The Upskilling Imperative

How can you keep your skills—and your team—relevant in a world that changes faster than ever? In The Upskilling Imperative, Shelley Osborne, Vice President of Learning at Udemy, argues that the only sustainable advantage in today’s workplace is the capacity to learn continuously. The new career mantra is simple: if you stop learning, you stop leading. Osborne contends that the modern world of automation, AI, and shifting technology makes learning inseparable from work itself, and that companies who fail to build learning cultures will fall behind.

This book is both a manifesto and a playbook for embedding learning into the DNA of organizations. Osborne moves beyond the outdated image of training as a boring, one-time compliance event and presents learning as a dynamic, shared responsibility that drives engagement, creativity, and organizational agility. She explores why traditional development programs no longer work, what science now tells us about how adults learn best, and how leaders can foster psychological safety where people can fail, reflect, and grow. Most importantly, she presents five core practices for creating a true learning culture: fostering agile learners, making feedback fuel growth, thinking like marketers, integrating learning into the workflow, and signaling its value daily.

From Job Security to Learnability

Osborne opens by diagnosing a major shift in the world of work: the half-life of skills has shrunk to about five years, while careers can last over five decades. In this new era, neither employees nor organizations can afford complacency. Upskilling—continually adding new competencies to stay relevant—is no longer optional. Rather than fearing the speed of technological change, Osborne sees it as an invitation to reimagine learning as an ongoing, energizing process that fuels satisfaction and innovation.

She calls this the “upskilling imperative.” Companies that embed ongoing learning into every level of their operations not only retain talent but also become more resilient. Employees, meanwhile, must see learning as a lifelong journey rather than a phase that ended with school. For them, professional joy and psychological safety come from staying in motion—constantly evolving their skills and perspectives.

Why Traditional Training Fails

Osborne draws on both her experience as a classroom teacher and corporate learning leader to expose why conventional training feels lifeless. It’s often mandatory, generic, and disconnected from real work. “Training,” she notes, has long been treated as punishment or reward, not a vital aspect of performance. In contrast, modern workers—especially Millennials and Gen Z—expect on-demand, personalized, engaging learning experiences that mirror the digital ecosystems they already use daily.

Learning science supports this shift. Osborne introduces research on the forgetting curve (Hermann Ebbinghaus), “spaced repetition,” and cognitive load theory. These show that true learning happens when we apply information in meaningful contexts, revisit it over time, and feel safe enough to experiment. Neuroscience and behavioral psychology confirm that fear and boredom kill learning, while trust, curiosity, and emotion ignite it. (This echoes insights from Carol Dweck’s Mindset and Brené Brown’s work on vulnerability.)

What a Learning Culture Looks Like

For Osborne, a learning culture goes beyond training programs—it’s a living ecosystem. Everyone, from executives to interns, “owns” learning. L&D professionals become facilitators, not gatekeepers. Learning becomes democratized; access to growth isn’t limited to top performers. Managers evolve into coaches, feedback conversations become everyday events, and growth mindset becomes the norm. Learning happens inside the flow of work rather than outside of it.

Osborne draws on examples from organizations like Udemy, Accenture, and PCL Construction. At Udemy, she institutionalized programs like DEAL Hour—Drop Everything And Learn—where everyone pauses work to learn together. Accenture’s “Durable Learning” model illustrates how learning science principles—like relevance, effort, spacing, and social learning—build long-term retention. At PCL Construction, continuous development is woven into career paths, with leadership programs for all employees, not just executives. These stories show that when learning becomes routine and visible, engagement and innovation skyrocket.

The Five Ways to Build a Learning Core

The book’s heart is structured around five powerful practices that any organization can adopt:

• Develop and Foster Agile Learners: Encourage lifelong adaptability and curiosity. Make learning accessible, self-directed, and visible at all levels.
• Feedback Is Fuel: Create a feedback-safe culture where growth replaces fear, honest conversation sparks improvement, and reflection builds momentum.
• Think Like a Marketer: Promote learning with creativity and storytelling—make it attractive, meaningful, and contagious.
• Put Learning into the Flow of Work: Remove barriers; make learning frictionless and intertwined with everyday tasks.
• Signal the Value of Learning: Let leadership model learning behavior and celebrate it publicly.

