In the business world, we have historically treated learning as a one-time event. But in the real world, it’s an ongoing process of exploration, growth, and discovery—one that unfolds over the course of a lifetime. Or in the context of this article, a career.
There’s no fixed destination or endpoint; it’s a continuous cycle of acquiring new skills, applying them in real-world situations, reflecting on the outcomes, and then building on those learnings in the next iteration.
So why do some organizations still treat learning and development (L&D) opportunities as formal, episodic, and isolated events? A class to attend, a workshop to complete, a box to check, so to speak. It’s time for L&D to move beyond the classroom and reflect how we learn in our daily lives: continuously and iteratively.
Align L&D with modern habits
Traditional is not inherently wrong. But traditional, curricula-heavy teaching methods are simply not reflective of how people learn today.
We are always learning—be it through quick internet searches, AI prompts, podcasts, TikTok scrolling, and any other quickly-accessible digital content. Then we apply and adapt this new knowledge through trial and error. Think: Watching a YouTube video and adjusting your golf swing, then tweaking that new approach to better suit your personal mechanics. Or experimenting with a bread recipe you found on Pinterest, gradually modifying time and temperature until those '20 minutes at 350F' work with your oven's unique build.
It’s iterative, self-directed, and inspired by the evolution of our natural behaviors.
For better or for worse, technology has rewired the way people address gaps in knowledge or skills and process new information. Organizations must find ways to cut through the tidal wave of constant content so they can reach their learners. Hint: It should be woven into the flow of work wherever possible.
"Early in my career, folks would have considered it rude to sit in a room with your laptop up, taking notes. Now, that's the way we learn and capture information in real-time. While you're talking, it's not rude for them to pull up and look at a learning module or look up a concept they didn't understand. It's real-time exploration and education. And with AI, it's not just real-time, but it's also about anticipating the next question and augmenting the traditional internet-search mindset.”
– Jeni Fitzpatrick, North Highland Chief People Officer (CPO)
L&D in a business setting shouldn’t fight against the way learning habits are trending, it should adapt to this natural shift toward “always-on learning”.
Consider the benefits of this approach in today’s business landscape:
Role-based change: Artificial intelligence (AI) is projected to create nearly 97 million new roles by 2025, not to mention the countless job descriptions being redefined in its wake. This implies that many existing role-based learning paths will become outdated if not altogether obsolete. An always-on approach helps organizations design learning in a way that is flexible and responsive, allowing them to quickly address shifting skill needs and support employees as their roles evolve.
Human-in-the-loop: Speaking of AI reshaping roles: The "human-in-the-loop" is becoming more influential 
than ever. This concept refers to the crucial role people play in training, overseeing, and enhancing AI systems. But here's the catch: The skills needed to effectively serve as the human-in-the-loop are constantly evolving as the technology advances. By providing employees with continuous, easily accessible learning opportunities, organizations can ensure their people are always equipped to work effectively alongside AI. We share details of our own always-on learning approach to AI in our blog, AI Odyssey: Learning Through Play.
“Organizations can't afford to spend ages perfecting learning programs or courses. The speed of technological changes, the advent of new skills, and sunsetting of old ones is too fast now.”
– Kylie Ray, Principal; Strategy Practice
Generational signals: Gen Z is set to make up 27 percent of the workforce by 2025—with a concerning workplace engagement rate of only 54 percent. But this issue runs deeper than you may expect; Gen Y (Millennials) and Gen X—nearly 70 percent of today’s workforce—report similar disengagement rates, only one and two points behind Gen Z, respectively. While the youngest workers may have earned a reputation as being the most vocal about it, the desire for change is cross-generational. But consider that the workforce actually spans four generations. Meaning that—on top of the clearly shared desire for new—each organization is filled with diverse learning preferences, styles, and paces. Iterative L&D does more than accommodate modern learners: It creates space for personalized experiences that can flex to individual needs.
But what does it mean to adopt an always-on, iterative learning approach? Let’s take a closer look.
Embrace iteration and experimentation
Rather than striving for perfection right out of the gate, organizations need to adopt a "try and apply" mindset that values progress over polish.
“Think about how we consume content in our personal lives—it’s often raw, unpolished, and deeply engaging. There’s a lesson there for L&D.”
– Jeni Fitzpatrick, CPO
Always-on learning requires adopting a fundamentally different approach from traditional L&D models—one that embraces experimentation, iteration, and even a degree of controlled failure. Get comfortable with putting out "minimum viable" learning products, testing them with real users, and rapidly iterating based on feedback. Run small pilots before investing in large-scale programs. And be willing to fail fast and learn from those failures. Essentially, L&D teams should embrace the same experimental mindset they aim to cultivate in employees.
On the other side of this approach lies more evidence-based L&D tactics and programs. Iteration and experimentation increase opportunities for testing new learning methods and the higher volume of touchpoints will generate a deeper well of organic insights on things like employee interests, knowledge gaps, and learning preferences. This feedback also paves the way for more strategic and effective upskilling—more on that later.
