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HOW TO PULL THEWINDOWS MIGRATION TRIGGER:
FIVE QUESTIONS EVERY CIOMUST ASKAn Olenick & Associates White Paper
March 2013
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How to Pull the Windows Migration Trigger: Five Questions Every CIO Must Ask
Contents
Executive Summary .................................................................................................................... 1
Isnt the Desktop dead? .............................................................................................................. 2Should I Target Windows 7 or Windows 8? ................................................................................. 3
How can I scope the problem? .................................................................................................... 5
Application Criticality.............................................................................................................. 5
Number of Target Computers ................................................................................................. 5
Configuration Diversity ........................................................................................................... 7
How can I Manage Migration Risk? ............................................................................................. 8
Application Risk Mitigation ..................................................................................................... 8
Configuration Risk Mitigation ................................................................................................. 9
User Community Risk Mitigation ............................................................................................ 9
How Can I Manage for Success? ................................................................................................ 10
Critical Success Factors ......................................................................................................... 10
Metrics and Key Performance Indicators............................................................................... 11
Conclusion ................................................................................................................................ 12
About Olenick & Associates ...................................................................................................... 12
Notes ........................................................................................................................................ 13
Copyright 2013 Olenick & Associates, Inc. All rights reserved.
205 W. Wacker Drive, Suite 2000
Chicago, IL 60606
312 332 0096
http://olenick.com
@OlenickIT
Additional copies of this white paper can be downloaded from
http://olenick.com/How-to-Pull-the-Windows-Migration-Trigger-Five-Questions-Every-CIO-
Must-Ask.pdf
Windows is a registered trademark of Microsoft Corporation in the United States and other
countries.
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How to Pull the Windows Migration Trigger: Five Questions Every CIO Must Ask 1
EXECUTIVE SUMMARY
Despite Microsofts well-publicized end of support for the Windows XP desktop operatingsystem and the attractiveness of replacements Windows 7 and 8, thousands of IT managers are
just now starting to embrace all this as inevitable. If youre one of them, youre not alone. As of
January 2013, about 43% of all Windows personal computers are running XP; 6% are still
running Vista or earlier Windows versions.1
For an organization with many thousands of XP PCs, migration to a new Windows OS will be a
significant undertaking. This white paper discusses some key questions that CIOs and
enterprise technology managers must consider as they decide how to meet this challenge and
create a migration strategy.
Isnt the desktop dead?Does the cloud and mobile revolution obviate the need fordesktop computers? Why migrate if there are better alternatives?
Should I target Windows 7 or Windows 8?Although the technical differences are wellunderstood, what are the operational and economic consequences of this choice?
How can I scope the problem?What are the key drivers of time, cost, and results? Whatdo I need to know to lay out an effective roadmap?
How can I manage migration risk?What can go wrong? How can I mitigate these risks? How can I manage for success?What management actions and tools will assure the
success of my migration project?
Of course, any final answer to these questions depends on your situation a simple cookbook
approach would certainly be wrong. Instead, we present lessons Olenick & Associates have
learned from migration projects for our enterprise IT clients as a framework for planning.*
*You may also be interested in our companion white paperWindows Migration Tips, Tricks, and
Gotchas.
http://olenick.com/Windows-Migration-Tips-Tricks-and-Gotchas.pdfhttp://olenick.com/Windows-Migration-Tips-Tricks-and-Gotchas.pdfhttp://olenick.com/Windows-Migration-Tips-Tricks-and-Gotchas.pdfhttp://olenick.com/Windows-Migration-Tips-Tricks-and-Gotchas.pdfhttp://olenick.com/Windows-Migration-Tips-Tricks-and-Gotchas.pdfhttp://olenick.com/Windows-Migration-Tips-Tricks-and-Gotchas.pdfhttp://olenick.com/2w7w8 -
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How to Pull the Windows Migration Trigger: Five Questions Every CIO Must Ask 2
ISNT THE DESKTOP DEAD?Lets consider some reasons why you might want to skip migration to a new Windows desktop
OS altogether.
Cloud-hosted SAAS offerings like Windows 365 are viable and proven alternatives. Cloud-based applications dont really need a personal computer any device that runs a
browser will do, including tablets and smartphones.
For some applications, virtualized hosted desktops and thin clients can replace physicaldesktops for significant cost reductions.
