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Digital Strength Course II | Who is responsible for Digital Transformation? | 1

Contents

Clicking on the titles will take you to the different sections.

About the Digital Strength Program

I. Introduction

II. Should Digital Transformation (DT) Be a Top-Down or

Bottom-Up Process?

III. Co-Creation is the New Name of the Game

IV. Is Digital Transformation an IT Initiative or a Business

Process?

V. Who Should Spearhead the Digital Transformation Process?

VI. The Key Attributes to Look for in Leaders of Digital

Transformation

VII. IT as the Enabler, But Not the Driver

VIII. Ensuring C-Suite and Board Buy-In

About HelloSign

About Ben Kepes

Digital Strength Course II | Who is responsible for Digital Transformation? | 2

About the Digital Strength Program

In this digital age, the pace of change is increasing exponentially and every organization
faces existential threats from new and existing competitors. The Digital Strength program
is crafted to give everyone within an organization – from the C-Suite to the production
line – an understanding of what digital transformation means within a global context, and
guidance to achieve the digital transformation journey in your own organization.

We will cover an explanation of what digital transformation involves, the roles and respon-
sibilities around digital transformation, as well as the cultural aspects of a digital change.
Over the course of the program we will detail tips and tricks, potential barriers, clues into
the ideation approach, and how to move towards seeing digital as an ongoing process.

By the end of the program, participants will be fully conversant about digital transforma-
tion, and will be armed to be the change agents within their own organization to imple-
ment digital broadly.

No matter whether you are just beginning the journey of transformation or are well on your
way, the guidance in this program will be useful to you. Early adopters, those mid-way on
the transformation journey or those yet to begin will all find something of value from this
program.

Welcome to the future!

Digital Strength Course II | Who is responsible for Digital Transformation? | 3

Course II: Who is Responsible for Digital Transformation?

I. Introduction

Now that we have a basic understanding what digital transformation is, it is time to think
about how your organization can prepare (or continue) its own transformation. Like any big
change project, digital transformation has many strands to it and it is important to put in
place a well thought out, robust process for your transformation journey.

In this course, we’ll look at the issues around who should hold ultimate responsibility for
the digital transformation journey, and whether it should be seen as a top down process or
a more democratic one led from the grassroots.

We’ll discuss the thorny issue around whether digital transformation should be seen as a
technology change, or something far deeper than that.

Finally we’ll look at what the leadership team – in particular the C-Suite and the board –
needs to do to develop their own “transformational muscle memory” to ensure the path to
digital is an effective one.

Digital Strength Course II | Who is responsible for Digital Transformation? | 4

II. Should Digital Transformation (DT) Be a Top-Down or Bot-
tom-Up Process?

Traditional organizations work on a centralized, top-down basis. Decisions are made by the
board, the CEO, or by management. Those decisions are then fed down through the chain
until, eventually, the line workers who are actually responsible for implementing whatever
change has been decided upon are finally appraised of the situation and tasked with exe-
cuting it.

Perhaps the most effective and striking example of top-down processes lies within Apple
and its co-founder, sometimes CEO, and generally accepted autocrat Steve Jobs. Jobs
was widely regarded as a tyrant who compartmentalized knowledge and information. His
approach was to control all aspects of design from the top – neither listening to internal
stakeholders nor customers. The result was the iPhone, a device and ecosystem borne of
laser-focused precision and control. Some suggest that had Apple been a more democratic
organization and encouraged product and service design with a bottom-up approach, the
iPhone would never have existed.

But while the Apple approach might be typical of most organizations in the industrial era,
it is becoming more atypical in modern times. Over the second half of the 20th Century
(and accelerating into this Century), there has been a shift. Many organizations are now
assessing their top-down approaches within the context of creating greater agility and
faster speed. The rise of bottom-up approaches have, at least in part, been a reaction to
the realization that day-to-day stakeholders have the best idea of customer needs, pro-
cess improvements, and a multitude of other factors which can be potential targets of
change.

The theory goes that by flattening structures and embracing bottom-up approaches, a
company can quickly benefit from the skills and knowledge employees have to offer. While
there are many advocates for this approach, it’s not without its critics. Those who advo-
cate against a bottom-up approach contend that it produces ad-hoc and scattered results.
The theory goes that an organization can’t simply add pieces as it goes along. Critics argue
that this kind of knee-jerk reaction to individual stakeholder requirements takes the orga-
nization on a haphazard journey with no clear direction. As a result, it doesn’t enable the
organization to truly respond to the broader market trends.

