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Preparing for Your
Migration to the Cloud

7 Steps to Success

Steve Francis

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Boston Farnham Sebastopol

Tokyo


Preparing for Your Migration to the Cloud
by Steve Francis
Copyright © 2018 O’Reilly Media. All rights reserved.
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Migration to the Cloud, the cover image, and related trade dress are trademarks of
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The views expressed in this work are those of the authors, and do not represent the
publisher’s views. While the publisher and the authors have used good faith efforts
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the publisher and the authors disclaim all responsibility for errors or omissions,
including without limitation responsibility for damages resulting from the use of or
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licenses and/or rights.
This work is part of a collaboration between O’Reilly and LogicMonitor. See our
statement of editorial independence.

978-1-492-03880-1
[LSI]


Table of Contents

Preface. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . v
Preparing for Your Migration to the Cloud. . . . . . . . . . . . . . . . . . . . . . . . . . 1
Introduction
What’s the Attraction of the Cloud?
Cloud Constraints and Challenges
Plan Your Approach
The Seven-Step Migration Plan
In Parallel with the Seven Steps

Cost Management in the Cloud
In Conclusion

1
3
11
15
18
43
45
46

iii



Preface

How to best take advantage of the cloud is a frequent topic of dis‐
cussion among all levels of an organization’s IT team. Often, the dis‐
cussion will be couched in terms of enterprise transformation, or
digital transformation, or datacenter consolidation, but at their
heart, these projects usually involve cloud migrations.
Cloud migrations can bring great benefit, but the technology is new
enough, and changing rapidly enough, that even if you develop an
accurate business case, your organization may not achieve those
benefits, since your staff is probably inexperienced in cloud migra‐
tions. That’s exactly the situation this report is intended to help with.
While there is no universal script for cloud migrations, there are
steps you should consider in planning any move to the cloud. One

of the big risks in any project is the “unknown-unknowns.” This
report won’t give you all the answers, but it will help you highlight
the questions that you should be asking in planning a cloud adop‐
tion. It is intended to be useful for everyone that is involved in, or
wants to advocate for, a cloud migration—from the CIO down to
the engineering staff. And I would posit that practically every orga‐
nization should be thinking about cloud migration in order to main‐
tain the agility it needs to be competitive. I would also suggest that
for technical staff, knowledge of cloud technologies and cloud
migration principles is as sure a thing for career advancement as
there is at the moment.
When LogicMonitor started, the cloud was in its infancy. Indeed,
virtualization was just becoming big. LogicMonitor has been able to
navigate the transition from bare metal, to virtualization, and now

v


the cloud, hybrid cloud, serverless, and whatever else technology
brings.
Much of the wisdom in this report is directly attributable to the
expertise, knowledge and insight of our customers, and their will‐
ingness to share and discuss their challenges and solutions.
For that, I will always be grateful.
Cheers,
Steve Francis

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Preface


Preparing for Your Migration to
the Cloud

Introduction
The cloud is everywhere.
You know that the cloud stats are trending up, but did you know
how fast? According to Forrester, the global public cloud market
will jump from $146 billion in 2017 to $178 billion in 2018. After
that, it is expected to grow at a 22-percent compound annual growth
rate (CAGR).
For comparison purposes, growth of the overall global tech sector in
2018 will be just five percent, and even if it smashed predictions it
would get only to the seven-percent-plus range. Thus, an increasing
proportion of global information technology spending will be on the
cloud. (According to IDC, global information technology spending
will reach $4.8 trillion in 2018.)
Not surprisingly, the cloud migration market is heating up, as well.
After all, these businesses investing in cloud technology generally
need services to help them succeed in their transformations. The
global cloud migration services market is predicted to expand from
$3.17 billion in 2017 to $9.47 billion by 2022, at an even higher
CAGR of 24.5 percent.
Most notable about all this is the move to the public cloud. Accord‐
ing to McKinsey, almost 80 percent of businesses plan to have more
than 10 percent of their workloads in the public cloud within three
years. According to Spiceworks, these workloads range from backup

1


(the most popular), to email hosting, to productivity apps, and
everything in between (see Figure 1-1).