Many workers now prefer to use their own tablet or smartphone. In some cases, thismeans you can eliminate the annual per PC spend of around $4,000 for licenses,
support, and power.2
Mobile devices are cheaper and in many ways, faster and better. Native apps can bedeveloped to perform the same functions desktop apps provide.
If you can run some or all of your business from a
tablet or smartphone, these points are worth
consideration. However, for many organizations,
dumping the desktop just isnt feasible.
Many apps/users rely on a keyboard, mouse, and a large screen. Tapping on a handheldis not ergonomic for writing in quantity, graphic composition, side-by-side reading, and
user multi-tasking.
Handhelds or browsers cant provide the bandwidth, storage, or number crunchingneeded for resource-intensive apps.
Mobile wireless networks that mobile devices favor are more expensive, slower, andless reliable than the typical wired network for desktops.
Laptop PCs are still the platform of choice for many road warriors. High-performanceand ruggedized laptops provide nearly all of the advantages of desktop hardware as
well as the unwired benefits of handhelds and tablets.
The cloud/mobile stack has new and different security hazards. Your current and potential workforce has skills in Windows apps on a Windows OS. You've built your business processes around apps that use a Windows OS. Disruption
would entail unnecessary costs and risks.
The cost of migrating legacy apps to a cloud/mobile stack can be prohibitive.
For many organizations,dumping the desktop just
isnt feasible.
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How to Pull the Windows Migration Trigger: Five Questions Every CIO Must Ask 3
SHOULD I TARGET WINDOWS 7 OR WINDOWS 8?
There are many analyses of the relative advantages of Windows 7
and Windows 8 the nearby sidebar lists a few.
We like both platforms. Migration scope, cost, and risk are about
the same, so operational effects for your organization should drive
the decision.
Microsoft has made great improvements in desktopreliability. Having been in the field for several years,
Windows 7 is now highly stable. Although Windows 8
users may encounter some new bugs, we expect Windows
8 to be as, if not more, reliable than Windows 7.
Windows 8 provides built-in cloud and mobile integration.We expect significant enhancements in this direction for
Windows 8, both from Microsoft and third parties. As
Windows 8 becomes the platform of choice, Windows 7
will trail this leading edge.
If you start with Windows 8 now, it may be another tenyears before youll have to go through another migration.
Although we cant say exactly when the future tipping
point for migrating from Windows 7 will occur, it will
probably be several years sooner.
Although the Windows 8 Metro user interface will initially take
getting used to, we see Windows 8 as a better technology that
best positions you for the future. However:
We dont recommend going to Windows 7 as a short-termpath to Windows 8. If your goal is Windows 8, then go
directly dont waste time and money with Windows 7.
If you are currently using Windows 7, stay there unlessthere are features in Windows 8 (like advanced security)
you must have.
The choice depends on your planning horizon. Exhibit 1 Windows 7
versus Windows 8compares some key operational effects. In the
longer term, Windows 8 is clearly a better choice. If your horizon is
the next few years, Windows 7 is arguably better.
Enterprise Upgrades: Five
Reasons to Focus on Windows 7
not Windows 8.This article
weighs the pros and cons of
Windows 7 and 8, and finds that
Windows 7 is a better choice for
the Enterprise.
DOD Awards First Joint Licensing
Agreement. After an extensive
internal study, the US
Department of Defense
committed to upgrading 700,000
of its Windows computers to
Windows 8, as they see it will be
substantially less expensive and
more secure than Windows 7.
Windows 8: Not for Old-at-HeartPCs.The Wall Street Journals
Walter Mossberg finds that
Windows 8 may require new
hardware too.
Microsoft Q&A: With Windows 8,
the Choice Is Yours.An interview
with Microsoft VP Antoine
Leblond about why Windows 8 isright for the enterprise.
