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In a world defined by constant change, organizational agility isn’t optional—it’s essential. But true agility doesn’t happen by chance. It’s built through smart, strategic upskilling strategies that align learning with business goals and equip people with the right skills at the right time.

Featuring insights from two D2L L&D experts, this blog explores how your organization can move from high-level strategy to hands-on skill development, empowering your workforce to not just keep up with change but lead it.

Start With the End in Mind

The most effective skills strategies begin by asking: What does our organization want to achieve? From there, it becomes easier to define the behaviors, knowledge and attitudes need to get there and the metrics, KPIs and milestones your organization will use to measure its progress.

“What’s overwhelming is that there are so many skills. Where do you start, and what do you say no to? Taking a strategic approach to L&D helps you get clear and focused,” says Kristina Tsiriotakis, senior director, learning and organizational development at D2L.

“It focuses on developing those essential skills that are needed for the organization to succeed,” reinforces Jenna Lauren, L&D partner at D2L. “If we don’t focus on them, the organization can’t achieve its vision, strategy and goals.”

Ultimately, strategic learning isn’t just about offering table-stakes training—it’s about enabling the behaviors that drive performance. 

Define a Clear Skills Taxonomy

Once goals are defined, the next step is building a clear and structured skills taxonomy. This typically includes:

  • core skills required by everyone across the organization
  • future-focused skills that support adaptability (like data fluency or AI literacy)
  • functional or level-specific skills tailored to different teams and roles

It’s also important to establish what proficiency looks like at different levels—competence, proficiency and mastery—so learners and leaders can track progress and plan development accordingly.

It’s so important that people know what excellence across a skillset looks like. It gets them hungry to grow and helps them recognize where they’re at and where they can go as well.
Kristina Tsiriotakis senior director, learning and organizational development, D2L

Design With Purpose and Flexibility

With the taxonomy in place, it’s time to design programs that meet learners where they are. “It’s important to think about the learning culture,” says Kristina. “Where, when and how are people learning currently? What capacity does your organization have to bring in new programming?”

You want to be able to balance how you deliver learning, blending synchronous (live) and asynchronous (on-demand) experiences.

Blending synchronous and asynchronous experiences helps cater to different learning needs and address barriers and constraints that people in your workforce might face.
Jenna Lauren L&D partner, D2L

It’s also important to remember that upskilling isn’t a one-time event. The most effective programs embed learning into the flow of work—combining formal instruction with on-the-job learning, peer collaboration and real-world application. “When you do that, what you’re really doing is setting your people up to build skills steadily over time and be able to show up and invest in their own development,” says Kristina.

Leverage Technology for Scale

Technology can be a force multiplier for learning. But as Kristina and Jenna say, your programs will only be as strong as your tools enable them to be.

That’s why it’s crucial to choose platforms that are purpose-built for skills development—with strong analytics, personalized learning paths and integrated social features—that empower your team to deliver timely, relevant and measurable learning experiences.

“When we want to instill competence and mastery, making the right choices when it comes to upskilling technology will help our people develop and our organization go further faster,” says Kristina.

Cultivate a Learning Culture

For upskilling to truly take hold, it must be rooted in culture. When employees understand how skill development contributes to both personal growth and organizational outcomes, they’re more motivated to engage and take ownership of their learning journey.

It’s also essential for L&D to operate as a connected part of the business. “Remember, we’re not an island,” says Kristina. “We are a center of excellence, but we can’t do this work alone. Connecting with HR, frontline leaders and senior managers is how you’re going to be able to create and communicate with inspiration and impact.”

“I would also add that it involves continuous learning on your end as an L&D practitioner,” Jenna continues. “Listening to and learning from your people can help you enhance, refine and iterate your programs over time.”

Upskilling for agility isn’t about overnight transformation—it’s about building a resilient, adaptable workforce one skill at a time. Whether you’re just starting or refining your strategy, keeping the end in mind and building intentionally will help you get there faster.

Don’t Delay Workforce Upskilling

To help your organization stay one step ahead, you need to be able to deliver effective employee learning that drives performance, engagement and builds business-critical skills quickly and at scale. See how D2L can help you deliver high-impact learning tailored for business growth.

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Table of Contents

  1. Start With the End in Mind
  2. Define a Clear Skills Taxonomy
  3. Design With Purpose and Flexibility
  4. Leverage Technology for Scale
  5. Cultivate a Learning Culture

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