Understanding

Patterns of Enterprise
Transformation
Investing in Continuous Improvement
for Your Business

Helen Williams & Jeremy Sutherland

Understanding Patterns of
Enterprise Transformation

Helen Williams and Jeremy Sutherland

Beijing Boston Farnham Sebastopol Tokyo

Understanding Patterns of Enterprise Transformation
by Helen Williams and Jeremy Sutherland
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978-1-492-02800-0
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 Table of Contents

Understanding Patterns of Enterprise Transformation. . . . . . . . . . . . . . . 1

Types of Transformation 3
Summary of Transformation Types 8
Approaches to Transformation 10
Transformation Approaches to Avoid 23
Transformation Leadership 27
Starting Your Own Enterprise Transformation 33

iii
 Understanding Patterns of
Enterprise Transformation

Transformation is ubiquitous. It seems that every business has done,

is doing, or is planning to “do a transformation.” Over the course of
the past decade, the idea of transformation has transcended the spe‐
cific organizations within which they exist to become a standalone
entity and industry. At the same time, being agile has become more
mainstream as countless organizations seek to emulate the successes
of industry standard-bearers like Spotify, Netflix, and Amazon. The
resulting explosion of growth that has supported this developing
industry has yielded a raft of new roles, certifications, courses, blogs,
books, webinars, meet-ups, and events.
This growth spurt is far from over. A recent survey noted that 64%
of CIOs now believe political, economic, and business uncertainty is
on the rise. Of these, more than half plan to respond by becoming
more agile, and 88% by continuing to invest heavily in digital as a
strategy. Crucially, these changes all necessitate ongoing investment
in people, practice, and technology to continuously adapt to an ever-
changing environment. In fact, transformation is becoming less of a
one-off event and is evolving in purpose to support the desire for
adaptability and responsiveness over longer-term planning for fore‐
casting. Transformation is a byword for investment in continuous
improvement.
However, this growing industry is not without its challenges. The
often-quoted and debated statistic that around 70% of transforma‐
tion programs fail highlights an inescapable fact—transformation is
extremely difficult. There are many variables and conditions that
can influence the ability of an organization to successfully (within its

1
own definition) transform, many of which are not within the con‐
trol of the people trying to effect the change. This should not cast a
dark shadow over an existing transformation program or dissuade
anyone from taking action where needed. In fact, this is excellent
news because it means that there is a lot of data and experience that
we can learn from. And it seems that many organizations are
putting this learning into practice. In a 2017 survey, it was reported
that 98% of organizations are realizing some successes through
Agile projects.
If you’re embarking on transformation program now, you might
think you’ve left it too late and are at the back of the pack as a “late
adopter,” or even—gasp—a “laggard.” But you have a secret weapon:
you have all of this experience and data from the organizations that
have come before you, which means the failures, successes, and
everything in between. You might even have data from another area
within your own organization.
Each transformation program is a snowflake. It is shaped by hun‐
dreds of variables that continuously change. However, through the
work of thousands of organizations that have undertaken a transfor‐
mation program, patterns have emerged that can help organizations
manage and anticipate challenges in transformation to gain more
out of their investments.
These patterns of transformation fall into three broad categories:
Types of transformation
In simple terms, this is what you are trying to achieve. Each
transformation seeks to be an answer to a specific problem.
Accordingly, not all transformation programs are seeking to
change the same things. Awareness of what you are trying to
achieve will set you on the right path and help others under‐
stand and embrace the journey. It will also help you better spot
the potential pitfalls and opportunities along the journey you
are taking.
Approaches to transformation
This is how you intend to approach the transformation of your
organization. There are multiple paths toward the ultimate des‐
tination. Being conscious of your organizational variables will
help you select the correct approach to transformation and get
the most change for your investment.

2 | Understanding Patterns of Enterprise Transformation

Transformation leadership
This is who will lead the charge and help drive the changes
through the people, practices, technology, and culture of an
organization. The level and type of leadership in an organiza‐
tion can either be the single biggest limiting factor or the great‐
est asset of a transformation program. A total of 45% of
organizations report that lack of leadership and managerial sup‐
port inhibits the adoption of Agile at scale. Understanding who
is backing your transformation will help you in shaping the type
of transformation and approach to it, or challenge your pro‐
gram to influence the leadership you need to transform in the
way you need.
Knowing your challenges and variables is the first step in identifying
helpful patterns in transformation and toward a successful outcome.
Klaus Schwab, executive chairman of the WEF, phrases it perfectly:
New technologies and approaches are merging the physical, digital,
and biological worlds in ways that will fundamentally transform
humankind. The extent to which that transformation is positive
will depend on how we navigate the risks and opportunities that
arise along the way.

Types of Transformation
Being explicit about what you want to achieve and therefore what
type of transformation you are embarking on will determine the
radius of impact for the change you want to make. For each type of
transformation, there are clear variables that will affect the likeli‐
hood of success (see Figure 1-1).
The types of transformation listed are set in ascending order of
magnitude in terms of organizational impact and potential value
opportunity to be gained.

Types of Transformation | 3
Figure 1-1. Finding the sweet spot for organizational transformation

As we increase in impact and value, it’s often the case that the type of
transformation is much more difficult to see and measure in terms
of change and success. For example, it’s quick and easy to see and
measure a change in where people are situated in the organization,
but a fundamental shift in how value is delivered to customers or
the underlying business model will emerge only over time.

Organizational Transformation
Organizational transformation typically focuses on how people are
organized around existing work and technology structures, and
attempts to optimize by changing this only. This consists of a change
to role descriptions and line management, and usually relies on a
target operating model to guide the transformation to a fixed end
point. We tend to see this kind of transformation most in rationali‐
zation or cost-saving exercises, so the radius of impact and value is
quite small compared to the disruption this kind of change introdu‐
ces.
Because of this low disruption-to-value ratio, organizational trans‐
formations can feel very frustrating to those affected. There is an
additional frustration in the other challenges within the organiza‐
tion that this shift will expose. Frequently, you will see changes to
team structure expose deficiencies or constraints in technology and
process.
This kind of transformation is like changing the driver of an old car
to see if you can make it drive faster or for longer.

