How to Upskill Employees: 7 Practical Strategies That Work

According to the World Economic Forum, approximately 39% of existing skill sets are expected to become outdated between 2025 and 2030. This puts pressure on businesses to upskill their employees to meet the evolving industry trends. 

However, designing upskilling programs that work for your employees can be a challenging task. More often, companies invest in generic training that fails to address skills gaps or meet business objectives. To make an impact, leaders must first understand how to upskill employees strategically and then design targeted upskilling programs. 

In this guide, we’ll define what employee upskilling means and outline seven practical strategies to help you upskill your team.

What Does Employee Upskilling Mean? 

Employee upskilling is the process of equipping your workforce with new knowledge and advanced training that expands upon their existing skill sets. Unlike reskilling, which prepares workers for entirely different roles, upskilling sharpens their current capabilities. This helps them excel in their current jobs while adapting to future demands. 

In today’s hyper-competitive industry, businesses that fail to invest in workforce development risk falling behind. In fact, skills gaps are considered to be the biggest hurdle to sustainable business growth. To manage this gap, almost 85% of employers worldwide plan to invest in employee upskilling actively.

7 Strategies to Upskill Employees at the Workplace

Companies that prioritize continuous learning always remain one step ahead. Upskilling employees not only benefits the workers through personal and professional growth, but also the business by enhancing productivity. Here are seven practical strategies to upskill your employees: 

Strategy #1: Conduct a Skills Gap Analysis

A skills gap analysis shows you one thing: Where your team is now vs. where they need to be.

Finding this answer isn’t optional, but critical. McKinsey & Company reports that 87% of organizations are either experiencing a skills gap or expect one in the near future. That means, if you’re not actively identifying these gaps, you’re already behind.

Here's how it can be done: 

• Skill assessment → Benchmark technical and soft skills against role requirements.
• One-on-one performance reviews → Identify strengths and development areas.
• Employee surveys → Capture how confident team members feel about their abilities.
• 360° feedback → Gather well-rounded insights from managers, peers, and reports.
• Performance data → Use KPIs and analytics to spot recurring weaknesses.

Strategy #2: Define Clear Goals and Objectives

When employees understand why they’re learning new skills and how those skills translate into opportunities, engagement and motivation naturally increase. 

Start by breaking down your workforce strategy into skill-based priorities. For example, if your business is moving towards automation, identify which roles need technical training and which require soft skills training for better adaptability. From there, set tiered objectives and divide them into short-term and long-term goals.

Make sure your managers and employees know:

• What skills are they expected to build?
• How will the progress be measured?
• The appropriate milestones for each objective.  

What Works Best :
Set SMART (Specific, Measurable, Achievable, Relevant, and Time-bound) goals for your organization. Instead of saying “We want employees to get better in data analytics”, set a goal, such as “Train 75% of employees in data analytics in the next 6 months.”

Strategy #3: Tailoring Training to Every Employee 

Every employee has unique strengths, weaknesses, and learning preferences. Some are eager to learn; some aren’t interested at all. And others only stay motivated when training feels fun, like through gamification.

Expecting all these different individuals to upskill from a single, one-size-fits-all program is unrealistic. You need personalized training plans, programs that adapt to each employee’s pace, style, and goals.

Here’s how to make it possible:

• Host one-on-one meetings → Uncover hidden strengths, career goals, and interests.
• Get feedback from the team → Use feedback to shape employee development plans.
• Mix learning formats → Blend microlearning, workshops, mentorship, and e-learning so everyone finds a method that fits.
• Recognize progress → Reward with incentives, certificates, badges, or public appreciation to inspire continuous upskilling.

Strategy #4: Upskill Smarter with Technology

Compared to static classroom training, digital tools allow organizations to deliver adaptive learning experiences at lower costs. In fact, IBM found that employees learn 5 times more material using e-learning techniques compared to classroom learning. This shows the importance of technology-driven upskilling for modern workforces. For example: 

• AI-powered Learning Management System: It allows you to build tailored courses, deliver content, track employee progress, and gather feedback, all with a few clicks.
• Knowledge Management System: KMSs make learning more accessible for workers. They centralize organizational expertise and ensure easy access to learning resources anywhere, anytime. 
• Collaboration Tools: Platforms, such as Slack, Microsoft Teams, and Zoom, encourage peer-to-peer learning and knowledge sharing.

Coursebox E-Learning Platform: Coursebox is an excellent option for training your employees and enhancing their skills. It offers advanced features like AI video generators, AI quiz chatbot trainers, and AI quiz generators. This helps deliver engaging, role-specific training in minutes. 

Strategy #5: Embrace Microlearning for Faster Results

Employees value training that fits into their workflow, not around it. Microlearning leverages this preference and breaks content into bite-sized modules, usually 5-6 minutes long. 

Research highlights that microlearning can make training 17% more productive than traditional methods. This is because, instead of pausing for hours of training, employees can complete a module between tasks or during short breaks. These modules can take different forms, such as:

• Short Videos: Helps with step-by-step instructions on tools or processes. 
• Interactive Quizzes: Test knowledge retention and decision-making. 
• Engaging Infographics: Aids quick scanning of data, workflows, or procedures. 
• Mini Articles or Flashcards: Works great for knowledge checks on updates and policy changes.

Strategy #6: Make Learning Practical and Actionable 

Hands-on learning experiences bridge the gap between theory and practice. 

According to the learning pyramid, people retain 75% of what they practice, compared to only 5% of what they hear in a lecture. This highlights the importance of building practical learning opportunities into every upskilling program.

You can put it into action through job rotations, giving employees exposure to different departments and roles to broaden their skill sets. Assign real projects so they can immediately apply new skills, and introduce stretch assignments that push them slightly out of their comfort zone. Consistent practice not only builds competence but also boosts confidence.