Figure 1-1. Budget breakdown of cloud spend (source: “The 2018 State
of IT,” Spiceworks)
What’s driving all this? Largely, businesses searching for cost bene‐
fits.
A recent study from 451 Research discovered that cost savings is the
top motivating factor for CIOs moving to the cloud model, with
38.8 percent of them naming that as a critical driver. (Resource scal‐

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Preparing for Your Migration to the Cloud


ability and time to market/agility rank high, as well, as both were
chosen by 32 percent of businesses. More on this shortly.)
But here’s the kicker: after the migration cloud costs become the
number one pain point.
According to 451 Research:
Cloud is an inexpensive and easily accessible technology. People
consume more, thereby spending more, and forget to control or
limit their consumption. With ease of access, inevitably some

resources get orphaned with no ownership; these continue to incur
costs. Some resources are overprovisioned to provide extra capacity
as a “just in case” solution. Unexpected line items, such as band‐
width, are consumed. The IT department has limited visibility or
control of these items.

Indeed, moving to the cloud is a fairly low-risk investment, and
accrues fairly moderate costs. According to one recent study, half
(50 percent) of the companies surveyed estimate the cost of migra‐
tion to be between $100 and $500 per machine, with just 17 percent
estimating it costs more than $500 per machine.
Unfortunately, there’s no how-to guide for creating an end-to-end
transition plan to prepare your enterprise for the cloud. IT profes‐
sionals are solving pieces of the challenge, but often in disconnected
silos that require retrofitting—often at great opportunity cost.
Make no mistake about it, moving to the cloud is a complex propo‐
sition. It will be worth it for your business in terms of increased agil‐
ity and other benefits, but there are a lot of pitfalls that you might
well run into—pitfalls, however, that you can learn to avoid.
This report takes a prescriptive look at the best practices and
sequential journey needed to ensure a successful transition. Cloud
migration experts also weigh in on the various stages of the journey.
The result: a how-to guide for an end-to-end transition plan to the
cloud.

What’s the Attraction of the Cloud?
Moving to the cloud offers many, many benefits, but in this report, I
focus on three: operational agility, strategic focus, and—possibly—
cost savings. Notice I hedged on cost savings and listed it last.
There’s a reason for that, which we get into later.

What’s the Attraction of the Cloud?

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3


Enable Operational Agility
Operational agility is the top advantage you gain by moving to the
cloud. That’s because the speed at which your developers can deploy
new software and the swiftness with which you can try new technol‐
ogies is much faster when you don’t have to wait for IT to provision
servers and storage and networking connections. You simply spin
up new instances for whatever workloads you need, and you’re set.
This gives your product teams and developers the tools to release
products, get feedback, and quickly iterate and improve them to
help you meet the needs of your customers. That’s what operational
agility is all about.
There’s also the fact that virtually every week, Amazon, Microsoft,
Google (currently the top three cloud providers), and other clouds
are rolling out new cloud-based services that, if you use them appro‐
priately, can give you a competitive advantage. Want to get into
machine learning? No need to build the capacity yourself—just use
Amazon’s new AI service. You’ll still need data scientists, of course,
but you won’t need someone to build out the infrastructure. You’ll
be able to get better products to market faster and roll out products
sooner—and that can be a large competitive advantage.
Whether you are deploying to the cloud through Infrastructure as a
Service (IaaS), Platform as a Service (PaaS), or Software as a Service

(SaaS), you stand to gain significant operational agility. Table 1-1
provides a synopsis.
Compare cloud to the alternative—the status quo. If you’ve invested
in owning your own on-premises environment, you are more limi‐
ted in the infrastructure that you can make available to your devel‐
opers. You’ve made a long-term commitment to a certain way of
doing things. This prevents you from being able to take advantage of
the latest and greatest technologies that are being brought to market.
Financially, on-premises environments typically come out of capital
expense (CapEx) budgets, whereas cloud purchases are usually an
operating expense (OpEx). Depending on allocation of budgets in
your company or department, one financial model might be prefera‐
ble over the other.