http://www.cio.com/article/717418/Enterprise_Upgrades_Five_Reasons_to_Focus_on_Windows_7_not_Windows_8http://www.cio.com/article/717418/Enterprise_Upgrades_Five_Reasons_to_Focus_on_Windows_7_not_Windows_8http://www.cio.com/article/717418/Enterprise_Upgrades_Five_Reasons_to_Focus_on_Windows_7_not_Windows_8http://www.cio.com/article/717418/Enterprise_Upgrades_Five_Reasons_to_Focus_on_Windows_7_not_Windows_8http://www.defense.gov/news/newsarticle.aspx?id=118887http://www.defense.gov/news/newsarticle.aspx?id=118887http://www.defense.gov/news/newsarticle.aspx?id=118887http://online.wsj.com/article/SB10001424127887323936804578229682529360570.htmlhttp://online.wsj.com/article/SB10001424127887323936804578229682529360570.htmlhttp://www.cio.com/article/708239/Microsoft_Q_A_With_Windows_8_the_Choice_Is_Yourshttp://www.cio.com/article/708239/Microsoft_Q_A_With_Windows_8_the_Choice_Is_Yourshttp://www.cio.com/article/708239/Microsoft_Q_A_With_Windows_8_the_Choice_Is_Yourshttp://www.cio.com/article/708239/Microsoft_Q_A_With_Windows_8_the_Choice_Is_Yourshttp://online.wsj.com/article/SB10001424127887323936804578229682529360570.htmlhttp://online.wsj.com/article/SB10001424127887323936804578229682529360570.htmlhttp://www.defense.gov/news/newsarticle.aspx?id=118887http://www.defense.gov/news/newsarticle.aspx?id=118887http://www.cio.com/article/717418/Enterprise_Upgrades_Five_Reasons_to_Focus_on_Windows_7_not_Windows_8http://www.cio.com/article/717418/Enterprise_Upgrades_Five_Reasons_to_Focus_on_Windows_7_not_Windows_8http://www.cio.com/article/717418/Enterprise_Upgrades_Five_Reasons_to_Focus_on_Windows_7_not_Windows_8http://olenick.com/2w7w8 -
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How to Pull the Windows Migration Trigger: Five Questions Every CIO Must Ask 4
In the longer term, Windows 8 is clearly abetter choice. If your horizon is the next
few years, Windows 7 is arguably better.
Operational Factor Windows 7 Windows 8
User learning curve Low Moderate
Legacy app compatibility Low
Lower
Typical hardware 64 bit, 4G RAM 64 bit, 4G RAM
Projected End-of-Life 2016 2020
Security Good Better
Cloud integration Good Better
Mobile integration Low Good
Third Party App compatibility Best now Best later
Stability Best now Best later
Development SupportVisual Studio,
Dot Net
Visual Studio,
Dot Net
Microsoft client apps: Office,
SharePoint, etc.Best now Best later
Microsoft Server apps: Exchange,
SQL Server, etc.Best now Best later
Exhibit 1 Windows 7 versus Windows 8
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How to Pull the Windows Migration Trigger: Five Questions Every CIO Must Ask 5
HOW CAN I SCOPE THE PROBLEM?Although there are hundreds of specific factors to consider, weve found that a few dominate
the scope of a Windows migration project: application criticality, number of target computers,
and configuration diversity.
Application Criticality
Some desktop applications or the user-
facing components of a multi-tier system
perform tasks that are the heartbeat of
your organization Enterprise Resource
Planning (ERP) is a prime example. They
may have been provided by a third party or
internally developed. Others are engrained
in daily workflow: document editing,
email, and collaboration tools. Others may have been picked up along the way, are personal
favorites, or simply obsolete.
The first step of migration is to inventory and then bucket apps accordingly to their operational
criticality. Exhibit 2Application Criticalityprovides a scheme to classify your applications.
Critical. You depend on these apps every day any disruption to them would have animmediate adverse effect on operations, costs, or revenues.
Essential. The usage profile is roughly the same as critical, but effects of an outage arenot as immediate or severe.
Special Purpose. Usage is limited to certain roles or times. User Specific. Usage is limited to certain persons; disruption impact is narrow. Deprecated. These apps should not be migrated they may be obsolete, unsecure, or
unsupported.
Youll almost certainly want to migrate all of your critical and essential applications and set
priorities for special-purpose and user-specific apps.
Number of Target Computers
While this may seem obvious, dont forget to count separately computers that can or will be
removed from service during the migration. It is usually easiest to have your vendor configure
new computers with the desired OS. However, you'll still have to transfer data and applicationsfrom the retired computer.
Although some older computers might meet the minimum hardware requirements for
Windows 7, the typical current configuration for either OS is a PC with at least 4GB RAM and a
64-bit processor.
