Almost two years ago, we published an article called "How To Staff Your Windows 10 Migration Team Properly" which walks you through the required team member roles and necessary skills for your Windows 10 Transformation project. Now that a significant number of enterprises have at least begun, if not completed, their migration, we thought we should have a look at how your team roles need to change to adapt to a continuous Servicing Update management model going forward. For many, this function will be assimilated into the Business As Usual team, a change which could have major impacts if not managed correctly.

For decades, large IT Transformation projects have been planned using manual spreadsheets or hand-cranked databases. All required steps were neatly visualized in a massive MS Project Gantt Chart — of course, with buffers built in right from the start because we knew there would be delays. We also knew that the real project devil would be in the asset readiness detail, something that couldn't be managed in a Microsoft project plan. However, we would still spend an exorbitant amount of time updating our scorecards and spreadsheets even though they would inevitably fall apart entirely at some point. It was slow and inefficient.

Now, with the Windows 10 Servicing model and its fast and continuous update cadence, attempting to manage thousands of readiness activities in multiple spreadsheets is useless because managing Windows-as-a-Service is more like juggling hundreds of balls at the same time. Not only do you have to keep the current release balls up in the air, you have to keep your eye on the future balls coming at you just as quickly!

In November 2015, I calculated the per device cost to migrate from Windows 7 to Windows 10 — a whopping $693 per seat for a manually delivered migration using spreadsheets or hand-cranked databases!  In comparison, Gartner had quoted somewhere between $1,035 and $1,930 per user depending on the level of desktop management in place, and Forrester estimated $1,000 as the average expense. 

With Juriba Dashworks software, we were able to reduce this figure significantly (on average to $493 per seat). While our Win 7 to Win 10 calculation was based on a hypothetical 10,000 seat migration project, it was built from real-world experience of having helped enterprises ready millions of devices for migration.

As companies move to continuous upgrades rather than big bang migrations, the focus of these calculations shifts as well. This week, Gartner has been first to market with a new cost model, the so-called "Windows 10 Feature Update Cost Model", which is available for purchase for $7,500 on the analyst company's website and consists of an Excel spreadsheet and an accompanying report. It outlines how the ongoing maintenance cost compares with the big bang migrations of the past. The goal is to allow large organizations to estimate the costs and labor requirements involved for managing one or two Windows 10 Servicing cycles a year.

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Over the past few years, we have seen our fair share of failed and dangerously inefficient enterprise attempts to keep Windows 10 and Office 365 servicing up-to-date. Often, the organization took longer than anticipated to run through the first initial migration, skipped an update to come up for air, just to drown under the workload of the feature update roll out, for which it had vastly underestimated the risk and work effort. Ever worse, these updates are often managed manually, with antiquated and inadequate project management practices!

TL; DR: In an attempt to slow down the pace of the required Windows 10 feature upgrades and to alleviate some of the pain, some enterprises have gone down the slippery slope of skipping every second update release. But while the approach makes sense on paper, unless delivered with great velocity, it potentially exposes a large number of business users in later broad deployment rings to being upgraded only after the to be upgraded version has reached its end-of-life. If this wasn't scary enough, add in the risk of Microsoft delivering the new update later than expected and we have quite a management headache to solve. 

(This article is part of an extensive blog series "The Definitive Guide To Windows 10 Servicing".)

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Over the past few years, we have seen our fair share of failed and dangerously inefficient enterprise attempts to keep Windows 10 and Office 365 servicing up-to-date. Often, the organization took longer than anticipated to run through the first initial migration, skipped an update to come up for air, just to drown under the workload of the feature update roll out, for which it had vastly underestimated the risk and work effort. Ever worse, these updates are often managed manually, with antiquated and inadequate project management practices!

If you recently tried to find anything on Microsoft Office — for example on the enterprise section of Office.com — you might have noticed that there isn't much mention of Microsoft's on-premise productivity application suite anymore.

The vast majority of Microsoft's marketing communication and sales conversation is about Office 365! This is not an oversight or a temporary marketing campaign — but rather a strategic push to move enterprise customers away from the perpetually licensed Office fat client and onto the subscription-based, always up-to-date Office 365. Moreover, now that Office 2019 is about to be released, many enterprises are asking themselves: "Should we consider Office 2019, or is it not the right time to switch to Office 365 ProPlus?"

