Windows 10 Rollout Project

Table of Contents

Proposal Overview......................................................................................................................................3

Problem Summary...................................................................................................................................3

IT Solution...............................................................................................................................................3

Implementation Plan................................................................................................................................4

Review of Other Work.................................................................................................................................5

Relation of Artifacts to Project Development..........................................................................................8

Project Rationale.......................................................................................................................................10

Current Project Environment.....................................................................................................................11

Methodology.............................................................................................................................................13

Project Goals, Objectives, and Deliverables..............................................................................................14

Goals, Objectives, and Deliverables Table.............................................................................................14

Goals, Objectives, and Deliverables Descriptions.................................................................................16

Project Timeline with Milestones..............................................................................................................19

Outcome....................................................................................................................................................20

References.................................................................................................................................................23
Windows 10 Rollout Project

Proposal Overview

Problem Summary

Midsize Law Firm LLP, is a medium-sized law firm based in Indianapolis, IN. They have

75 attorneys and 100 support staff divided between 5 different offices for a total of 175

employees. Each employee is issued a laptop so they can work from any of the 5 satellite offices

or home. Due to Microsoft’s sunset of the popular Windows 7 operating system, it is necessary to

refresh all equipment in the firm so that the firm can utilize Windows 10 and continue to receive

vital security updates from Microsoft. All equipment currently in use at the firm was purchased 7

years ago, is currently past all manufacturer warranty dates and not capable of running Windows

10. There is currently no standard model laptop or monitor and all technology is a mixture of

different model monitors and laptops purchased over the last 10 years. The Executive Committee

has tasked the Director of Information Technology and his team with upgrading and

standardizing the current technology environment. Upgrading technology across the firm’s 5

offices will include ordering new laptops, docking stations, monitors, creating a Windows 10

image, deploying it and lastly training the firm’s employees on the changes in Windows 10.

IT Solution

The Director of Information Technology has recommended using the internal IT

Department to create a Windows 10 environment, contracting Electronic Strategies Inc.(ESI) to

purchase equipment and dispose of outdated resources, and contracting Traveling Coaches to

assist in creating a training program to prepare all attorneys and support staff for the changes in

Windows 10. While a significant change to an organization can be frightening it’s important to

remember that the equipment refresh and migration to a more modern operating system are

unfortunately mandatory due to Microsoft’s decision to stop supporting Windows 7. As of this

Windows 10 Rollout Project

time Midsize Law Firm LLP is operating in an environment that has no mainstream or even

extended support as of January 14th, 2020. This means the firm is no longer receiving security

patches, bug-fixes or improved functionality in our Windows environment. This puts the firm

and client data at risk of a malware attack or a data security breach.

Implementation Plan

The IT Department will handle the Windows 10 Rollout Project in three phases that align

with the three main goals of this project and will last no longer than 16 weeks. The first phase is

anticipated to last 5 weeks and will primarily involve the IT Department and a small cross-

section of support staff and attorneys who will act as our “testers”. Phase 1 will focus on creating

a Windows 10 image for our new equipment, having the test group test that image, collecting

feedback and fine-tuning our image then lastly preparing for deployment.

The Windows 10 Rollout Project Phase 2 is estimated to begin no later than the second

week of May and is expected to last no longer than 8 weeks. In phase 2 of our Windows 10

rollout, we will be focusing on new asset deployment, old asset collection, and user training.

Each office location will receive no less than 1 full week of attention from our IT Department

and the Travelling Coaches the firm will contract to assist in user training. There will be

mandatory training sessions and sign-up sheets at each location however additional training can

be scheduled during Phase 3.

The final phase of our Windows 10 Rollout Project will primarily consist of “cleanup”

activities and is expected to last 9 weeks at the most. These activities will include but are not

limited to the inventorying of old assets, disposing of old assets, completing any outstanding

deployments and additional training. We also have an additional two weeks built into Phase 3

listed as “Buffer Time” that can be redistributed amongst the previous phases if necessary, to
Windows 10 Rollout Project

complete all aspects of this project within our suggested 16-week timeline. If the buffer time is

not necessary for project completion, we will close out the project and consider the Windows 10

Rollout Project complete.

