CLOUD READINESS

CHECKLIST

www.Seaside-Soft.com * 347-627-0004 * info@seaside-soft.com

Moving to the cloud is more than just upgrading servers and

software. It represents a fundamental shift in the way that you
manage technology. This transition gives you a rare opportunity to
align technology with your overall business vision, which in turn can
help you grow your business, improve productivity, and reduce
costs.

This document is designed to help you outline your business goals

and desired capabilities, document your infrastructure, and
understand the set of cloud-relevant skills in place in your
organization.
 Cloud Readiness Checklist

This information can be used to develop a plan for moving to the

cloud that is clear, understandable, and measurable, and one that
helps bring your business vision to reality.
About Seaside Software Solutions
Seaside Software Solutions is a Microsoft Partner here to provide
you an amazing customer service experience as you work to solve
key business challenges and move to the cloud.

You can leverage our 25+ years of experience in Microsoft

technologies (starting way back at Windows 3.1 - we even know
mainframes), as you leverage technology to become more agile,
improve productivity, enable collaboration across devices and
locations, reduce costs, and maintain compliance.

As your organization prepares for the move to the cloud, you can
feel confident knowing that we bring the expertise required to
assess the current state of your infrastructure and applications, and
help you design and implement your cloud.

We have worked on projects from large to small, across a wide

variety of technologies including Microsoft, Oracle, IBM, and more.

What some of our customers have to say:

Outstanding IT professional with mastery level technical, analytical, and

architectural skills. Has the unique blend of technical and soft skills that
enable him to engage with anyone at any level and produce excellent
results. A true pleasure to work with!
-- Mendy Moskowitz, Systems Manager, Consolidated Edison of NY

Conrad is a meticulous, thorough and detail-oriented person. He is

reliable and professional, and he delivers.
-- Kevin Mann, Accenture

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Contents
INTRODUCTION................................................................................................................... 5
CHECKLIST STEPS ................................................................................................................. 5
Notes ........................................................................................................................................................... 6
Step 1: Outline Business Goals .............................................................................................................. 8
Step 2: Perform Infrastructure Assessment........................................................................................... 9
Software Licenses .................................................................................................................................. 9
Physical Hardware ................................................................................................................................ 9
Purchased Software ........................................................................................................................... 10
Developed Software.......................................................................................................................... 10
Skills Assessment.................................................................................................................................. 11
Step 3: Evaluate Results ....................................................................................................................... 12
Step 4: Define Project .......................................................................................................................... 13
Step 5: Develop Project Plan .............................................................................................................. 14
Step 6: Build Baseline Cloud ............................................................................................................... 15
Step 7: Develop and Test .................................................................................................................... 16
Step 8: Go Live ...................................................................................................................................... 17
Step 9: Implement Post-Go-Live Plan ................................................................................................ 18
Step 10: Hold Post-Go-Live Reviews ................................................................................................. 19
CONCLUSION .................................................................................................................... 20

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INTRODUCTION
This document, sponsored by Seaside Software Solutions, provides a 10-point checklist for moving to the
cloud. We hope that you find this information helpful, and that you consider working with Seaside Software
Solutions (a Microsoft Partner), as you begin your move to the cloud.
The document contains a series of checklists that help define your business goals and desired capabilities,
outline the status of your infrastructure (servers, software, services), and understand the set of skills that exist
in your organization in regard to a move to the cloud.

CHECKLIST STEPS
The following table outlines the general set of steps used to plan for and implement a move to the cloud. The
steps and participants for individual organizations will vary, but these steps can serve as a guideline.

# Step Description Who

1 Outline Business Goals
2 Perform Infrastructure
Assessment
3 Evaluate Results
Outline the business goals and capabilities that Executive Team
should be in place once a migration to the Business Team
cloud is complete. Technology Team
Note: A typical migration takes place in
phases, so start by listing all goals and
capabilities, and later work to prioritize/assign
to phases.
Assess the state of the corporate infrastructure. Business Team
This includes an inventory of hardware, Technology Team
software, etc., and an understanding of the
cloud-relevant skill sets in place at your
organization.
Once steps 1 and 2 are complete, set up a Executive Team
meeting with all participants to review and Business Team
evaluate the results. Technology Team

4 Define Project
5 Develop Project Plan
Define the scope of the project to begin Executive Team
moving to the cloud. This includes features and Business Team
functionality, high-level steps, timeline, and Technology Team
budget.
In this step, a detailed project plan is Business Team
developed. This includes the Technology Team
features/applications/databases to be
implanted in the cloud, and the steps to Reviewed by:
develop/migrate/implement. This also includes Executive Team
developing a post-production support process.