The first step of migration isto inventory and then bucket
apps accordingly to their
operational criticality.
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How to Pull the Windows Migration Trigger: Five Questions Every CIO Must Ask 6
You may want to review your equipment budget and expensing policy to determine what
economic effect speeding up or deferring retirement of target computers would have. Ideally,
you can set your rollout schedule accordingly. However, if youre just starting this process,
Microsofts termination of regular XP support in April 2014 may limit your options.
Level App Profile Outage Impact
1
Critical
Integral component of essential
workflow
Enterprise resource planningclient (ERP)
Email, DocumentManagement
Payment processing Catalog definition Order processing
Essential operations halted
Company-wide productivityis compromised
Material adverse cost or saleseffect
Public, wide-spread damageto organizations reputation
2
Essential
Essential operations degraded
Customer dissatisfaction Compliance violation Significant employee
productivity degradation
Damage to organizationsreputation
3
Special
Purpose
Specialized or infrequent usage Year-end reporting Audit compliance
Some operations degraded Indirect customer
dissatisfaction
Moderate employeeproductivity loss
4
User
Specific
User selected/installed
Analytics Graphics
User operations degraded
Impact typically limited toprimary user
5Deprecated
Unauthorized/unsupported Legacy apps to be replaced Security risk
Continued use poses a hazard,
creates waste or excess cost
Exhibit 2 Application Criticality
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How to Pull the Windows Migration Trigger: Five Questions Every CIO Must Ask 7
Configuration Diversity
The physical configuration of your PC fleet is just as important as its application profile. A
partially automated census of all computers in your fleet is the best way to determine this.
Automated or not, youll need this to create an effective migration plan. Exhibit 3 Configuration
Scope Driverslists factors that determine project scope and may call for special attention.
You may also find it useful to evaluate other
improvement opportunities. Are any items
based on obsolete assumptions? Is this structure
adequate for future changes?
For many reasons, you may have PCs that are
dedicated to running only a single app. For
example, hundreds of PCs in a warehouse are
only used to check stock status. Instead of
continuing to use a general purpose PC for asingle app, it may make sense to host the app in
a cloud and replace the PC with a thin client.
Configuration Item
Roles
How many role-specific configurations are there?
Management, technical specialist, clerical, field sales, etc.?
How many Active Directory profiles are there?
Offices/ Locales
How many physical sites are there?
Where are they located?
How many localization profiles are needed?
Images
What versions of Windows OS are there: DOS, NT, Windows 9x,
2000, XP, XP SP1, Vista, etc.
How many of each?
Platforms
What kind of computers are there?
Desktop, laptop, or workstation?
CPU type?
Memory?
HD size?
Video Device TypesWhat kinds of display devices are used?
Resolution?
Printer and Multi-Function
Device Types
What types of printers
What kind of multi-function devices (e.g., fax/print/scan
combo)?Exhibit 3 Configuration Scope Drivers
Instead of continuingto use a general
purpose PC for a single
app, it may make sense
to host this app in a
cloud and replace the
PC with a thin client.
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How to Pull the Windows Migration Trigger: Five Questions Every CIO Must Ask 8
HOW CAN I MANAGE MIGRATION RISK?We see two primary business risks.
Underestimating either thedifficulty or impact of a
migration project.
Delaying migration. After April8, 2014 there will be a
substantial increase in
Microsoft support costs.4 The
sooner you start, the lower
these costs will be.
Like any large IT project, many things
can go wrong in a Windows migration.
Problems related to applications, configuration, and users are common in our clients migrationprojects. You can avoid delays and unexpected costs with focused quality assurance, proactive
management, and effective monitoring during the migration project.
Application Risk Mitigation
Application risk includes all of the problems that can occur when you transfer an existing
application to a new platform. Compatibility testing is the first step for mitigation, followed
with testing each installation package on the target platform(s).
A typical PC has scores of applications that must be re-installed on top of the new OS.
Application packaging is the bundling of installation files into an industry standard format such
as MSI or App-V. This minimizes compatibility problems and per-PC conversion cost. Although
package design, implementation, testing, and development life cycle coordination can be
challenging, all are essential for risk mitigation.
