Office 365: Operation Migration

Operation Migration
Six lessons learned from migrating
20,000+ Microsoft®
Office 365™
mailboxes
A conversation
with Tim McKellips
and Mack Ratcliffe
of Softchoice.

Connect with us today 1.800.268.7638 | www.softchoice.com | @softchoice 2
Software as a Service (SaaS) has revolutionized enterprise IT,
changing the way companies manage and deliver applications,
as well as enhancing end-user productivity by providing new
ways of consuming data and enabling collaboration across
multiple devices from virtually any place, any time.
With the introduction of Microsoft Office 365, many companies
are taking the opportunity to address their larger SaaS strategy,
which introduces new business process and technology
challenges. As Microsoft Practice Leads at Softchoice (one of
the world’s leading managed service providers) Tim McKellips
and Mack Ratcliffe have led SaaS implementation initiatives
for hundreds of companies, and have learned six valuable
lessons along the way.
Operation Migration | Introduction

Tim McKellips
Twitter: @Mckellip
LinkedIn: Tim McKellips
Tim McKellips has spent his entire 16-year
IT career in the Microsoft technology and
professional services arena, starting as an
Exchange 5.5 and Windows NT consultant, then
serving as the director of a Microsoft practice
in Central and Eastern US before coming to
Softchoice in 2007. Tim leads the Technical
Services team at Softchoice, defining strategy
and methodology for complex Professional
Services solutions—with a focus as the
Microsoft Practice Lead for North America. 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 northern Wisconsin.
Mack Ratcliffe
Twitter: @mack_ratcliffe
LinkedIn: Mack Ratcliffe
As a Services Practice at Softchoice, Mack
Rackcliffe is responsible for setting the technical
strategy for Softchoice’s SaaS business and
developing managed services for Microsoft
Office 365 and Azure platforms. Over the course
of his 15-year career, Mack has worked in a
variety of sales and technology focused roles.
He has provided application support for custom
B2C and B2B ecommerce platforms, served
as a Senior Systems Engineer responsible for
designing and managing Microsoft and VMware
infrastructure. When Mack first joined Softchoice
he worked as a Senior Microsoft Solutions
Architect. Mack loves travelling, surfing in
Southern California and holds a Master’s of
Science in Information Systems.
About Tim and Mack.

Migrating from on-premise infrastructure to cloud-based infrastructure is a
significant undertaking, due in part to more substantive integration of cloud and
mobile technologies into companies’ key business processes and systems than
ever before. Gone are the days where we could spend most of our time building
in a server room and cutting planning time short. The old carpentry maxim “plan
twice and cut once” has never been more important than in these complex
cloud-based systems. And once we understand and meet the technical business
requirements, there are other considerations.
Yes, with these requirements identified, now we need to understand any
necessary regulatory or compliance issues that must be considered along the way.
When key systems are moved outside an organization’s firewall into a SaaS model,
customers often overlook the differences and unique requirements of designing
Authentication versus Authorization or Access. Providing Single Sign-On (SSO) for
end users and developing a company-wide identity-management solution that
accounts for both current and future SaaS or IaaS initiatives is absolutely crucial to
putting a winning technology solution in place.
1 Careful
planning is
the key to
success.
Planning Must Be a Priority.
Lesson 1
Tim
Mack

Right. A foundational aspect of a network is making sure that only the right
people have access to the right resources, and that you have the ability to audit,
report, and re-certify the access permissions over time. When you only focus
on Authentication (i.e. you are who you say you are) without thinking about
Authorization (i.e. what you have access to), you miss the point. It’s like this: you
might have a valid driver’s license, but that doesn’t mean you get to drive my car!
The Authorization issue is key. And it’s important to think about this in the
context of future SaaS implementations. By design, SaaS applications are very
easy for users to acquire and use. All of a sudden your users’ lives are easier,
but those same application’s could be causing compliance issues or exposing
important company data. It’s crucial that the IT team spends time planning how
to manage and extend their organization’s identity management strategy into
those applications. It’s no longer just about Office 365—it needs to be about your
SaaS strategy for the next three to five years. These aren’t new concepts for IT
management, but they’re the details that can be overlooked if companies don’t do
proper planning. It really comes down to this: we have to be more diligent as we
trust the cloud more and more.
For many customers Office 365 is just the first of many ‘sanctioned’ SaaS
applications, so it’s a good time to establish security and governance best
practices for the dozens of other cloud-based applications that are already in your
environment or coming soon. In our experience, Office 365 is often the compelling
event that pushes organization to establish a longer-term SaaS management
strategy, as well as a great end-user experience through things like SSO.
“
”
It really comes down to this: we have
to be more diligent as we trust the cloud
more and more.
Tim
Mack
Tim
Operation Migration | Lesson 1: Planning Must Be a Priority.