It is important to note that some of our phases will overlap as some activities take place

in tandem. This will be more clearly outlined in our Project Timeline and Deliverables section

While a 16-week timeline may seem excessive for this project we would like to caution against

shortening the timeline. For this project to be successful and for the firm to experience the least

amount of difficulty in transitioning to our new Windows environment the IT Department will

require as much time as possible during each phase of this project.

Review of Other Work

During the IT department’s planning and preparation for the Windows 10 Rollout Project,

we’ve researched and investigated different techniques other companies have utilized during a

company-wide upgrade. Below we will summarize 4 different companies and what specific

learning opportunities they are providing us within our project. The learning opportunities we are

utilizing originate from Intelliteach which is a Managed Service Provider (MSP), Scantron which

is an educational assessment company, Juriba which is an IT migration consultation company,

and NewEggBusiness which is a free resource library written for tech professionals and business

leaders engaged in information technology.

 Intelliteach is an MSP based out of Atlanta, Georgia. Their online article “Upgrading to

Windows 10 and Office 2016 for Law Firms” has provided several good points to keep in

mind during our upgrade process. The article covers the steps that Intelliteach

recommends to all law firms consider when they are considering upgrading their

environment. The first point you should recognize from the overview of the

Implementation Plan on page 4 of this proposal. Intelliteach recommends considering a

Windows 10 Rollout Project

hardware refresh when upgrading. From their experience, if a computer does not exceed

the minimum requirements of an operating system then a company will see system

slowness and other system crashes. This will, of course, cause adopters of new

technology to have a negative view of the new software and start an already stressful

process on an even worse note. Another point that Intelliteach recommends is also

something that we have included in our Implementation Plan which is conducting

widespread user training and having floor support available for users to reach out to

quickly should they need help.

 Scantron is an educational assessment company based out of Minneapolis, Minnesota

and in their article “Do you know what old hardware is really costing you?” they discuss

criteria that need to be considered when deciding to either refresh hardware or not. The

author of the article, Dave Koopmans discusses what kind of hardware lifecycle needs to

be considered when working with technology. The author covers a brief history of

operating system upgrades and discusses the hardware requirements that have come with

each upgrade. In his experience, a hardware 3-year life cycle is a good rule to follow

when deciding whether to upgrade a piece of hardware or not. He does, however, make a

special caveat that if the hardware that is being considered is a laptop then the rule should

be a 2-year life cycle. Whichever rule we as a firm decide to follow moving forward, we

need to remember that at this time all the current equipment in the firm was purchased

when Windows 7 was the mandatory Microsoft upgrade. Meaning that every piece of

equipment in the firm was originally designed to run Microsoft Windows XP, Vista or 7.

Our current hardware infrastructure is currently 5 years behind where it should be

according to the author of this program. Some of the critical points that are made in this

article as to why we not only need to upgrade our operating systems but also our

hardware itself are that new hardware is faster and has more capacity, older hardware is

more mechanical and breaks down more, newer hardware is smaller and takes up less
Windows 10 Rollout Project

space, and new products are designed to take the most advantage of the newest operating

system and its features. The hardware refresh recommendations and reasons why we need

to adopt them are more than worth consideration towards the approval of this proposal.