Later chapters expand on how to make the business case for learning—connecting upskilling to measurable results like retention, agility, and innovation—and how to maintain momentum over time. Osborne argues that learning cultures are organic and must be continuously refreshed. Like organisms, they survive through curiosity and adaptation.

Why This Matters Now

Osborne’s message arrives in the age of remote work, automation, and rapid disruption. When uncertainty is the norm, learning is no longer the supportive “side dish” to work—it’s the main course. The organizations that will thrive are those whose people feel both confident and curious about change, not rattled by it. The same applies to individuals building careers that must span multiple decades and industries; learnability is now the ultimate form of job security.

In short, The Upskilling Imperative is both an invitation and a challenge. It asks: are you willing to make learning a natural part of who you are and how your organization operates? If the answer is yes, then what follows is a clear roadmap for doing just that—one that blends science, heart, and strategy into a vision for work that’s both human and future-ready.

Osborne opens by confronting the reader with a simple truth: the pace of change is outpacing traditional education. A degree can be obsolete before the ink dries. Skills expire. Automation and AI make entire job functions irrelevant overnight. Yet, as she says, “learning is happiness”—our deepest satisfaction comes from growth. The challenge lies in reinventing how we approach learning at work so it’s continuous, accessible, and democratized.

The End of the One-and-Done Model

Old-school corporate training relied on compliance checklists and rigid schedules. Employees sat through marathon PowerPoints, bored and detached. L&D teams acted as content gatekeepers, delivering prepackaged knowledge rather than facilitating curiosity. The result? Employees saw training as either punishment or reward, not an investment in their potential. Osborne likens these sessions to “the overhead projector era”—a relic from her early days as a schoolteacher.

Modern learners crave autonomy. They want choice, relevance, and application. They expect learning to fit into their workflow, not disrupt it. As Osborne emphasizes, “Learning can’t live outside of work anymore.”

Democratizing Opportunity

One of Osborne’s most radical propositions is that learning must be democratized across an organization. It can’t be reserved only for high performers or senior leaders. Every employee—regardless of role or tenure—has a right and responsibility to grow. Limiting learning to a select few sends the toxic message that not everyone’s development matters. By contrast, an inclusive learning ecosystem signals trust and equality: everyone’s growth fuels the organization’s success.

Shared Accountability

A learning culture only thrives when accountability is shared. Employees own their learning journeys, managers coach and amplify growth, L&D curates tools and strategy, and executives set the tone. Table 1.2 in the book lays this out clearly—each level has distinct roles but mutual responsibility. This echoes cutting-edge HR philosophies like David Ulrich’s model of HR as a strategic partner driving capability building, not compliance management.

Learning into the Flow

Osborne insists that learning must become “in-the-flow-of-work.” It can’t be a separate phase or an afterthought but something people access anytime they need it—during a project, while troubleshooting a problem, or preparing for a role change. Modern platforms like Udemy for Business enable this kind of microlearning, offering personalized recommendations powered by machine learning. The key is relevance: learning on demand, in context, builds retention and motivation.

Learning, Osborne concludes, is no longer HR’s side project. It’s the core business strategy. It drives retention, innovation, and competitive edge. When learning becomes daily work rather than disruption, both individuals and organizations win. That’s the essence of the upskilling imperative.

Osborne transitions from why we need new learning cultures to how humans actually learn most effectively. Drawing lessons from teaching teenagers and professionals alike, she demystifies the cognitive science behind learning and applies it to the modern workplace. Her central point: learning isn’t about information dumping; it’s about connection, repetition, and emotion.

Why “Necessity is the Mother of Learning”

We learn when we need to. Osborne revisits Hermann Ebbinghaus’s “forgetting curve,” showing that people forget most content almost immediately unless they practice it in real-world contexts. Learning sticks when it’s tied to necessity—when you must apply it right away to solve a problem or take on a new challenge. This principle is echoed by modern learning experts like Will Thalheimer, who popularized spaced practice as critical to long-term retention.

Pedagogy Over Novelty

Osborne warns that chasing shiny tech like VR or AI will fail if instructional design is poor. Good pedagogy—clear goals, context, and interactive engagement—matter far more than delivery tools. She cites researcher Richard Clark’s famous line that “media are mere vehicles that deliver instruction but do not influence learning any more than the truck that delivers our groceries causes changes in our nutrition.” In other words, technology amplifies good learning design; it doesn’t replace it.