4 | Understanding Patterns of Enterprise Transformation

Technology Transformation (Replatforming)
This transformation represents an investment in the IT systems of
an organization and quite often occurs when the technology sup‐
porting the organization becomes so old and congested that it is the
single biggest limiting factor to the organization’s success. In other
words, technology is a burning platform.
The key differentiator between this and any other type of transfor‐
mation is that it is a change to systems, tools, and technology only.
There is no need to change team structure to achieve this. There is
no prerequisite to adopt other ways of working. This transformation
simply addresses a very narrow issue within an organization.
This type of transformation does not happen as often as it once did.
Organizations are now cognizant of the missed opportunity in
addressing only one small area and are tending toward greater sys‐
tems thinking in resolving core organizational challenges. Added to
this is the growth in credibility of Agile and Lean ways of working in
getting value to customers more quickly. It is more appealing to
adopt this way of delivering new technology, along with the varying
degrees of organizational change that implies. As Conway’s law says,
“Any organization that designs a system (defined broadly) will pro‐
duce a design whose structure is a copy of the organization’s com‐
munication structure.”
Therefore, technology transformations that limit their radius of
impact to system only will miss a potential value opportunity to
design an architecture that supports the business, and not current
technology team structure.
This kind of transformation is like putting a brand-new engine in a
rusty old car. It might get you somewhere much faster, but you’ll
worry if the body is up to the task!

Delivery Transformation
As its name implies, delivery transformation focuses on the part of
the organization responsible for delivering products and services to
the customer. This means that our radius is extended beyond sys‐
tem, tools, and technology into people and practice. It makes the
part of the organization that builds and delivers products and serv‐
ices more effective, with continuous delivery, data-driven decisions,
and a culture of continuous improvement. In many cases, this is

Types of Transformation | 5
where the first signs of transformation emerge in an organization, as
product and service delivery teams are often at the sharp edge of the
pain organizations feel when technology, practice, and culture are
poorly aligned.
The value of achieving this type of transformation is limited, how‐
ever, by the lack of integration with core business functions around
product/service ownership and the customer focus this provides.
Organizationally speaking, this type of transformation is still local
optimization. We can still invoke Conway’s law as we are limiting
the radius of impact, and therefore the opportunity potential, to the
delivery function. In some organizations, this extends somewhat
into the business to find product representation, but in many exam‐
ples (financial services organizations are often guilty of this) we find
the radius limited to within the IT organization only.
Let’s not overlook that this type of transformation does solve some
great problems within organizations. In addition to potentially solv‐
ing a “burning platform” issue, it can introduce thinking that signifi‐
cantly improves delivery of value of customers not only in terms of
speed to market, but also quality in market and overall responsive‐
ness to feedback.
Ultimately, however, a successful delivery transformation will cause
cultural dissonance between the areas included within the transfor‐
mation, and the areas looking at the transformation. Without
addressing leadership from the top, organizations remain at risk of
increasing flow but still delivering things of relatively low value,
fighting competing and continuously changing agendas, and man‐
aging too much work in progress.
Delivery transformation is akin to having a fast car with a powerful
engine, but with loose suspension and steering and a driver who is
not sure where they are going!

Digital Transformation
Digital transformation is focused on the aspects of an organization
that ensure a high-quality, continuous delivery of value to the cus‐
tomer. It integrates the product and service ownership functions
with delivery and is structured around delivering customer value.
Continuous innovation is supported by lightweight decision making
at product level, adaptive programs, and evolutionary architecture.
This type of transformation, as with the delivery transformation,

6 | Understanding Patterns of Enterprise Transformation

tackles technology, people, practice, and culture, but it does so with
a wider radial impact across the organization. Here, organizations
take advantage of new channels and technologies so that customers
can experience products and services in a new way.
There is less cultural dissonance across the organization horizon‐
tally; more organizational capabilities are typically involved with
digital transformations. Vertically, however, this kind of transforma‐
tion can still reveal challenges across leadership. Digital transforma‐
tion is limited by lack of clarity in organizational purpose and
vision, heavyweight/waterfall decision-making processes, and lack of
clarity or consistency associated with it. This type of transformation
is possible only with the direct support and involvement of the
entire leadership team.
Digital transformation is akin to having a fast car with a powerful
engine and good suspension and steering but a driver with poor
reflexes and sense of direction!

Business Transformation
Business transformation focuses on making the entire organization
adaptive. All aspects—from adaptive leadership and clarity of pur‐
pose at the executive level, through customer focus, product, and
service-aligned teams and evolutionary architecture at the design
level, to continuous delivery at the delivery level—are aligned to
deliver customer value.
This is essentially a composite of all transformation types that have
come before with an added focus on really interrogating the why of
organizational purpose and leadership. This is especially useful for
organizations that have existed for many years and are beginning to
level off in the current marketplace, or have seen many smaller com‐
peting organizations begin to chip away at what makes them unique.
As all levels interact and reinforce one another, it is possible for
these types of transformations to deliver change more effectively
than either digital or delivery transformations. The organization not
only aims to deliver value to customers more effectively and cross-
functionally, but also to learn and evolve from the data it generates.
This creates a resilience and adaptiveness that makes an organiza‐
tion more robust in times of change and uncertainty.

Types of Transformation | 7
Business transformation takes time and it can take much longer to
reap the rewards than a delivery or organizational transformation. It
necessitates strong and courageous leadership to hold their nerve in
the face of learning through failure as well as investors’ and boards’
questions.
This transformation is like having the best racing car and a trained
driver that can use it well!

Summary of Transformation Types

Each transformation type has a varying radius of impact (see
Figure 1-2), but across all kinds of transformation, there are two key
patterns:

• The widespread adoption of Lean and Agile practices, coupled

with the desire to embrace the digitalization of the Fourth
Industrial Revolution, means that organizations are now more
likely to begin at delivery transformation and move toward digi‐
tal and even business transformation.
• The key factor in deciding to do this is the ratio between antici‐
pated disruption versus value opportunity. The value is decided
primarily by the type of transformation, whereas the amount of
disruption can be managed through the approach to transfor‐
mation.