 Juriba is an IT migration consultation company based out of Boston, Massachusetts. In

his article “The Basics of Planning Your Enterprise Desktop Migration to Windows 10”

author Barry Angell provided us with a wealth of project management information to

consider when deciding whether this project could be run through the internal IT

department. In part 3 of his article, he discusses how to decide if our firm’s IT department

has the necessary bandwidth, skills, and resources to run this project internally. The

Director of IT has considered this and believes without a doubt his department can run

this migration to a new hardware and software environment successfully. The article does

recommend utilizing both internal and external resources for a widespread hardware

migration and the Director of IT has considered that. As discussed on page 4 under the

Implementation Plan, we will be utilizing a company named Travelling Coaches to assist

us in working with our users. Traveling Coaches will augment our current IT department,

function as additional trainers and provide floor support for users at each site during our

week-long deployment at every office. In part 5 of this article, the author highlights some

areas of success when creating, testing and managing a new system image. Some lessons

we’ve taken away from this section are that we need to get a workable test out to our test

groups immediately. We can’t afford to keep our Alpha and Beta versions of the system

image existing until they are “perfect”. The only way for us to find out what needs to be

adjusted, if anything at all, is to get a working copy out to our test users as soon as

possible. The IT department will be referring to this article regularly as our plans

continue to take shape and we consider possible adjustments.

Windows 10 Rollout Project

 NewEggBusiness is an online resource for tech professionals based out of City of

Industry, California. In his article “How to Plan Your Windows 7 to Windows 10

Upgrade” author Adam Lovinus discusses some of the new tools that Microsoft

has made available to companies to help automate the process of upgrading or

provisioning a new Windows environment. One of those tools is the Assessment

and Deployment Toolkit (ADK) which was built specifically for Windows 10.

This tool offers an interface that will help design a Windows 10 system image and

will even allow us to remove features from the base Windows 10 operating

system to better suit our environment. On top of the ability to help us create our

system image, it will also assist us with deploying that image across the more than

175 laptops that we are currently recommending the firm purchase. Utilizing

ADK we will be able to run multiple concurrent installations of Windows 10

which will speed up our imaging process for our final push to deployment. This

tool will also allow us more granular control over modifications to the system as

we collect information from our Alpha and Beta testers.

Relation of Artifacts to Project Development

 Intelliteach: This article is relevant to our project from its position on hardware refresh

requirements and user training. Hardware in our current environment is already several

years old so it’s important to factor that into how we believe Windows 10 will perform if

we decided to leave our current laptops in place and just upgrade the operating system

themselves. Since the systems meet the minimum requirements it’s possible, they may

run Windows 10 however we will not be able to take full advantage of everything our

upgraded system can offer us without the hardware refresh. Intelliteach also gives us

good recommendations regarding user training. They suggest conducting new user
Windows 10 Rollout Project

training and keeping trainers on the floor as available support personnel for the new users

during our rollout.

 Scantron: This company may be better known for working in educational environments,

but their article makes a very strong case for why a hardware refresh for a company

should be mandatory. According to the author of the article, we need to adopt a 2-year but

not more than a 3-year lifecycle on all hardware. Keeping this in mind we are

recommending a hardware refresh so that we can take full advantage of the features

Windows 10 can offer our firm. This will also help us cut costs with future upgrades

since our system will not be as far behind technologically. It may be possible in a future

upgrade to perform only RAM and hard drive upgrades which would save the firm

thousands of dollars.

 Juriba: The recommendations by this company have helped shape some of our stances

towards the use of external assistance to help augment our internal staff. In as much, we

will be contracting a company named Travelling Coaches. This company will assist us in

creating a training program for all users. These training modules will be no more than 90

seconds a module and will cover the most frequently asked questions by new users of

Windows 10. We will also be utilizing Travelling Coaches as floor support during our

week-long deployment at each office to make sure that every user gets the additional

attention they require.

 NewEggBusiness: The new tools offered by Microsoft are going to streamline our

deployment process. The Assessment and Development Toolkit (ADK) will allow

our team to create a more robust and customized system image for our firm. ADK

will also allow us to image multiple machines at a time which should help us keep

our deployment timelines. This streamlined process will help free up additional
Windows 10 Rollout Project

resources within the IT department so we can focus on user training and old asset

collection/destruction.