Strategy #7: Monitor Progress and Adjust Training

Upskilling is an ongoing journey, not a single event. As your business goals and market conditions change, your training programs need to adapt and evolve. This can be done by monitoring key performance indicators (KPIs).

These KPIs are metrics that measure how well your employees are learning, applying new skills, and improving performance. Tracking them helps you see what’s working, what’s not, and where to adjust your training. KPIs you should track include: 

In addition, regular feedback sessions also help identify what’s working for your employees and guide adjustments to the content. You can monitor their progress by re-running the skills gap analysis to see the real impact of your program and identify areas that require more attention.

Why is Upskilling Important for Employees?

When organizations prioritize upskilling, they create a competitive workforce that can take on future challenges with ease. Let’s take a look at why upskilling is essential in workplaces: 

1. Improves Employee Retention

When employees feel their growth is supported, they are more likely to stay committed to the organization. Upskilling demonstrates that the company values its people beyond their current roles and is willing to invest in their careers. 

According to research, companies offering development opportunities are twice as likely to retain their employees. This reduces the recruitment cost and minimizes loss of top talent, and productivity. Ultimately, these factors combine to drive almost 11% higher profitability. 

2. Provides a Competitive Advantage

Companies that invest in their employees' learning and development gain a clear edge over their competitors. This is because upskilling helps your team get familiar with emerging technologies, implement best practices, and innovate faster. 

Organizations that continuously upskill their employees are better positioned to respond quickly to market changes. Whether it’s adapting to new regulations, embracing digital transformation, or meeting customer expectations, skilled employees keep your business running smoothly. 

3. Continuous Learning Environment 

Upskilling doesn’t end after the skills gap has been identified and filled. In fact, it creates a culture of continuous learning where employees see change as an opportunity rather than a threat. A workplace that encourages learning and development also appeals to the employees, which increases their retention, productivity, and job satisfaction. 

According to a Gallup study, more than 57% of workers in the US express a strong interest in upskilling programs. By leveraging their interest, employers can train their workforce to tackle unexpected challenges.

4. Prepares Employees for the Future

According to the World Economic Forum, automation is expected to displace 85 million jobs by 2025. But it will also create 97 million new roles. The difference between those who thrive and those who struggle lies in one thing: skills. 

By investing in upskilling today, businesses can prepare employees for future advancements. When individuals are equipped with adaptable skills, they feel more confident navigating change. This reduces resistance to innovation and also positions organizations to lead the rapidly evolving industry.  

5. Higher Productivity 

Employees who are confident in their abilities complete tasks more quickly and make fewer errors. This efficiency translates into measurable gains in both productivity and profitability. 

In fact, research consistently shows that upskilling leads to improved employee engagement, and engaged employees are significantly more productive. Thus, it’s a win-win situation. The employees feel empowered, and companies enjoy sustainable results.

Real-World Examples of Upskilling Programs

Upskilling strengthens internal talent pipelines, which enhances organizational resilience. Let's take a closer look at some big names in the industry upskilling their employees:

1. Amazon Upskilling 2025 Program 

Amazon’s Upskilling 2025 is one of the largest corporate commitments to workforce development. With a massive investment of $1.2 billion, Amazon pledged to upskill 300,000 employees by 2025. 

It comprises 12 upskilling programs that majorly focus on high-demand areas such as machine learning, IT support, and data science. By opening doors to technical careers, Amazon ensures its workforce remains relevant in the age of automation. 

2. Mastercard Upskilling Program

Staying ahead of the competition in the fintech industry requires keeping up with innovations. Mastercard has responded to this by offering three types of training: Foundational Training, Tailored Job-Specific Training, and a Reskilling Program. 

They actively encourage employees to learn skills that match their interests and career goals. This approach makes the employees feel valued and increases their engagement and loyalty. As the VP of Global Talent Development at Mastercard explains:

“We want our people to bring their best self to work – and sometimes that means learning skills that are unexpected.”

Build a Future-Ready Workforce (Innovate Like 92% of High-Performers)

Leading companies are investing heavily in training, and for good reason. A Deloitte study found that high-performance organizations with continuous learning cultures are 92% more likely to innovate.

This clearly shows that continuous upskilling is no longer optional. Falling behind in learning and development puts organizations at risk of losing their competitive edge and missing opportunities, something no one wants (including us).

That’s why we created Coursebox. It is an AI-powered platform that makes creating engaging upskilling programs effortless. Whether you need outlines, quizzes, gamification, or AI-generated videos with avatars, Coursebox helps you design training that actually sticks and drives results.

Start your free trial today and discover how to upskill employees using an AI-powered platform. 

FAQs

1. What is the best way to upskill employees?

The best way to upskill employees is to analyze where they lack. Once you run a skills gap analysis, you’ll know what skills they need to stay productive and competitive. Provide them personalized training using advanced digital tools and track their progress for continuous improvement. 

2. What is a skills gap analysis?

A skills gap analysis is a process that identifies the difference between employees’ current skills and the skills they need to excel in their roles. It helps organizations detect weaknesses, provide targeted training, and prepare the workforce for future needs. 

3. What is the difference between upskilling and reskilling?

Upskilling means enhancing an employee’s current skill set to perform better in their existing roles. This usually involves learning how to adopt new tools or techniques. Reskilling, in contrast, focuses on training employees for a completely new role or career path, typically in response to evolving business needs or technological changes.

4. How does technology help in upskilling employees?

Technology enhances employee upskilling by making learning scalable, flexible, and personalized. With tools like Coursebox, an AI-powered LMS and training platform, businesses can upskill their employees conveniently. It offers training that is tailored to individual learning needs, tracks progress, and provides real-time feedback.