Figure 1-2. Radius of impact for transformation types

8 | Understanding Patterns of Enterprise Transformation

The approach to transformation, and therefore how organizations
can manage the disruption that comes along with it, is reliant on the
characteristics of the organization and the people within it.

Case Study: Government Digital Services—Supporting

the Digital Transformation of the Public Sector in the
UK
In 2010, Martha Lane-Fox published a letter to Francis Maude, a
Member of Parliament who was responsible at that time for work‐
ing with the Efficiency and Reform group to make government
departments more efficient. Lane-Fox was, herself, involved with a
government initiative to make the public at large more computer
literate. She had extensive experience with technology, having
founded lastminute.com in the late 1990s.
In short, the letter challenged the government to become more
service-oriented for citizens and to centralize digital services, using
Agile practices and an iterative mindset, with a chief digital officer
role being created within government to oversee the transition of
all government services to a more user-centric offering.
The reply was an emphatic “yes” and a promise to support and help
realize the recommendations. A department called Government
Digital Services (GDS) was created in early 2011 to address the
much-needed revolution in how citizens consumed government
services. Using Agile practices and tools, an alpha prototype version
of the website GOV.UK was launched, with the beta following in
early 2012; much of the work was to form the template for govern‐
ment service design in the coming years. During the next years, the
service standards, design standards, and role modeling of this gov‐
ernment department began to influence and drive change through‐
out other large-scale bodies such as the Ministry of Justice and Her
Majesty’s Revenue & Customs (HMRC; the UK’s IRS).
Many IT initiatives within government had a terrible reputation of
delivering little value for customers, providing poor service, and
always being late and over budget—in short, not good value for
money. There was also a lot of outsourcing within government, so
IT solutions were not being built or maintained by service experts.
In this environment, GDS was a revolution and helped to influence
a real digital transformation over continuous technology and
organizational-flavored change.

Summary of Transformation Types | 9

 In later years, GDS would act as a central team to ensure compli‐
ance from other government agencies and support 25 exemplar
programs of change. This was to ensure that they could take advan‐
tage of the learnings of GDS and maximize the investment in
change, therefore assuring their transformations would move from
the delivery to the digital space.
Here’s what the GDS did well to support this:

• Exemplified behavior by developing a deep pool of experience

and expertise from which to draw.
• Created principles to support change rather than tell organiza‐
tions how to change. This way, organizations would experience
their own transformation, add to the principles already created,
and feel ownership for their own transformation.
• Operated on a coaching/advisory model, because the point
wasn’t to do the work for the organizations. GDS simply helped
existing organizations to shape and deliver work, or put them
in touch with agencies and people who could supplement their
capabilities where needed.

Approaches to Transformation
Now that the type of transformation required has been identified, it’s
time to understand the best way to achieve it within the organiza‐
tion. There is no right or wrong way to approach this big, gnarly
problem. The characteristics of the organization, the goals the orga‐
nization wants to achieve, the people within the organization, the
leadership support, the technologies that support it, and the external
factors that affect it will make some approaches more suitable than
others.
Most organizations will manage transformation, for whatever type
and in whatever form, through a program. Put simply, in return for
an investment of time and money, the organization will deliver
change. Transformation is treated exactly like every other kind of
product and service delivery program in this sense—we outline
what we expect will happen over a timeframe we think is reasonable
and a budget that will cover it. This is the first big constraint to
acknowledge when selecting an approach because it sets up expecta‐
tions that are founded on little but will still be enforced. More

10 | Understanding Patterns of Enterprise Transformation

enlightened organizations choose to experiment a little at the begin‐
ning to examine how this change will be received within the organi‐
zation, then build up to a longer-range view of transformation.
Selecting the right approach for an organization can be the differ‐
ence between success and failure! A less-suitable approach can make
the transformation process frustrating and exclusionary, and fuel
negativity and doubt over time. A better-suited approach can create
and foster safety for learning and experimentation in a collaborative
environment.
Simply put, what kind of disruption can the organization withstand
to get the maximum value for this investment?

Approach 1: Boiling the Ocean

You’ve probably heard this stalwart of business-speak many times. It
signifies [“link:http://bit.ly/2BAZOzIan impossible task or project or
to make a task or project unnecessarily difficult”] or just generally
making something much bigger and more difficult than it needs to
be. You might be wondering what this is doing in a list of
approaches to transformation; however, this approach is more com‐
mon than you would think.

What does it look like?

This kind of transformation program tries to effect change every‐
where at the same time. Typically, it can look quite chaotic and
unfocused, with lots of changes happening across multiple areas at
the same time. To coordinate this program, there is likely to be a
central team. These kinds of programs can feel very pressured, as
such a wide radius of impact necessitates high investment, and along
with it an expectation of high-impact change over a relatively short
time. However, the wide radius of impact often results in a low or
superficial penetration of change (see Figure 1-3).

Approaches to Transformation | 11
Figure 1-3. Boiling the ocean

In this kind of program, organizations usually push very visible

change to assure leadership and investors that change is happening
—for example, story walls, charters, ceremonies, and visible data to
support the program.
Boiling the ocean is usually a vehicle for practice change and is most
likely to be used to achieve a delivery transformation.

What is it good for?

It’s inclusive
Because the focus is very large, it means more people are part of
the program and there is less chance that it will be labeled as
exclusive or an ivory-tower change. This is an approach for
keeping morale high and people on your side.
It can be a good pathfinder
Sometimes, conditions make it unclear where a good starting
point for change in an organization might be:
• Tightly coupled or monolithic technologies prevent organi‐
zations from breaking out distinct areas on which to focus.
• Lack of leadership commitment to change in business areas,
or all leaders wanting to be included simultaneously.

12 | Understanding Patterns of Enterprise Transformation

 • Lack of support or expertise to select a starting point within
an organization.

