THE

5 WAYS TO MAKE
LEARNING CORE TO
THE WAY WE WORK

SHELLEY OSBORNEVP, LEARNING AT UDEMY

and PATRICIA WITKIN

9781260466683_Osborne_PASS4a.indd 1 5/15/20 3:59 PM

 Copyright © 2020 by Udemy, Inc. All rights reserved. Printed in the United
States of America. Except as permitted under the United States Copyright
Act of 1976, no part of this publication may be reproduced or distributed
in any form or by any means, or stored in a database or retrieval system,
without the prior written permission of the publisher.

1 2 3 4 5 6 7 8 9  LCR  25 24 23 22 21 20

ISBN: 978-1-260-46668-3
MHID: 1-260-46668-X

e-ISBN: 978-1-260-46669-0
e-MHID: 1-260-46669-8

Library of Congress Cataloging-in-Publication Data

Names: Osborne, Shelley, author. | Witkin, Patricia, author.
Title: The upskilling imperative : five ways to make learning core to the
way we work / Shelley Osborne, VP of learning at Udemy and Patricia
Witkin.
Description: New York : McGraw-Hill Education, [2020] | Includes
bibliographical references and index.
Identifiers: LCCN 2020007040 (print) | LCCN 2020007041 (ebook) |
ISBN 9781260466683 (hardback) | ISBN 9781260466690 (ebook)
Subjects: LCSH: Occupational training. | Employees--Training of.
Classification: LCC HD5715 .O83 2020 (print) | LCC HD5715 (ebook) |
DDC 658.3/124--dc23
LC record available at [Link]
LC ebook record available at [Link]

McGraw-Hill Education books are available at special quantity discounts

to use as premiums and sales promotions or for use in corporate training
programs. To contact a representative, please visit the Contact Us pages at
[Link].

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 CONTENTS

Foreword v
Acknowledgments vii

PART I Introducing the Era of Continuous Learning

Why Are We Talking About Learning at Work?
1 3
What Have We Learned About Learning?
2 13
Building a Learning Culture Means Getting
3
Comfortable with Change 39

PART II Five Ways to Make Learning Core

to the Way We Work
Develop and Foster Agile Learners
4 59
Feedback Is Fuel for Learning Cultures
5 83
Think Like a Marketer to Drive Learning
6
and Development 99
Put Learning into the Flow of Work
7 117
Signal the Value of Learning
8 131

PART III Making Upskilling Imperative to Your Business

The Business Case for a Learning Culture
9 157
Care and Maintenance of Your
10
Learning Culture 179

Notes 195
Index 201

iii

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 FOREWORD

I
n our world, competition is fierce, and the nature of
the work we perform changes fast. To thrive, we need
to get back to the most fundamental of all human
skills: the ability to learn. Small problem: Many of us
have been habituated—through our organizations, those
around us, and society—to believe that learning officially
ends with formal education. We’re unaccustomed to the
scariness (and the thrill) that comes from starting at the
beginning again and again.
That’s where The Upskilling Imperative comes in. I love
Shelley Osborne’s message that learning must be con-
tinuous and prioritized. I’m in absolute agreement that
investing in upskilling is the path to better performance,
better organizations, and more meaning in our work.
I study an incredibly diverse set of organizations
around the world, from high-end boutiques and restau-
rants to bustling chains serving millions. Most recently,
I’ve focused my attention on “rebel talent”—rule breakers
who change the nature of their work, their organizations,
and their industry, sometimes with spectacular results
and sometimes less so. One key attribute shared by suc-
cessful rule breakers is the willingness to courageously
and continuously learn. You can’t just rebel; you need to
draw on skills to devise solutions and keep pushing until
you succeed. Through continuous learning, we channel