Risk MitigationApp not compatible with
new OSEvaluate and test application compatibility
In-house applications dont
work
Perform compatibility and packaging testing prior to
deployment
Validate virtualized stack for non-compatible apps
Application packages
corrupted
Packaging team verifies packages before deployment
Rollout distribution covers all critical applications
Application security
incorrect
Packaging and testing team verifies security before deployment
Rollout distribution covers all critical security verifications
Applications install but
dont launch
Packaging team tests that the application will launch and is
usable with an active non-admin user ID.
Exhibit 4 Application Risks and Mitigation
An IT manager toldComputerworld that Microsoft hadquoted his company $1 million forthe first year of custom support to
cover 5,000 Windows XP machines,
$2 million for the second year, and
$5 million for the third.3
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How to Pull the Windows Migration Trigger: Five Questions Every CIO Must Ask 9
Configuration Risk Mitigation
Configuration risk refers to potential incompatibility of your existing IT infrastructure with your
new OS and its configuration. Mitigation requires stabilizing applications on reference PCs
followed with systematic testing of peripherals and configurations, prior to rollout.
Risk Mitigation
File systems dont work
Image testing verifies that file systems are accessible and
operational post installation
Rollout covers all file system instances
Printers dont work
Test images to verify that printer systems are accessible
and operational post installation
Test all printer system instances
WAN/LAN latency or outage
Provide24x7 network support, special staffing per
installation location as necessary
Test with images to determine network load duringimage installation (can be quite large, up to 15GB) as well
as the network impact at each location
Set up transfer stations and conduct conversions on
isolated network
PC failure during transferRollout team maintains access to an inventory of spares
with the normal desktop refresh / troubleshooting team
Domain access privileges missingImage testing verifies domain access configuration
Exhibit 5 Configuration Risks and Mitigation
User Community Risk Mitigation
User risk includes problems that can occur when users are not adequately prepared for the new
OS and other changes. Even if they are, timely support to resolve issues and help desk capacity
to answer questions will facilitate broad acceptance of the new systems.
Risk Mitigation
Users are not able to work on new
Windows / Office version
Provide user training and job aids for new features of
Windows and Office
Establish a robust help desk with added staff to meet
spike in Windows and Office questions
Pre-rollout usability testing to understand problem areas
and structure resulting job aids appropriately
User PC unavailable at scheduled
time
Site coordinators and supervisors ensure that user PCs
are present for the scheduled upgrade time
Allow time contingency for scheduling user PCs
Rollout team has remote access to perform upgrades.
Exhibit 6 User Community Risks and Mitigation
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How to Pull the Windows Migration Trigger: Five Questions Every CIO Must Ask 10
HOW CAN I MANAGE FOR SUCCESS?
Critical Success Factors
Reflecting on our migration projects, we see common management actions that lead tosuccess. In our experience, these actions are necessary for a successful migration.
Critical Success Factor Best Practice
Integration with other
processes/initiatives
Identify impacts and dependencies on other projects or
initiatives
Incorporate key elements from other work streams (e.g.
Active Directory, Exchange) in the migration plan
Change management and
communication
Establish change management function
Communicate benefits of the upgraded desktopTrain migration team to communicate value to users
Project management
Project Manager with migration experience
Set PMO expectations at outset of engagement
Project schedule and staffing
Adequate and experienced team
Adjust staffing based on metrics and KPIs
Agile deployment
Develop multiple deployment solutions to accommodate
business and technical constraints
Conduct testing at technology commit point
Tracking and reporting
Implement detailed tracking of schedule, deployments,
issues, lesson learned
Report deployment status using a centralized dashboard
Application readiness
Establish a Windows compatibility validation process and
application readiness checklist
Integrate application readiness reporting with Windows
upgrade reporting
Manage performance
expectations
Baseline desktop performance for troubleshooting and
support
Training and support
Provide end user training on new OS and App versions
Establish help desk to handle user questions
Increase help desk staffing temporarily
Exhibit 7 Critical Success Factors
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How to Pull the Windows Migration Trigger: Five Questions Every CIO Must Ask 11
Metrics and Key Performance Indicators
Defining and tracking basic migration metrics is an
effective way to mitigate risks and keep the project on
track to successful completion. When you checkmigration progress at regular intervals, reliable
estimates of time to completion and fact-based
reallocation of resources are possible.
