TO A SEAMLESS MIGRATION TO WINDOWS 10 - AN EXECUTIVE'S GUIDE A succinct guide containing strategies, tools, tactics and key insights ...

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TO A SEAMLESS MIGRATION TO WINDOWS 10 - AN EXECUTIVE'S GUIDE A succinct guide containing strategies, tools, tactics and key insights ...
AN EXECUTIVE’S GUIDE
TO A SEAMLESS
MIGRATION TO
WINDOWS 10
A succinct guide containing strategies, tools, tactics
and key insights decision-makers need to know about
successfully migrating to Windows 10.
TO A SEAMLESS MIGRATION TO WINDOWS 10 - AN EXECUTIVE'S GUIDE A succinct guide containing strategies, tools, tactics and key insights ...
With Windows 7 end of life fast approaching,

IT’S TIME TO GET SERIOUS
ABOUT TRANSITIONING YOUR
ORGANIZATION TO WINDOWS 10.
This guide can help by providing you with the strategies, tools, tactics and key
insights that migration experts regularly use to deliver successful migrations.
Obviously, there is a great deal at stake when you are migrating your entire
organization’s operating system. Depending on the IT resources you have on hand,
you may be inclined to do this migration in-house. The critical question is:

Just because you can, does it mean you should?
Keep this important question in mind as you digest the content that follows.

This guide is divided into 3 sections (business briefs) for easy consumption:
Brief 1 covers 4 key considerations when planning your migration; Brief 2 explains
how to leverage Microsoft tools that will make the migration easier; and Brief 3
shares important timing considerations for your transition to Windows 10.

Let’s get started…

                                           2
TO A SEAMLESS MIGRATION TO WINDOWS 10 - AN EXECUTIVE'S GUIDE A succinct guide containing strategies, tools, tactics and key insights ...
TABLE OF CONTENTS
          Business Brief 1:
          4 Key Considerations When Planning your Windows 10 Migration

           5   Business Brief 1 Intro           10    Hardware Compatibility

           7   4 Key Considerations When        12    User Acceptance
               Planning Your Windows
               10 Migration                     14    User Data

           8   Application Compatibility        15    Conclusion

          Business Brief 2:
          How to Leverage Microsoft Tools to Make Your Windows 10
          Migration Easier

          17   Business Brief 2 Intro           20    Small- to Mid-Size
                                                      Businesses
          18   Migration Preparation
                                                20    Larger Companies
          19   Executing the Migration                & Enterprises

                                                21    Conclusion

          Business Brief 3:
          Timing Considerations for your Windows 10 Migration

          23   Business Brief 3 Intro           29    Stage 3: Execution

          24   4 Stages of Migration            29    Stage 4: Close-Out

          26   Stage 1: Initiation              30    Timing Chart

          28   Stage 2: Preparation             31    Overall Conclusion
                                                      & Endnotes

                                 3
TO A SEAMLESS MIGRATION TO WINDOWS 10 - AN EXECUTIVE'S GUIDE A succinct guide containing strategies, tools, tactics and key insights ...
KEY CONSIDERATIONS
   WHEN PLANNING YOUR
  WINDOWS 10 MIGRATION
        Business Brief 1

            4
TO A SEAMLESS MIGRATION TO WINDOWS 10 - AN EXECUTIVE'S GUIDE A succinct guide containing strategies, tools, tactics and key insights ...
Are you ready to make the transition to
 Windows 10? If your answer is “no,” you are
 not alone. As of October 2018, 46.7% of
 personal computers that are running
 Windows are currently running Windows 7.1

 The multitude of users still on Windows 7
 was the impetus for creating our series,
                                                           46.7%
 Seamless Migration to Windows 10 — and
 providing you with helpful content and tips
 along the way. Our goal is to arm you with
 valuable insights that will help you increase
 the success of your Windows 10 migration
                                                        46.7% of PCs that are
                                                        running Windows are
 In this business brief, we will share four key
                                                         running Windows 7.
 considerations when planning your migration to
 Windows 10. But first, let’s quickly review why
 this particular migration is so critical.

“Today, Windows 7 does not meet the requirements
    of modern technology, nor the high security
         requirements of IT departments.” 2
                   Markus Nitschke, Head of Windows at Microsoft Germany

                                                   5
TO A SEAMLESS MIGRATION TO WINDOWS 10 - AN EXECUTIVE'S GUIDE A succinct guide containing strategies, tools, tactics and key insights ...
TICK-TOCK: AS TIME RUNS OUT ON
WINDOWS 7, RISKS AND COSTS INCREASE
January 14, 2020 marks the official end-date for usefulness of Windows 7 and Server 2008/2008r2.
For companies unable to migrate to Windows 10 by this date, Microsoft will offer extended support for
Windows 7, but beware: It will cost you dearly. Ever-increasing monthly fees from Microsoft could end
up costing your company hundreds of thousands of dollars — or more — annually.3 Worse still, this
expense is only one of several negative impacts your business may experience if you fail to migrate to
Windows 10 before 2020.