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 Foreword

our inner rebel to push past our discomfort and grow our
organizations and ourselves.
I first met Shelley at an event where we were both
speaking, and I was immediately struck by how Shelley
drew in the audience. In her book, she does the same.
As someone who studies and prizes authenticity, I love
Shelley’s voice. She’s encouraging, pragmatic, and clear.
And she’s the right messenger to get us all on board with
spending time every day pushing ourselves to grow.
Make no mistake: it’s not easy to make learning part
of our every day. Shelley’s book, however, will help each
of us do just that. It’s full of the very best kind of advice:
straightforward and supremely doable ideas that you
can put into practice right away—and that will make an
actual difference.
—Francesca Gino, Harvard Business School professor and
author of Rebel Talent and Sidetracked

vi

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 ACKNOWLEDGMENTS

M
y husband, Tom: My original editor and
thought partner. Relentlessly willing to give
me feedback and help me be my best. Also
happens to be my best friend. Thank you for
encouraging and believing in me.

My family: My mom and dad, my brother and sister-in-law.

Patricia: I am so incredibly honored and will be forever

grateful to have worked with you on this book. You gave
your everything to will this book into reality.

Shannon: You believed in me and this book from day one,

and you made this book possible. Thank you for always
having my back and making me better every single day.

Devon: For being a “clutch” performer, as usual and

always. I would literally be lost without you, and I trust
you with my life.

Every teacher I’ve ever had (particularly Mr. Kilarski for

my first lesson in growth mindset) and every student of
mine—child and adult (who were also my teachers).

My Learning Team: For joining me and creating this cul-

ture of learning together. It is a privilege to work with
each of you.

vii

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 Acknowledgments

All Udemates everywhere: The most earnestly authentic,

smartest people working at a place where I am challenged
to do my very best work.

Jenn Farris: For teaching me that my voice has power and

encouraging me to use it for its highest and best use.

Darren: For changing the trajectory of my career, from

the original opportunity to work at Udemy and every
opportunity since.

For everyone who contributed to this book: I am inspired

by all of you and learned so much from each of you.

McGraw-Hill.

Canada: Yep, the whole darn country.

viii

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 R T I

NG T HE PA

O DUCI U S
T R
IN CONTINU O
A O F
ER EARNING
L

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 Up until a few years ago, there was a simple pathway
from school to work. You graduated, found a job,
and never really needed to look back. For better or
worse, life is no longer that simple.
The “future of work” is already here, and front-
loading your education is not enough to launch
a career, let alone sustain it over decades. We’ve
entered the era of continuous learning, a new way of
working that requires all of us to rethink how we view
our jobs, our skills, and ourselves.
In Part I, we’ll talk about why now is the time
to bring learning into our workplaces, better
understand what it takes to learn something new,
and explore why getting comfortable with change is
a necessary ingredient for building a learning culture.

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 1

Why Are We Talking

About Learning at Work?

O
ur lives, inside and outside of work, have
changed. Automation and machine learning
are infiltrating more industries and chang-
ing (or eliminating) more job functions.
New technologies are evolving more quickly, challenging
workers to keep up if they want to stay employed.
At the same time, employers find themselves having
to devise new strategies for closing their own skills gaps,
developing (and retaining) adaptable workers, supporting
upskilling efforts, and preparing workers for whatever
comes next. But most aren’t there yet.

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 THE UPSKILLING IMPERATIVE

Meanwhile, employees find themselves in unfamil-

iar territory. They don’t know which skills they should
be learning, how to demonstrate their competencies
to supervisors and hiring managers, or how to ensure
they’re really retaining and applying newly gained
knowledge. These working professionals may be years
out of school and no longer consider themselves “in
learning mode.” Even recent grads have fears and doubts
about what it means to be lifelong learners in a work
setting.
Nevertheless, these individuals will have to embrace
learning, become more adaptable and proactive, and,
essentially, learn to learn. This is what we’re talking about
when we refer to the upskilling imperative.
The good news: we’re at our happiest and most pro-
ductive when we’re growing and developing!

Out with the Old

Estimates indicate that a career launched today could last

as long as 50 years.1 Meanwhile, skills stay relevant for
only about five years.2 Do the math and it’s clear: we all
need to be learning continuously or risk falling behind
and having our skills become dated.
Smart companies respond to this trend by doing more
to help employees navigate winding career paths and
gain the skills that will keep them moving forward. Not
simply a “nice” thing to do, supporting employee learn-
ing and development is a proven business driver.3

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 Why Are We Talking About Learning at Work?

