10 Tips

for Managing Digital

Transformation in the Real World
With Gene Kim & Bret Piontek
 ABOUT THE
CONTRIBUTORS
ABOUT US
2
GENE KIM
Author, Researcher, and Founder
of IT Revolution
Gene Kim is a multiple award-winning
CTO, researcher and author, and
has been studying high-performing
technology organizations since 1999.
He is the founder of the DevOps
Enterprise Summit and he has written
six books, including his most recent
release, The Unicorn Project.
BRET PIONTEK
Enterprise Lean/Agile
Transformation Leader
Bret Piontek is a Certified Professional
Scrum Master, a SAFe 4.0 Program
Consultant (SPC4), and a PMI-certified
Project Management Professional.
He is currently an Agile Program
Manager at Levi Strauss & Co, where
he leads Scaled Agility and Lean
program initiatives.
 Digital transformation is a journey. And for Agile leaders, Scrum Masters,
project managers, and other change agents in the organization, the
road can be rocky. DevOps enthusiast, Gene Kim, and Bret Piontek,
Enterprise Lean/Agile Transformation Leader at Levi Strauss, offer
some real-world advice for those of you with boots on the ground,
driving change and transforming your organizations.

The following is excerpted from the Digital.ai webcast, Deliver More Customer
Value with Value Stream Management. View the webcast on-demand now.

“SILOS WILL OPTIMIZE AROUND

SILO GOALS, NOT MISSION GOALS.

3 1 GETTING THE ORGANIZATION TO

WORK TOGETHER AROUND THE
MISSION CAN LEAD TO AMAZING
OUTCOMES.”
– GENE KIM

ALIGN AROUND VALUE

Create a customer-centric, value-driven engineering environment
where everyone is aligned around common, strategic goals. This
approach is a great way to break down silos and get everyone
focused on what matters.
 “TEAMS LIKE SECURITY AND QA

2 WOULDN’T BE SAYING NO AS MUCH

IF THEY WEREN’T TREATED AS AN
AFTERTHOUGHT AND BROUGHT IN
AT THE LAST MINUTE.”
- BRET PIONTEK

GIVE PEOPLE A SEAT AT THE TABLE

Bring people into the digital transformation process early, give
them context and visibility, and in return they are more likely to be
receptive to change, more engaged, and more likely to bring great
ideas to the table.

4
“IT IS ALL ABOUT ENABLEMENT,

3
SO THAT EVERYONE ON THE TEAMS
CAN DO MEANINGFUL WORK, MAKE
DECISIONS, AND SOLVE PROBLEMS
CLOSEST TO WHERE THEY ARE
BEING FELT.”
- GENE KIM

PUSH DECISION-MAKING DOWN AND OUT TO

THE EDGES
Once everyone has a strategic view of the business, decision making
can spread throughout the organization. Empowering teams at
all levels of the organization leads to faster and better decisions,
which has an immediate and positive impact on the business.
 “IT STARTS WITH PEOPLE, HEARTS

4
AND MINDS, AND GETTING PEOPLE
INSPIRED TO LOOK AT THINGS
DIFFERENTLY.”
- BRET PIONTEK

TAKE A PERSON BY PERSON, TEAM BY TEAM,

PROGRAM BY PROGRAM APPROACH
In the real world, digital transformation is not something you create
and roll out in one grand gesture. To be successful, you need to
show people how to see things from a customer perspective, not
a release or defects perspective.

5
“I’M NOT MARRIED TO A

5
PARTICULAR METHODOLOGY… I LIKE
BEING ABLE TO APPLY WHAT I NEED
AT A GIVEN TIME.”
- BRET PIONTEK

ONE METHODOLOGY DOESN’T FIT ALL

Stop trying to select the “right” methodology to apply to your
entire digital transformation initiative. The reality is you’re going to
need more than one. And you need to be able to pivot to different
approaches depending on the situation, goal, team skill level,
existing environment, etc. Treat methodologies like tools and be
willing to apply the right one for the job at hand.
 “CULTURE IS HIGHLY CORRELATED

6 TO OUTCOMES. PSYCHOLOGICAL
SAFETY IS CRITICAL TO SUCCESS.”
- GENE KIM ON THE 4TH IDEAL IN THE
UNICORN PROJECT

CREATE AN ENVIRONMENT OF TRUST

Lack of trust between individuals, teams, and levels within the
organization is one of the biggest challenges to overcome in a
digital transformation. Building trust and creating an environment
where people at all levels feel safe speaking openly and honestly
is critical.