Rolling out Office 365 can be very exciting considering the value it will add to your organization in terms of unified communication, collaboration, and business processes! But it can be equally terrifying if you think about all the dependencies of users, mailboxes, delegates, mail archives, public folders, groups, instant messaging, ... the list goes on and on.

After the initial migration is completed, Microsoft will release two larger Office client feature updates and monthly security updates to increase productivity for your end users and tighten security. However, just like Windows as a Service, these larger feature updates will need to be rolled out effectively as they can also be considered a mini-migration.

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.

On January 14th, 2020, the extended support for Windows 7 ends, which means that enterprises have about 26 months to fully roll out Windows 10. Similarly, Microsoft expects that at least two-thirds of its Office business customers will move to Office 365 by fiscal year 2019. Since a migration project of that size will take, on average, more than 124 man weeks to complete, it is about high time to get serious about upgrading!

According to our own research, only 44% of organizations are set on managing this IT Transformation internally; 28% are about to issue a Request-for-Proposal, 14% have not decided yet, and 14% have already engaged with a service integrator to outsource this massive project.

I don't know about you, but I don't know of any single enterprise-size organization that does not do some formal application compatibility testing as they roll out a new OS — except one: Microsoft.

According to a webinar, Microsoft's application portfolio consists of 1,650 applications, 96% of which are browser-based. That leaves them with about 250 business critical apps, but surprisingly the company hasn't undergone a formal app compatibility testing program since rolling out Windows 8. Instead, the software giant has been able to roll out at least four Windows 10 versions to 95% of its full-time employees in less than nine weeks by running a 20,000 device pilot phase in which issues are tracked through the help desk, Feedback Hub, and Yammer before rolling it out company-wide. 

If that makes you feel a bit queasy (or full-blown anxious), stick with me as I walk you through what choices organizations have to manage their application packaging and testing efforts in an Evergreen IT mode, what the prerequisites are for doing so successfully, and what an optimized process would look like. At the end, I will also include some general pointers to keep in mind.

In the past week, Microsoft asked me to speak at the Windows Partner Deployment Day about the infrastructure, project management & readiness support for effective Windows-as-a-Service deployments. Juriba Dashworks consumes and enhances the valuable Windows Analytics and Upgrade Readiness data feed with a robust command and control system to help manage Evergreen initiatives. 

We also spoke a lot about AutoPilot and Microsoft's "Modern IT Management" agenda which the software giant has been pushing for the past three years. The premise is that strategic-minded IT teams strive to increase user productivity and security on any device while contributing to the company's bottom line by driving Digital Transformation and innovation — but they are met with constant challenges, such as more sophisticated cybersecurity threats, disruptive business models, and consumerization of IT. This leads IT to having to do more with less — and one way to do so is to move more applications and infrastructure into the cloud which often requires a different IT management approach that enables them to manage any device with almost zero-touch. 

2018 started with a bang for those in cyber-security — and almost everyone else running a device that uses an Intel, AMD or ARM chip made from the mid-nineties till today. News broke (and spread like wildfire) that three security flaws, named Spectre (Variant 1 and 2) and Meltdown, could be exploited by ransomware and other malicious code to extract sensitive information by utilizing the chip's way to speed up processing. 

The intricacies of how this works and why this has not been made known before have been discussed at large by much bigger cyber-security experts than myself. After giving you the must-know facts about Spectre and Meltdown, I'd much rather focus on who's affected, how to fix it, at what cost, and how to prepare for the future when other decades-old flaws are found.

If you ask a bunch of different CIOs what is the biggest barrier to achieving his/her goals, you will likely hear the same answer: the current IT skill gap! 

However, this isn't as simple as the IT skill gap that the industry faced in the past 2 decades. For twenty years, we encouraged young men and women in universities around the globe to learn about Object-Oriented Programming, Network Technologies, Web Services, and Service-Oriented Architecture, and within a few years, there were plenty of programmers, network specialists, and other IT professionals available to satisfy the demands. 

In 1876, a plant new to the United States called Kudzu, was introduced at the Japanese Pavillion at the Centennial Exposition in Philadelphia. Due to its fast growth, the Soil Conservation Service encouraged farmers to plant Kudzu as a ground cover to prevent soil erosion during the Great Depression.