Digital Strength Course II | Who is responsible for Digital Transformation? | 5

Both leadership approaches can be (and have been) applied to digital transformation. Yet
there’s a third approach which is arguably more effective.

Current thinking suggests that while it is appropriate to have a single person leading the
digital transformation process, it is better to have a group of people, all of whom are
deeply involved in the project and process and who will jointly drive the outcomes. Ideally
this group consists of people from across the organization, and even from outside of the
organization where appropriate. In this way, individuals can apply their particular specialty
to the task at hand, while still focusing on the overall transformation goal. This third ap-
proach is called “co-creation.”

This notion of co-creation brings the best of both top-down and bottom-up approaches
with few of the negative aspects.

III. Co-Creation is the New Name of the Game

Rather than a rigid top-down or bottom-up approach, organizations looking for the most
effective and efficient digital transformation should strive for an organization-wide per-
spective that combines strategic transformational goals with the subject-matter expertise
that exists inside and outside of the organization.

Sonja Kresojevic, co-founder of the lean consulting organization Spinnaker, was formerly
SVP and Chief Product Officer at Pearson. In an interview1 before an Intrapreneurship Con-
ference, Kresojevic talked at length about this top-down or bottom-up conundrum.

In her opinion:

“I truly believe the only way to do this is co-design. I also think you need
to have a small leadership team – I wouldn’t even call it a leadership team,
more a transformation team – that’s driving it forward, that’s clearly commu-
nicating the message. That way transformation becomes a center of gravity

1 Lean Enterprise Transformation - Top Down or Bottom Up? (2017, November 28). Retrieved February 13, 2018, from
https://innov8rs.co/toronto/lean-enterprise-transformation-top-down-or-bottom-up

Digital Strength Course II | Who is responsible for Digital Transformation? | 6

 for the organization. They’re doing everything from coordinating the efforts,
communicating, mobilizing the troops, working with communities of best
practice inside and outside the organization.

I can’t emphasize enough how important the role of leaders is. Unless you
have a leader that is willing to sacrifice some of the short term goals and
gains for the long term future of the company, real transformation doesn’t
happen.

But in terms of the change that happens you have to co-create, you have to
co-design. There is so much expertise in the business already – you have to
bring those people on the journey, they need to feel like they’re part of the
process. So when you are designing your financial processes and approvals,
you need the finance team on the journey with you, you can’t do it for them.
You need to have people doing that with you who are a natural part of that
process.

It’s equally important to create those communities at different levels. Those

communities become change agents, they push change throughout the
organization. I also suggest you reach out or collaborate with external com-
munities of best practice, because you are not operating in isolation.”

There are many names for this co-creative approach: holistic design, design-led thinking,
360 degree design. No matter the name, it is increasingly seen as the best way to drive
digital outcomes for organizations of all sizes.

Before we dive into what the ideal co-creation team looks like, let’s consider where full
digital responsibility used to lie (and why it is evolving).

Digital Strength Course II | Who is responsible for Digital Transformation? | 7

IV. Is Digital Transformation an IT Though cloud computing is now
enjoying massive adoption there
Initiative or a Business Process? is still debate about what it actu-
ally is. The definition most people
use currently is that provided by
Traditionally, everything “digital” has been under the The National Institute of Science
purview of the IT department. This is hardly surprising and Technology (NIST). NIST’s
definition runs to several hundred
given that IT, in its infancy, was the domain of lab-coat-
words and while undeniably
ed technicians working in cavernous basements with comprehensive, no one could ever
highly specialized equipment. Tools of technology – like accuse it of being brief or easy
to read.
punch cards, mainframes, servers – required operational
knowledge of highly technical machines. And even as It’s for this reason that I prefer
to use a definition devised by
technology becomes more democratized, there still exists none other than Dave Nielsen,
a seemingly inexhaustible list of reasons why technolo- one of the founders of Cloud-
Camp. Dave has the following
gy decisions should rest with the IT department. Some
pithy definition2 that removes the
examples include cybersecurity, governance, risk, and mystery surrounding Cloud and
compliance. articulates it in ways that anyone
can understand.

