By David Kelly

This is a guest post by David Kelly – L&D Executive, Advisor, Speaker, and Writer. Kelly is the former Chairman and CEO at the Learning Guild. He has over two decades of experience in learning and performance leadership and consulting. Kelly’s work constantly explores the convergence of learning and technology, demonstrating a profound commitment to transforming workplaces and enriching lives through innovative learning strategies.  

When you ask most learning leaders what keeps them up at night, the answers are rarely about tools. They are about relevance, alignment, and impact. Are we focusing on the right problems? Are we supporting the work that actually matters? Are we preparing the organization for what comes next without chasing every new idea that appears?

The challenge heading into 2026 is not a lack of insight about where the field might be going. There is no shortage of predictions. The challenge is deciding how to navigate that future with intention rather than reaction. In that environment, questions often matter more than answers.

The following three questions are not a roadmap or a maturity model. They are a diagnostic. They are designed to help leaders assess whether their learning strategy is intentionally designed or simply a collection of activities.

Question 1: What problem is our learning strategy actually designed to solve?

Many learning strategies begin with good intentions and end up as collections of initiatives. New programs are launched, platforms are added, and content libraries grow, often without a clear line of sight to the problem they are meant to address. Over time, activity becomes a proxy for progress.

This question forces clarity. What problem is learning meant to solve for the organization right now? Is it improving performance in critical roles? Building future capability? Reducing risk? Supporting transformation? The answer matters less than whether there is alignment around it. When different stakeholders describe the purpose of learning in different ways, design breaks down.

This becomes even more important as AI and other technologies enter the picture. When intent is unclear, technology scales confusion. When intent is clear, technology can accelerate focus and consistency. If your learning systems disappeared tomorrow, what problem would immediately become visible? That answer often reveals more than any strategy document.

Question 2: Where does learning actually show up in the flow of work?

Learning that lives outside the work has always struggled to change behavior. People do not fail because they lack access to information. They struggle because the right support is not available when it is needed. That gap becomes more costly as work grows more complex and less predictable.

In many organizations, learning still shows up as an interruption rather than an enabler. Courses, programs, and events pull people away from work instead of supporting them within it. The future of learning, however, is increasingly defined by proximity. Learning shows up closer to the moment of need, embedded in tools, systems, and workflows.

This shift challenges traditional assumptions. In some cases, the most effective learning solution may not look like learning at all. It may look like better design, clearer processes, or smarter systems that recognize struggle and provide support in context. When learning supports work rather than competes with it, performance improves in ways that formal training alone rarely achieves.

Question 3: What are we asking humans to do that technology could do better?

As automation and AI continue to advance, this question becomes unavoidable. Not all work benefits equally from human effort. Some tasks are repetitive, administrative, or analytical in ways that technology can handle more effectively and consistently. The mistake is not in using technology. The mistake is in using it without intent.

This question is not about replacing people. It is about being deliberate about human contribution. What work requires judgment, sense-making, empathy, and decision-making? What work benefits from human accountability? Answering those questions clarifies where technology should support and where it should step back.

Organizations that use technology well tend to do so in service of better human work. They automate what can be automated so people can focus on what cannot. When this balance is designed intentionally, learning shifts from teaching people how to do tasks to helping them make better decisions in complex situations.

What These Questions Reveal When Taken Together

These questions are interconnected. A lack of clarity around the problem learning is meant to solve often leads to learning that sits outside the work. Poor integration with work makes it harder to decide what should be automated and what should remain human. The result is fragmentation rather than progress.

What these questions ultimately reveal is not tool maturity, but design maturity. Organizations that answer them well tend to have learning ecosystems that feel coherent, even if they are not perfect. Those that struggle often have capable teams and strong tools, but lack shared intent.

Most learning challenges are not capability problems. They are design problems in disguise.

A Diagnostic, Not a Deadline

There are no universally correct answers to these questions. Context matters. The right answer today may not be the right answer a year from now. What matters is the discipline of revisiting them as conditions change.

The future of L&D will not be defined by how quickly new ideas are adopted. It will be defined by how clearly leaders understand what they are trying to enable and how intentionally they design learning to support it. These questions are a starting point, not an endpoint.

The real work begins in the conversations they provoke.

Kelly brings his passion to life in his daily work as a dynamic strategist, speaker, and writer – inspiring others to view their work through a fresh, technology-enhanced lens. If you’d like to read more from David Kelly, check out his LinkedIn and subscribe to his newsletter.