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Preparing for Your Migration to the Cloud


Table 1-1. How cloud enables operational agility (Source: Taken from
“2018 SaaS Industry Market Report: Key Global Trends & Growth
Forecasts,” FinancesOnline.)
Flexible infrastructure

Dynamic
applications

On-demand services

Efficient
management

• Get infrastructure
programmatically
provisioned

• Build applications
that are quick to
deploy, and
optimize use of
resources

• Cloud providers have • Cloud adoption
many “ready-to-run”
can force
services (such as
programmatic
queuing systems,
management and
databases, etc.)
best practices, due
to imposed
constraints

• Reduced cost of
additional capacity
• Shorter time to
provision new

resources
• Geographically
distributed
infrastructure
• infinite scalability

• Faster time to
feedback
• Faster time to
deploy changes
• Shorter release
cycles can lead to
faster product/
market fit

• Complex services
immediately
available for use by
application
developers
• Don’t need
specialized expertise
in running things
like Elasticache
• Faster monetization
of innovation

• Automated flexible
management
• Lower cost of

monitoring
• Reduced
downtime

With a cloud infrastructure, you get access to the best equipment
available: the newest Intel processors, the most optimized RAM
memory, solid-state drive (SSD) storage, arrays of graphics process‐
ing units (GPUs), and even cloud-programmable hardware. This
comes with a wide ecosystem of software platforms to choose from:
managed databases and warehouses, orchestration platforms, cach‐
ing, queuing systems, and just about anything you need for any soft‐
ware architecture.
The impact on your business when you move to the cloud can be
immediate, especially if you operate in a competitive market that is
advancing swiftly.
Capital One moved one of its largest customer-facing apps—its
mobile banking app—to Amazon Web Services (AWS) in 2016. Said
Jason D. Valentino, director of reliability engineering at Capital One
Digital, “The move to AWS was a way of removing the constraints
preventing them [Capital One developers] from developing their
ideal applications. The move was neither an edict nor a product
What’s the Attraction of the Cloud?

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5


goal. It was a way to build the best application using our best skills
and tools.” Valentino went on to say:

“Moving forward, Capital One Mobile (as well as the other
consumer-facing products owned by our team) will have infrastruc‐
ture that moves at a speed that keeps up with the needs of our prod‐
uct. In the months to come, we look forward to further exploring
the advantages the cloud continues to bring. As well as redefining
our own team definition of what it means to ’ship early and ship
often.’”
In another example, Walgreens achieved significant organizational
agility by recognizing that it could use the cloud to meet its custom‐
ers’ demands the way they wanted them met: on their mobile devi‐
ces. Consumers are now used to, and even prefer, app-driven
interactivity compared to traditional ways of interacting with the
retailer. Today, Walgreens’ mobile app drives about 40 percent of the
retailer’s digital traffic, with cloud-based features like Refill by Scan
and QuickPrints helping to completely transform the business and
helping it nimbly stay ahead of competitors in an industry that is
being rapidly disrupted by innovation.
To give a counter-example, here’s how not being into the cloud chal‐
lenges you: We were talking to a company that eventually became a
customer of LogicMonitor. The reason the company initially came
to us is because they were in a merger and acquisition (M&A) sce‐
nario, in which the company it was acquiring was geographically
separate from LogicMonitor and running its own datacenters. The
company couldn’t figure out a way to monitor the other company’s
remote on-premises infrastructure within the time constraints of
closing the M&A deal. With its existing on-premises monitoring
software, LogicMonitor was stuck with slow on-premises systems
that required it to provision new servers, ship them out physically,
and install them on the remote premises simply to get visibility into
the other company’s infrastructure. This caused the deal to fall apart

—a very expensive side effect. The cloud would have solved this, of
course.

Maintain Strategic Focus
The second benefit that moving to the cloud gives you is strategic
focus on your business.

