide whether the capability exists in-house or if you need to bring some people in.

Red Flag! The telltale sign that your project does not have the right skillset is that it has been running a few months and you are without a proper plan, process or prioritization matrix. You are spending money but there is a distinct lack of progress.

2) Adequate Tooling

One of the most essential success factors in an efficacious migration project is your tooling. You wouldn't start any home improvement without buying the requisite tools to do the job. For DIY IT migration, it starts in the discovery phase as you are trying to get an accurate view of what you are dealing with. You need to know what state your IT landscape is in. For example:

  • Achieving an accurate inventory
  • Understanding hardware age and compliancy with the Windows 10 requirements
  • Knowing which of your applications are compatible out-of-the-box, have a forward-path, or need further testing

In addition to the discovery, you will need to manage your project with a command and control tool that allows you to not only get an accurate view of where you are (single source of truth) and how much progress you have made, but actionable insights into your planned vs. actual project delivery items.

In addition to project management and command and control, you also have to consider your deployment and application management. How will you group devices, users or locations into deployment groups and so on? Handing around dozens of out-of-date spreadsheets or hand-cranked databases will lead to instant chaos as they are inadequate to handle projects this complex.

In home improvement terms, it's about understanding the requirements for the job, ascertaining the tools that you need, and building a proper plan of action that you can manage. After all, you wouldn't (or at least shouldn't) start knocking down a partition wall before you have determined whether or not it was load-bearing! Equally, you wouldn't take a small hammer to the job — you would need the proper equipment.

Red Flag! If your project team cannot answer questions about 'how' your organization is going to deliver their migration plan, you are likely to be in DIY disaster territory.

3) Communication 

A big home improvement project generally involves some external expertise that has to be scheduled and monitored — maybe a builder, electrician or plumber. Communication with these individuals is important because it ensures that you get the job you wanted done and it is essential to achieving a complete project.

Anyone who has been part of an IT Transformation management project before knows that effective user communication and training is absolutely critical to the success of your migration. Without the user's buy-in and adoption, you will receive a lot of push-back, which can negatively impact project perception!

If you decide to take the DIY route, you must ensure that you have a plan for managing and tracking your user communication across multiple channels. Even if your entire rollout process only requires 5-6 emails, consider tracking those across 50,000 users — you could be sending over 300,000 emails! And that is without any rescheduling!

You should also consider a self-service component which, for example, allows your end users to volunteer for early migration, validate data and application usage, enter out-of-office dates and much more — leading to a faster and more efficient migration.

Red Flag! If you have to employ dedicated communications resources, or are struggling to keep up with the volume of scheduling, then you are not managing this project as effectively as you could be.

4) Dependency Tracking

Most home improvement projects involve a complex sequence of events that often have dependencies. For example, you can't put a new shower unit in if the plumbing and tiling has not be done ahead of time.

The same is true for asset migration readiness in IT migration projects. You cannot migrate a user or device until all of the dependencies have been met. 

By going down the DIY route, you need to ask yourself how you will be handling and tracking all dependencies, such as devices, users, locations, departments, procurement, and so on. Even with only several thousand end users this becomes an unmanageable monster if you are using spreadsheets!

Without a method and tools to efficiently track dependencies, you may end up in the costly situation of having tradesmen turn up at your door and be unable to do any work!

Red Flag! If your project is continually rescheduling user migrations, or your project team is passing around lots of spreadsheets, it is likely to be out of control and headed for DIY overspend.

5) Application Compatibility & UAT

How often do we test our home improvement properly before we let our tradesmen off site? Not enough is the common response. We often want the job completed as quickly as possible, but then suffer the snag list consequence. And the same is true of IT migration. If we rush ahead to get deployment numbers without the corresponding due diligence on the environment that we are provisioning, then we are headed for a huge end-of-project snag list.

As a DIY IT migration house, you need to address the concern of application compatibility and user acceptance testing. Despite Microsoft's claims that this isn't an issue with Windows 10 anymore, more than 1 out of 3 IT project managers name application compatibility their biggest obstacle! In many cases the app might work, but it might also be out of support, or need repackaging to a new format like AppV. First, you need to be able to determine which applications are compatible, which have an upgrade path, which are incompatible and which applications are unknown and need further testing. Only then can you go ahead and put together a plan of how you will deploy your devices.

The DIY migration horse often falls early in the race when the project manager is overburdened with application work.  It takes its eye off the fence and unseats its rider. To ensure that you stay on your DIY horse, you need to surround yourself with tools that can help manage the app testing with you.

Red Flag! If your project team cannot quickly identify the applications in scope, the migration path for each of them, and the impact that each one has on your deployment plan, there is likely a DIY disaster ahead!

Don't Turn Your DIY Project Into A Case For 'DIY SOS'

In conclusion, don't be discouraged to go ahead and roll out Windows 10 in-house. It is very much possible, and we have seen some excellent success stories. But, before you start, think of our home renovation example. You wouldn't undertake a project like a kitchen remodel with a hammer and a box of nails. You must have the right tools, skills, and framework in place — or you'll hit the wall at some point and will have to call in the experts to fix the mess, which will cost you a pretty penny.

For those considering a DIY route, you could do a lot worse than look towards Juriba Dashworks as the platform from which to control the Windows 10 migration project. 

If you want to learn more about how to accelerate your DIY Windows 10 migration by using Juriba's Enterprise IT Transformation management tool, download our eBook below:

Click here to accelerate your Windows 10 Migration ebook

Barry Angell

Written by Barry Angell

Barry is a co-founder of Juriba, where he is focused on using his experience in IT migration to help drive product strategy, pre-sales and service delivery. He is an experienced End User Services executive that has helped manage thousands of users, computers, applications and mailboxes to their next IT platform. He has saved millions of dollars for internal departments and customers alike through product, project, process and service delivery efficiency.

Topics: Windows 10/Desktop Migration