The Bottom Line: Doubling down on highly structured and formal learning approaches can waste resources on programs that may be obsolete before deployment. An iterative and experimental approach on the other hand…
- Accelerates time-to-competency by quickly identifying what works, allowing you to swiftly capitalize on new opportunities or meet evolving customer needs.
- Generates necessary feedback that allows you to refine and improve learning approaches while uncovering gaps.
- Boosts engagement and knowledge retention by modeling a continuous learning mindset and aligning learning initiatives with how people naturally absorb information.
- Reduces investment in programs that don’t resonate by testing and validating before full-scale implementation.
- Normalizes experimentation and fosters a culture of innovation.
Democratize learning
Cultivating always-on learning also means redefining the relationship between employees and their own development. It’s about transferring agency to the individual and empowering them to take the driver’s seat.
Initiating this requires shifting from a "push" to a "pull" model. Instead of relying solely on prescribed learning paths and compliance-driven training, leaders should focus on enabling self-directed learning. In other words: Democratizing L&D.
Next, let’s go through three key tenets of democratized learning, using one of our own initiatives—Seasons of Skills—to offer real-world examples.
Transparency: Provide clear visibility into the skills valued by the organization, both currently and in the future. This allows employees to make informed decisions about their own development and align their learning with business needs. This tenet regularly conveys how skill relevancy is evolving to guide employees' learning choices. 
At North Highland, this means translating the work in our pipeline into in-demand skills that would help consultants capitalize on opportunities and get staffed onto upcoming projects. This incentivizes firm members to proactively adopt skills that will position them well for future work.
Accountability: Foster a shared sense of ownership for learning by encouraging employees to proactively communicate their skill development interests and goals. Regularly discuss how these aspirations align with organizational needs and co-create personalized learning plans. Provide support and resources, but ultimately empower individuals to drive their own career growth. Consultants participating in our Season of Skills are empowered to co-create learning paths with internal subject matter experts (SMEs). Rather than simply being handed training plans or modules, they become responsible for owning their development. And the SME partnership simultaneously ensures learning remains aligned with market trends, business needs, and client demand.
Mobility: Enable employees to apply newly acquired skills through fluid internal mobility. It’s critical to connect learning experiences to actual work opportunities, such as projects or gigs, to facilitate practical application and mastery. Remember: Real-time feedback is both a characteristic and benefit to always-on learning. Encourage managers to support skill development through timely, contextual coaching and feedback in the flow of work. The inaugural Season of Skills initiative targeted employees not currently staffed on client projects. The intent was that focusing on skills tied to our pipeline would create a well of knowledge that could be deployed as pipeline projects kicked off. As we iterate on this initiative and it grows in sophistication, we can take it a step further and staff projects according to skills gained through the program.
"There should be transparency about the skills we need as an organization, the skills that are becoming more or less important, and where they sit in our roles. Providing this information empowers people to make informed decisions about their own development. It's about ensuring learning channels are available but putting the onus on individuals to decide what skills they want to build and how they want to apply them in their role, based on the direction the organization is headed."
– Kylie Ray, Principal; Strategy Practice
The goal here is to create a learning ecosystem where employees feel empowered to take charge of their growth, and where development is seamlessly integrated into the daily flow of work and company culture.
The Bottom Line: Shifting from passive training to active learning isn’t just an engagement driver—it’s a business imperative. Here’s why:
- It fosters individual accountability for continuous skill development, which can also help broaden the organization’s scope of capabilities.
- Retention rates will improve as employees have clear visibility into growth opportunities and career paths.
- Stronger internal mobility will allow you to remain competitive even when talent resources are limited.
Leverage people data & analytics
The right learning platforms and tools can help organizations to:
- Curate and disseminate bite-sized content
- Facilitate social and collaborative learning, and
- Personalize development based on individual needs and preferences
But the real power lies in leveraging the data and analytics (D&A) from these platforms to understand the skills landscape at a granular level. At North Highland, we are currently leveraging two key platforms: One to identify and track skills needs according to existing and evolving client needs, and another to maintain awareness of existing skills throughout the organization. The key is connecting the data to create a clear view of supply and demand—enabling us to proactively address gaps between current capabilities and future needs.
"The data aspect is key. You're going to go down a path of understanding what skills you have, because you have to define what you want those to be. A lot of companies won't even know. You ask them, 'What skills do you have? What skills do you want to know and how do you want to know it?'"
– Amy O’Rafferty, Director; Office of the CPO
Analyzing workforce performance and learning data helps to build a comprehensive picture of the skills the organization has, the skills it needs, and how to best close the gap between the two.
The Bottom Line: Without clear visibility into your talent landscape, development investments become a shot in the dark. A data-driven approach prevents this from happening. You’ll see:
- More accurate workforce planning, backed by real-time insights into organizational capabilities.
- Reduced project delays by proactively identifying and addressing critical skill gaps rather than being forced to play catch up.
- Greater returns on learning investments by targeting development resources where they’ll have the strongest impact.
- Enhanced ability to track and measure the direct ROI of learning initiatives.
- Creation of an accurate baseline of current capabilities, enabling more strategic and purposeful learning roadmaps.