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| Preparing for Your Migration to the Cloud


Effectively, strategic focus builds off agility because you needn’t
worry about having to run a datacenter. After all, managing a data‐
center is difficult and complex. You need good, smart people to han‐
dle the provisioning and figure out the data management and
security, among other tasks. Power management, space planning,
cooling, contracts with ISPs—these are all complex tasks that
require not-insignificant resources allocated to them. Managing
storage and networks in particular are very specialized skill sets. If
you could repurpose these valuable employees on initiatives that are
more strategic to your business, such as developing applications or
designing customer- and employee-facing systems rather than
putting energy into keeping infrastructure running, you’re naturally
more competitive.
Philip Tuttle, a cloud consultant for London-based Orange Business
Systems, provides cloud migration services for customers as part of
a broad portfolio of IT consulting services. He says that his custom‐
ers are primarily looking to take advantage of the cloud to move
away from a constant construct-and-refresh cycle of on-premises

physical systems. They particularly want to turn a CapEx investment
cycle into a more effective OpEx financial model so that they can
plow cash back into their core businesses. “That’s probably still the
biggest driver,” says Tuttle. “They don’t want to have to manage and
refresh their own infrastructure hosted in their own datacenter.
They want to leverage the financial benefits of moving to the cloud,
the scalability, the stand-up times, and basically shift from this lead
weight of having to manage or maintain their own infrastructure to
better managing their core business.”
This is definitely the trend. According to IDC, global spending on
public cloud services and infrastructure will exceed $160 billion in
2018, an increase of 23.2% over 2017, reflecting the rapid shift to
OPEX from CAPEX business models.
“First and foremost, you take a huge burden off the shoulders of
your IT staff,” agrees James Bell, integrated global services general
manager of Long View Systems, an information technology services
and solutions company based in Calgary, Canada.
“When you think of old monolithic IT organizations with hundreds
of IT people supporting them, that’s just not sustainable anymore
for a variety of reasons,” says Bell. Among other things, it involves
keeping track of all of your own hardware and software licensing

What’s the Attraction of the Cloud?

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7


requirements, your own warranty information, and having to con‐

stantly care and feed that infrastructure. It takes focus away from
your business, he says.
“If you’ve got the right cloud provider and your data is safe and is
secure and is auditable and your cloud provider is doing all the right
things, all of that overhead is taken away from you,” says Bell.
“Without all of that pain and suffering, your life is a heck of a lot
easier.”
Consuming IT infrastructure as a utility frees you up to concentrate
on what really matters, says Bell.
“Running IT infrastructure isn’t the core business of most compa‐
nies,” says Bell. “If we look at core versus context, running IT infra‐
structure is just context.” He stresses that making money or driving
value for shareholders or delivering services to the market is what’s
important. “I personally think that’s the number one benefit of mov‐
ing to the cloud,” he says.

(Possibly) Cut Costs
Businesses have great expectations of the cost-cutting potential of
the cloud. As we mentioned earlier, they cited it as their primary
driver for moving to the cloud, according to 451 Research’s 2018
study on cloud adoption.
However, it doesn’t always work out that way. Costs often rise. 451
Research found that the main reason for this was that companies
consume more compute, storage, and networking resources after
they’ve moved to the cloud. In other words, it’s there, and easy to
provision, so they use it. And not all wisely. Wasting cloud resources
was the second reason that cloud spend increased, according to the
survey.
451 Research called this the “Jevons Paradox,” in which ease of
access to technology and lower costs drive companies to consume

more of it. Unit costs might be lower, but overall costs rise.
451 Research thus concluded that in hoping to cut costs by moving
to the cloud, businesses find that “reality doesn’t match expecta‐
tions.” Indeed, costs, initially the driver of most cloud adoption ini‐
tiatives, become the number one pain point following migration.

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Preparing for Your Migration to the Cloud


How much money you could even theoretically save also depends
on the type of workload you are moving to the cloud. For example,
if you are running a server that has 64 GB of memory and an array
of SSDs, and you need that server constantly up to run a businesscritical workload—for example, global order processing on a 24/7
basis—it’s going to be much more expensive, by most metrics, to run
that in the cloud than it is to run it in your own datacenter.
After all, you can buy a server like that for approximately $7,000
from Dell, whereas renting it from Amazon costs about $1,200 a
month. In most cases, it would be much cheaper to spend the $7,000
upfront and run it yourself. Of course, running it yourself requires
datacenter space and power and air conditioning and so on, but still
at a net cost on any kind of scale, it’s going to be significantly
cheaper to run your own IT infrastructure than to run it in the
cloud over an extended period of time.
But if your IT infrastructure has any type of variable component, the
cloud could be a benefit from a cost perspective. Suppose that you
need 50 servers for your application, but only during business hours