Project Rationale

Midsize Law Firm LLP specializes in corporate law whose clients are banks, hospitals,

and state governments. The firm and its employees have access to confidential data that is

protected under various State and Federal laws that include Healthcare, Intellectual Property,

Real Estate, and Finance. Since the firm’s clients are from heavily regulated industries with

stringent auditing and reporting standards, data confidentiality and protection are of the utmost

importance. As such having a computer environment where the primary operating system used

firmwide is no longer supported by the vendor is not only dangerous to the firm but a violation of

the firm’s contractual obligations with their clients. The impetus and the rationale behind

approval of this project rest on two points; the first is that an outdated operating system opens the

firm to attacks by malicious outsiders and the second we could be legally and financially liable

for data loss containing client sensitive information.

Microsoft officially ended all support of the popular Windows 7 operating system on

January 14th, 2020. This means that the firm’s systems are now vulnerable to any “bugs” or

security vulnerabilities. Given the popularity of the Windows 7 operating system and the sheer

number of computing devices in the world it is a sure bet that malicious outsiders will attempt to

seek out and exploit any system found running this obsolete operating system. The firm can not

afford to be a target.

Midsize Law Firm LLP represents Religious Alliance Hospitals, a national hospital

organization with hundreds of locations across the country and millions of patients. Religious

Alliance Hospitals are bound by HIPAA regulations regarding client health data integrity,
Windows 10 Rollout Project

confidentiality, and accountability. HIPAA violations can incur fines ranging from a few hundred

dollars to millions of dollars per violation. These fines are only a minor part of the damage a data

breach can cause. The damage to the firm’s reputation could also be irreparable if the data breach

is shown to originate from the firm. The firm also needs to consider our contractual obligations

with our other clients that require we store all client data securely. The firm can scarcely consider

data secured if the very foundation of our IT systems is running unsupported and outdated

software.

Current Project Environment

In the following sections, we will provide a brief overview of the current technological

state of Midsize Law Firm LLP. This will help illustrate the need for our Windows 10 Rollout

project.

Current Technology

 Number of Desktops: 60 x Dell Optiplex 709 with i5 processors and 8 GB of

RAM.

 Number of Laptops: 115 x Dell Latitude 6430 with i5 processors and 8 GB of

RAM.

 Current Operating System: Windows 7

 Number of Monitors: 350 total with no common model

There are several issues with the state of the current environment chief among them is

that Microsoft as of January 14th, 2020 is no longer offering any level of support for Windows 7.

This opens us up to vulnerabilities like cyber-attacks, malware issues, and potentially worst of all

a data breach. Microsoft releases regular updates to their products. These updates can range from
Windows 10 Rollout Project

correcting simple flaws in the way a program runs to closing critical security holes in their

system that could open us up to a potential data breach.

The next significant issue with our system is that we are utilizing equipment that was

released in 2011. After contacting our hardware providers at Dell we have verified that none of

our desktops or laptops have been under a manufacturer’s warranty in over 2 years. While it may

be possible to run Windows 10 on our current technology, we pay out of pocket for all hardware

replacements. This puts additional strain on the firm’s budget for technology, stretches our

current technology supplies thin, and puts extra pressure on our IT department to keep equipment

that should have long since been retired in working order.

The final issue is that our monitors are also woefully out of date. A thorough inventory of

our equipment shows that none of our monitors can support a modern digital video and audio

connection like HDMI or DisplayPort. Each employee of the firm receives either a laptop or a

desktop and two monitors to perform their duties. In our current environment, no one has two

monitors of the same model. This causes issues not only for our employees but for our IT

department who frequently troubleshoot video issues over the phone. As of this time, the IT

department could find themselves supporting over 10 different models of monitors at any time.