Nearly 70% of the systems                               These risks come with high costs. Perhaps the
affected by the ubiquitous                              most costly are those that directly weaken your
                                                        company’s data security, increasing your exposure
2017 WannaCry ransomware                                to data breaches.
were running Windows 7.4
                                                        These end of life realities alone should be more
Indeed, continued use of Windows 7 at end               than enough to convince organizations everywhere
of life is likely to have disastrous consequences       that now is the time to start planning their
on your day-to-day operations and data                  Windows 10 migration. Let’s get into it now…
security, including:

•   Software, utilities and features become
    incompatible with upgrades
•   Applications no longer receive updates
                                                             Average total cost
    that apply to Windows 7
•   New devices (e.g., printers, webcams) may
                                                             of a data breach:

•
    be unable to connect with Windows 7
    Antivirus may not be updated, and
    third-party virus protection software will
                                                             $3.86 Million                               5

    eventually stop supporting Windows 7
•   Software bug fixes are no longer patched,
    leaving systems open to exploitation
•   Online banking transaction systems may
    expire if their authentication and encryption
    methods cannot be supported by Windows 7

                                                    6
TO A SEAMLESS MIGRATION TO WINDOWS 10 - AN EXECUTIVE'S GUIDE A succinct guide containing strategies, tools, tactics and key insights ...
4 KEY CONSIDERATIONS WHEN PLANNING
YOUR WINDOWS 10 MIGRATION
As with every project, thoughtful upfront planning is key to slaying your Windows 10 migration on-time
and on-budget, while also satisfying users and other stakeholders. A great way to begin planning is by
considering the impacts and implications that the following four factors will have on your migration:

        Application Compatibility                          Hardware Compatibility

              User Acceptance                                         User Data

                                                                             Let’s take a look at each of
                                                                           these factors more closely...

                                                  7
TO A SEAMLESS MIGRATION TO WINDOWS 10 - AN EXECUTIVE'S GUIDE A succinct guide containing strategies, tools, tactics and key insights ...
APPLICATION COMPATIBILITY:
                             THIS IS WHERE TO START
Take a moment to reflect on the multitude of applications that exist in your environment — everything
from installed software used throughout your extended organization to application packages (MSIs and
APP-Vs) to every application that all your users may have downloaded over time. Only once you have a
clear picture of everything that’s being used in your environment will you be able to thoroughly test
application compatibility.

80% of application                                    Fortunately, you can test the compatibility of
                                                      your applications using a free tool from Microsoft
compatibility concerns                                called Application Compatibility Toolkit (ACT),
can be addressed with ACT.                            which is part of the Windows 10 Assessment and
                                                      Deployment Kit (ADK). ACT can help evaluate your
                                                      IT estate both before and after upgrading to assess
                                                      software and hardware compatibility against the
                                                      current release of Windows 10.

                                                      The key tool within ACT, the Compatibility
                                                      Administrator, provides updates to many Windows
                                                      applications by leveraging an extensive built-in
                                                      application list. There’s a high probability that
                                                      if there is an application you need to run within
                                                      Windows 10, the Compatibility Administrator
                                                      knows what is needed to make it work. The tool
                                                      also provides shims you can apply to applications
                                                      to make those applications run in Windows 10.

                                                  8
TO A SEAMLESS MIGRATION TO WINDOWS 10 - AN EXECUTIVE'S GUIDE A succinct guide containing strategies, tools, tactics and key insights ...
Understanding your current environment’s
                                                          ACT can address most,
compatibility status with Windows 10 is only
part of the process. You’ll also need to dig              but not all application
deeper into areas like application consolidation,       compatibility testing you’ll
OS imaging, deployment planning and end user
                                                          need. Contact us about
engagement which are all vital to ensuring a
successful migration.                                     smoke screen testing.

                                                          Our experienced team
                                                         can help you rapidly and
                                                           thoroughly test your
                                                          applications to ensure
                                                         successful functionality.

                                                    9
TO A SEAMLESS MIGRATION TO WINDOWS 10 - AN EXECUTIVE'S GUIDE A succinct guide containing strategies, tools, tactics and key insights ...
HARDWARE COMPATIBILITY:
                                 FREE MICROSOFT TOOLS MAKE IT EASY
By now, you’ve cataloged your software and should feel comfortable about application compatibility —
but do you know if your current hardware will support Windows 10? The last thing you want to do is push
out a new operating system only to learn that users are hampered by a bad driver, or a lack of processing
speed or disk space.

