In 2025, the future of work isn’t just about technology. It’s about people adapting to it and performing at their best with it. At the heart of this shift are their skills.

One eye-opening fact from IBM really got our attention: general skills have a half-life of just five years, and technical skills even less—under three years. Skill demands are changing faster than ever.

What once required proficiency in Microsoft Office, now demands the ability to use AI to get things done quicker & smarter.

That’s why upskilling isn’t optional anymore—it’s a necessity. In fact, CEOs now rank the lack of good upskilling programs as one of the top three threats to business growth.

The challenge is clear for L&D leaders and training managers. With digital transformation, hybrid work, and evolving needs, your employees demand training programs that don’t just check boxes but truly develop skills.

This blog is here to help. We’ll cover top best practices, real-world success stories and much more to help you upskill employees, bridge critical skills gaps, and future-proof your workforce.

We’ll cover it in two parts. [Feel free to skip the basics if you’re here for actionable insights]

The Basics [What, Why, When]

• What is Upskilling?
• What is Reskilling?
• Upskilling vs. Reskilling: What’s the Difference?
• Why Do You Need an Upskilling Strategy?
• When is Upskilling Employees a Must?

The Practical Guide

• 5 Best Practices to Start Upskilling Today
• How Do You Measure Upskilling?
• What About AI Upskilling?
• Three Inspiring Upskilling Success Stories
• The Upskilling Advantage: Where To From Here?

The Basics [What, Why, When]

What is Upskilling?

Upskilling is the process of learning new skills or improving existing ones to keep up with changes in your job or industry. It helps people stay competitive in their careers by acquiring knowledge or abilities that are in demand. Companies must upskill employees regularly to keep pace with technological advancements.

Benefits of Upskilling Employees:

• Boosts Employee Productivity, Morale and Engagement
• Reduces and Closes Skill Gaps
• Encourages Creativity & Innovation
• Better Customer Experience
• Builds Internal Talent Pipelines
• Saves Costs on Recruitment

What is Reskilling?

Reskilling is learning new skills to switch to a different job or career. It’s like starting over in a new field by gaining the knowledge and abilities needed for that new role.

Benefits of Reskilling Employees:

• Adapts to Industry Changes
• Retains Valuable Talent
• Saves Hiring Costs
• Boosts Employee Loyalty
• Promotes Business Agility

There’s so much to say about the benefits of upskilling and reskilling, but the real focus should be on understanding their distinct purposes.

Upskilling vs. Reskilling: What's the Difference?

In the Navigate 22 virtual summit , Caroline Ford, previously Global Head of Skills at Novartis, and Michael Landers, Founder of Culture Crossing, broke down the nuances between upskilling and reskilling employees:

Upskilling: Think ‘T’

• The vertical line? That’s deep, specialized skills in a specific domain. Think of it as the core expertise an employee brings to the table.
• When upskilling employees, you’re helping them strengthen the vertical line of their ‘T.’

For example:

• Take a sales rep. They’re great at creating Excel reports. Upskilling means teaching them AI integrations to make reporting faster and smarter.

Goal: Make them a master of their craft, empowering their expertise.

Reskilling: Think ‘M’

Now imagine an ‘M.’

• Two vertical lines of the ‘M’ are skill sets in entirely different domains, while the connecting middle represents the transferable skills that tie everything together.
• When you reskill an employee, you’re essentially moving them from one vertical (their current expertise) to another vertical (a new domain).

For example:

• A factory worker’s job gets automated. Reskill them for IT support or customer service—completely new skills for a new path.

Goal: Equip them to thrive in an entirely new career space.

The Bottom Line

• Upskilling: Dive deeper. Sharpen the skills they already have.
• Reskilling: Pivot to something new. Open doors to fresh opportunities.

Both are about growth—just in different directions.

Why do you need an upskilling strategy?

Alright, you’ve landed on this blog—so we know you already get that upskilling matters. But let’s cut to the chase and spell out the top three reasons why having a strategy is non-negotiable:

Keeping Employees Loyal

• Job hopping is the new normal. So, what makes employees stick around?
• According to a LinkedIn Learning survey, 94% of employees will stay longer if they feel their career development is supported.
• Upskilling gives them that reason to stay. They’ll see growth, learn valuable skills, and feel invested in your organization.

Bridging the ‘Digital’ Skill Gap

• AI, automation, and advanced tech are taking over—fast.
• If your team can’t adapt to these tools, you’re putting your organization at risk of falling behind.
• Upskilling helps your workforce stay tech-savvy and future-ready, turning challenges into opportunities.

The Baby Boomers Are Leaving

• Retirement is coming, & with it, the exit of a huge chunk of experienced talent.
• The aging workforce means gaps will open up, and filling them won’t be easy if you’re not proactively upskilling your workforce.
• Upskilling ensures that your younger workforce is ready to step in and keep things running smoothly.

The Big Picture: Too often, training strategies focus on the ‘how.’ But without a clear ‘why,’ you’re just going through the motions. Nail your ‘why,’ and you’re on the path to creating a workforce that’s engaged, adaptable, and loyal.

When is Upskilling Employees a Must?

Short answer: Always.

Upskilling isn’t a one-and-done deal. You can’t train employees once and expect them to stay ahead forever.

Here's the thing - we live in a world where spreadsheets are practically vintage. These days, your employees’ average workday probably involves juggling a whole alphabet soup of tools - CRM, HRMS, POS... (huh, enough with the acronyms already!)