If you look at how IT traditionally spent its investment dollars, there would be a distinct requirement for a positive return on investment by the end of the first three years. Many were long-term IT investments that would determine how you would operate in the next ten to twelve years, and resulted in the definition of many established IT management practices.

But those ancient IT processes and policies used to manage legacy apps are inadequate to handle modern technology updates. Today, most enterprises are much more agile, having moved applications into the cloud, or utilizing the power of Software-as-a-Service. However, most are still maintaining a layer of dinosaur legacy applications and other mission-critical on-premise software in massive data centers. Since most IT organizations are unable or unwilling to change how they manage IT, they still use IT processes and policies that date back more than twenty years!

The quality of customer service has a massive impact on how consumers interact with the service provider — whether that provider is an internal department, an outsource partner, or a company providing goods and services externally. Studies have shown that one out of two customers will stop doing business with a company because of a poor service experience.

That is why most consumers, 71% in fact, prefer firms that give them the ability to solve most service issues on their own. While this might not surprise you, it might shock you to know that an astonishing 38% of consumers would rather clean a toilet than speak to a customer service representative!

This article was also published on The Technology Record magazine here.

You know you are in a pickle when you are six months into your migration project and you still haven’t gotten any numbers on the board. As the responsible project manager, you are frustrated. There are a thousand questions running through your head: What went wrong? Where did the time go? What can I do to get this back on track? Is there a way I can accelerate this to get back on schedule? Should I increase the number of resources dedicated to this project?

Throwing more people at it certainly seems like the right thing to do. After all, you need to be seen to be doing something! This is the route that many a project manager has trodden! But what most project managers have come to realize after the fact is that throwing more people at it doesn’t always translate into a faster project. Only automation and appropriate tooling will do that.

When it comes to technology, one thing is true: change is constant. In fact, technology today is changing faster than ever before. It changes the way we pay, shop, interact with other people, and even how we work. For businesses, this means they have to adapt — and fast — to exceed their shoppers' expectations by providing an outstanding omni-channel and digitally supported customer experience. Companies across all industries have to constantly push the innovation envelope to reach new customers and keep existing ones from wandering off to the competition. 

Despite the political and economic uncertainties within the past 12 months, CEOs around the globe are prioritizing growth (58%) — a huge jump from last year's 42%.  These growth innovations to improve customer experience and save costs are commonly known as "Digital Business Transformation" and often target a plethora of opportunities to outpace your competitors and reap untold savings. But achieving successful transformation is a journey full of potential roadblocks. In this blog we look at what those roadblocks are, and how to avoid them.

Getting a new work PC should be a “magical experience for an employee,” as it shows the employee that he or she is valued and that the organization is investing in his or her productivity and user experience — at least according to Microsoft's marketing material. You might think that this refers to working in Windows 10 or Office 365, but the software giant is taking it even one step further: to the unboxing of a brand new PC! 

Microsoft recently announced a new zero-touch, self-service deployment service called AutoPilot. It sets out to empower IT to customize the Windows 10 out-of-box-experience. This announcement does not come entirely unexpected as the last Windows 10 updates already included enhancements and improvements to prepare for this step. 

Also part of the announcements were exciting Mobile Device Management enhancements as well as the new Device Health features (agent to optimize UX on Windows) in Windows Analytics. 

In the last few years, enterprise IT departments have faced a unique set of challenges: On the one hand, they have morphed from a supporting entity to a business enabler, and are maintaining increasingly complex IT landscapes whilst battling significantly larger cyber security threats than ever before. On the other hand, they have to manage more change with fewer resources and stagnant or minimally-increasing budgets.

A few weeks ago, we spoke about the Digital Workplace and how it came a long way from being an abstract concept that a lot of companies saw value in, but did not have the technology to support their needs properly, to becoming a reality for a lot of enterprises as they embraced server-hosted virtual desktops.

As organizations are now embarking on their Windows 10 migrations, as well as considering Evergreen IT as a long-term IT goal in order to become more agile, scalable and flexible, Virtual Desktop Infrastructure is experiencing a technology-induced revival. It's been a much slower adoption than many analysts expected, but more companies are now virtualizing desktops than ever before!