Emotions, Fear, and Engagement

One of Osborne’s strongest lessons comes from her classroom days: fear kills learning. When students—and employees—feel judged or unsafe, they shut down. Drawing on linguist Stephen Krashen’s “affective filter” hypothesis, she explains that high anxiety blocks input at a neurological level. A culture of psychological safety, where mistakes are normalized and curiosity is rewarded, is essential to effective learning. Carol Dweck’s growth mindset and Brené Brown’s research on vulnerability both reinforce this human truth.

Instead of rewarding perfection, Osborne says, leaders should reward learning attempts. Fear kills experimentation; trust brings discovery. This principle underpins the entire feedback culture she later advocates.

Gamification and Motivation

To make learning engaging, Osborne embraces gamification—not as gimmickry, but as behavioral science. She references BJ Fogg’s B=MAP model (Behavior = Motivation × Ability × Prompt) and Yu-kai Chou’s Octalysis Framework, which explores eight core drives of human motivation such as meaning, accomplishment, and social influence. For example, Udemy’s internal onboarding game, Udemy GO, uses augmented reality and “choose your own adventure” design to encourage exploration and collaboration. Employees earn points and prizes like “I’m Kind of a Big DEAL” hoodies for achieving learning goals. It’s fun, but more importantly, it taps deep motivational drives like mastery and belonging.

Learning by Doing

Finally, Osborne invokes Malcolm Knowles’s theory of andragogy—adult learning. Adults learn best when they understand why they’re learning something, can apply it immediately, and learn by doing. This is why experiential, collaborative, and problem-based learning works so well at work. “You don’t learn to swim in a library,” she quips. Whether teaching teenagers Spanish through trips to Spain or training managers through simulations, she shows that immersion trumps memorization every time.

One of Osborne’s most urgent ideas is that the modern career depends on what she calls change agility. Companies can’t hire their way out of the skills gap; they must empower employees to adapt internally. Change agility means seeing change not as a threat but as a chance to learn. This mindset protects employability even as roles evolve or vanish.

The Five Building Blocks of Agility

Osborne, inspired by McKinsey’s research and neuroscience, identifies five building blocks individuals and teams must develop:

• 1. Be Ready for Anything: Expect uncertainty. The brain craves predictability; by acknowledging change as normal, you reduce threat response and keep clarity.
• 2. Think Outside the Box: Combat your brain’s energy-saving bias. Seek discomfort intentionally—it’s how creativity and resilience grow.
• 3. Reduce Subjectivity: Learn to reframe setbacks objectively using cognitive reappraisal. Naming emotions helps control them.
• 4. Tolerate Ambiguity: Train decision-making frameworks so you can move forward even with incomplete data.
• 5. Communicate in Change: Overcommunicate context. People prefer clarity about bad news to silence about uncertainty.

These habits build “organizational muscle” for adaptation—a phrase Osborne borrows from her engineering-minded husband, who taught her to use agile methodologies for continuous iteration. It’s not about perfect systems; it’s about flexible ones.

The People Side of Agility

Change agility isn’t merely procedural; it’s relational. Osborne uses her early experience at PCL Construction to show what learning-embedded organizations look like. At PCL, L&D is integrated with HR so deeply that every manager sees themselves as a teacher. Senior leaders—most of whom “grew up” in the company—model lifelong learning. This shared responsibility aligns with Carol Dweck’s growth mindset at an institutional level: everyone believes talent can be developed through effort and coaching.

For individuals, change agility is emotional work. It requires embracing vulnerability and curiosity, and letting go of control. Osborne puts it simply: “You can’t expect others to change if you can’t change yourself.” By staying close to others’ needs, communicating transparently, and iterating quickly, agile learners become agile leaders. Over time, agility replaces fear as the organizational default.

If one theme defines Osborne’s method, it’s feedback. She calls it “fuel”—the energy that powers continuous improvement. Yet, in most organizations, feedback still triggers anxiety or defensiveness. She aims to flip that script completely by rooting it in psychological safety and growth mindset. Feedback, in her model, is not something done to you—it’s something you use to grow.