Give users the best Windows experience and               Hopefully your organization follows a 3-year
enable faster adoption by ensuring hardware              hardware refresh cycle. Regardless, before you
compatibility upfront. Start your compatibility          execute your Windows 10 migration, ensure you
assessment by taking an inventory of all end-            know the maturity and compatibility of every
devices in your network. You may discover a              end-device in your environment. Microsoft offers
kiosk device that you weren’t aware of, or a             two free tools to help with this:
laptop that had been forgotten about.                    •   Microsoft Assessment and
                                                             Planning Toolkit (MAP)
                                                         •   Windows System Assessment
                                                             Tool (WinSAT)

Minimum hardware requirements
to run Windows 10:          6

•   Processor: 1 gigahertz (GHz) or faster processor or SoC
•   RAM: 1 gigabyte (GB) for 32-bit or 2 GB for 64-bit
•   Hard disk space: 16 GB for 32-bit OS 20 GB for 64-bit OS
•   Graphics Card: DirectX 9 or later with WDDM 1.0 driver
•   Display: 1024x600

                                                     10
MAP                                                  WinSAT
MAP is an agentless, automated, multi-product        WinSAT is a module of Microsoft Windows Vista,
planning and assessment tool for quicker and         Windows 7, Windows 8 and Windows 10 that
easier desktop, server and cloud migrations.         you’ll find in the Control Panel under Performance
It provides detailed readiness assessment            Information and Tools (except in Windows 8.1 &
reports with extensive hardware and software         Windows 10). It measures various performance
information, and actionable recommendations          characteristics and capabilities of the hardware
to help you accelerate your organization’s IT        it is running on and reports them as a Windows
infrastructure planning process and gather           Experience Index (WEI) score. The WEI includes
more detail on assets that reside within your        five sub-scores: processor; memory; 2D graphics;
current environment. MAP makes it easy by            3D graphics; and disk. The base score is equal to
consolidating all the information into a SQL         the lowest of the sub scores and is not an average
database and providing recommendations on            of the sub scores. WinSAT reports WEI scores on
hardware you’ll need to set up and configure         a scale from 1.0 to 5.9 for Windows Vista, 7.9 for
in your environment.                                 Windows 7, and 9.9 for Windows 8 and Windows
                                                     10. Knowing the scores gives you a good idea about
                                                     device performance, which is helpful for making
                                                     business decisions about purchasing new hardware.

                                                       Need help assessing your
                                                        hardware for Windows
                                                          10 compatibility?

                                                            Contact our experienced
                                                                 team at HMB.

                                                11
USER ACCEPTANCE:
                              Plan for it now
 All too often, little thought is given to user acceptance prior to migration. Change is never easy on
 users. As much as you know that your organization needs to make the change, getting users to
 embrace Windows 10 could prove challenging. This is especially true for legacy users, whom you
 need to convince to give up processes, shortcuts and workarounds they’re very comfortable with.

 Devoting time and attention to end users now can help facilitate a smoother transition.
 These tips will also help:

EDUCATE AND                                              Engage early
LISTEN TO USERS                                          adopters NOW
It is much easier for users to get on board if           Most likely there are a few key users in your
they understand why the change is happening              company that are familiar with and excited
in the first place. Clearly explain the business         about transitioning to Windows 10. Ask them
drivers behind the change, help them visualize           to advocate for the coming change —
what is coming and how they will benefit.                not only to leadership, but also to their peers.
Also, ask them to express their concerns and             Encourage them to engage with other users
address them appropriately.                              to share their knowledge, provide insights on
                                                         best practices and calm fears of the unknown.

                                                    12
Workers increase
productivity
by 86% when
coaching is added
to training.7                                           Use User-friendly Language
                                                        and Highlight Benefits
                                                        Remember that people don’t like change. If
                                                        your message communicating the Windows 10
                                                        migration includes buzzwords like “innovation”
                                                        and “game-changer,” users may put up their
                                                        defenses to engage them. They’ll be less resistant
                                                        if you use inclusive, user-friendly language to
                                                        engage them, and highlight the benefits they
                                                        will realize personally from adoption.

DON’T SKIMP ON                                          LAUNCH A COMMUNITY
USER TRAINING                                           FOR COLLABORATING
User training is all too often a topic of               Employ collaboration tools such as Microsoft
conversation that gets pushed to the end of             Teams or Slack to serve as a venue for users to
the project, when timelines and budgets are             ask questions, post best practices and share tips.
squeezed. Because successful user adoption              Have early adopters champion it and moderate
is dependent upon effective user training, take         the conversations. If employees feel like everyone
time up front to plan and budget for proper user        is rallying around a tool, they will be more willing
training, personal coaching and hands-on labs.          to accept it. It also frees up time of the IT team,
                                                        as questions and concerns aren’t flowing solely
                                                        through one department.

