How to choose a Microsoft Office 365™
Moving to the Cloud without Risking Productivity, Collaboration or Security
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Not all Microsoft Office 365 migration partners are equal.
You often find partners who look good on paper and realize – after
it’s too late – they’re missing the mark. Sometimes issues arise
when a project isn’t accurately scoped out, or when Office 365’s
value (and limitations) are not properly communicated at the
outset. In other cases, not enough thought is given to what
happens after day two and beyond.
Everyone has bad days. The challenge for many organizations is
how do you separate the wheat from the chaff?
I’ve assembled what I believe are the best practices and key
considerations for evaluating a great migration partner. This is
based on direct experience managing the migration of more than
20,000 mailboxes (and counting). In each section, I outline key
considerations and what to look for during every phase of a
migration. I hope it serves you well on your journey to the cloud!
Choosing a Microsoft Office 365™ Migration Partner | Introduction
Manager of Technical Services
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LinkedIn: Tim McKellips
About Tim McKellips
Tim McKellips has spent his entire 16-year IT career in the Microsoft
technology and professional services arena. He started as an Exchange 5.5
and Windows NT consultant before serving as the director of a Microsoft
practice in the Central and Eastern U.S. Tim joined Softchoice in 2007 and
today leads the company’s Technical Services team, defining strategy and
methodology for complex Professional Services solutions, with a special focus
Tim relishes living the stereotype of a gadget and technology enthusiast.
For fun, he and his family are slowly renovating their century old cottage in
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When you invest in Office 365, you’ll find lots of vendors who will tell you how they want to execute
your project. The reality is, the planning and design process is more about understanding your needs
and environment in order to tailor the right solution.
During the planning and design phase, I recommend the following:
Assess your current state
Understanding the health of your current systems before you plan for your end state is essential.
Many people skip this step and then deal with delays and failures during the actual migration. The
reality is your structure is only as strong as your foundation.
In my experience, the most important thing to do is make sure your Active Directory is healthy
and doesn’t contain errors. For instance, IT administrators often build exchange servers and fail to
remove them from Active Directory when they are no longer needed. This causes errors when these
servers are shut down and bad data is moved to Office 365.
1 BE ACCURATE
Planning and Design
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Choosing an Office 365 Migration Partner | Phase 1: Planning and Design
Consider the gap state
I’ve seen many IT decision makers look at Office 365’s features and decide what they want to achieve.
What often gets lost is the work involved in moving from point A to point B. This route – or the space
between your current state and end state – is the gap state and requires careful planning and design.
How to mind the gaps?
• Don’t squeeze your business into a narrow definition of Office 365. Instead, a partner should help
you think about creative ways to make Office 365 work for your business.
• Decide how Office 365 will help you achieve your business goals. For example, if uninterrupted
service is part of your migration goals, how will you maintain uptime during the gap state?
• Determine how migrating to Office 365 will impact your SLAs. Revisit your SLAs and key policies
as part of the migration plan. This includes evaluating how Office 365 will impact your uptime,
archive policies and recovery time objectives. I also like to use a migration to recommit to business
SLAs and potentially raise them.
If you fail to consider SLAs as part of your gap state, you will get bitten. Some IT professionals
underestimate their mailboxes and create a plan without the right diligence. This can triple the
effort of a migration.
• Determine the impact circle. Email runs the engine of your business, so you must understand how
it impacts productivity in your organization. I’ve seen IT professionals actually shut off access to email
during a migration. While some organizations can get away with this, if you don’t want to face the
wrath of your co-workers, plan to migrate without service interruptions. This also means understanding
how other systems and hardware – such as fax machines – may be affected by the migration.
The space between your current state
and end state is the gap state and requires
careful planning and design.
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Envision your end state
The best end states are agile. At the end of an Office 365 migration, you should be more flexible
and have a working strategy that you will change over time. Clients often ask me if they should
keep all of their mailboxes on premise or move them all to the cloud. The reality is it’s not an all or
nothing situation. You will find a happy middle ground by keeping sensitive mailboxes on premise
while moving the rest to the cloud to achieve cost savings. This may also help you comply with SLAs,
address regulatory concerns and enable easier disaster recovery.
Build a global identity strategy
Many organizations use Office 365 as the compelling event to spur a larger SaaS management
strategy. Office 365 gives you the opportunity to think about how you will manage a global SaaS
identity strategy. When you migrate to Office 365, you should consider:
• How will you enhance user productivity while keeping your data secure? Will you allow users to
log in via Active Directory to gain secure access not just to Office 365 but to all of their SaaS apps?
• How will you provision and deprovision access? How will you turn off an employee’s access to
your other SaaS apps when they leave the organization?
• How will you manage external identities? What are the best ways to manage customers, partners
and vendors who need to access your apps and portals?
These are important questions and figuring out your strategy here can pay big dividends in terms of
improved security, governance and productivity over the long-term.