Still, learning and development (L&D) programs them-

selves need to evolve with the times as well. Traditional
training approaches were built for a world we don’t live
in anymore and are even less engaging for twenty-first
century workers accustomed to consuming digital con-
tent on their own terms (see Table 1.1).
But even more than modernizing the L&D experience,
companies need to transform at every level into learning-
driven organizations, where working and learning are
inextricably linked.

TABLE 1.1  Old vs. New Training Modes

WHAT OLD TRAINING WHAT LEARNING MUST BE
WAS LIKE IN A LEARNING CULTURE

Static, quickly dated On demand, self-driven

Scheduled, mandated by Intrinsic part of work

Human Resources

One-way push Democratized across the

organization

Completion as proxy for Up-to-date, relevant content

learning and experiences

Programmatic, episodic Anticipatory

A True Learning Culture

Is Democratized

Learning can’t be reserved for only those employees of a

certain rank or tenure. Consider the message that sends:
only some people’s growth and development are worth

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 THE UPSKILLING IMPERATIVE

investing in. That’s a surefire way to kill enthusiasm and

impede results.
But everyone also has to stay accountable and has a
part to play in the culture’s overall success. Table 1.2 is
a snapshot of what that means at different levels. We’ll
explore this idea in greater depth later in the book.

TABLE 1.2   ccountability for Learning,

A
by Job Title
Individual Employees
■ Commit to developing a growth mindset; don’t be afraid to make
a mistake
■ Bring the culture of learning to your work

■ Share your experiences with others

■ Advocate for your own learning needs

■ Don’t fall for myths, e.g., you can only succeed with one

“learning style”

Managers and Teams

■ Embrace your role as career guide for your direct reports
■ Experiment with social learning, peer-to-peer learning, and
other formats
■ Work to develop a team with balanced skills, where individuals

complement each other

■ Give honest, constructive feedback—and receive it graciously

Organizations (Human Resources, Chief Learning Officer,

Chief Executive Officer)
■ Put employees in the driver’s seat
■ Hire for learning agility and growth mindset
■ Make it safe to learn and ask for help

■ Think like a marketer to get people excited about learning

■ Build the infrastructure to make it work

■ Signal the importance of learning

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 Why Are We Talking About Learning at Work?

A High-Level View of a
True Learning Culture

Learning is not something that can happen outside of

work anymore. Things are moving too fast, and employee
needs and wants vary too much, especially with five gen-
erations soon to be in the workforce at once.4 One recent
survey commissioned by my company, Udemy, found
that 51 percent of employees said they would quit a job
where they weren’t offered necessary training,5 while
millennials in particular cited learning and development
opportunities as the second-most important benefit, after
salary, they expect from an employer.6
Historically, training initiatives have come out of the
L&D or human resources (HR) departments. That needs
to change. While the L&D team should serve as facili-
tators, individuals, managers, and organizations share
responsibility for building, upholding, and participating
in the learning culture.
Here are the main components for a successful learn-
ing culture, which we will explore in greater detail later
in the book.

1. Develop and Foster Agile Learners

When leaders embrace change and are open and adapt-
able to what comes next, they position themselves and
their teams for the twenty-first century workplace. As
a foundation for creating a culture of learning, leaders
must help their employees develop into agile learners

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 THE UPSKILLING IMPERATIVE

who embrace change and growth. To create agile employ-

ees, organizations should empower individuals to access
learning resources in their moment of need, even as
those needs change and evolve, and then allow people to
engage with learning when, where, and how they prefer.
There are numerous elements of the learning agility
puzzle—coaching workshops, career development con-
versations, durability principles, and the like—that can
be done to support individual learning that is specific to a
team, role, or stage in the employee life cycle. For leaders,
it’s time to think differently about their responsibility to
build the organizational muscle for change and foster a
workforce of agile learners.