—during off hours you can rely on just 10 servers. If you scale up in
the day and down at night, yes, cloud can be much cheaper.
However, there’s another consideration. With cost, there’s also the
problem of cloud litter. These are the cloud instances that are spun
up and then forgotten. It’s very difficult to get a handle on these. For
example, when your developers release a new system, they might
spin up a new cloud instance. They might provision elastic block
storage volumes on the cloud that are rather costly. But then they
decide they need a bigger system so they spin out another, larger
cloud instance, move everything over to that, and then forget to shut
down the other one. That’s very, very common.
Then you get a giant bill, due to the fact that you have 1,200 instan‐
ces instead of the 1,000 you need. No one goes through and checks
them—the operations teams often don’t see the bills, and the finance
team has no insight into what servers are actually needed. So even if
you engineer your cloud infrastructure for cost savings, it’s quite
likely that you won’t end up with any. Because cloud resources are so
easy to provision and so easy to pay for, it’s very difficult to maintain
good cloud hygiene.
It makes sense that businesses are searching for savings in the cloud.
It’s one of the most proclaimed benefits of migrating. “Most IT
What’s the Attraction of the Cloud?

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9


departments are squeezed for budget, looking for cost optimizations
across the infrastructure, and they think the cloud is an easy answer

to that,” says Orange’s Tuttle.
“It’s the responsibility of people like myself as consultants to reset
expectations and to try to explain to customers where they can gain
cost benefits, but indirectly rather than directly,” he says.
Yes, there are some potential cost benefits that can be had from
moving to the cloud. Utilizing the right cloud services can reduce
your operational overhead and reduce the need for IT infrastructure
headcount or expertise.
“In traditional infrastructures you’ve got fairly static monolithic
workloads which are unmoving,” says Tuttle. “Why move those to
the cloud? You’ll only pay more.”
Indeed, using the most popular mode of shifting to the cloud—“lift
and shift”—it’s especially tricky to get the payback you anticipate.
“Whereas if you shift highly varying workloads, you pay only for
what you use at the times you use it. That will save you,” says Tuttle.
Many companies eventually resign themselves to the fact that cloud
costs will be higher. They realize that the operational agility that they
get out of it makes it worth it. So they’ll accept the fact that it’s going
to cost them 50 percent more in their IT budget for the infrastruc‐
ture component,” says Tuttle. “They’re satisfied with the advantage
that they can develop apps much quicker, that they can release faster,
and they can learn faster, so they actually bring in revenue rather
than holding up the business through infrastructure “plumbing.”
When in their cloud journeys do businesses experience this “aha”—
that the chief benefits are not cost savings and indeed might not be
easily quantifiable?
Tuttle has found that businesses get fairly deep into their journeys
before they truly understand how the cloud will benefit them. One
challenge he’s experienced with customer engagements is that most
cloud transformations begin with the infrastructure rather than the

applications team. “It can be difficult to get access to the people who
are building or managing the applications, yet that’s where the real
benefits are going to begin flowing in,” says Tuttle.
If an enterprise is looking to cut costs by simply moving infrastruc‐
ture, that’s difficult, says Tuttle. “So you need to start digging into

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the application state, the application architecture, and these things
tend to take time to understand,” he says. But after you get to the
point at which you can explain how they can optimize application
development processes, how they can deploy quicker, how they can
streamline development to deployment, and how they can optimize
application architecture to scaling for higher-level services that
reduce operation overheads, “that’s when businesses begin to realize
the true benefits,” says Tuttle. “It’s a matter of resetting expectations.”