                                                   13
USER DATA:
                                  EASILY TRANSFER IT TO WINDOWS 10
The last thing you want during your migration is to be slowed down unnecessarily.
Seamlessly transitioning user profile data between operating systems will help reduce
negative impacts on the user experience.

Two of the easiest tools for seamlessly transferring user data between systems at scale are
Microsoft’s User State Migration Tool (USMT) 10.0 and OneDrive.

USMT 10.0                                                     command in Windows Preinstallation
USMT 10.0 streamlines and simplifies user state               Environment (WinPE) or you can perform
migration during large deployments of Windows                 migrations from previous installations of
operating systems. USMT captures user accounts,               Windows contained in Windows old directories.
user files, operating system and application                  For more information about migration types,
settings, and then migrates them to a new                     see Choose a Migration Store Type and
Windows installation. You can use USMT for both               Offline Migration Reference.
PC replacement and PC refresh migrations.
                                                           ONE DRIVE
USMT enables you to do the following:                      An often-overlooked Microsoft solution for
•   Configure your migration according to your             keeping your user data intact is OneDrive. It
    business needs by using the migration rule             allows users to back up their content, settings
    (.xml) files to control exactly which files and        and preferences and seamlessly integrate those
    settings are migrated and how they are                 items to their new environment and hardware.
    migrated. For more information about how to
                                                           This useful solution has one important caveat,
    modify these files, see USMT XML Reference.
                                                           however: OneDrive consumes extra network
•   Fit your customized migration into your                bandwidth. Therefore, ensure that you have the
    automated deployment process by using the              necessary bandwidth to support OneDrive as
    ScanState and LoadState tools, which control           an enterprise-wide user data solution before
    collecting and restoring the user files and            committing to it.
    settings. Learn more at User State Migration
    Tool (USMT) Command-line Syntax.                       For more information, check out
•   Perform offline migrations. You can run                Common Migration Scenarios.
    migrations offline by using the ScanState

                                                      14
CONCLUSION                                               ABOUT HMB
The countdown to Windows 7 and Server                    HMB is an IT solutions firm that helps mid-to-
2018/2018r2 end of life is well underway. If you         large-sized enterprises deliver custom technology
haven’t done so already, it’s time to get serious        solutions that solve their biggest challenges.
about planning your Windows 10 migration.                We specialize in providing Professional Services,
Our series, Seamless Migration to Windows 10,            Fax & Digital Transformation solutions and
will help you get started.                               developing niche software products.

In this brief, we covered four key considerations
                                                                          Contact Us
when planning your migration to Windows 10.
                                                                          Phone 614.221.6831
The factors you should focus on are:                                      Email sales@hmbnet.com
                                                                          Web     hmbnet.com
1. Application Compatibility
2. Hardware Compatibility
3. User Acceptance
4. User Data
                                                               Contact us to set up a
Microsoft offers a variety of tools to help you
with compatibility testing, and HMB is here to                 personalized session to
answer your questions and provide assistance                   customize a Windows 10
along the way.
                                                               environment for your team.
Watch for more Seamless Migration to
Windows 10 content from HMB.

                                                    15
HOW TO LEVERAGE
MICROSOFT TOOLS
AS PART OF THE SEAMLESS
MIGRATION TO WINDOWS 10
       Business Brief 2

           16
HOW ARE YOUR WINDOWS 10
MIGRATION PLANS COMING ALONG?
In our previous business brief, 4 Key                In this brief, we share our favorite
Considerations When Planning Your                    free and premium tools from Microsoft
Windows 10 Migration, we reviewed
                                                     that will make it easier for you to both
important factors to consider early in your
                                                     prepare for and execute your Windows
migration planning. We also spelled out the
potentially disastrous consequences that
                                                     10 migration. We know these tools well
companies may face if they fail to transition        and are very familiar with the value
to Windows 10 before January 2020.                   they bring to the migration process.

Running Windows 7 at end of life can
weaken data security and increase
exposure to data breaches. With the
average cost of a breach estimated at
$3.86 Million8, it’s not worth the risk.

These risks come with high costs. Perhaps
the most costly are those that directly
weaken your company’s data security,
increasing your exposure to data breaches.

                                                                            Let’s take a look
                                                                              at them now…
                                                17
MIGRATION PREPARATION:
FREE TOOLS THAT AID PRE-MIGRATION PROCESSES
Microsoft offers two free toolkits that are exceptionally useful in helping
you execute important pre-migration tasks:

Microsoft Application                                       Microsoft Assessment
Compatibility Toolkit (ACT)                                 and Planning Toolkit (MAP)
ACT is a free life-cycle management tool that               MAP is an agentless, automated, multi-product
can help you identify and manage your overall               planning, assessment and reporting tool that
application portfolio. Using it to determine                enables quicker and easier migrations. It provides
compatibility of your applications with Windows             detailed inventory and readiness assessment
10 before deployment helps reduce the time and              reports with actionable recommendations to
cost associated with compatibility issues. It also          help you streamline and accelerate your IT
helps speed deployment of the new operating                 infrastructure planning process.
system. Learn more in this blog.