Recommended Solution

Our recommendations for fixing the issues in our current environment are to modernize

and standardize all equipment in the firm. While the primary concern is that we are running on

an outdated operating system there is also the secondary issue that there are too many different

models of equipment and a tertiary issue that none of our hardware has a manufacturer’s

warranty. Our proposal will first task the IT department with creating a new Windows 10

environment utilizing the most current technology available. We also propose standardizing the
Windows 10 Rollout Project

entire firm on matching equipment. In this case, we recommend issuing everyone a laptop and

two monitors. This will reduce the amount of time the IT department needs to spend researching

any hardware issues, allowing them to target the root cause faster and of course call the issue in

for manufacturer warranty coverage. Our recommended solution will not only resolve our

immediate problems but will also help the firm save time and money on future upgrades when

we only need to update the environment from the past 2 years instead of the past 9.

Methodology

The IT Department will be utilizing the Rapid Application Development Methodology or

RAD approach to this project. RAD is an AGILE management strategy that emphasizes fast

project turnaround, which given our current environment is something we need. Two key

benefits of RAD methodology are a focus on regular communication with constant feedback

from our users and regularly producing prototypes for our users to test. RAD methodology

follows four main phases; Requirements Planning, User Design, Rapid Construction, and

Cutover.

 Phase 1 - Requirements Planning: We will be holding an IT department meeting with the

InfoTech Committee to discuss refreshing our hardware and upgrading to Windows 10.

From this meeting, we will clearly define our scope for the project moving forward. At

this time the key points the Director of IT would like to discuss are; hardware

requirements for new equipment purchases, attorney and support personnel requirements,

and our recommended timeline. The results of the InfoTech Committee meeting will be

forwarded to the Executive Committee for final approval or requests for additional

revisions.
Windows 10 Rollout Project

 Phase 2 – User Design: The IT department will regularly meet with a representative of

the InfoTech Committee and our test users. In this phase, we’re going to focus on

constructing a working prototype of our system image and applying it to a group of test

machines. This phase of our work is iterative meaning we will repeat or revisit our

previous steps as necessary. For example, we construct an Alpha version of our system

image, our testers utilize it and give us feedback, we take that feedback and repeat the

construction of the Beta version. Since we will be focusing heavily on prototyping and

user feedback at this phase, we should be able to complete a working final copy within 3

weeks.

 Phase 3 – Rapid Construction: The focus of this phase is to take the feedback from the

previous phase, applying it to creating a final system image, uploading it to our SCCM

server for deployment to our new hardware. This process will take place at our

Indianapolis, IN offices where the IT department is based. During this phase, we will still

invite feedback and last-minute changes to the system image. As with previous phases,

this phase is also iterative, and we will revisit the previous phases if necessary.

 Phase 4 – Cutover: This is the implementation phase where we complete mass imaging

machines, transporting equipment to outer offices, deploying to users, training users,

collecting old assets and preparing old assets for destruction. The Cutover phase is the

longest phase and will involve the IT department and Travelling Coaches working

together at each satellite office to ensure the final deployment is successful.