2Do No Harm.
Lesson 2
Consider
the impacts on
existing systems and
future SaaS
implementations.
Tim
Mack
To ensure a successful migration, smart companies need to first understand
what the solution can and can’t do before determining its feasibility. This
includes understanding the potential impacts on existing systems and business
processes. So, before adopting an appropriate cloud strategy, always consider
the organization’s short and long-term strategic goals around messaging, unified
communications, and collaboration. When migrating from Exchange to Office
365, for example, it’s critical for companies to fully understand the intricacies of
how various systems and applications interface with email beyond just employee
communications. Application and system interaction with a messaging platform
is often vitally important for an organization to consider in determining the most
appropriate future state architecture and migration plan.
And as we mentioned earlier, there may be additional requirements around
authentication, identity, and security that impact existing systems, and companies
may need to consider additional SaaS management infrastructure to support these
new requirements. The challenge with SaaS is that it’s really fast and easy to get
things up and running—but you need to understand the ramifications of what
you’ve let loose in the world.

Sure, and it’s different for every company. The only consistent thing about any two
Office 365 migrations is that everyone ends up on Office 365. Where they start is
completely unique, like a fingerprint. Differences come into play with what type
of business it is, what their current systems are, how the company interacts with
customers, the business requirements around uptime, things like that. A fertilizer
company and a ticket reseller use email completely differently. We’ve never had
two customers that are similar enough to reuse the same exact steps, though we
do use our well-tested methodologies, which are critical to success.
It’s important to remember that the individual business commitment is what
drives the architecture you need to build and deploy. Minutes of downtime for one
kind of company would be catastrophic, and would require an entirely different
architecture than might be required by a company that is less reliant on email. You
need to work backwards to meet your SLA requirements. A fast food restaurant
and a catering company both need kitchens, but they’re open different hours,
serve different customers and have different needs entirely.
What we’ve found in working with so many different customer environments is
that there’s often opportunity to think creatively about schedules and budgets
when you consider the entire application ecosystem. We had a customer who
wanted to migrate to Office 365, but couldn’t justify the spend. We helped them
look at their environment and we identified another application that would
become redundant if they migrated, so they were able to free up budget dollars
without losing key network functionality.
Tim
Tim
Mack
“
”
The challenge with SaaS is that it’s really
fast and easy to get things up and running—
but you need to understand the ramifications
of what you’ve let loose in the world.
Operation Migration | Lesson 2: Do No Harm.

Migrating a system of any kind introduces complexities into the entire
environment. Even with careful planning, a major implementation project
is usually more challenging than it might appear in the documentation and
project plans. It’s impossible to test every possible scenario and real-world
use case thoroughly. Here’s an example we came across recently; there’s a
messaging protocol used by many different applications (MAPI), and Microsoft
no longer supports server-to-server MAPI with Office 365. Companies that
are migrating from earlier versions of Exchange will need to consider any
application that uses email, from scheduling to ERP or whatever systems
they rely on every day, and make sure they have a plan for messaging with
these applications.
The good thing is that Microsoft has always been open to collaboration.
Office 365 works well with a wide range of third-party systems to fill in the
gaps around your specific business needs. But you need to work with people
who really understand both what problems you’re trying to solve and what
other applications can help you get there. This is part of the solution we offer
through the Softchoice Cloud.
3Nothing Exists in a Vacuum.
Lesson 3
Cloud-based
technologies bring
some specific new
challenges and
opportunities.
Mack
Tim

Mack
Tim
Understanding the ecosystem of SaaS applications can be especially important
to address some of the net new challenges that arise when you move from
on-premise to the cloud. One issue that comes up frequently for our clients is
the question of data encryption at rest. Office 365 encrypts data in transport, but
doesn’t encrypt data at rest on the disk. This isn’t an issue for everyone, but for
companies with this specific compliance requirement, it can be a showstopper. In
this case, we’d recommend a third-party solution like CipherCloud, who we partner
with, to add this functionality.
With the shift to the cloud, IT management responsibilities evolve from the
traditional realm of overseeing machines to managing larger business processes.
This introduces significant new responsibilities in the areas which security,
authentication and identity, access control, and application workflow, can be
enormously challenging for teams who had previously focused mostly on server
performance and uptime. We see a lot of challenges around data residency, data
privacy, regulatory, and compliance issues.
4Moving from On-Premise to the Cloud
Brings New Challenges.
Lesson 4
Acknowledge
the net new
challenges that
occur during cloud
migration.