                          Not sure where to start? Contact Terry Every, HMB’s Director
                          of Infrastructure Services. With hundreds of migrations
                          under his belt, he will get you started in the right direction.

                                                     1818
EXECUTING THE MIGRATION:
FREE AND PREMIUM TOOLS THAT MAKE IT EASIER
When you are ready to execute the migration, Microsoft offers a variety of free and premium tools that
allow you to standardize your Windows 10 environment and automate deployment. These tools can help
you realize a smoother deployment with fewer issues, an improved user experience and faster adoption.
Though not an exhaustive list, the following is a snapshot of the tools you are likely to find most helpful:

Microsoft Windows Assessment and Deployment Kit (ADK)
ADK is a free toolkit that contains everything you need to customize Windows images for large-scale
deployment and test the quality and performance of your system. Tools within ADK include:

Windows Assessment Toolkit                                Windows System Image Manager (WSIM)
Helps determine the quality of a running operating        Enables administrators to create
system, components and applications with regard           unattended Windows Setup answer files.
to performance, reliability and functionality.
                                                          User State Migration Toolkit (USMT)
Windows Performance Toolkit                               Streamlines and simplifies user state migration by
Provides in-depth analysis of both application            capturing user accounts, user files, operating system
performance and operating system performance.             and application settings, and then migrates them.

Windows Configuration Designer                            Volume Activation Management Tool (VAMT)
Makes it fast and easy for IT administrators to           Allows administrators to manage and apply
configure end-user devices without imaging.               Microsoft licenses to products like Windows OS
                                                          and Microsoft Office over the network.
Windows Pre-installation Environment (WinPE)
A simple, very basic operating system used                User Experience Virtualization (UE-V)
to install, deploy and repair Windows 10.                 and Application Virtualization (App-V)
                                                          Provide virtualization capabilities that
Deployment Imaging and                                    prior to now were not available free to
Servicing Management (DISM)                               the general public.
Allows administrators to make changes to a
base image (e.g. a specific background image)
before deploying it to all users.

                                                     19
FOR SMALL- TO MID-SIZE BUSINESSES
Microsoft Deployment Toolkit (MDT)                       to be done remotely, eliminating the need to set
is a free toolkit for Windows deployments                up each computer individually. A computer can
at small-to mid-size businesses (fewer                   be taken from bare bones to a fully imaged, fully
than 300 devices). MDK is a dynamic, fluid               configured Windows device quickly, allowing
deployment mechanism; unlike other                       users to become productive immediately.
deployment solutions that are static
and inflexible.                                          MDT with WDS does have some limitations,
                                                         however. Because of this, it is not recommended
In conjunction with Windows Deployment                   for organizations running Windows on 500 or
Services (WDS), MDT saves administrators                 more devices.
time by allowing network-based installations

                    FOR LARGER COMPANIES AND ENTERPRISES
System Center Configuration Manager                      so a new application can be sent out immediately
(SCCM) is a premium (pay for use) Microsoft              to all devices and users can begin using it
deployment tool designed specifically for                immediately.
larger companies and enterprises. It is a unified
management console with an automated                     The User State Migration Tool (USMT)
set of administrative tools for deploying                is fully integrated into SCCM, making it easy to
software, protecting data, monitoring health,            transfer user data. Some of our own technicians,
and enforcing compliance across all devices              however, prefer to use OneDrive* for user data
in an organization. It allows you to not only            transfers. Contact us if you’d like to discuss which
standardize your environment, it also provides           tool may be best for your migration.
you with more direct control over your
                                                         *HMB recommends this solution for transferring user data
environment going forward.

SCCM makes it easy to manage software                    Based on the thousands of device
updates, inventory of all devices and usage.             Migrations, HMB consultants truly
Importantly, it allows administrators to deploy          understand the value that SCCM
applications outside of the imaging process —            brings to migration.

                                                    20
CONCLUSION                                          ABOUT HMB
As you plan your Windows 10 migration,              HMB is an IT solutions firm that helps mid-to-
it’s important to know about the variety of         large-sized enterprises deliver custom technology
proven Microsoft tools that are available           solutions that solve their biggest challenges.
to make your journey more successful.               We specialize in providing Professional Services,
While a majority of the tools are free, more        Fax & Digital Transformation solutions and
comprehensive tools come at a premium.              developing niche software products.
Which tools are right for you depends on
the size of your organization and your                               Contact Us
requirements. HMB has a great deal of                                Phone 614.221.6831
experience with all of the Microsoft tools                           Email sales@hmbnet.com
covered herein, and many more. We’re here                            Web     hmbnet.com
if you have any questions or need help with
your migration to Windows 10.