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6 Build Baseline Cloud Implement the initial non-production version of

7 Develop and Test
8 Go Live
9 Implement Post-Go-Live Plan
10 Hold Post-Go-Live Reviews
the cloud with a limited set of features and
small set of users. Review with all teams to
ensure that what is being implemented matches
the overall vision.
Note: This is the step in which to implement key
features such as hybrid cloud functionality,
device enablement, etc.
This is an iterative step during which
applications, databases, etc. slated for
implementation in the cloud are
developed/upgraded and tested.
Once testing has completed, applications,
databases, and features and switched on in
production. There can be an iterative
approach versus turning on everything at once.
Once the cloud is live, the post-production
support plan is implemented.
For a period of time after the cloud systems go
live (usually 2 or more months), post-go-live
review meetings are held with all teams to
address issues and plan upcoming
enhancements.

Notes
Moving to the cloud is not an all-or-nothing event. There are normally multiple projects phases during which
functionality is implemented. The implementation of a “hybrid cloud” allows you to keep some applications on
premise (as they exist today) and some in the cloud. This allows you to move step-by-step to the cloud while
maintaining business continuity.
The tables in this document are designed to help get you started assembling the necessary information to
prepare for a move to the cloud. If your organization already has mechanisms in place to inventory servers,
software, etc., there is no need to fill out the tables in this document, but instead you can utilize the inventory
reports generated by these systems. Excel is the preferred format for inventory reports whenever possible.
Building a full inventory of licenses, servers and software can be a daunting task, especially for organizations
where not much is documented. If you have a large number of undocumented servers and software
applications, start by listing the ones most closely associated with the business processes that you are
considering moving to the cloud.

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Step 1: Outline Business Goals

This checklist helps you document your business goals and desired capabilities, including items that you would
like to be able to achieve today but cannot.
Below are some examples to get you started (your list is not limited to these items or topics):

 “allow employees in the field to run our applications on mobile devices”

 “more easily manage information related to projects. We currently use email and file folders.”
 “develop useful business reporting that allows us make effective decisions about the business”
 “allow employees to use their own mobile devices for work, but easily manage security”
 “Improve the system for sending order information to suppliers (electronically versus by fax or email)”
 “have a way to search for all documents, emails, etc. related to a topic or project.
 “stop going back-and-forth with customers in emails with attachments. Is there a better way?”
 “improve our data backup process. Can backups be stored in the cloud?”
 “move our customer service application to the cloud so it can be used from anywhere.”
If you are not sure whether to add an item, add it - you can always remove it later.
List the business goal or desired capability in the first column, and in the second column, the challenges that
you face achieving this goal (if it is not easy to list the challenge, list why this is not yet implemented).

# Business Goal / Desired Capability Current challenges / reasons not implemented

1 

2 

3 

4 

5 

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Step 2: Perform Infrastructure Assessment

The next step is to document your current infrastructure. This includes building a list of your servers, software,
subscriptions, etc., to gain a full picture of your technology. This information is critical for helping you
determine the best path forward.

Software Licenses
List of software licenses that the company owns. This includes manufacturer, name of the software, version,
purchase date, license expiration date, cost (if known), and any comments you have about the software.
For example:

Manufacturer Name Version Purchase Date Expiration Date Cost Comments

Microsoft Office 2003 2006 Expired $356/user Expired

Intuit QuickBooks 2008 2008 Not sure $120/user/yr. Want to move

online

Manufacturer Name Version Purchase Date Expiration Date Cost Comments

Physical Hardware
List of the company’s physical hardware. Includes workstations, servers, network devices, backup devices, and
any other hardware that you feel is important. If you have a great deal of hardware (larger numbers of
servers, a large number of network and backup devices, etc.), summarize as opposed to listing each
separately.
For example:

Manufacturer Name Purchase Support Annual Purpose Comments

Date Expiration Support
Date Cost

Dell PowerEdge 2008 2011 $1200 10 servers

2850
3rd party support contract:
$100/month

IBM IntelliStation 2005 2009 82 workstations. 62 running

285 Windows 7; 20 running
Windows XP.

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Purchased Software
This is the list of purchased software actively used in your company. Includes applications such as Microsoft
Office, QuickBooks, etc. If your workstations or servers came pre-installed with software that you definitely do
not use, leave that software off of the list.
For example:

Manufacturer Name Version Purpose Comments

Intuit QuickBooks Handle customer taxes. Would like to have a way besides
Import tax information sent email for customers to send
via email by customers. information.

Oracle PeopleSoft 11 Corporate payroll system

Manufacturer Name Version Purpose Comments

Developed Software
List the software developed by your organization or a third party developer for use in your organization. For
example, your IT department may have developed desktop or web-based applications, or a third party
company may have developed an application for you.
For example:

Application Name Type Platform / When Purpose Planned Enhancements Comments

Language Developed / Challenges

Company Web Application C# and SQL 2007 Informational Would like to

Website Server improve

Timekeeping Desktop Visual Studio 2004 Used by employees Need rewriting. Developed by
System Application 2003 / VB to enter hours Would like to third party in
integrate with our Visual Studio
payroll system. 2003.