The list is not exhaustive, but where the path forward is not known,
unclear, or cannot be agreed on, it can be valuable to begin a trans‐
formation program by going wide and testing where there is sticki‐
ness for the changes required. It can also act to validate some early
hypotheses about how the organization will react to change and help
shape the remaining program.
In this sense, it is much like the approach one might take to a cha‐
otic situation in the sense-making framework Cynefin, where you
might act first (in this case try to change as much as possible) and
then sense and respond with a more informed strategy.

What it’s not so good for

It’s high investment for low value
Just as its name suggests, you need a lot of energy to heat up (let
alone boil) such a large body of water. At the beginning of a pro‐
gram, where you will be expending a lot of energy (and there‐
fore money) to try to get some of the changes to stick, it might
appear as though there is little return for such an investment.
This can be the first big test of leadership in transformation.
Centralization over localization
In larger organizations, the resources required could be phe‐
nomenal in scale. This often necessitates an additional layer of
people to manage the transformation resources and justify the
spending on an ongoing basis. This can cause the people affec‐
ted by the change to feel less ownership for it because of this
influence.
It’s one size fits all
Organizations that don’t test and learn during their transforma‐
tion can tend to adopt a one-size-fits-all approach to coaching,
strategy, training material, and so on, which can be off-putting
to some areas of the business. This makes it much more difficult
to come back to that area over time and reintroduce them to
Agile and Lean practices and thinking if their initial experience
has been negative.

Approaches to Transformation | 13
Do this when…
You need to find out how or where to start a transformation pro‐
gram, what your next steps will be, or test the environment. Then,
move onto another approach when you have more data about how
the organization responds to this change.
This is an approach that you can use to overlay existing work rather
than change the portfolio of work to deliver transformation.
Also do this in conjunction with other approaches (e.g., hot spots)
as a secondary approach that can help inclusivity. Where more
focused approaches might have other strengths, they can ignore the
rest of the organization. Using the spirit of boiling the ocean, organ‐
izations can benefit by introducing some smaller changes across the
organization to minimize the cultural impact of creating a newly
transformed section of the business versus the old business.

Don’t do this when…

This is your only approach. This will quickly run its course and
leave you feeling burned out with little deep penetration of change
into the organization overall. Because of this, it’s also a poor
approach if you are constrained by time, budget, or expectations.
High expectations of change in a short amount of time, or with a
relatively modest budget, are not best served by boiling the ocean.
Overall, this is a high-disruption approach that does not work well
in change-fatigued organizations or organizations that are already
experiencing high degrees of change in uncertainty (merger, regula‐
tory change, etc.).

Approach 2: Focusing on Hot Spots

Transformation programs that effect change through hot spots do so
to take advantage of preexisting areas and people who are already
changing or demonstrate a predisposition to change. Building on
and incubating organizational success is a sound strategy for trans‐
formation and can develop meaningful change in the affected areas.
However, you must take care so that those areas that are not targeted
do not experience cultural dissonance, leading to suspicion and
resistance to change. This is partly why many organizations often
find it difficult to find a path to scale successes beyond the hot spots.

14 | Understanding Patterns of Enterprise Transformation

What does this look like?
This will be obvious in the organization because there will be areas
of very visible change next to the existing processes and practices. It
is likely that the hot spots of change will create friction within the
existing organization as key organizational capabilities try to operate
next to new and old practices; this will manifest obviously around
areas like the project management office (PMO), finance, and HR
(see Figure 1-4).

Figure 1-4. Hot spot

Hot spots are commonly used as a starting point in an organiza‐

tional, delivery transformation, or occasionally a digital transforma‐
tion. Due to the difficulty in joining the hot spots together, this
approach inevitably fails or evolves into an “extract and enhance” or
“strangler” transformation approach.

What is it good for?

Show and grow success
This approach is a great way of showcasing success in transfor‐
mation in a relatively short amount of time. Hot spots usually
contain people who are good at finding ways around organiza‐
tional constraints to deliver value. They are people who have
been brought in because of a background in Lean and Agile
practices or who have sought out their own education to sup‐
port continuous change within their own areas or teams. In
short, hot spots can show change with comparatively little
investment and build organizational confidence.

Approaches to Transformation | 15
Localized change
Whether the hot spot is a project, program, or a team, the
change is often controlled and developed locally. This means
less influence from a centralized team and more sense of owner‐
ship within the area effecting the change.

What it’s not so good for

Organizational goals over local optimization
It is very easy to lose the balance between building a trans‐
formed organization and optimizing for the program, project,
or team.
An organizational journey
Hot spots, by definition, are small areas of change within a
larger organization. This creates dissonance between the exist‐
ing organization and the areas of change. Unchecked, the hot
spots can be treated like an exception, or a virus, which the
organization seeks to eradicate.
A path to scaling
Although hot spots are great at showing how things can be suc‐
cessful, they are not always indicative of how this success might
look or be achieved across the organization. Hot spots are typi‐
cally not cross capability; that is, they usually are exceptions that
do not include elements of finance, HR, operations, and other
key functions, and they are not representative of a scaled orga‐
nization and cannot provide data to help scaling Agile and Lean
practices.

Do this when…
If you have areas of change within your organization, program,
business line, and so on, it’s worth using the hot-spot model to
explore what conditions would make a transformation successful in
that area. The more organizational capabilities you have in your hot
spot, the better and more meaningful the data will be to help you
scale this successfully.
This is a great approach for tentative organizations that are looking
for data to prove that Agile practices, tools, and mindset will work to
support further investment. It’s also a good approach when you are
looking for an opportunity within an existing portfolio of work to
deliver something using new practices.

16 | Understanding Patterns of Enterprise Transformation

Don’t do this when…
You’re looking to scale directly from some localized hot spots to
organizational agility.

Approach 3: Extract and Enhance

Extract and enhance as an approach to transformation is perhaps
the most complex from a delivery perspective. It requires deliberate
planning, experienced leadership, and many short feedback loops to
course-correct. The approach itself is based on an approach from
technical architecture aimed at breaking up a technical monolith.