            Contact us to schedule a custom demo of any of these
             Microsoft tools. We’re here to help ensure that your
                     Windows 10 migration is seamless.

                                               21
TIMING
CONSIDERATIONS
TO MAKE YOUR WINDOWS 10
    MIGRATION EASIER
       Business Brief 3

            22
INTRODUCTION
With the end of life for Windows 7 drawing closer every day,
we want to provide you with useful tools to smooth your
organization’s transition to Windows 10.

Hopefully you’ve gained some helpful insights from previous content
in this series, particularly 4 Key Considerations When Planning Your
Windows 10 Migration and How to Leverage Microsoft Tools to
Make Your Windows 10 Migration Easier.

This brief builds on those publications, as we attempt to answer
a question frequently asked by many clients these days:

HOW MUCH TIME SHOULD WE ALLOW
FOR OUR WINDOWS 10 MIGRATION?
The short answer is: It depends; usually between 5-11 months. Read on to fully
flesh the answer out, and discover how we plan for and execute migration projects
successfully within the time frame scheduled. It’s a planning methodology that
works and we’re happy to share it with you.

                                            23
4 STAGES OF MIGRATION:
TIMING AND TASKS
When considering timing for your Windows 10 migration,
it’s helpful to start by dividing the migration itself into 4 stages:

 1                               2                            3                    4

     Initiation                      Preparation                  Execution            Close-out

Each stage involves distinct processes and tasks that must be accomplished regardless of the size
of the migration. The amount of time you should set aside for each stage, however, varies depending
on the size and complexity of the organization and the number of end devices to be migrated.
For purposes of our discussion, we will define organization size as follows:

     Organization Size                   Noted As                 Number of End Devices

     Small                               S                        ≤ 99

     Medium                              M                        100-299

     Large                               L                        300-799

     Enterprise                          E                        800 ≥

                                                      24
Many important IT projects still
fail due to a lack of strategic
vision, realistic expectations
and resource and planning.
As a failed project, that CRM
implementation hardly stands
alone. The Project Management

                                                 28%
Institute’s 2017 Pulse of the
Profession report found that...

                                             of strategic initiatives overseen
                                               by survey respondents were
                                                deemed outright failures.

                                  Inadequate resources, overly aggressive
                                  timelines, underestimated costs, overlooked
                                  requirements, unanticipated complications,
                                  poor governance and human mistakes such
                                  as bad code can all lead to project failure.9

                                      25
INITIATION                        S    1 Month      M     1 Month           L   2 Months     E    3 Months

During Stage 1: Initiation, you will conduct discovery and make decisions regarding what the Windows 10
migration will look like and the tools you will use to accomplish it. You should allot 1-3 months for this stage,
depending on the size and complexity of your organization. Key tasks to be accomplished during this stage
are listed below.

• Identify All Applications your organization                   DETERMINE WINDOWS 10 DEPLOYMENT
  is using. Determine who is using what, and                    SOLUTION, including the tools you will use to
  consolidate apps with duplicate functionality.                prepare for and execute the migration, how you
  Using the free Microsoft Application                          will handle user data, and where and how you’ll
  Compatibility Toolkit (ACT) to identify and                   perform the migration. The following information
  manage your application portfolio speeds and                  should help with these decisions:
  ensures a high-quality process.
                                                                Free Microsoft Tools
• Identify Devices and use the opportunity to                        • ACT, the same free tool you used to identify
  take a physical inventory. Track the make and                         applications, can be used to test application
  model of drivers and check remaining warranties.                      compatibility with Windows 10. It saves
  Using the free Microsoft Assessment and Planning                      time and costs associated with compatibility
  Toolkit (MAP) can help speed the process.                             issues, and is appropriate for organizations
                                                                        of all sizes.
• Identify User Groups to be migrated and start
                                                                     • Microsoft Deployment Toolkit (MDK) is
  scheduling. Be sure to identify blackout dates
                                                                        useful for small- to mid-size companies
  for the company, divisions, business units and
                                                                        deploying Windows 10 on fewer than
  teams. Also identify early adopters that may be
                                                                        300 devices. It is a flexible and fluid solution
  willing to test applications.
                                                                        for standardizing and securely deploying
                                                                        desktop and server images.
• Review Active Directory Group Policies to check
  for potential operating system conflicts or issues.
                                                                     • Windows Deployment Services (WDS)
                                                                        works in conjunction with MDK to decrease
                                                                        the time, complexity and cost of deploying
                                                                        Windows 10 for companies with fewer
                                                                        than 300 devices.