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Understand your user roles and use profiles
As IT professionals, we worry a lot about user profiles. While these are still important, we now must
separate them into users and profiles. To get the most from an Office 365 investment, we must
identify not only who is using the technology but how.
Let me give you an example. Do you have mobile workers who want to use Office 365 on their
iPads? A mobile worker is a ‘role’ and the fact that they’re using an iPad represents a distinct
‘profile’. If we don’t support this profile, users will go outside of IT to get their work done.
This is also where licensing comes into play. The choices you make around users and profiles when
planning an Office 365 migration will affect your licensing options and also your costs.
Be aware of Office 365’s strengths and limitations
While Office 365 offers a powerful suite of services, it may not meet all of your needs. You may
want to archive both on-premise and cloud workloads for Office 365 and on-premise collaboration
data. Since Office 365 can’t do both, you may want to bring in a third-party service, such as
Mimecast to provide this capability. You may also require additional layers of security and
encryption. Understanding the ecosystem surrounding Office 365 is important, particularly if you’re
in a highly regulated industry.
The best end states are agile. At the end
of an Office 365 migration, you should be
more flexible and have a working strategy
that you can change over time.
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2Design and Implementation
Everyone has the same goal for an Office 365 migration: a successful move to the cloud. What’s
unique is your starting point. You may be coming from Google Docs or Lotus Notes. Perhaps you’re
transitioning from older versions of Office. Broad experience in terms of understanding these
platforms and where you’re coming from is key.
Appreciate how you are different
It’s one thing to know Office 365 best practices. But it’s more important to apply them to your
unique requirements and objectives. Are you regulated by HIPPA? What are your data encryption
needs? How will your data be archived? These and other factors impact how you arrive at your final
Ensure the implementation runs smoothly
Most employees shouldn’t be aware that a migration is even happening. To ensure a smooth
transition, you need to determine the impact circle – or who will be affected by the migration.
One key to success is testing Office 365 with a pilot group before rolling it out. Create a coexistence
strategy that allows employees to use Office while the migration is taking place.
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Think beyond day one
When you’re strapped for time and resources, training is often the first thing to go.
Make no mistake: no migration can be considered successful unless Office 365 is actually being used.
Before you move to migration and testing, you need a plan for ‘Day two’. How will you teach
employees about Office 365’s new features? How will you ensure usage? An adoption and support
plan will empower users to get the most out of Office 365. This will help your move to the cloud be
more successful in the long-run.
Everyone has the same goal for an Office
365 migration: a successful move to the
cloud. What’s unique is your starting point.
Choosing an Office 365 Migration Partner | Phase 2: Design and Implementation
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Many partners test Office 365 during a migration. If it looks like it works, they move on. What
they often don’t do is validate that everything is working according to the original plan.
For instance, you may create dummy mailboxes, send some test emails to them and proceed
with your migration confident that everything is ship-shape. However, you need to make sure
that all of your users have working email.
The rule of thumb here is ‘expect, then inspect.’ A good plan, poorly executed results in failure.
You need to test, then action, then validate.
3Migration and Validation
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The post-migration phase is the time to set yourself up for long-term success. This includes executing
a support plan that states how you will manage changes in your organization going forward. What
will happen if critical people in your organization leave? Your support plan should include all of the
documentation that new users and IT staff need to pick up where others have left off.
What Role Does Support Play in Your Vision for Office 365?
Good documentation is enough for many organizations. If you’re moving to the cloud to eliminate
support to focus on other priorities, it may make sense to move your support to the cloud as well.
In the on-premise world, your staff responds to tickets and resolves incidents. With Office 365, your
tickets go to a dedicated support center. Instead of resolving incidents directly, IT takes on the job
of managing the escalation of issues with an external provider. It is also challenging to provide your
mobile users with the round-the-clock support that they expect.
If you don’t have the bandwidth to manage Office 365 in house, managed services – such as
Softchoice’s Keystone Services – may make sense. This provides you with “always-on” monitoring,
support and incident management for Office 365. A good managed services offering also includes
regular business technology reviews and ongoing mentorship from Office 365 professionals who
understand your environment and can help you plan for the future.
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I’ve covered a lot of ground. Hopefully this gives you a good sense of the most important
considerations when evaluating a migration partner. In summary, a successful migration
requires the following:
Choosing an Office 365 Migration Partner | Overview
BE READYBE CLEAR
PROPERLY PLAN ASSESS THE
PROJECT’S SCOPE, TIMEFRAME
EDUCATE YOURSELF ABOUT OFFICE
365’S VALUE AND LIMITATIONS.
CREATE MAINTAIN A
GET PREPARED FOR ANYTHING THAT
COMES UP DURING THE MIGRATION
AND BE READY TO PROVIDE SUPPORT
ON DAY TWO.