What does it look like?

The approach involves analyzing the organization and its associated
technology systems estate to identify “seams” that you can use to
break out organizational capabilities so they can be transformed. In
practice, this typically involves splitting out functional elements of
the business (e.g., finance), as the functional silos in the organiza‐
tion represent the most easily accessible seams due to organizational
ownership, structure, and technology (remember Conway’s law?).
The extracted function then is transformed while continuing with
its ongoing business function, which necessitates significant integra‐
tion with the untransformed elements of the business. This is often a
significant limiting factor, as this need for integration will limit the
amount of real change that can be made. An organization taking this
approach will likely have to go through many cycles of change for
each extracted function or capability before the old organizational
and technological constraints are eliminated (see Figure 1-5).

Approaches to Transformation | 17
Figure 1-5. Extract and enhance

What is it good for?

This approach is best suited for organizations that have very specific
targeted areas in need of change rather than those that are looking
for more widespread change because it will typically focus attention
on one area of the business at a time.

What it’s not so good for

This is generally not a good approach for radical transformation
because any change is fundamentally limited by the need to support
ongoing business operations and integrate with the existing technol‐
ogy systems estate. Broad-scale organizational change is likely to be
slow, and resistance to change within the untransformed elements of
the business might create a “us versus them” culture.

Do it when…
Take this approach when you are looking for targeted change in spe‐
cific elements of the organization.

18 | Understanding Patterns of Enterprise Transformation

Don’t do it when…
Don’t take this approach when you are looking for fundamental
change in the overall organization.

Approach 6: Organizational Strangler

This is the most significant and impactful approach to change
within an organization. It is an effective method of transforming
every element of an organization while maintaining the same brand,
people, and purpose. It is typically done in parallel with the
business-as-usual services, and thus creates an incremental transfor‐
mation approach in which new services, products, and capabilities
are introduced but fit into the wider ecosystem. The strangler effec‐
tively creates a business within a business and seeks to draw in old
service, products, and capabilities over time until none remain in
the legacy space. This is the key differentiator between this approach
and the “start again” approach—the change occurs within the organi‐
zation and therefore is both limited and amplified by the organiza‐
tion’s characteristics.

What does it look like?

This approach will be highly prioritized within an organization
because it will use many of the organization’s best people to get the
work done. The strangler begins with a small cross-organizational
piece of work and gains momentum as more data is collected and
understood, so the number of people required to complete a trans‐
formation of this approach increases over time (see Figure 1-6).

Approaches to Transformation | 19
Figure 1-6. The organizational strangler

Usually, organizations will create different areas for these teams to

work together, meaning there might be a new or transformation feel
versus a legacy feel within the organization. Lastly, this approach
requires some diligence at the beginning, so there is likely to be a
phase in which discovery is undertaken to form an evolutionary
view of the business and technical architecture, along with some
adaptive planning to understand operational and user impact when
the transformed capabilities are released over time.

What is it good for?

Cross-organizational agility
Because the strangler fundamentally targets entire propositions,
all capabilities within the organization involved with delivering
the service must become part of the transformation. This

20 | Understanding Patterns of Enterprise Transformation

 approach can introduce much higher levels of organizational
agility and adaptability because of this.
Promoting systems thinking
This approach can work only where teams deliver an end-to-
end capability. Operations, technology, users, channels, and
everything else needed must be factored into thinking from the
beginning.
Learning
As we start small and test something across the entire organiza‐
tion, we learn a lot more about how change affects the business
and the approach to transformation than we do in an isolated
change program. This approach scales with the data the pro‐
gram gathers, and so over time becomes very adaptive and
robust.

What it’s not so good for

Hesitant or misaligned leadership
Because this is cross-organizational, the leadership must buy
into this approach. They will be expected to support some key
people from their areas being dedicated primarily to transfor‐
mation over business as usual. This sounds like a sensible
request on paper, but in the event of major operational inci‐
dents, the pressure will be on to remove those people from the
program.
Harmonious culture
The organization will begin to break into the new and legacy
factions. It will be obvious where the importance and invest‐
ment lies from the new tools, support, focus, and facilities a
transformation program will have to support it. This prevailing
culture will try to quash the emerging culture. Although this
can be mitigated, it is always a fine balance to walk and takes a
lot of energy to tackle.

Do it when…
When organizational constraints can be managed by isolating areas
of the business one by one, the leadership can make difficult calls
and keep the various areas of the business allied to the program.
This is very well suited to organizations looking to effect large-scale
change while managing an operational business.

Approaches to Transformation | 21
Don’t do it when…
Leadership is not completely bought into the approach—the stran‐
gler approach necessitates too much sponsorship to work without
this.

Approach 7: Start All Over

This approach initially might seem extreme, but in the right situa‐
tion, it’s actually very sensible. If an organization is barely surviving
and is being attacked by long-standing competitors as well as start‐
ups, making changes to your organizational structure and delivery
methodology is unlikely to have a big effect. If the organization has
many legacy systems, relationships, processes, political baggage, or
cultural toxicity, working within these constraints will limit any
transformation that takes place within the organization.
In this situation, the sensible option is to start again. This approach
is rarely taken by the established organization. Politically, it is rarely
seen as a viable option because it means recognizing that the current
organization is coming to its end of life. It takes a bold executive
team to admit this, even among itself.
Crucially, unlike the organizational strangler, this change is effected
outside of the existing organization completely and therefore has
minimal factors from the existing environment that can influence
the transformation.

What does it look like?

New premises. White labeling. Lots of outside help. New practices.
New technology. Different culture. It’s an opportunity to start again,
so expect the essence of what made the organization successful ini‐
tially but with a new mindset and zero constraints (see Table 1-1).

What is it good for?

Reset
This is perfect for organizations that have lots of baggage—tech‐
nical debt, process debt, and organizational debt that make it
feel as though the organization is wading through molasses.
Trying to effect change through transformation in any other
way would be extremely difficult and time-consuming. Do this
to move faster and deliver value.