Project Goals, Objectives, and Deliverables

Goals, Objectives, and Deliverables Table

Goal Supporting objectives Deliverables enabling the project objectives

Windows 10 Rollout Project

1.a. Create a Windows 10 Image 1.a.i. Hold a planning meeting with

InfoTech Committee and Testers 1.a. i
* All deliverables within this 1.a.ii. Create an initial test image on a group
Objective are iterative meaning of test machines 1.a.ii
that they will be repeated until a 1.a.iii Test and Revise within the IT
final system image is completed* Department 1.a.iii
1.b.i. Present initial system image to
Migrate to a Testers1.b.i
1 Windows 10 1.b.ii. Collect Feedback 1.b.ii
1.b. Test and Revise the Image
Environment 1.b.iii. Revise System Image and Deliver to
Testers 1.b.iii
* All deliverables within this
1.b.iv. Hold a meeting with InfoTech
Objective are iterative meaning
Committee to present the final system
that they will be repeated until a
image 1.b.iv
final system image is completed*
1.b.v. Hold a meeting with Executive
Committee to present the final system
image 1.b.v
2.a.i. Deliver ESI quote to the Executive
Committee for approval 2.a.i
2.a. Equipment Procurement. 2.a
2.a.ii. Place order with ESI 2.a.ii
2.a.iii. Receive all ordered equipment 2.a.iii
Upgrade the
2.b.i. Image all laptops 2.b.i
Firm’s
2 2.b.ii. Inventory and assign all assets by
Hardware 2.b. Equipment Deployment 2.b.
office and user2.b.ii
Technology
2.b.iii. Deploy all assets 2.b.iii
2.c.i. Collect all old assets 2.c.i
2.c. Old Asset Collection 2.c 2.c.ii Inventory all old assets 2.c.ii
2.c.iii ESI collects old assets 2.c.iii
3.a.i Meet with Travelling Coaches to
3.a. Create a User Training discuss their recommendations for user
Program 3.a training 3.a.i
3.a.ii Create initial training program 3.a.ii
3.a.iii Train the test group 3.a.iii
3.b.i Meet with Testers and Collect
Feedback 3.b.i
3.b Refine the Training Program
3.b.ii. Revise the training program 3.b.ii
3 User Training
3.b.iii Present final training program to
Travelling Coaches 3.b.iii
3.c.i Conduct User Training During Each
Office Deployment 3.c.i
3.c.ii Solicit Feedback Regarding Training
3.c Conduct User Training 3.c
Program 3.c.ii
3.c.iii Prepare a final training program from
the Feedback 3.c.iii
Windows 10 Rollout Project

Goals, Objectives, and Deliverables Descriptions

The Windows 10 Rollout Project has three main goals with a number of objectives and

deliverables within each. Our three main goals for this project are to; Migrate to a Windows 10

Environment, Upgrade the Firm’s Hardware Technology, and User Training. Each Goal,

Objective, and Deliverable will be explained in greater detail below.

Goal 1. Migrate to a Windows 10 Environment

The first goal of this project is to migrate the firm to a Windows 10 environment. At

present, the firm is running in a Windows 7 environment which as of January 14th, 2020 is no

longer supported by Microsoft. This has placed the firm in a position where we are no longer

receiving critical system updates, bug fixes, and security patches.

Objective 1. Create a Windows 10 Image

Creating a Windows 10 image is the first step in migrating the firm to a Windows 7

environment. The IT department will need to survey our current environment and begin crafting

a Windows 10 environment that will continue to meet the needs of our organization. The

Windows 10 Image creation process will start off with a meeting involving the InfoTech

Committee and our testers who will be comprised of attorneys and support staff. During this

meeting, we will discuss the system image creation process and deliver our timeliness on when

our users can expect the first test machines, what the testing criteria will be, and what feedback

we will need to revise our image. The IT department will then begin creating the initial Windows

10 system image and testing it within the IT department to confirm stability before releasing the

first test machines to our users.

Objective 2. Test and Revise the Image

Windows 10 Rollout Project

During this objective, the IT department will largely be performing the same steps

repeatedly until a finished image is approved by both our users and the InfoTech Committee. We

will present a test machine to our users, allow them several days to test the machine, document

their feedback and then from that feedback, the IT department will create the next version of the

Windows 10 image. The final deliverable of this objective will be the completed system image

which will be presented to the Executive Committee after all test user feedback has been

processed and applied to our final system image. Upon final approval from both the Executive

Committee and the InfoTech Committee, the IT department will move on to the next goal of

Upgrading the Firm’s Hardware Technology.

Goal 2. Upgrading the Firm’s Hardware Technology

The second goal of this project is to upgrade the firm’s hardware technology. The last

time the firm saw a system-wide refresh of equipment was in 2013. That refresh included

purchasing new laptops, monitors, and docking stations. Given the age of our equipment and the

wide variety of equipment brands that are in the office, the IT department is recommending the

same level of equipment refresh during this project.