Cloud Constraints and Challenges
Of course, there are the inevitable challenges and drawbacks of
adopting any new technology. You need to consider these when
evaluating when—and what—to move to the cloud.
Your biggest constraint will be finding the right people—people who
know how to use this incredible resource called the cloud, and how
best to take advantage of it. This is a significant problem. There cur‐
rently is a general shortage of IT workers, and, especially, a shortage

of cloud experts.
If you’re thinking of moving to the cloud, you need to foster a learn‐
ing mindset in your team because new technology will always be
foisted on you. Always. And the cloud is no exception. It is evolving
month by month, and you must stay on top of it.
Indeed, a recent study by the London School of Economics and
Political Science, sponsored by Rackspace, found that enterprises
globally are losing more than 5 percent of their revenue annually
due to a lack of cloud expertise. The study also found that the cloud
skills gap is stifling creativity, with two-thirds (65 percent) of busi‐
nesses saying they could innovate faster and more effectively if they
had the right cloud insight.
Nearly three-quarters (71 percent) of businesses report that their
organizations have lost revenue due to a lack of cloud expertise.
Beyond missing out on innovation and growth, 4 in 10 (42 percent)
of them believe a lack of skills is causing them to fall behind their
competitors. And the majority (71 percent) say that they need to
invest more in their workforces and train them to understand and
take advantage of the cloud.
This is all sobering. After all, if you don’t have experienced people,
you’re going to have to buy, rent, or grow them. Unfortunately, the
Cloud Constraints and Challenges

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11


situation a lot of companies are in is that they don’t know what they
don’t know.

One customer of ours had moved its applications into the cloud—
into Amazon. It had done a reasonably good job, but mistakenly
thought that the cloud offered it unlimited resources that it could
use to scale as demand grew. The company didn’t realize that Ama‐
zon imposed constraints on the number of machines it could have at
any one time. These service limits make sense for both the cloud
provider and the customer—it’s all too easy to imagine a situation in
which a buggy provisioning system continually requests machines,
possibly depleting the available machines that AWS can offer other
customers and presenting the erroneous requester with a very large
bill.
This particular customer was unaware of the service limit concept—
it thought it had infinite scalability. But as it turned out, the com‐
pany was within two machines of its current service limit. It needed
to request an increase on the service limit—but until the company
adopted LogicMonitor and received an alert about the fact that it
was close to hitting its limit, the people there were unaware that this
was an aspect of cloud deployments that they even needed to be
aware of. This could have been a very expensive lesson if the com‐
pany had exceeded its limit during a busy period when it needed to
scale. In the end, the problem was directly related to the fact that the
company’s engineers weren’t experienced with the cloud.
The bottom line is that without expertise, you’re likely to do it
wrong. This can lead to cloud retrofitting: moving applications to
the cloud only to move them back again. I’ve seen this happen quite
a few times. The usual reason is simply that businesses have not
optimized their applications for the cloud, and they find that they
are paying an excessive price for cloud services but getting no bene‐
fit.
Gartner calls this a nonlinear approach to IT. It argues that because

innovation is causing such massive disruptions in today’s globally
connected businesses, IT and business leaders alike need to have a
flexible and dynamic approach to utilizing new technologies. This
means taking a proactive, nonlinear architectural approach for con‐
tinuous evolution and what Gartner calls “complete reversibility.”
“You have to determine the degree to which your organization can
reverse investment commitments and apply scenario planning to
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Preparing for Your Migration to the Cloud


forecast risk and responsibilities while focusing on ‘good enough’
rather than ‘ideal,’” Gartner advises.
According to this model, you might move some workloads, then
you move some back and then you move other bits. It’s nonlinear
migration in that it’s not just one directional. You’re bouncing things
around because you’re learning as you’re doing it. Many of your ini‐
tial trials will be wrong. Although that’s reasonable—you’re new to
this, after all—if others have already made mistakes, you can learn
from them.
Let’s look at one common scenario: Suppose that a business has an
application running in its own datacenter. Typically, this application
would be on VMware. The business could spread it among several
machines. This is important, because if a node is on a server that is
taken down for maintenance, it needs to continue running some‐
where else in the virtual infrastructure. It’s a question of high availa‐
bility.

