Why Your Skills Training Will Fail (Unless You Fix These 5 Things First)

With an increasing need to help employees master new approaches and tools—in particular, AI—reskilling and upskilling are top of mind for learning and development professionals.

But many find that their efforts aren’t yielding the impacts they’d hoped for. They teach the skills. They provide an opportunity to use them in a supervised setting. They verify that the learning has been well-received and that the learning objectives have been achieved.

Yet, when employees return to the job, they fail to produce the expected output. Worse, it doesn’t take long before employees give up using these new approaches and tools altogether.

What gives?

Systems vs. Motivation

While many are quick to point to a lack of motivation among employees or a resistance to learning new technology they fear may replace their jobs, most companies actually don’t have a motivation problem. They have a systems problem.

That systems problem is more pervasive and potentially more costly than a perceived lack of employee motivation. If it persists, it threatens to quietly but quickly undermine companies’ technology and training investments.

My research indicates that individual motivation accounts for approximately 7 percent of performance, while organizational learning systems contribute roughly 23 percent—more than three times the impact. For CEOs and senior leaders, that gap is the difference between blaming employees and redesigning the conditions that actually drive results.

Unfortunately, if L&D focuses on getting people “more motivated” without changing the conditions that shape their choices, the result is frustration for everyone involved.

Five Opportunities for L&D Influence

L&D professionals have an opportunity to significantly influence how well organizations adapt their systems to improve learning outcomes. It’s not just about creating and delivering training programs. It’s about working with leaders to ensure that the organization and its managers create a culture where learning is likely to transfer to on-the-job performance.

Here, I provide a practitioner-oriented framework for designing simple interventions and conversations that shift the system.

1. Make the environment safer and easier to learn in.

A supportive learning environment is more than a “growth mindset” slogan; it’s the day-to-day experience of whether trying something new is safe and feasible. For instance, in my upskilling work, IT employees often report that they want to experiment with new tools but avoid doing so because errors are treated as failures rather than learning data.

Practical steps for L&D:

• Build in opportunities for practice after training has been delivered. Work with managers to ensure employees have the opportunity to apply and refine their new skills in a real-world setting. Ensure they’re able to do this in an environment where it’s okay to make mistakes.

• Make trying and failing the norm. Encourage leaders to share stories about times when they tried a new method, broke something, and fixed it—with a focus on what they learned. Use these as opening vignettes in workshops and town halls.

• Coach leaders on their language. Provide a one-page guide with phrases that invite learning (“What did we learn from this?”) and ones that shut it down (“We can’t afford mistakes”). Encourage sponsors to model the former in debriefs.

2. Turn vague priorities into visible skill paths.

Most organizations say things like “we need more AI skills” or “data literacy is important,” but employees can’t see how that translates into concrete expectations for their role. It’s important to help them move from abstract capabilities to clear, observable behaviors along a path.

Practical steps for L&D:

• Create an example based on a single role (for example, data analysts or frontline managers). Map a process for applying what they’ve learned. Work with subject matter experts to create a simple three-level path: baseline, proficient, and advanced, that’s described in terms of specific activities and outputs.

• Publish “from–to” skill snapshots. Instead of a dense competency model, give learners a one-page “today versus six months from now” snapshot: specific tasks they’ll handle differently, decisions they’ll make, or problems they’ll be able to solve.

• Tag learning to the path, not the catalog. In your LMS or portal, organize resources under those path levels (“Start here if you’re at baseline”), so learners can see how each asset moves them closer to the expectations for their role.

3. Redesign jobs so practice is part of the work.

Employees often leave training feeling enthusiastic and eager to apply what they’ve learned. But when they return to their jobs, they discover that there’s zero allowance for experimentation. They have real work to do!

Focusing too stringently on efficiency and productivity leaves employees feeling that any effort applied to using new skills is a risk. That can be especially true in IT and other project-based environments.

Practical steps for L&D:

• Build a “practice budget” into the training effort. Explicitly ask leaders to agree to a specific number of hours/days upfront that employees will be encouraged to spend practicing their new skills.

• Incorporate new application tasks into existing work instead of making them an add-on. For instance, maybe one sprint each quarter, a team uses the new analytics dashboard instead of the old spreadsheet.

• Flag conflicting metrics. Think about a support team: if they’re measured only on volume and handle time, asking them to slow down to apply new skills will fail. Use intake conversations to identify where performance measures need temporary adjustments to make practice viable.

4. Equip managers to reinforce, not just remind.

Managers and supervisors can either help or hinder their employees’ ability to transfer what they’ve learned back to their jobs. When managers protect time for learning, provide timely feedback, and connect new behaviors to opportunities, transfer improves. When they don’t, even excellent training erodes.

Practical moves for L&D:

• Give managers a “before and after” playbook. For each major program, supply managers with a short guide that outlines what to do before the training (set expectations, clarify outcomes) and after (observe one behavior, offer specific feedback, remove one barrier).

• Make feedback easier and more immediate. My work on feedback timing underscores that while perfectly immediate feedback is rare in real workplaces, feedback that is specific, behavior-focused, and tied closely to the next opportunity to perform can still powerfully shape behavior. Provide simple observation checklists or prompts managers can use in regular one-on-ones.

• Measure managers on development behaviors. Partner with HR to add a couple of indicators—such as the frequency of development conversations or the percentage of team members applying new skills—to manager scorecards, and provide that feedback to them regularly.

5. Make new skills “pay off” in your system.

Learners quickly pick up on whether using new skills changes anything about their work life. My research mapping training and firm performance shows that when organizations treat training as an isolated event without linking it to recognition, career opportunities, or better work, the signal to learners is clear: this is optional.

Practical steps for L&D:

• Tie skills to visible opportunities. Work with talent management to pre-define ways new capabilities will contribute to employee opportunities they care about, such as eligibility for specific projects, internal gigs, or communities of practice. Advertise those links in your program materials.

• Audit your recognition system. Run a quick scan: in the last six months, how often have promotions, bonuses, or shout-outs explicitly referenced someone applying a new skill from training? If the answer is “rarely,” partner with leaders to change the narrative in town halls and reviews.

• Track behavior and outcome metrics, not just completions. In my professional experience in designing upskilling, effective frameworks start by defining behavioral indicators and pairing behavioral indicators (for example, frequency of using a new tool) with business metrics (like error reduction or cycle time) to demonstrate real payoff. Use those stories to reinforce that the organization takes new skills seriously.

Summary

One fundamental point is clear: performance is engineered, not trained into existence. For L&D professionals, that’s not a threat to your role: it’s an invitation to expand it and move from content creator to system designer. It’s a more strategic role that will benefit you, your learners, and your organization.