From Fear to Fuel

Drawing inspiration from Carol Dweck’s research, Osborne contrasts fixed and growth mindsets. In fixed cultures, employees fear feedback because it’s seen as judgment of ability; in growth cultures, they view it as insight for learning. Stanford’s data shows that workers in growth-mindset environments report higher trust, stronger ownership, and more willingness to take risks—key ingredients for innovation. Her message: if you want curiosity, you must normalize imperfection.

Building a Feedback-First Culture

At Udemy, feedback is embedded everywhere—post-training surveys, hackathons, all-hands Q&As, anonymous suggestion tools, and day-to-day coaching. Employees even read “Mean Feedback” scripts—a humorous internal video series modeled after Jimmy Kimmel Live’s “Mean Tweets”—to show that feedback can be both fun and valuable. These initiatives make feedback less taboo and more conversational.

She encourages using the phrase “I’d like to share additional thoughts” instead of “I have feedback for you.” This small linguistic shift disarms defensiveness. Equally vital is frequency: feedback must happen continuously, not as an annual ritual.

Practical Feedback Skills

Osborne offers step-by-step guidance. For receiving feedback, she says: assume good intent, listen before reacting, and ask clarifying questions. Treat it as data, not doctrine. For giving feedback, be specific, timely, and goal-oriented. Have face-to-face conversations when possible; avoid hiding behind Slack or email, where tone gets lost. Timing matters: don’t dump criticisms before weekends or vacations. Above all, tie feedback to growth opportunities, not personal flaws.

In this vision, feedback becomes an organizational rhythm: everyone shares, listens, adapts, and improves. When feedback moves from fear to fuel, learning becomes unstoppable—and cultures become self-renewing.

“If learning has a bad brand,” Osborne writes, “then it’s time for a rebrand.” The analogy fits: after years of uninspired training, employees treat development like a chore. To reverse this, L&D must steal tactics from marketing. It’s not enough to create great programs—you have to sell them. That means captivating your learners before, during, and after the learning experience.

The Five-Step Creativity Framework

Osborne’s “Five-Step Framework” helps learning teams spark innovation:

• Consume: Constantly observe the world for inspiration. Her own example—turning the Pokémon Go craze into an AR onboarding game at Udemy—came from playful curiosity.
• Flip the Script: Identify what’s broken in your current approach and imagine the opposite.
• Incubate: Step away and let your subconscious connect ideas. It often sparks creativity—like when shower thoughts lead to breakthroughs (Britt Andreatta’s “Wired to Grow” explains this neuroscience).
• Connect the Dots: Align creativity with instructional purpose—pedagogy over novelty.
• Follow: Implement and iterate, gathering learner feedback to refine.

Marketing Tactics in L&D

Osborne applies classic marketing tools—segmentation, storytelling, scarcity, and social proof—to learning programs. For example, her team launched DEAL Hour using posters styled like vintage travel ads declaring “Where will your learning take you?” They left chocolate bars on desks with wrappers reading “Eat your own chocolate”—a playful twist on the tech saying “eat your own dog food.” They also created anticipation with teaser campaigns and celebrity “endorsements” from internal influencers.

The message is clear: learning should feel exciting, not obligatory. By combining marketing psychology with authentic storytelling, L&D professionals become evangelists. They make learning contagious—and transform education from compliance to community.

The best training won’t matter if it’s disconnected from daily routines. Osborne insists that real learning cultures bake learning into “the flow of work.” When learning becomes as habitual as checking email, it ceases to feel like extra work—it becomes how work gets done.

Norms for Continuous Learning

Employees must own their learning, managers must act as coaches, and L&D must enable access through multiple modalities—online, peer-to-peer, experiential. Microlearning platforms like Udemy for Business allow self-paced, moment-of-need learning. Managers can then discuss lessons during one-on-ones, turning learning into natural conversation rather than assignment.

Programs that Bring Theory to Life

Udemy built workshops like Career Navigator for career conversations, Change Agent for navigating uncertainty, and Bomb Squad, a playful VR-based activity for understanding work style diversity. Each combines gamification, group dialogue, and reflection to translate learning into behavior. The Udemy Coach program trains managers to use coaching questions and the GROW model (Goals, Reality, Options, Will) in every performance review.