Design a purpose-driven roadmap
And underlying all these shifts is the need to align L&D strategies with strategic priorities and convert those objectives into a clear plan.
“If the ‘how’ and the ‘why’ behind designing and deploying these iterative learning components isn’t there, then the ideas of this approach are moot points.”
– Amy O’Rafferty, Director; Office of the CPO
Amid emerging technologies and market uncertainty, the ability to quickly and accurately upskill teams through always-on learning can be a competitive differentiator. But this only works if L&D is iterating in step with the strategic priorities of the organization, because real transformation is unlikely if it’s not rooted in purpose.
At a high level, L&D leaders should be executing three key actions:
#1 Gain clarity on strategic objectives and translate them into skill needs.
L&D should stay in lock-step with organizational goals and use them to identify skills that will move the business forward. This requires working closely with executive leaders to gain a clear picture of where the organization is headed—and it should be an ongoing process as priorities can change quickly, requiring new capabilities to maintain a competitive edge.
#2 Assess the current capability landscape and pinpoint urgent gaps.
With target skills defined, take an unflinching look at the organization’s current state. Thorough evaluations and skill inventories are essential for identifying areas of development that need the most attention. And as you repeat this step, don’t forget to utilize the iterative feedback and data & analytics mentioned earlier.
#3 Apply design thinking to create a roadmap with flexible learning paths.
Once the current state and desired skills are clear, L&D can create targeted but flexible learning content that can adapt as needs evolve. Remember, this is not about producing the perfect curriculum. The emphasis should be on rapidly deploying impactful learning experiences that develop must-have capabilities.
#4. Design for engagement.
Strategic alignment alone can’t guarantee higher motivation to learn. Behavioral science shows that engagement stems from tapping into natural human drives—which is the primary objective of always-on learning, anyways. Ways of achieving this include:
- Making skill development transparent and attainable by communicating the value of needed skills and their connection to growth opportunities.
- Reducing friction by embedding learning moments into existing workflows.
- Enabling real-time exploration by encouraging employees to look up concepts and learn in the moment, like they would outside of work.
- Fostering experimentation and curiosity by encouraging teams to “try and apply” new methods in their day-to-day.
As to be expected with an iterative approach, this is not a one-and-done, isolated practice. The steps outlined here should be repeated regularly to ensure L&D remains aligned with the ever-evolving strategic needs of the business as it evolves. Only by making this alignment process a consistent, ongoing discipline can organizations harness the full competitive power of always-on learning.
The Bottom Line: If L&D isn’t iterating in tandem with strategic initiatives, organizations won’t have the skills they need, when they need them. A purpose-driven learning roadmap delivers value by…
- Preventing revenue loss from missing opportunities due to skill gaps.
- Prioritizing and aligning skilling initiatives with the most pressing real-world needs.
- Creating a clear line of sight between learning investments and business outcomes.
- Ensuring your learning roadmap fulfills its main objective: inspiring action.
Get started
Cultivating an always-on learning culture is no small undertaking. It requires challenging deeply ingrained mindsets, rewiring long-standing processes, and fundamentally reimagining the role of L&D.
It’s also a non-linear process. As the name suggests, adopting this always-on, iterative style of L&D requires iteration in and of itself. You’ll need to experiment, gather feedback, refine, and repeat in order to continuously improve. However, here are a few ways to start initiating an always-on learning approach:
#1. Target natural experiences. Look for organic opportunities that align with the actual work and skills needed in your organization. By identifying authentic learning moments connected to real business needs, you can avoid the trap of generic L&D programs that feel disconnected from day-to-day work.
“Consider the spaces where you're bringing people into the organization. You can reset expectations pretty quickly. Changing everything everywhere is quite hard, but if you can isolate the initial learning experiences and focus on ‘What does that look like?’ and ‘How can we try some new things?’, you have a powerful opportunity to experiment.”
– Jeni Fitzpatrick, CPO
#2. Start with new talent and entry points. Rethinking your onboarding process provides a clean slate to introduce new hires to an always-on learning culture from day one. It sets the tone that continuous growth is the norm and an expectation.
#3. Communicate intent and ask for grace. Adopting an always-on approach requires a culture and mindset shift for the organization and employees. Be transparent that you are experimenting with new ways of learning. Bringing people along on the journey and creating psychological safety to try new things is key to truly cultivating a culture of always-on learning.
The Bottom Line
Moving forward, organizations that embrace an always-on, iterative approach to learning and development will be the ones that thrive. The traditional, episodic L&D models of the past are simply no longer sufficient to keep pace with the evolution of skills, market demand, and employee preferences.
It requires a willingness to experiment, iterate, and even fail in the pursuit of continuous improvement. But in return, organizations stand to gain:
- A culture of innovation and continuous growth that attracts and retains top talent.
- The agility needed to swiftly meet shifting business needs with the right skills.
- Empowered employees who take ownership of their development and align it with strategic goals.
- Data-driven insights that allow you to forecast skill demand, measure direct impact of learning initiatives, and make informed investments in upskilling for maximum ROI.
- A future-proof workforce ready to seize emerging opportunities and navigate change.
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