Gartner expected the hosted virtual desktop market to grow to 76 million users by the end of this year. And it seems the growth is not slowing down anytime soon. Most analysts forecast anywhere from 8.9% CAGR (IDC for the entire VCC market) up to 27% (depending on the analysts' definition of VDI) during the period 2016-2020. 

As more and more enterprises are starting to embrace Virtual Desktop Infrastructure to save costs, tighten security and improve manageability and compliance as well as give their employees more device flexibility and accessibility options, many fail to consider the generational change in the workforce that is happening right now. 

Traditionally, User Acceptance Testing (UAT) is performed at the end of a long software development cycle by the intended audience under real-world conditions. By then, engineering has performed a battery of technical tests to ensure the software works as expected. However, in some cases, engineering's understanding of the business requirements and user needs versus what the user was actually looking for are two very different things. This is where UAT usually comes in.

Today, we are wrapping up our 3-part blog post series about Evergreen IT by taking a closer look at software catalogs.

(If you have missed the previous blog posts you can find them here: Software Asset Lifecycle Management - Dream or Reality as well as How Important Is Application Normalization For Your Next Windows 10 Migration And Evergreen IT?)

As your organization evolves, and demand for business flexibility increases, the proliferation of applications each end user works with tends to grow in volume as well. Consequently, your IT department works to cope with an increasingly complicated application environment, and you begin to dream of initiating a Software Asset Lifecycle Management project that will bring order to the chaos. 

What’s the name of that application Employee A is running on her desktop? Is it the same as the similar title running on another computer by Employee B in a nearby department? You cannot get an accurate idea of how much software you have deployed if you don’t know the names and locations of each installed application.

If software is not named consistently, you might see one copy that includes the name of the vendor and another that has a truncated or abbreviated version of the same name, or a different vendor entirely (think Macromedia and Adobe - both now Adobe Systems). It might seem like you have five applications when actually you only have five names for the same thing.

A stressed out, harried IT department is a sign that your organization has bitten off more than it can chew. There’s no need to have circumstances lead to the point where your IT professionals are pulling out their hair in frustration and growing ragged from lack of sleep because of the burden that comes from launching one big bang project after the other.

Instead, gradual, incremental changes to your mission-critical software assets will be much more effective and will help your organization stay on track. Many larger organizations have recognized this not only as a possible way to gain a long-term competitive advantage but also a way to significantly cut cost and resources. 

In this 3-part series, we are exploring vital stepping stones that pave the way to achieving this. Last week, we talked about software asset lifecycle management, and today we will look into application normalization. In a few days, we will take a closer look at software cataloging. With that in mind, you may be wondering how important application normalization is to your Windows 10 and Evergreen IT projects.

Today, enterprises need to be able to adapt faster to changing environments to fend off competitive pressure; they need to be able to grow faster or scale back when needed — all while reducing costs and increasing the value of the services offered.

There is not a week that goes by where I don't have at least one conversation about Evergreen IT or managing IT change as "Business as Usual" with prospects, customers or partners. 

The demand for managing information technology assets on a continual basis reflects a natural consequence of software developments (e.g., cloud computing, software-as-a-service) as well as changing business demands. Think about your Apple or Android phone constantly updating applications in the background, or Windows 10 and its regular patches.

But back in the corporate world, the requirement for control of the environment is a significant hurdle to adopting the most adaptive change methodologies. Imagine if an untested change brought down your main trading application! The challenge is how to take a better approach but retain control. Ideally, Evergreen IT results in increased efficiencies, more agility and better scalability across the entire enterprise. For example, IT transformations could be managed in an agile fashion (business as usual), rather than in one-off big bang migration projects. 

Let me start by explaining that I have spent a significant part of my career in the application packaging space, and currently work for a company called Revacom who are an application packaging expert.

At Revacom we support the application packaging for multiple large OS rollouts across different enterprise organizations. In most of these projects, the applications are the major blocker to deployment progress. 

 With the Windows 2003 Server end of life time bomb now passed on July 14^th 2015, we thought we would take the time to document our advice for Server 2003 migration project planning activities based on our own server migration experience. Download our Server 2003 Project Plan for free.

With Windows 7 approaching end of support in January 2020, most enterprises are accelerating plans to migrate to Windows 10 in 2018 to take advantage of the new or improved cyber-security capabilities, and avoid an expensive custom support agreement  with Microsoft. However, at this time, fewer organizations than expected have taken the plunge because they dread the Windows-as-a-Service servicing model that requires continuous upgrades and a more agile, Evergreen IT management approach.