                 Learn more about migration tools that are readily available.
      Download the infographic, 8 (Mostly) Free Tools You Need in Your Windows 10 Migration Toolbox.

                                                         26
To increase adoption, let users know why the company is
                                 moving to Windows 10 and explain how they will benefit.

Premium Microsoft Tool                                     determine how you will handle device refreshes.
The needs of large companies and enterprises               DETERMINE ORGANIZATIONAL CHANGE
often can’t be met by the MDK/WDS solution. For            MANAGEMENT (OCM) SOLUTION
them, we recommend the premium tool System                 Remember that change isn’t easy for most
Center Configuration Manager (SCCM), a unified             end-users. Your OCM solution should include a
management console that makes it easy to                   communications plan to educate and keep users
standardize, manage and control your Windows               informed. Consider creating a series of emails
environment and gain long-term benefits.                   that, at minimum, includes:

Moving User Data                                           • An Initial Broadcast Email to announce the
There are two viable tools for migrating user data.          upcoming migration to the company. State why
The first is Microsoft OneDrive whose Known                  the migration is happening and how users will
Folder Move (KFM) feature allows users to move               benefit. Include the migration schedule. If you
their own documents, desktop and photos to                   decide to hold an Open House to allow users to
OneDrive quickly, and access them from any                   interact with Windows 10 before migration,
Microsoft application. The second is Microsoft’s             include information about it.
free User State Migration Tool (USMT), which
safely migrates user accounts and operation                • 7 Days Prior Targeted Email to the user group
systems and application settings.                            to let them know what to expect during the
                                                             next week’s migration.
Deployment Methodology
Your deployment method should be fairly simple to          • 1 Day Prior Targeted Email to the user group to
determine. If the number of devices is manageable,           remind them about the next day’s migration.
you may decide to do the deployment at each
user’s desk. Or you may decide to set up a depot           • 1 Day After Targeted Email to the user group
in a conference room, perform the migration, and             to see how the migration went and remind
hand the devices back; then take the next group. If          them where to go for support.
you have a distributed network, you may decide to
perform the entire migration out of one location,
with or without a depot. Finally, you also need to

                                                      27
PREPARATION                             S    2 Months      M     2 Months      L    2 Months          E   4 Months

When all the Initiation tasks are complete, you will move into Stage 2: Preparation. During this stage, you will
use the determinations made in Stage 1 and move forward with them. You should plan approximately 2-4
months for this stage, depending on the size and complexity of your organization.

TASKS TO BE COMPLETED:

• Build Deployment Solution using the tools                    • Collect Device Drivers for the make/models
  determined in Stage 1. Develop task sequences                   of devices identified in phase 1 (Initiation)
  based on the various end result configurations
  and software combinations.                                   • Build Base Image for the organization
                                                                  and default configuration for all devices.
• Update Active Directory Group Policies
  to eliminate OS version issues.                              • Define Detailed Schedule for deployment
                                                                  by user group.
• Test Application Compatibility and conduct
  any necessary remediation.                                   • Host Open House sessions for users,
                                                                  if applicable.
• Begin Procurement Process for devices that
  need replaced.                                               • Start Executing OCM solution as determined
                                                                  in Phase 1.

                                                               • Set Up Imaging Depot, if required.

                                                        28
EXECUTION                              S   1 Month     M     1 Month        L    2 Months      E      3 Months

After all the preparation work is done, it’s finally time to execute the migration. Stage 3: Execution, typically takes
1-3 months, depending on the size of your organization and number of end devices. Don’t be fooled by the short
length of the to-do list for this stage; a great deal of work needs to be accomplished during this time.

TASKS TO BE COMPLETED:

• Execute Deployment Schedule and keep                           • Provide One-on-One User Support that includes:
  user groups apprised if the timing changes.                        • Setting up email
                                                                     • Verifying network drives
• Image The Devices based on decisions made                          • Verifying user data
  in Stage 1 and work done in Stage 2.                               • Validating applications
                                                                     • Providing quick introduction to Windows 10

                                                                 • Address Issues as they arise.

            CLOSE-OUT                              S   1 Month     M     1 Month        L    1 Month       E      1 Month

The fourth and final stage of migration is typically the shortest in length; typically, no longer than a month,
regardless of company size. The to-do list below includes both tasks you must complete to ensure proper
close-out, as well as additional tasks that we conduct to ensure successful completion for clients.