The Space to Learn

Osborne reminds readers that learning needs physical and mental space. People can’t learn when stressed or distracted. She compares quiet learning zones to train “quiet cars”—spaces where noise and interruptions are off-limits. Even essentials like snacks and ergonomic setups affect focus and recall. These small environmental choices send a big message: learning time is sacred.

By the time you finish this chapter, it’s impossible not to see that every email, meeting, and feedback chat can be an act of learning. When companies give employees permission to pause and reflect—whether through DEAL Hour or supportive coaching—they unlock growth at scale.

All the strategy in the world falls flat if learning isn’t visibly valued. Osborne devotes a powerful section to how leaders, managers, and peers can signal that learning matters. Culture reflects what leaders celebrate—and silence communicates as much as speech.

Leaders Who Learn Out Loud

Senior leaders must model learning behavior. At PCL Construction, executives publicly share their experiences in leadership academies and celebrate learning through companywide awards like the Valedictorian and Excellence in Construction prizes. At Udemy, executives like Darren Shimkus embody “learn out loud” leadership by sharing what they’re currently studying, where they’ve failed, and what they’re improving. This vulnerability is contagious; it gives teams permission to do the same.

Turning Failure into Growth

Osborne argues that learning cultures must normalize failure. Most employees play it safe because failure feels fatal. Drawing on research from DDI, she notes that only 7% of managers report their companies embrace failure as a learning opportunity. The remedy: reframe “failure” as data. Hold learning debriefs instead of postmortems. Replace “What went wrong?” with “What did we learn?” This small shift drives psychological safety and innovation.

Recognition That Matters

Celebrating learning reinforces its value. Osborne describes Udemy’s annual Demmy Awards—a lively event honoring top learners—and the Sizzle & Spice Award at Udemy for Business, which started as a hot sauce trophy passed among high performers. These playful traditions make growth social and joyful. The company also invests tangibly, offering each employee a $1,500 ULearn stipend for external development. Rewards, she writes, must be meaningful or risk signaling that learning is low priority.

Ultimately, Osborne defines success as cultural osmosis: when learning is “like the air itself—it’s just there.” Once that happens, organizations no longer need to enforce learning; it becomes who they are.

In her final chapter, Osborne emphasizes that learning cultures are living systems, not projects. They require care, energy, and evolution. “You can’t set it and forget it,” she warns. Stagnation is the enemy. Keeping a culture of curiosity alive means continuously renewing content, updating tools, and nurturing relationships.

Avoiding Stagnancy

New employees bring fresh perspectives; established ones need new sparks. L&D must update programs regularly and retire outdated material. Hard and soft skills evolve alike—yesterday’s programming language or leadership style can become obsolete quickly. Staying current demands curiosity from everyone, not just the L&D team.

Distributed Learning Without Chaos

Osborne celebrates employee-led learning initiatives but warns against duplication. When teams build ad-hoc trainings, they may waste effort or create inconsistency. The solution is visibility and partnership, not policing. L&D must be approachable and collaborative, supporting grassroots learning while ensuring alignment. Her Udemy example of working with the “Culture Crew” to co-develop a mentorship pilot shows how partnership, not rigidity, keeps cultures healthy.

Agile Improvement

Borrowing from her husband’s world of software engineering, Osborne brings agile methodology into L&D. “The perfect is the enemy of the good,” she reminds readers. Nothing is ever final; everything iterates. Teams should collect feedback surveys (more than “smile sheets”), release versions, and treat programs as living prototypes. Quality is defined not by internal standards but by learner satisfaction and outcomes.

Hiring for Growth Mindset

To sustain the culture, hire learners, not knowers. PCL Construction, for example, screens candidates using behavioral questions like “Tell me about a time you received unexpected feedback—what did you do with it?” These reveal curiosity and resilience more than credentials. Osborne urges teams to evaluate candidates through a learning lens, emphasizing adaptability, diversity, and empathy.

Her final message loops back to inclusion: learning cultures must also be diverse learning cultures. Training content must represent all voices, accommodate all learners, and make education as accessible as an elevator. Learning, she concludes, is the surest way to navigate the unpredictable future—because, at its core, every company is a human company, and humans learn.