Objective 1. Equipment Procurement

The IT department will contact our partners with Electronic Strategies Inc. (ESI) and

request a quote for 175 laptops, 350 monitors, 175 docking stations. Once we have received this

quote from ESI we will deliver this to the Executive Committee for approval. After we’ve

received approval for the purchase ESI has confirmed they can have all equipment to us within

two weeks. We will begin preparing for deployment as soon as we receive our final order.

Objective 2. Equipment Deployment

Windows 10 Rollout Project

Equipment deployment will begin with imaging all laptops the IT department receives

with the completed and approved Windows 10 image. At this stage changes to the final system

image are no longer possible as we will be preparing our deployment schedule with each of our 5

offices. All laptops, monitors and docking stations will be asset tagged and assigned to each user

for asset tracking and inventory purposes. Finally, all equipment will be deployed to each office

and old equipment will be collected.

Objective 3. Old Asset Collection

The final objective of our second goal will be Old Asset Collection. The IT department

will collect and inventory all old equipment as we deploy new equipment. All equipment will be

shipped to our Indianapolis, IN headquarters for final inventory and disposal. ESI has already

agreed to securely dispose of and recycle all old assets as part of our new equipment order with

their company.

Goal 3. User Training

The final goal of this project is to train our users in the changes they can expect with

Windows 10 which should help improve the overall user experience post new equipment

deployment. At the end of this goal, we plan to not only have better-educated users but a well-

established training program built upon our observations and feedback we collect from our

training sessions.

Objective 1. Create a User Training Program

The firm has partnered with Travelling Coaches to help augment our IT department

during this project. Travelling Coaches will assist our own internal training team with creating a

training program that will help our users adjust to the changes in Windows 10. Our deliverables

with this objective will be the initial creation of a training program and training of our test users.
Windows 10 Rollout Project

Objective 2. Refine the Training Program

One of the most important objectives of user training is to create a training program that

is thorough, understandable and is reusable. Our second objective is will involve working closely

with our test users and revising our training program based on their feedback. This feedback will

be vital during our deployments at each office.

Objective 3. Conduct User Training

Our final objective will be to conduct user training at each location. The IT department
and the firm’s management have agreed that user training is critical to the success of this project.
As such user training is mandatory for all attorneys and support personnel. Training at each
location will be conducted over the span of Monday and Tuesday of each deployment week
leaving Wednesday through Friday open for follow up training sessions. Travelling Coaches and
the internal training team will all walk around each office offering to assist users with their
training needs. It is important that our trainers be seen and make themselves available so each
user’s needs are met. At the end of each deployment, feedback will be collected from each site
and if time permits we will revise our training for our next deployment. After all new user
training is completed we will collect all feedback and create a new user training program for
future employee onboarding.

Project Timeline with Milestones

Milestone or Deliverable Duration Projected Start Date Anticipated End Date

Initial Image Creation 2 weeks March 30th, 2020 April 10th, 2020
Equipment Purchase/Delivery 2 weeks March 30th, 2020 April 13th, 2020
Construct and Test 1st Image 1 week April 13th, 2020 April 20th, 2020
Revise and Re-Test Image 1 week April 20th, 2020 April 27th, 2020
Final Image Creation 1 week April 27th, 2020 April 29th, 2020
Image all new laptops 1 week April 29th, 2020 May 8th, 2020
Chicago Deployment 1 week May 11th, 2020 May 15th, 2020
Merrillville Deployment 1 week May 18th, 2020 May 22nd, 2020
South Bend Deployment 1 week May 25th, 2020 May 29th, 2020
Carmel Deployment 1 week June 1st, 2020 June 5th, 2020
Indianapolis Deployment 1 week June 8th, 2020 June 12th, 2020
Inventory Old Equipment 1 week June 15th, 2020 June 19th, 2020
Dispose of Old Equipment 1 week June 15th, 2020 June 26th, 2020
Outstanding Deployments 1 week June 15th, 2020 July 22nd, 2020
Additional Training 1 week June 15th, 2020 July 22nd, 2020
Runover Time 1 week Used as Necessary July 22nd, 2020
Windows 10 Rollout Project