22 | Understanding Patterns of Enterprise Transformation

What it’s not so good for
Continuous improvement
If the organization is delivering value to customers and simply
wants to optimize this through changing technology, practice,
or structure, starting again is not necessary.
Hesitant leadership
Starting again is not for the faint-hearted. This is not a suitable
approach if your executive sponsorship is not invested com‐
pletely. Start small and build data to prove the approach rather
than using this as a jumping-off point for a transformation.

Do it when…
Organizational constraint would mean the investment in delivering
change through any other transformation approach would signifi‐
cantly outweigh the potential value of the program.

Don’t do it when…
The leadership team does not support this approach. It needs execu‐
tive sponsorship and active participation as a starting point and will
not work without it.

Transformation Approaches to Avoid

You can execute the aforementioned approaches to transformation
with a range of mindsets and strategies. They can, individually or in
combination, amplify both positive and negative elements within a
transformation. There are some key indicators that the execution of
a transformation strategy will amplify the negative elements of the
program. These “bad smells” are important to recognize and neu‐
tralize quickly!

The Checklist
Beware the checklist! This could be an actual checklist or a list of
pre-agreed things that are hidden in plans and story walls. If you are
doing something because the transformation program has commit‐
ted to it or because it has appeared on program material, not
because it is the right thing to do, you are checklisting.

Transformation Approaches to Avoid | 23

Transformation mentality should welcome change and adapt to new
data. Following a plan or list because you have one, not because it’s
the right thing to do, is a warning sign that things have not really
changed. Resist the false comfort of creating lists that will quickly
become obsolete.

Headless Change
Leadership is vitally important to transformation programs, and it’s
not just executive-level sponsorship that counts. Transformations
need leadership that is present and accessible. If your leadership is
asking for reports, has a chain of command, and is not visible
around the office, chances are that they are not close enough to the
program to really lead it effectively.
Organizations need leadership that can defend in times of doubt
and adapt to changing circumstances quickly. Neither can be
achieved if the leadership is distant from the program.

Outside Bias
Many organizations will seek outside support and expertise, no mat‐
ter which type and approach of transformation they are undertak‐
ing. This is a sensible strategy to supplement both numbers and
knowledge. However, too many contractors and consultants swarm‐
ing onto one area can make existing teams and people feel threat‐
ened and out of control. A bias toward external people delivering
transformation also does nothing for internal capability building.
The people within the organization must experience the end-to-end
process and do the difficult stuff as well—this is how we build
organizational resilience.

Centralization
Another fine balance that can have a significant impact on a trans‐
formation program is how we govern the program. Typically, a pro‐
gram of any significance will have a centralized capability to support
shared learning, shield from outside influence, and course-correct
toward the overall goals and vision. Central teams that push change
to areas of the business will eventually undermine the transforma‐
tion program’s effectiveness. To succeed, the transformation must
successfully engage the people within an organization. To survive
the initial investment and program, the people in the organization

24 | Understanding Patterns of Enterprise Transformation

must see the value in what they are doing, and want to do it. It is
highly unlikely that people will be inspired by a transformation that
is done to them.

Installation (Before Experimentation)

Many organizations select a scaling framework because it helps
articulate to the organization what an end state might look like in
terms of process and organizational design. Selecting a scaling
framework necessitates careful consideration of an organization’s
characteristics, the characteristics of the various frameworks, the
constraints within which it would operate, and how the organization
adopts change.
Installing a framework into an organization too early on in a trans‐
formation program will detract from the main goal and vision of
transformation. Like everything else, it is a tool that can help an
organization become a better version of itself. However, it is unlikely
this tool will be helpful without much investigation into what makes
change successful within the organization and what the limiting fac‐
tors of the organization are. Moreover, focusing on installing a
framework tends to override the cultural changes and dictate the
organizational structure prematurely.
Now we have established the “why” that determines the type of
transformation, and considered the best approach to effecting
change within the organization. The last remaining pattern to con‐
sider is leadership, or who is going to create the runway so you can
land the change?
What ostensibly started as a digital transformation is, in fact, more
of a delivery or technology transformation. Digital transformation is
about finding ways of delivering existing services and products to
customers via new channels. This necessitates taking what an orga‐
nization currently offers and finding new ways customer can con‐
sume it through digital channels—at minimum an evolution and at
best a revolution. Get Me There is an example of where services
have been digitized with little or no change—in other words, a digi‐
tal “lift and shift,” making visible the tensions between the current
services and the services customers want.

Transformation Approaches to Avoid | 25

 Case Study: Get Me There—How the Digital
Transformation for Manchester’s Transport System
Never Quite Made It
Anyone who has used public transport in London, or in most big
city transit systems, will be familiar with the smart ticketing
options. From the Oyster card to contactless and smartphone solu‐
tions, there are numerous ways for you to pay without needing to
get a physical ticket. It’s simple and makes commuting just a little
bit easier.
When it was announced back in 2012 that Manchester, the UK’s
third largest city, would be getting a smart ticketing solution, this
was not a surprise. However, the Get Me There solution got off on
the wrong foot with Mancunian commuters, with thousands sign‐
ing a petition to change the name. In the intervening five years or
so between the decision to create a ticketless solution and the
launch in 2017, one might have expected many prototypes, cus‐
tomer engagement, and learning for the ever-evolving picture of
smart travel across the country. However, the Get Me There service
launched with some challenges:

• The main offerings of an app and a card did not talk to each
other and did not span all forms of transport. In fact, the app
and card data were held in two separate databases. The onus
was on the customer to fight through the complexity in order
to use the service, rather than the customer being at the heart
of the experience.
• The service did not span all forms of transport. Tram users
could use the app. Bus users could use the card. Train users
were not accommodated. Again, this puts the onus of having
multiple accounts on the customer.
• The service was driven on customer data and ticketing. Unlike
the Oyster card, and other smart ticketing systems, which rely
on cost per journey, the service is constrained by ticket types
and having customers register an account.
• The world had moved on and the service could not scale and
adapt to meet more modern payment solutions such as con‐
tactless and smartpay. The reliance on customer accounts and
ticketing will only make this more challenging to adopt.