Then, suppose that the company decides to consolidate datacenters
and move the application to the cloud—either Amazon or Azure.
Typically, a company will do this via “lift-and-shift”—because sim‐
ply moving to running the virtual machines (VMs) in the cloud is
easy. Yet unless the company does a fair bit of work to redesign the
application, the business won’t get the same level of availability it
had in its own datacenter.
That’s because a lift-and-shift initiative will generally not give you
the same availability you had in your datacenter. In your datacenter,
you can specify policies for critical applications, control mainte‐
nance windows, and even set up VMware high availability so that if
the guest VM or the ESXi host running the guest goes down, the
guest VM will be automatically restarted on a different node.
In the cloud, changes to, and rebooting of, the underlying hypervi‐
sor machines is outside of your control. Your application might run
successfully for two months. But Amazon might send out an email
notice that it’s going to retire some of the instances you use for this
application. Many people miss these emails among all the clutter in
their inboxes. So, Amazon goes ahead and retires those instances,
shuts them down, you lose two-thirds of your capacity, and experi‐
ence an outage.

Cloud Constraints and Challenges

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13


If your company has strong configuration management and provi‐

sioning systems, it should be able to quickly spin up new instances
to replace the capacity, but the outage can leave a bad impression on
users. And without a scripted ability to build systems, the outage
can be even more severe to both your company and to people’s jobs.
This type of experience is very common. According to one recent
study, although most companies (66 percent) surveyed utilize both
redesigning and lift-and-shift cloud migration strategies, there is a
clear preference (68 percent) for a simple lift-and-shift. This tells us
that most companies are not making the most of the cloud.
Redesigning your applications for the cloud can result in increased
availability, and greater agility. But it’s also a lot of work. If your
application is designed to expect highly available hardware—such as
clustered nodes, shared file systems, or redundant memory—you
have relied on high-availability designed hardware, not software.
Such hardware is not available in the cloud, so the task of shifting
the tolerance for failures into software is nontrivial.
A truly well-designed cloud application can tolerate instances, or
even an entire availability zone or region, becoming unavailable, and
still provide the application service. Of course, not every application
needs this level of reliability, which comes at a cost, both in terms of
resources, development time, and, significantly, agility. Any applica‐
tion that is designed for very high levels of reliability, whether onpremises or in the cloud, will be slower to change and develop than
less-engineered systems. For this reason, some of the benefits of a
cloud migration can come from specifying the actual availability
requirements—which might be lower than the availability the sys‐
tems currently support. This can itself lead to substantially greater
agility.
Security always comes into play when discussing the cloud. Almost
half (47 percent) of businesses list it as a major concern post–cloud
migration, according to 451 Research.

In one sense, your data and applications are more secure in the
cloud. Cloud service providers such as AWS, Google Cloud Platform
(GCP), and Snowflake fully understand that thousands of businesses
trust them. They thus strive to exceed the highest security standards
in the industry as set by healthcare, financial, and governmental
institutions. You might be pleasantly surprised that it’s easier to get
certifications like SOC2, ISO27001, HIPAA, and PCI in the cloud
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because your applications will be running on a computing infra‐
structure that is already certified.
You’ll also find authentication, authorization, logging, and auditing
built in to all major cloud platforms. Additionally, security measures
like network and application firewalls, Distributed Denial-of-Service
(DDOS) protection, and identity management are standardized, tes‐
ted, and made available for setup and configuration. The cloud pro‐
viders even send out notifications of incorrectly set up security
configurations—such as opening up Secure Shell (SSH) ports to the
world, or databases that accept connections from anywhere.
However, although cloud environments have secure computing lay‐
ers, and the virtual (or logical) computing layers possess all neces‐
sary enterprise-grade security measures, you’re still responsible for
making sure you have the right security policies for your architec‐
ture—just as you would in an on-premises setup. Effectively, the
cloud provider will give you infrastructure and services you can use

to execute your security policy. However, defining the security pol‐
icy for your application, and ensuring it is appropriate and sup‐
ported, is still up to you. It is likely that the policy for your
application will not change, even if you move it to the cloud—your
practice of destroying Personally Identifiable Information (PII)
when a customer leaves, for example. However, the practices you use
to do so might change in the cloud. (You might destroy all the cloud
instances that the customer’s account lived on, for example.)