Outcome

The close of this project will result in an up to date IT environment with a more

knowledgeable user base. Attorneys and support staff alike will have access to faster more

reliable equipment that is covered by a manufacturer’s warranty. The firm equipment will receive

the latest security updates from both hardware and software manufacturers. Our users will be

more adept at utilizing the new technology and should experience little to no downtime. Most

importantly the firm will find itself in a stronger position to protect both firm confidential and

client confidential data from security breaches.

Our proposed method for measuring the success of this project will take place over 60

days following the final deployment of this project. It’s important to align all success criteria

with the goals of the project. Our first goal “Migrate to a Windows 10 Environment” will be

measured on how much time it takes to create a Windows 10 image, get the image in front of the

testers and receive final approval from the Executive Committee to move forward with our

deployment schedule. Keeping this in mind the IT department has estimated this process to last

no more than 5 weeks. In light of that timeline, the first goal will be considered a success if the

deliverable is met within a 5-week timeframe.

Our second goal “Upgrade the Firm’s Hardware Technology” success will be measured

with a combination of user surveys and timeline adherence. We will create a survey that will

anonymously survey the attorneys and support staff at each office to give us their feedback on

the deployment process. We will be interested in their opinions on whether they approve of the

new hardware’s performance, how disruptive the deployment process was, and how professional

the deployment team was. These results will be measured on a 5 point scale, offer additional

comment sections and to help achieve maximum survey completion we will hold a drawing at
Windows 10 Rollout Project

each office for a $50 visa gift card. If the final total average survey score across all offices shows

an approval rating of 85% or greater the metric will be considered a success. The second metric

we will measure is timeline adherence. The IT department expects the deployment process to last

no more than 8 weeks from the time equipment is delivered for imaging to the time it is deployed

to the user. Any amount of time less than 8 weeks total will be considered a success.

The final goal of “User Training” will be measured solely on user surveys. The success of

this particular goal is very perception based. We will conduct two surveys over a span of 60 days.

The first survey will be delivered after training has been delivered during each office’s

deployment week and will offer scoring scales of 5 points and sections for additional comments.

We will again offer a drawing for a $50 visa gift card for successful survey completion. 60 days

after training completion we will send out another survey and again offer a similar reward. In our

second survey, we will be looking to see if the users still feel the overall training received during

the deployment was sufficient and if they feel there was anything missing in the training that

should be added. If approval ratings between both surveys average out to be 85% or greater we

will consider training to be a success.

The final results of the Windows 10 Rollout Project success criteria will be presented in a

formal report to the Executive Committee for final review, feedback, and approval. The final

determination of the Executive Committee will be presented to the firm in our quarterly firm

“All Hands On Deck” meeting.

Windows 10 Rollout Project

References

Friedel, C. (2019, March 20). Windows 10 Upgrade For Law Firms. Retrieved March 15, 2020,

from https://www.intelliteach.com/windows-10-upgrade-for-law-firms/

Koopmans, D. (2020, January 16). Is It Time for a Hardware Refresh? Retrieved March 15,

2020, from https://www.scantron.com/blog/is-it-time-for-a-hardware-refresh/

Angell, B. (n.d.). The Basics Of Planning Your Enterprise Desktop Migration to Windows 10.

Retrieved from https://blog.juriba.com/the-basics-of-planning-an-enterprise-desktop-

migration-to-windows-10

Lovinus, A. (2019, February 2). How to Plan Your Windows 7 to Windows 10 Upgrade.

Retrieved from https://www.neweggbusiness.com/smartbuyer/windows/plan-windows-7-

to-windows-10-upgrade/