26 | Understanding Patterns of Enterprise Transformation

Transformation Leadership
Leadership is the single most important factor in determining how
far the impact of a transformation program can go.
Already considered are the transformation type and approach,
defined by two factors:

• The scope of the transformational vision—the why

• The characteristics within which the transformation will be
delivered—the how

The final pattern of transformation is the biggest limiting factor of

all three. The simple truth is this: it is virtually impossible to sponsor
transformation in an aspect of the business for which you are not
responsible. Therefore, the leadership supporting the transforma‐
tion program will limit the overall scope and success of a program
no matter how compelling the vision and suitable the approach.
The leadership within an organization is like a fingerprint—it is
unique to that environment and cannot be replicated elsewhere.
However, there are some key roles and characteristics we can iden‐
tify that can help organizations understand exactly how far their
executive sponsorship can get the transformation.

Executive Leadership and Transformation Type

Organizations will form executive teams around the key capabilities
required to ensure success. With so many organizations now evolv‐
ing to embrace digital solutions and technologies at the core of the
business strategy, it’s not surprising that we have seen the inclusion
or creation of new roles at an executive level. The number of organi‐
zations employing a chief digital officer has increased from 7% in
2014 to 25% in 2017—this is a staggering change both in terms of
volume and in changing the dynamic of executive teams. Other rela‐
tively new roles at this level include chief data officer (information
as an enterprise asset), chief scientific officer (technology advisory
across the enterprise), and chief product officer (product strategy
across the enterprise). Moreover, the balance of power is moving
around the executive table with 71% of CIOs stating their strategic
influence within an enterprise has grown significantly over the past
year.

Transformation Leadership | 27
In this environment of new roles and shifting power, what does the
correlation of transformation type and executive sponsorship look
like? Table 1-1 provides an overview of the kind of sponsorship
required per transformation type.

Table 1-1. Sponsorship requirement by transformation type

Transformation type Executive sponsorship
Organizational Chief People Officer and C-level of any affected department
Technology CTO or CIO
Delivery CTO or CIO and CPO
Digital CDO or CTO, COO, and CPO
Business CEO and all other members of the executive

Organizational transformation
As this kind of transformation is primarily motivated by efficiencies,
and therefore cost savings, it necessitates the approval of any C-level
member whose departments are being affected. It’s often the case
that even though organizational transformation requires approval
from C-level sponsorship, the rest of the program is conducted in a
fairly light-touch manner.

Technology transformation
This is a much more delineated change and necessitates any C-level
sponsor who falls into the information or technology moniker
(CIO/CTO) to lead, and broad alignment with the CDO and/or
CSO if they exist within the enterprise. Potential sources of friction
can occur where the CDO’s strategy is not aligned with the technol‐
ogy changes required in this transformation.

Delivery transformation
Here, we need sponsorship and leadership again from the CIO/CTO
with at least buy-in if not full leadership from the CPO. This is to
ensure that we can deliver “products” or items of value to customers.
Again, the biggest source of friction will be any misalignment with a
digital strategy.

Digital transformation
For this kind of transformation, we need much broader sponsorship
from the executive team. We will require the technology leadership,

28 | Understanding Patterns of Enterprise Transformation

product or digital leadership (potentially both if they coexist), and
operational leadership. This is to support the new ways the organi‐
zation will deliver value to customers (new channels, retiring prod‐
ucts and channels, options for minimum viable product [MVP]
delivery, etc.).

Business transformation
This requires the broadest buy-in from executive teams. This must
be led by the CEO with full support from the rest of the executive.
Only the CEO can represent a team that is looking to fundamentally
challenge and change the business model of the organization. The
CEO must work with the team to build a vision and support the
organization to deliver toward it, but the CEO alone will be respon‐
sible for defending the work, obtaining the investment, and manag‐
ing stakeholders at the highest level.
If your transformational vision exceeds the scope of your organiza‐
tional authority, all is not lost. There is no linear path through trans‐
formation, and it is not always the executive leadership that starts
this journey. This is where the approach can help build confidence
and pave the way for the desired transformation type. In this case,
beginning with some small hot spots of delivery transformation is
perfect for demonstrating how changes might work at small scale,
generating data, and testing out where the key challenges will lie.
The roles, and therefore the correlating type of transformation, are
only half the picture. The characteristics of the executive leadership
team can also be a limiting factor of the approach to transformation.
The key role of the executive sponsorship team within the change
program is to remove enterprise-level blockers and constraints.
Without this, we cannot achieve significant change in the way
organizations deliver value to customers. Therefore, the characteris‐
tics of the executive team will help determine the approach to trans‐
formation that is most realistic at any point in time. It is important
to use feedback here because it might be possible to change the
approach to transformation based on the data available to help lead‐
ership teams make better-informed decisions (see Figure 1-7).

Transformation Leadership | 29
Figure 1-7. How leadership influences the transformation approach

Hostile and Reluctant Leadership

These kinds of leadership will generally amplify the negative charac‐
teristics of a transformation program and do not lend themselves
well to change approaches that require more collaboration, courage,
and confidence. Hostile leadership can manifest when some, but not
all, of the executive team are on board with the transformation
vision. The opposing leaders can cause friction at board level when
faced with large-scale organizational changes like creating cross-
functional teams, streamlining ongoing work, and making key hires.
Reluctant leadership can be rooted in a difference in views between
the executive team but can also be found where the leadership feels
the changes included in the transformation program are forced
upon them. This can happen when external bodies recommend the
adoption of new practices and tools rather than the need being gen‐
erated internally. In this situation, leaders can feel like the change is
being done to them—much like the effect an overly powerful central
team might have on teams within a transformation program.
These characteristics lend themselves more to certain approaches
that are less organizationally risky but have high complexity or
lower potential for value. Boiling the ocean is often the starting
point for organizations with reluctant or hostile leadership because

30 | Understanding Patterns of Enterprise Transformation

no decision on a starting point, measures for success, or how to
effect change can be reached. Hot spots can form when there is a
desire for change but no executive sponsorship, or where the execu‐
tive seeks data to inform future decisions. Interestingly, the extract-
and-enhance approach is also selected by leadership lacking in
confidence and commitment as a way of making a large digital
change with minimal impact to business as usual or to take advan‐
tage of a new capability within the transformation timeline.