Over the past decade, however, we have seen massive Under Dave’s definition, Cloud is
OSSM, meaning that Cloud Com-
changes in the way technologies – and by extension
puting is a computing resource
those responsible for it – work. The advent of cloud com- that is:
puting has resulted in an existential change for IT. Where-
• On-demand: the server is
as in the very recent past, acquiring technology resource already setup and ready to be
still required a technician (perhaps sans the lab coat deployed

these days) to supply a piece of physical hardware or • Self-service: the customer

install some technical software, acquiring IT assets today chooses what they want, when
they want it
is as easy as visiting a website and purchasing them on a
• Scalable: the customer can
credit card.
choose how much they want and
ramp up if necessary

This democratization of IT, both in terms of ease of use • Measurable: there is metering
and ability to acquire, has resulted in IT decisions splin- and reporting so you know you
are getting what you pay for.
tering away from central IT. Increasingly, it’s the line of
business that has the mandate to find and acquire solu-
tions that meet their particular requirements.
2 Pereira, D. (n.d.). Dave Nielsen explains
why cloud computing is OSSM (awe-
It is very much a case of the (digital) cat being out of the some). https://www.ibm.com/developer-
works/community/blogs/d8524a57-
bag; IT no longer has total control of technology deci- 3a71-4212-93e6-29a440e8f425/entry/
dave_nielsen_explains_why_cloud_com-
puting_is_ossm_awesome

Digital Strength Course II | Who is responsible for Digital Transformation? | 8

sions, and technology is, at least in part, the enabler for digital transformation. It should
therefore be obvious that leaving digital transformation to be an IT department deliverable
simply isn’t an option. Transformation is a process that needs to have input across the
organization.

V. Who Should Spearhead the Digital Transformation Process?

As we have seen already, effective digital transformation occurs when an organization has
a committed leader and a wide range of participants involved in the project. But if that is
the case, who is the right person to lead the project, what should their title be, and does it
matter?

Much angst has occurred when organizations have tried to determine whether the digital
transformation leader should come from the technology or the business side of the house.
Proponents of the former suggest that since digital transformation is fundamentally inter-
ested in applying digital technologies to an organization’s products, services, and process-
es, only a technologist will have the requisite skills to run the project successfully.

These people point out that without a deep understanding of the technology platforms
and systems upon which digital transformation will be built, the organization risks embark-
ing on ephemeral concepts that have no real chance of being executed.

Advocates of the opposing view, however, point out that IT-driven digital transforma-
tion too often ends up being siloed as a technology project, and may well miss the busi-
ness-wide opportunities that exist. This camp suggests that having a business leader
spearhead the process is the best way to broaden the impacts and best ensure success.

People point out that IT practitioners may not have the broader business level experience,
and that their communications may be couched in a technical vocabulary.

In much the same way that a zero-sum perspective on the top-down, bottom-up question
is unhelpful, so too is a black and white assessment on who should lead digital transforma-
tion. Clearly it is important for whomever is in charge to deeply understand the technology
platforms on which their transformation will occur. Similarly, it is critical that they have a
deep understanding of the business paradigm. So it could be the CEO, the COO, the CTO

Digital Strength Course II | Who is responsible for Digital Transformation? | 9

or a range of other titles but far more important are the attributes needed to make the
process work.

So with an understanding that the ideal leader will have both technology and business
skills, what are the key skills they should demonstrate?

VI. The Key Attributes to Look for in Leaders of Digital

Transformation

Despite digital transformation having been a topic of conversation for many years, there
is a lack of good solid best-practice guidelines for who should lead it and how to do it.
Indeed, this very Digital Strength program is all about creating a body of work that will arm
participants with the knowledge, skills, and processes for effecting good change.

It is therefore important to begin any digital transformation project with an understand-

ing of the right people to have involved in the process. This is especially the case when it
comes to leadership. While digital transformation is, as we have already explained, a pro-
cess of co-creation, the leadership position is still one of utmost importance.

In an interesting MIT Sloan Management Review and Deloitte University Press report,
“Aligning the Organization for Its Digital Focus”3 , 3,700 business executives were asked
what traits were consistent with the most mature companies.

Across the respondents there were some common themes as to what effective digital
transformation leaders excel at:

1. They cultivate a dynamic culture.

2. They integrate the organization’s digital strategy into the overall one.
3. They hire leaders who are change-agents.
4. They attract, engage, and retain talent with their digital focus.
5. They aspire to be something more.