TASKS TO BE COMPLETED:

• Validate 100% deployment of Windows 10                         • Long-term imaging solutions and recommendations
  on every device.
                                                                 • Application standardization results
• Ensure Automated Update schedule is active,
                                                                 • Assurance that company personnel are familiar with:
  if using SCCM
                                                                    • Application packages and deployment processes
Note that as IT consultants, our Stage 4 to-do list                 • Operating System Deployment Task Sequence
also includes a great deal of knowledge transfer.                   • Full System Center Configuration Manager
To ensure that we leave our clients with viable,                       solution (i.e. Boundaries, Distribution Points,
long-term solutions for maintaining their Windows                      Collections, Security, etc.)
10 environment, we provide the following:

                                                          29
WINDOWS 10 MIGRATION TIMING (MONTHS)

 Organization Size               Small          Medium           Large         Enterprise

 Noted As                          S               M               L               E

 Number of                       ≤ 99          100-299          300-799           800 ≥
 End Devices

 Initiation (Ph1)               1 Month         1 Month         2 Months        3 Months

 Preparation (Ph2)             2 Months        2 Months         2 Months        4 Months

 Execution (Ph3)                1 Month         1 Month         2 Months        3 Months

 Close-out (Ph4)                1 Month         1 Month         1 Month         1 Month

 TOTAL TIME                    5 Months        5 Months        7 Months        11 Months

With Windows 7 end of life swiftly encroaching, it’s imperative that you understand and plan for
the time required to transition your organization to Windows 10. The migration typically takes
between 5-11 months, depending on company size and the number of devices. Within that
time frame, you will move through 4 distinct stages of the migration: Initiation, Preparation,
Execution and Close-out. Using the lists of tasks within this brief will help ensure that you set
aside the appropriate amount of time for each stage and not miss any critical steps.

       Do you have any questions or need help with your Windows
         10 migration? Contact the experts at HMB. We can help
               ensure a seamless migration to Windows.

                                                   30
CONCLUSION
 Your organization’s transition to Windows 10 needs to happen sooner rather than later in order to avoid
 serious and costly Windows 7 end of life risks. Now that you know what’s involved in making this critical
 migration happen, you need to determine if you will go it alone or engage a migration partner. Large
 migrations are complicated. If it’s not something that your in-house team does every day, they are likely
 to experience countless unforeseen issues and delays along the way. This is why we recommend that
 if you are not extremely confident in your organization’s ability to pull off the migration seamlessly, you
 should engage a reputable migration partner. If you do decide go the partner route, below are some key
 questions to include as part of your vendor evaluation:

 • How many Windows migrations have you successfully completed for organizations our size?
 • What is the skill and experience level of your technicians?
 • What is your migration process and timing?
 • What technology tools will you use to assist with the migration?
 • How will you ensure a high rate of user adoption?

 If you’re seeking a strategic partner rather than just a vendor for your transition in Windows 10, start
 by asking these questions of HMB. Our answers will give you a solid baseline with which to compare
 other potential migration partners.

       Request a FREE Windows 10 Migration Workshop hosted by HMB’s experts.
                          You’ll walk away with a clear understanding of how best to get
                                    started in your migration (minus the headaches).

           [1] Keiser, Gregg. Windows By The Numbers: Windows 10 Backtracks, Windows 7 Remains Resilient, Oct. 2, 2018,
ENDNOTES

               https://www.computerworld.com/article/3199373/windows-pcs/windows-by-the-numbers-windows-10-backtracks
               -windows-7-remains-resilient.html
           [2] Kelly, Gordon. Microsoft Warns Windows 7 is Dangerous to Use, Jan. 17, 2917,
               https://www.forbes.com/sites/gordonkelly/2017/01/17/microsoft-windows-7-security-hardware-support-problems/#3e39952decdb
           [3] Kelly, Gordon. Why Windows 7 Has a New Monthly Charge, Sept. 15, 2018,
               https://www.forbes.com/sites/gordonkelly/2018/09/15/microsoft-windows-7-monthly-charge-windows-10-free-upgrade-cost-
               2/#a980ab740b02
           [4] Roberts, Paul. Behind Breaches: Lots of Outdated Software, July 26, 2017,
               https://digitalguardian.com/blog/behind-breaches-lots-outdated-software
           [5] IBM, 2018 Cost of a Data Breach Study by Ponemon,
               https://www.ibm.com/security/data-breach
            [6] Huculak, Mauro. Windows 10 Questions and Answers You Need to Know Before Upgrading, June 13, 2015,
                https://www.windowscentral.com/windows-10-questions-and-answers-you-need-know-upgrading
           [7] “Maximizing the Impact of Executive Coaching: Organizational Outcomes, and Return on Investment,”
               The Manchester Review, 2001, Volume 6, Number 1, http://www.slideshare.net/patweiland/coaching-roi
           [8] IBM, 2018 Cost of a Data Breach Study by Ponemon, https://www.ibm.com/security/data-breach
           [9] Success Rates Rise, Transforming the high cost of low performance (PMI’s Pulse of the Profession® - 2017)
               https://www.pmi.org/-/media/pmi/documents/public/pdf/learning/thought-leadership/pulse/pulse-of-the-profession-2017.pdf

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