2. Feedback Is Fuel for Learning Cultures

In a work culture that celebrates personal growth, peo-
ple should feel safe to share honest, constructive feedback
with colleagues. And they need the time and space to
think about feedback they’ve received and what they can
do to improve.
This isn’t about telling someone what they’re “bad at”
and then telling them to fix it. Instead, the objective is
to maximize strengths and encourage people to become
their best selves. Indeed, people stop putting forth their
full effort if they believe others will accept nothing
less than perfection; it has to be okay to talk about our
mistakes.
To be clear, this is decidedly not the same as going
through performance reviews. For starters, learning,

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 Why Are We Talking About Learning at Work?

feedback, and reflection coexist and should be happen-

ing all the time, not according to a company-mandated
schedule.
Rather, organizations need to normalize feedback and
build reflective structures into how people work. They
need to provide training that helps people understand
how to give and receive feedback and make room for
people to reflect during their day.
In addition, individuals need to get comfortable asking
for and hearing candid feedback. As I like to say, feed-
back is fuel! Without open channels, you won’t know
where you have opportunities to grow.

3. Think Like a Marketer to Drive

Learning and Development
Years of poor training initiatives have caused employees
to consider workplace learning a necessary evil, rather
than a professional imperative. As we all know, when a
product or business has a bad reputation, the first step
is for marketing to swoop in and educate the market. It’s
time to channel that same mindset to rebrand learning
and create a tangible culture around it.
Thinking like a marketer is a chance to get creative
with learning, but it’s also a way to take a customer-centric
approach that resonates with employees’ needs. The best
way to retain learners is to understand their needs and
wants, get creative about how you engage them in learn-
ing experiences, and market to them before, during, and
after learning or training to keep them interested.

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 THE UPSKILLING IMPERATIVE

4. Put Learning into the Flow of Work

A learning culture doesn’t just happen by magic; it needs to
be created and nurtured in each employee. It starts with a
companywide recognition that we all can and should want
to continue growing; we are never “finished” with learning.
Needing to learn isn’t viewed as a weakness or deficiency in
such an environment. On the contrary, it’s accepted as a nat-
ural part of the career journey and a sign of self-awareness.
One of the most important tenets of the learning cul-
ture must be that access to professional development
opportunities is democratized throughout the organi-
zation. No one should need to have a certain job title or
tenure to take full advantage of available opportunities.
All employees should know they have the freedom and
opportunity to learn whenever they need or want. They
should also be empowered to decide what they should be
learning and how.
Understanding that not everyone is a naturally self-
driven learner, the organization needs to put mechanisms
in place to encourage learning and make it desirable.
Managers need additional training so they can help their
direct reports discover their learning interests and guide
them to the best resources.

5. Signal the Value of Learning

Although more and more companies now recognize the
upskilling imperative, they’re not exactly sure how to act
on that information. Traditional training programs have
left corporate leaders skeptical about investing more time

10

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 Why Are We Talking About Learning at Work?

and resources into initiatives with unclear outcomes.

They’re looking for new approaches that see significant
employee engagement and improved performance with-
out disrupting productivity.
At the same time, individual employees know they
need to gain and maintain new skills but aren’t always
sure where to start or how best to do it. Or, they may not
work for organizations that support their learning needs
or connect them to useful resources. This is a stressful
place for workers with many years of employment ahead.
This book lays out the business case for why a learning
culture is the answer to the many challenges posed by
rapid technological change facing every company, team,
and individual. From there, we will see how some real
people and companies are taking action and leveraging
learning as a strategic asset to:
■ Close the skills gap
■ Retain head count and attract new hires
■ Improve engagement and job satisfaction
■ Spur innovation and cross-team collaboration
■ Move more quickly and nimbly

•••
Harnessing the power of learning isn’t as simple as roll-
ing out more training modules or sending people off to a
bunch of workshops. It takes careful thought, planning,
and commitment. But, when done right, the culture of
learning you create will yield benefits at all levels and
position you and your team for future success.

11

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