“I HELP START CONVERSATIONS

6
IN MANY POCKETS OF THE

7
ORGANIZATION. I AM ALWAYS
LOOKING FOR WAYS TO BRING US
TOGETHER.”
- BRET PIONTEK

BE A CATALYST FOR COMMUNICATION AND

COLLABORATION
During your digital transformation journey, you will run numerous
workshops, present in untold number of meetings, and meet people
in your organization you never knew existed. Use this time as an
opportunity to seek out teams and individuals hungry for learning
and change. Bring them together with other motivated teams
and individuals, and give them a means to form relationships – no
matter where they sit in the organization.
 8
“THERE ARE NO HEROES IN AGILE.
I’M NOT THE ONE ON THE GROUND
DOING THE WORK.”
- BRETT PIONTEK

STOP BEING A CONTROL FREAK

What worked in one situation, won’t necessarily work in the next.
Be willing to adapt and learn. Have conversations. Get input before
you start prescribing new processes, approaches, tools, etc. And
check yourself frequently to see if what you are putting out there
is resonating.

7 “I USED TO GET REALLY

FRUSTRATED IF THE SCRUMS DIDN’T
WORK THE WAY I WANTED THEM
TO. BUT I’VE LEARNED IF YOU MEET
PEOPLE WHERE THEY ARE, THE
9
REST TAKES CARE OF ITSELF.”
- BRET PIONTEK

LET GO OF PERFECTION
In any people-first endeavor, perfection is purely aspirational. As
people, we are imperfect by nature, and digital transformation
is no exception. Focus on understanding people’s needs and
aspirations, and then meet them where they are.
 “IT AND BUSINESS CAN BE

10
PARTNERS NOT ADVERSARIES. THEY
ARE TWO SIDES OF THE SAME COIN,
AND THEY CAN WORK TOGETHER.”
- BRETT PIONTEK

AGILE IS NOT JUST FOR IT AND DEVELOPMENT

One of the biggest roadblocks in the digital transformation journey
is the gap between IT and Business. Alignment of operational and
business value streams is a core concept for successful digital
transformation.

LESSONS FROM COVID-19

8
COVID-19 has turned our lives – personal and professional – upside
down. One thing it has taught us is even the largest, most entrenched
organizations are capable of change. And changing rapidly.

“COVID-19 HAS FORCED US TO LOOK AT THINGS DIFFERENTLY. NOW

WE KNOW OUR BUSINESS IS ABLE TO SHIFT AND MAINTAIN OUR
MOMENTUM WHILE PREPARING FOR WHAT COMES NEXT – SUCH AS
WHEN OUR RETAIL STORES REOPEN.” - BRETT PIONTEK

“COVID-19 HAS TAUGHT US THAT WE CAN BREAK ALL THE RULES

AND STILL DO THINGS IN A SAFE WAY. I THINK THESE ARE LESSONS
WE’RE GOING TO BE INTEGRATING INTO THE WAY WE WORK FOR
YEARS TO COME.” - GENE KIM
Ready to add an Agile practice to your digital transformation initiative or expand
your existing Agile practice? Check out the How to Get What You Want From Your
Enterprise Agile Transformation whitepaper.
 ABOUT US

ABOUT DIGITAL.AI
Digital.ai enables enterprises to focus on outcomes instead of outputs, create
greater business value faster, and deliver secure digital experiences their
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the disparate tools and processes across the various value streams, uses data
9
and AI/ML to create connective tissue between them, and provides the real-time,
contextual insights required to drive and sustain successful digital transformation.
With Digital.ai, enterprises have the visibility they’ve been seeking to deliver
value, drive growth, increase profitability, reduce security risk, and improve
customer experience.

Learn more at www.digital.ai

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