Number of application packages complete Number of PC upgrades completed to date (total, per site) Number of PC upgrades remaining (total, per site) Number of PCs ready for upgrade (total, per site) Number of PC upgrades scheduled this week (total, per site)
While progress metrics help to stay on track, Key Performance Indicators (KPIs) evaluate
efficiency and results.
PC conversion rate (actual vs. planned) Total duration and direct hours to upgrade a PC Ratio of high versus low touch upgrades5
For example, Exhibit 8 Managing Risks with Metrics shows weekly progress of packaging of
applications for installation on a new OS.
Exhibit 8 Managing Risks with Metrics
0
20
40
60
80
100
120 Application Packaging Progress
Total Apps Non-packageble AppsApps to be packaged App Packages DoneApp Packages Tested Apps Released for Installation
While progress metricshelp to stay on track, Key
Performance Indicatorsevaluate efficiency and
results.
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How to Pull the Windows Migration Trigger: Five Questions Every CIO Must Ask 12
CONCLUSION
The clock is ticking towards much higher XP support costs. A very good business case can be
made for migrating to Windows 7 or Windows 8 the sooner the better. Either platform offersimproved productivity and efficiency. You may be able to migrate some apps into a cloud and
cut or avoid substantial costs. More energy-efficient PCs can reduce power costs and help your
organization to be greener.
A Windows migration project will probably touch every IT user in your organization, so it has
high visibility and impact. This will entail many kinds of risks, with special considerations for
applications, configuration, and your user community.
Achieving a successful migration requires getting many things right, including coordination,
compatibility testing, packaging, benchmarking, and support. Defining and monitoring
progress metrics and key performance indicators are critical.
While there are a host of technical issues, they can be resolved. Focused testing and quality
assurance at each step in the process mitigates these risks. The other key lesson weve learned
is that Windows migration is not just a technical challenge it requires a focused management
approach to get priorities, timing, and resources right.
ABOUT OLENICK & ASSOCIATES
We published this white paper to help CIOs and IT executives understand the rationale, scope,and risks of a Windows desktop migration project.
In our experience, many managers underestimate this challenge. To find out more about how
ourAssured Windows Migration solution can support your migration, please contact Bill Mertes
at 1 (312) 804-5793 or via email [email protected].
To learn more about ourAssured Windows Migration solution, please visit us at
http://olenick.com/2w7w8.
mailto:William%20Mertes%20%[email protected]%3e?subject=Assured%20Windows%20Migrations:%20Five%20Questions%20Every%20CIO%20Must%20Askmailto:William%20Mertes%20%[email protected]%3e?subject=Assured%20Windows%20Migrations:%20Five%20Questions%20Every%20CIO%20Must%20Askmailto:William%20Mertes%20%[email protected]%3e?subject=Assured%20Windows%20Migrations:%20Five%20Questions%20Every%20CIO%20Must%20Askhttp://olenick.com/2w7w8http://olenick.com/2w7w8http://olenick.com/2w7w8mailto:William%20Mertes%20%[email protected]%3e?subject=Assured%20Windows%20Migrations:%20Five%20Questions%20Every%20CIO%20Must%20Askhttp://olenick.com/2w7w8 -
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How to Pull the Windows Migration Trigger: Five Questions Every CIO Must Ask 13
NOTES
1Desktop OS by Version, February 2013. Net Market Share.http://www.netmarketshare.com/
2Gartner Says Effective Management Can Cut Total Cost of Ownership for Desktop PCs by 42 Per cent.
Gartner Group.http://www.gartner.com/newsroom/id/636308. This 2008 Gartner report states that
average annual total cost per PC runs from $3,413 to $5,867. The full report is available at
http://web.citrix.com/go/m2l/hi/pdf/GartnerReport.pdf
3Microsoft gooses Windows XP's custom support prices as deadline nears. ComputerWorld, 2/21/2013.
http://www.computerworld.com/s/article/9237019/Microsoft_gooses_Windows_XP_s_custom_support_
prices_as_deadline_nears
4Windows XP SP3 and Office 2003 Support Ends April 8, 2014. Microsoft.http://www.microsoft.com/en-
us/windows/endofsupport.aspx.
5
A low-touch upgrade is possible when an existing PC can be converted to the target configurationremotely and automatically. A high-touch upgrade requires hands-on work to achieve the same result.
For details, seehttp://technet.microsoft.com/en-us/windows/pilot-and-deploy-windows-7.aspx.
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