Ahead of the game is Pillsbury Winthrop Shaw Pittman LLP, an international law firm recognized by the Financial Times as one of the Most Innovative Law Firms three years running. Today, I want to share a little sneak peek at our latest customer case study and tell you the story of how Dashworks transformed this dreaded Windows 10 migration experience into an IT Transformation initiative that the 700+ lawyers and their staff could not only get behind, but actively participate in!

Rolling out Office 365 can be very exciting considering the value it will add to your organization in terms of unified communication, collaboration, and business processes! But it can be equally terrifying if you think about all the dependencies of users, mailboxes, delegates, mail archives, public folders, groups, instant messaging, ... the list goes on and on.

After the initial migration is completed, Microsoft will release two larger Office client feature updates and monthly security updates to increase productivity for your end users and tighten security. However, just like Windows as a Service, these larger feature updates will need to be rolled out effectively as they can also be considered a mini-migration.

One of the most frequent questions we get when we talk to potential customers about tooling is: "What about Microsoft Upgrade Readiness? How does Dashworks compare to that?" It's a very valid question since the Microsoft tool is available free of charge and also built by Microsoft. Since no one knows Windows 10 as well as Microsoft does, one can assume that they also know how to best ready and deploy it using proven industry practices.

This article was also published on The Technology Record magazine here.

You know you are in a pickle when you are six months into your migration project and you still haven’t gotten any numbers on the board. As the responsible project manager, you are frustrated. There are a thousand questions running through your head: What went wrong? Where did the time go? What can I do to get this back on track? Is there a way I can accelerate this to get back on schedule? Should I increase the number of resources dedicated to this project?

Throwing more people at it certainly seems like the right thing to do. After all, you need to be seen to be doing something! This is the route that many a project manager has trodden! But what most project managers have come to realize after the fact is that throwing more people at it doesn’t always translate into a faster project. Only automation and appropriate tooling will do that.

Microsoft Inspire is now over and with so many announcements we think it is a good time to collect the big news all in one blog post. Many great discussions took place in Washington D.C. in July and with almost 18,000 attendees it was the biggest Microsoft partner event ever! As Microsoft CEO Satya Nadella said in his Vision Keynote address on Day 1, "Attendees at Microsoft Inspire come from 140 different countries, and the joint efforts of all these partners create 17 million jobs worldwide". With so many different technologies and new announcements, let us summarize what we learnt from the show...

Alliance Extends Ability to Deliver Integrated Solutions that Accelerate IT Migrations and Optimize Time and Budget.

LONDON – June 27, 2017 – World Wide Technology (WWT), a market-leading technology solution provider, announced today that it has formed a strategic partnership with Juriba, the company that has redefined Enterprise IT Migrations.

“Forging a strategic alliance with Juriba extends our ability to deliver truly innovative, integrated solutions to help our customers manage their IT Migrations, with Juriba Dashworks, WWT CPMigrator® and supporting tools like Tanium giving us a unique stack of technologies and services” said Bob Olwig, WWT’s vice president of business development and innovation.

Microsoft's biggest event of the year is now just over one month away and we couldn't be more excited! Not only will we have a booth (#1132), but many of the partners that use our Dashworks software daily will also be there, as well as hopefully some new partners interested in combining their services with our products. Formerly known as the Microsoft Worldwide Partner Conference, the show was renamed Microsoft Inspire to align with other flagship conferences, including Microsoft Build and Microsoft Ignite.

Microsoft Inspire is scheduled to run July 9 to July 13 in Washington, D.C. at the Walter E. Washington Convention Center. As usual, current and future partners can look forward to connecting and also attending sessions and Vision Keynotes, which are slated to run from 8:45 a.m. to 10:45 a.m. on July 10-12. The keynotes that have been announced so far are those by Satya Nadella, Ron Huddleston, Judson Althoff, Gavriella Schuster, Toni Townes-Whitley, CVP, Public Sector and Industry; Kirk Koenigsbauer, CVP, Office Marketing, who will be presenting at the Verizon Center. Also, make sure you don't miss this year's Partner Celebration with Carrie Underwood on July 12 from 7 to 10.30pm at the Nationals park!