Customer Service Mainframe COBOL and 1977 Handles customer Cannot enhance (too
Application Application DB2 service for 4000 old/no skills in house)
customers

Application Type Platform / When Purpose Planned Comments

Name Language Developed Enhancements

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Skills Assessment
List the skills in place in the organization relative to implementing and maintain a cloud computing
environment. Also list areas where they are challenges.
For example:

Skill Details

Development Our developer currently use Visual Studio 2010 but have not done anything with the cloud.

Database Most of our databases are SQL Server 2008. Our database developers are very good and we have a team that
supports our 80 SQL Server databases.

Mainframe We have a mainframe that runs older but important applications (COBOL/DB2), but only have a couple of people that
can support it.

Skill Details

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Step 3: Evaluate Results

Once you have completed steps 1 and 2, you have the basic information necessary to begin formulating a
plan to move to the cloud.
The next step is to evaluate the results of the infrastructure assessment, and begin the process of developing
the plan for the cloud.

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Step 4: Define Project

Now that you have an understanding of your business goals and current infrastructure, the next step is to
define a project. Depending upon your organization, this can involve determining the set of features to
implement, allocating resources, setting timelines, and setting budgets. In some cases there may need to be a
review with company officers.

In regard to the project implementation, start by building a list of the features that will be implemented in the
cloud (functionality/applications/databases/etc.), prioritizing the features based on a number of factors
including complexity, timeline, and cost, and developing a point-by-point technical implementation and
business transition plan (if required) for each.

Next, determine which feature will be implemented, and on what timeline (for example, one or more phases).

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Step 5: Develop Project Plan

Once the set of features has been approved, the next step is to develop a complete project plan. This
verbosely outlines the tasks to implement each feature, and includes the duration of the task and the person
who is completing the task.

Developing a project plan can be complex, and there are many choices of tools. Microsoft Project is a great
tool, but we have also seen very (very) complex project plans effectively implemented in Excel.

Once the initial project plan is completed it should be stored and versioned. For example, a SharePoint site
can be created for the project and the project plan stored on this site. This type of approach makes it easier
to view the plan, handle versioning, and manage security (who can view/edit the plan).

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Step 6: Build Baseline Cloud

The project plan should be structured so a baseline implementation of the cloud is the first thing developed.

The items implemented in the baseline build depend on the size of the organization and number of
applications, databases, etc. For example, a baseline version could include some or all of the following:

- Office 365 for 5 users

- Azure Initial Setup (storage, Active Directory)
- One Virtual Machine
- Active Directory synchronization for 5 test users
- Device management for 5 test devices
- One SQL Database (non-VM)
- One .NET Application
- One mobile application (mobile service)

Once these elements are in place there should be an end-to-end review with all teams present. This is key to
helping people in the organization understand what is being implemented (versus thinking of the cloud as
being something “out there somewhere” that they don’t understand).

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Step 7: Develop and Test

During this step, the cloud is fully implemented, applications are developed or upgraded, databases
implemented, etc. Many of the tasks are similar to a standard software development effort.
In a typical software development project, computer source code is developed, stored in “source control”, and
later moved to “production”.
Many of the Microsoft software development, database, and version control tools have been implemented in
the cloud. These tools allow for the development of applications that connect both to the cloud and on premise
(existing) systems.
Once a system is developed, several rounds of testing are performed. Our recommendations is that multiple
rounds of both functional and technical testing are performed.

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Step 8: Go Live
As testing completes, systems are moved to “production”. As mentioned earlier, this can be an iterative process
(in steps or phases), versus all at once.

Here are some key points about go-live:

- An end-to-end go-live timeline should be developed. This lists everything that is happening in regard to
going live, and when it happens. Ideally, this should be practiced in the form of a “table top drill” (act
like you are taking the steps but don’t really take them) to make sure that the necessary coordination is in
place.

- Depending on how each system is implemented there can be a conversion of data (movement of data
from the old system to the new system) prior to go live.

- The old and new systems may run in parallel for a period of time. Once the new cloud system is
operating as expected, the old system is either turned off, or set to read-only.

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Step 9: Implement Post-Go-Live Plan

Once the system goes live the post-go-live plan should be implemented. This consists of an ongoing (daily if
not hourly) review of the infrastructure and systems to make sure that everything is operating as expected.

Additionally, this is the point at which the system support plan should be put into place.

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Step 10: Hold Post-Go-Live Reviews

For a period of time after the systems go live (usually 2 or more months), post-go-live review meetings should
be held to address issues and plan upcoming enhancements.

As issues are identified they should be put on a list (a ‘bug tracking system’ accessible by everyone is a good
approach).

It is important to take time during these sessions to understand issues, because they can be opportunities in
disguise.

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CONCLUSION
This document, sponsored by Seaside Software Solutions, provides a 10-point checklist for moving to the
cloud. We hope that you find this information helpful, and that you consider working with Seaside Software
Solutions, a Microsoft Partner, as you begin your move to the cloud.

Seaside Software Solutions

www.Seaside-Soft.com * 347-627-0004 * info@seaside-soft.com

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