3 Gerald C. Kane, Doug Palmer, Anh Nguyen Phillips, David Kiron, and Natasha Buckley. (n.d.). Aligning the Organization
for Its Digital Future. Retrieved February 13, 2018, from https://sloanreview.mit.edu/projects/aligning-for-digital-future/

Digital Strength Course II | Who is responsible for Digital Transformation? | 10

 6. They break down departmental barriers.
7. They invest in innovation.
8. They drive decisions with data.
9. They plan to disrupt rather than be disrupted.
10. They embrace and aspire to ‘digital congruence’ – the point at which
culture, people, structure, and tasks are aligned with each other,
company strategy, and the challenges of a constantly changing digital landscape.

The strong takeaway from this work, then, is that whomever is leading the digital transfor-
mation process cannot be a specialist in any one area without having a broad understand-
ing, the empathy to include differing views, and the strategic mind to think of the long
term implications.

With those attributes ticked off, it is worthwhile to take one last quick look at the myth of
digital transformation being all about technology.

VII. IT as the Enabler, But Not the Driver

At the risk of laboring the point, it is vitally important that people embarking on the Digital
Strength program are completely aware that digital transformation is not something that
IT completes in isolation and then “throws over the wall” to the business.

Digital transformation is a business process and, as such, it should be run by individuals

that understand the business drivers and strategies. While that may be an IT practitioner
or leader, it isn’t necessarily so.

The key requirement, which should be obvious but is often overlooked, is that whoever
runs this process should have a deep understanding of technology and its application in
various areas. It is something of an urban legend, the story of executives who have their
PA print out their emails for them, only to scrawl a response on the printout before the
aforementioned PA emails it back. But alas, while an exaggeration, it isn’t much of one.

Digital Strength Course II | Who is responsible for Digital Transformation? | 11

The business world is filled with executives who have had largely static careers, and ha-
ven’t explored the broader world out of their organization. Even more challenging, these
leaders can be conservative, and slow to embrace new ways of thinking, working, and
living.

Digital transformation leaders don’t need to be digital natives themselves, but an under-
standing of, and appreciation for, digital technologies certainly makes a successful project
more likely.

So how do we ensure that the very highest levels of the organization – the C-suite and
board – also embrace this process?

VIII. Ensuring C-Suite and Board Buy-In

Anyone who has worked within a traditional organization will be well aware that successful
change is predicated on having sufficient buy-in to ease the process. Digital transforma-
tion, which often has massive impact on a broad scale within the organization, is no excep-
tion.

And while the C-suite and board will likely not be spearheading the process, it is vitally
important that they are kept involved and realize the value and the criticality of digital
change.

It is therefore vitally important that the board and C-suite embark on their own process
– not so much to explore the future of their own organization (although that is also valu-
able), but to explore the meaning of digital transformation in the broader sense.

Leveraging programs such as this one, inviting external parties to run sessions about dig-
ital transformation, and even site visits to various other organizations who are exemplars
in digital transformation, are all good ways to up-skill the boardrooms and corner offices of
your organization.

Digital Strength Course II | Who is responsible for Digital Transformation? | 12

About HelloSign

HelloSign simplifies work for millions of individuals. Over 60,000 companies world-wide
trust the HelloSign platform – which includes eSignature, digital workflow and electronic
fax solutions with HelloSign, HelloWorks and HelloFax – to automate and manage their
most important business transactions. For more information visit http://www.hellosign.com

About Ben Kepes

Ben Kepes is a business leader, a technology evangelist, an entrepreneur, and a commenta-

tor. Ben covers the convergence of business and technology. His areas of interest extend
to leadership development, startup activity, digital transformation, and enterprise software,
as well as articulating technology simply for everyday users.

He is a globally recognized subject matter expert with an extensive following across multi-
ple channels. His commentary has been published on Information Week, Computer World,
Forbes, Wired, ReadWriteWeb, GigaOm, The Guardian and a wide variety of publications –
both print and online.

Ben’s insight into the business of technology, and the technology of business has helped
organizations large and small, buy-side and sell-side, to navigate a challenging path to a
successful future.

Ben is passionate about technology as an enabler and enjoys exploring that theme in vari-
ous settings.

Digital Strength Course II | Who is responsible for Digital Transformation? | 13

 Course II – Who is Responsible for Digital Transformation

hellosign.com/digitalstrength

Author: Ben Kepes

© 2018 HelloSign, Inc

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