Committed and Extreme Leadership

Committed and extreme leadership will amplify more positive char‐
acteristic within a transformation program. Committed leaders are
fully invested into the transformation and will do all reasonably in
their power to remove organizational barriers and make the pro‐
gram work. Extreme leaders are the rare breed that will take the
opportunity to really embrace the journey toward organizational
adaptability and invest in their own self-development to better serve
others in the organization. Both leadership types are needed for dig‐
ital and business transformation.
Digital transformation requires a profound shift in how an organi‐
zation is structured to deliver value to customers more effectively. It
also necessitates breaking down the fourth wall between the busi‐
ness and the customer. This generally means a high degree of organ‐
izational flux during the program, which the leadership team must
navigate through while keeping the business running.
Business transformation is even more extreme because it involves all
of the above while fundamentally questioning the validity of the
organization’s business model and propositions. This kind of leader‐
ship requires visioning, storytelling, defending, and exhibiting pas‐
sion that few leaders possess.

Transformation Leadership | 31
 Case Study: The Business Transformation of Lego
In 2003, Lego was facing extinction. Its sales were down 30% year
over year, and it was in debt to the tune of $800 million. Neverthe‐
less, by 2015 Lego overtook Ferrari as the world’s most powerful
brand and 2016 profits were the highest ever. So what happened
between 2003 and 2015? Here we find two examples of business
transformation.
The first was consultant advised and consisted of rapid expansion
and diversification, based on the premise that the actual brick that
had made Lego successful for so long was obsolete. What followed
was hundreds of new lines and a foray into theme parks. However,
the situation did not improve.
Jørgen Vig Knudstorp, CEO of Lego, described the company as a
“burning platform” and knew that radical change was the only
option for survival. What followed was a business transformation
that consolidated what was great about Lego, while stopping what it
could not demonstrate success or expertise in. Simon Cotterrell of
Interbrand noted, “This is where a lot of companies go wrong. They
don’t understand that sometimes it’s better to let go than to hang
on.”
So what did Lego do?

• Stopped investment in things that weren’t working for it,

including selling the Lego theme parks and rationalizing prod‐
uct lines by more than half.
• Spotted patterns of success and sought to amplify them. Most
notably, it was always the case that Lego sets associated with
films sold well, so partnerships were formed that have led to
the recent Lego movie franchise.
• Broke down the fourth wall to customers by crowdsourcing
designs and investing heavily in usability studies globally with
their target audience. Lego designs are created with the user at
the heart of the product, and Lego is unafraid to iterate until it
is loved by the user.

Finally, Lego was supported by extreme leadership to pave the way

for radical changes that allowed the organization to test and build
on successful practices.

32 | Understanding Patterns of Enterprise Transformation

Starting Your Own Enterprise Transformation
Understanding the three key transformation patterns and the rela‐
tionship between them is a powerful tool for any organization con‐
sidering transformation. There are combinations that will make the
program more effective and efficient. As described shortly, certain
types and approaches—for example, a digital transformation—will
always need strong visionary and committed leadership. Others can
begin to pave the way for change without such leadership, and form
part of the overall strategy to engage the executive team.
Some approaches are excellent, but for short-term goals and as part
of a wider strategy, approaches such as hot spots can be great ways
of gaining data and confidence, but rarely join up to cohesively
transform an entire organization.
Mentality is the overriding factor across the three key patterns. Be
honest, be brave, and select a starting point that is representative of
the need and conditions within the organization. Inspect and adapt
the environment and move between approaches where necessary to
move the organization further toward its goals.
Transformation is just a tool that should help an organization
become a better version of itself. It should never be considered the
end point or a goal in and of itself. Transformation is only meaning‐
ful in the context of a clear and well-articulated narrative and vision.
Because of this, measuring progress through a transformation pro‐
gram will never be the same as measuring how successful the trans‐
formation actually is.

Starting Your Own Enterprise Transformation | 33

Figure 1-8. Essential patterns for shaping organizational transforma‐
tion

Recognizing patterns in transformation will make the process of

reaching organizational goals easier, but the journey will still be long
and challenging. The aim must not be to become an organization
that is good at transformation; rather, you should look to become an
organization that is adaptive, flexible, and able to move quickly and
deliver value to customers. A transformation program might be a
necessary first step in this journey, but the adaptive mindset it leaves
behind is what ensures enduring success.

34 | Understanding Patterns of Enterprise Transformation

About the Authors
Helen Williams spent over a decade working in the public sector
before she was involved in her first transformation program seven
years ago. This convinced her that organizational adoption of Lean
and Agile practices and mindset is the only way a modern business
can deliver value to users in the face of continuous change.
Subsequent experience in over a dozen transformation programs
has led her to understand that real and lasting transformation can
only be achieved when the entire enterprise embraces change.
Helen specializes in the creation of transformation programs, sup‐
porting leadership teams in embracing new ways of working and
building teams of purpose. Helen lives in Surrey with her partner,
Jeremy, and their two rabbits. Read about her experiences in trans‐
formation at www.theadaptiveorganisation.com.
Jeremy Sutherland has a diverse background ranging from user
experience, business analysis, product definition, and project man‐
agement to organizational design and business transformation. He
specializes in understanding user and business needs and distilling
them into a clear roadmap for delivery.
With over 20 years’ experience in the technology sector across many
domains, Jeremy has spent the last 12 years working at Thought‐
works, where he is a principal consultant specializing in business
architecture and transformation. Jeremy’s focus of recent years has
been predominantly on helping businesses define, lead, and execute
transformations.
Jeremy lives in Surrey with his partner, Helen, and his interests
include modern history, model making, and skiing.
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