Plan Your Approach
One of the first—and biggest—questions you will face as you begin
your cloud migration is whether you will take a bottom-up or topdown approach.
Top-down is when you make decisions at the top of the organization
—at the executive level, typically. You involve the CIO and his or her
organization, and IT leads the effort.
Bottom up is when the impetus, the ideas, the creativity, and even
the hands-on work happen in the business units. The people who
have specific business or implementation needs that can be solved
with cloud applications drive the migration.
In the perfect world, of course, the business users and IT and senior
management are all synchronized.
Plan Your Approach

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Unfortunately, it’s not always that way. Says Long View Systems’ Bell,
“It’s the classic Hatfield-and-McCoy situation. Cats and dogs fight‐

ing. IT guys are criticized by the business because they either can’t
deliver something or they can’t deliver it fast enough. And the busi‐
ness guys are sitting there with plans that they have to meet, dead‐
lines, product launches, revenue targets, and profitability targets.
They’re trying to get things to market and online as quickly as possi‐
ble.”
The bottom line: if a cloud strategy is not built collaboratively from
the ground up with buy-in from both engineers and the CIO’s office,
and has the corporate buy-in and the corporate support, it’s not
likely to deliver the results that everybody’s trying to get out of it. It
must include both.
If you try to force a top-down approach on your organization, with
constraints imposed centrally that the engineers disagree with, the
business becomes frustrated, IT gets frustrated, and this is where
shadow IT begins to be a problem. Gartner estimates that shadow IT
is 30 to 40 percent of IT spending in large enterprises, and Everest
Group goes even further, finding it comprises 50 percent or more.
Jordan Hager, senior director of IT operations and systems architec‐
ture, at Q2, a maker of digital banking platforms and solutions for
banks and credit unions based in Austin, Texas, experiences shadow
IT firsthand. He says that today his company is on multiple clouds:
GCP and AWS, and also Microsoft Azure.
“If you look at it in terms of workload distribution, you’d probably
consider it to be less than five percent of all workloads are in public
cloud, but it’s spread across three different clouds,” says Hager. “That
was not by design but rather virtue of acquisition and developers
getting frustrated with waiting on IT, so they went and spun instan‐
ces up so they could learn on their own.”
“The philosophy was, ‘the beauty of the cloud is that if I have a
credit card I can go and spin up a cloud service and I’m off and run‐

ning,’” says Hager. He doesn’t see a fragmented approach like this as
being an advantage to any business. “I think we would absolutely
love to be in one cloud so we don’t have to train employees on how
to support multiple clouds and would also reap economies of scale
through consolidation and vendor partnerships,” he says.

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“Our core competency is hosting our online banking application
and not necessarily hosting a number of back-office applications,”
says Hager. “If we would have to recover from a disaster or some
type of large outage, we wanted to focus on our core business, not
on worrying about getting an accounts payable system back online.”
Again, there are experts out there who specialize in such things, says
Hager. “So, what if you train someone to get good at it—they leave
to work elsewhere and you’re stuck retraining someone else for a
task that isn’t that relevant to your business’s core strategy.”
For example, Q2 is evaluating the possibility of using Apache Kafka
as a messaging bus. Says Hager, “We don’t want to have to run Kafka
in our private datacenters because to set it up, to make sure it’s
monitored properly, configured to be highly available, and sized
appropriately are really critical things. We’d much rather leverage
Kafka as a service where somebody manages the operational tasks
behind the scenes.”
Hager admits that the IT group in charge of the firm’s private data‐

centers will get requests for something from a business unit. “And
when we say, ‘It’s going to be a couple of weeks,’ they say, ‘I don’t
have two weeks, can we just spin this up in AWS?’”
Although management at Q2 knows it could go faster and be more
agile if it went 100 percent cloud, it is also a financial services com‐
pany that has banks and credit unions as customers, and needs to
remain mindful of the compliance requirements that go along with
servicing them.
“It’s not that we think that cloud is less secure, because we believe
they’re far more secure,” says Hager. “The investments made in secu‐
rity by cloud providers surpass the investments we could afford to
make in a given year. And we definitely realize and understand the
benefits of agility in a public cloud. But we have contractual obliga‐
tions that our cloud is not only a secure cloud, but a compliant
cloud. Data governance is a concern and our customers depend on
us to be mindful of where their data is hosted.”
Hager hopes that in five years, everything will be in the cloud. “I
would surely hope so. I think we’d be disappointed if it weren’t,” he
says.
Scott Pelletier, CTO at Lewan Technology, a provider of managed IT
services, printer and copier management, and business technology
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