Here’s another example: many companies have a regulatory requirement to save a
copy of every email that comes in and goes out of the organization. The traditional
way to do this is with a practice called, “journaling.” This saves a copy of every
message to a separate mailbox, which in some cases gets archived, sometimes
not. You can’t do this in Office 365 because there’s a 50GB limit on the mailbox
size. That particular mailbox would get filled up instantly. So customers who don’t
want to manage this on-premise—and can’t journal into Office 365—are forced
to figure out alternatives. This is one of the reasons why we’ve partnered with
Mimecast. Mimecast is a leader in security and archiving—and is a solution we
offer through Softchoice Cloud.
Mack
“
”
IT management responsibilities
evolve from the traditional realm of
overseeing machines to managing
larger business processes.
Operation Migration | Lesson 4: Moving from On-Premise to the Cloud Brings New Challenges.

5Mind the Gap.
Lesson 5
The people we work with are generally very smart IT executives. They have
a sophisticated understanding of both the current state and future state of
their enterprise environment. What can be more challenging, however, even
for the smartest folks, is understanding exactly what is needed to support the
organization as it moves between these two states.
This gap state can be a real challenge. Companies who can plan appropriately
for this period are better positioned to encourage adoption of—and compliance
with—new business and technology processes. We worked with a customer
who migrated thousands of employees from Exchange to Office 365.
Because of their own internal support requirements, they opted to migrate
one department at a time. Although they prepared appropriately for email
to function during the transition, they assumed it would be acceptable for
interdepartmental scheduling to be unavailable during the brief transition as
each department came on board. They found out the hard way from angry
users that this was not acceptable.
And for most of these kinds of situations, there are tools we can recommend
for managing uptime and system availability during a migration. There are
ways to get creative about this, and to make sure users feel supported. It’s all
about working together to make a sustainable migration plan.
Tim
Mack
Tim
Ensure
a smooth
transition period
between your current
and future
states.

6Planning for Day 2 and Beyond
is the Key to Success.
Lesson 6
Plan for
post-launch
insights, support,
and success.
Mack
Tim
We also make sure to remind clients that once the excitement of a successful
launch day is past, that’s when the real work begins. Changes in business and
technical processes will require additional help desk and training support for end
users. There will be new usage and storage quotas to track. In addition to new
ongoing licensing and user management procedures. Companies may no longer
need to purchase additional servers to run on-premise software, but will continue
to need investment and oversight in maximizing Internet capacity—and managing
network edge devices.
Another thing to keep in mind is that migration is a great opportunity for business
intelligence. We encourage companies to use the data that Office 365 and other
SaaS applications provide to gain actionable insights on usage and trends across
their environment. This kind of thing can be a big win for IT management within
the rest of the organization—by not only understanding the creation of data, but
how that information is consumed as well.

Implementing Office 365 and other SaaS applications
can be challenging. Mack, Tim, and the other experts at
Softchoice have migrated tens of thousands of customer
mailboxes to Office 365, and offer some valuable
takeaways for companies considering migration:
Operation Migration | Overview
Careful
planning is
the key to
success.
Consider
the impacts on
existing systems and
future SaaS
implementations.
Cloud-based
technologies bring
some specific new
challenges and
opportunities.
Acknowledge
the net new
challenges that
occur during cloud
migration.
Ensure
a smooth
transition period
between your current
and future
states.
Plan for
post-launch
insights, support,
and success.
Lesson 1
Lesson 4
Lesson 2
Lesson 5
Lesson 3
Lesson 6

About Softchoice.
With over 40 locations across the U.S. and Canada, Softchoice
is one of North America’s largest providers of IT solutions
and services. The company’s holistic approach to technology
includes solution design, implementation, and managed
services. Through unique offerings like Softchoice Cloud, and
deep expertise in Microsoft Office 365, Softchoice makes it
easy for organizations to source, implement, and manage
the right cloud solutions for their business.
©2014 Softchoice. All rights reserved.
All trademarks are the property of their respective owners.
Other guides in this series:
»How to choose a Microsoft Office 365™ Migration Partner : Moving to the Cloud without Risking
Productivity, Collaboration or Security
»The Essential Guide to Licensing Microsoft Office 365™ in the Cloud

Office 365: Operation Migration

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