Plus, when companies undergo digital transformation, it's not just about throwing new tools at your employees. You need to make sure, you have these two key ingredients:

1. Always keeping those communication channels wide open
2. Making learning actually fun (because, let's face it, boring training = zero engagement)

We love what Shelley Osborne (former VP of Learning at Udemy) says in her book "The Upskilling Imperative" - the secret to keeping pace with change is to make continuous learning a top value for every person on the team so when change happens, everyone is prepared.

And get this - skills aren't one-size-fits-all! Every role needs its unique mix of competencies. That quiet junior team member? They might be hiding some serious leadership potential. But you'll never know unless you give them chances to grow through both learning opportunities and hands-on experience.

Check out the diagram below (or imagine one) to visualize job competencies and their associated skills. Each circle highlights a key area where your employees can grow.

The digital world isn't slowing down anytime soon, so why should your learning?

The Practical Guide

5 Best Practices to Start Upskilling Now

Focus on Skills Gap Analysis

Managers play a key role in identifying areas where they can upskill employees. And skill gap analysis can help them do that. A thorough skills gap analysis gives you a clear picture of your workforce’s current skill levels.

Further, they can compare these skills to what’s required to achieve your business goals. Then, they can identify where your employees are lacking—be it technical expertise, soft skills, or industry-specific knowledge.

Without knowing the gaps, L&D/training managers can’t plan upskilling program.

Pro tip: Collect actionable data using tools like surveys, self-assessments, and performance reviews.

Also, you can use this → Template by Gyde - Skill Gap Analysis

Prioritize Skills Training Areas

Not all skill gaps need to be addressed immediately, so it’s always an upskilling best practice to prioritize training based on urgency and impact. In fact, the provided skill gap analysis template also has a section that lets you monitor priority.

Begin by evaluating the urgency of the skills needed—prioritize those critical to meeting immediate business needs or deadlines. Next, a cost-benefit analysis will determine the return on investment for different training options.

Here’s how you might prioritize training areas:

• High Priority: Focus on skills directly linked to core business functions and critical performance indicators (KPIs). Significant skill gaps could affect operational efficiency or customer satisfaction in these areas.
• Medium Priority: Address skills that support long-term strategic goals. While these may not immediately impact, they can enhance employee engagement and retention.
• Low Priority: These skills are beneficial but not essential for current operations. Training in these areas can be deferred or outsourced as needed.

Remember: Training sessions to upskill employees should focus on both technical and soft skills.

Monitor Industry Standards & Trends

Think of industry standards as your "must-have" checklist. These are the skills and practices that keep you in the game with your competitors. Like having a user-centric tech stack in 2024 - it's not exactly optional anymore, right?

Then there are trends - the flashy new things everyone's talking about. While they can give you quick wins and attention, here's the catch: they need to fit your brand like a glove. Nobody wants to be that company that jumped on the AI bandwagon just because everyone else did!

So how do you stay in the know? Here's your cheat sheet:

• Explore market data (it's gold for spotting where jobs are heading)
• Get social at industry conferences (ATD and Gartner run some great ones!)
• Become known with those industry reports landing in your inbox

Pro tip: Keep a living document of all these insights. Think of it as your industry playbook - it'll help you make smarter decisions about what skills your team really needs to level up on.

Remember: The goal isn't to chase every shiny new trend, but to build a solid upskilling strategy that makes sense for YOUR company and YOUR people.

Use Digital Tools for Every Upskilling Need

If you’re serious about upskilling your workforce, you need the right kind of upskilling software tools. Here’s a quick breakdown of what works best for different learning needs.

1. LMS (Learning Management Systems)

These are your all-in-one training hubs. Employees get access to detailed courses on any topic. Training managers can track progress and hand out certifications. Bonus? Employees see this investment as career growth.

Learn more about Learning Management Systems ➡️

2. DAP (Digital Adoption Platforms)

These are digital upskilling software that help your employees directly within the applications they use. Features like walkthroughs, help articles, and videos pop up right inside the app interface. They provide on-the-job training for all kinds of software application – may it be in cloud, browser based or web-based!

Explore how Digital Adoption Platforms work ➡️

3. Work Instructions Software

Use these tools for step-by-step clarity. They have screenshot-based guides for explaining work processes. You can easily share guides with a simple link or download them for offline use.

Discover the benefits of Work Instructions Software ➡️

4. Adaptive Learning Platforms

These upskilling software platforms help you take a tailored approach to learning. Based on user's activity, they adjust learning content and deliver personalized recommendations, saving time & effort. Perfect for cutting down repetitive L&D tasks.

Read more about Adaptive Learning Platforms ➡️

5. Knowledge Base Platforms

These can be your organization’s centralized storage for training documents, help articles, and more. Tagging makes it easy to find expert insights in seconds. Employees get instant access to answers, anytime.

Get insights on Knowledge Base Platforms ➡️

The right tool can make upskilling less of a chore and more of a game-changer. Start matching your needs to the right tech, and watch your team level up!

Make Flexibility the Core

“It’s 2025; the pandemic is ancient history!” – many might say this. But its impact on the workplace? Still very real. It forced companies to rethink where they stood and how to move forward.

Josh Bersin’s report nails it: during the pandemic, survival came first. But as businesses shifted to growth mode, one key lesson stood out—actively caring for employees is non-negotiable.

About 46% of organizations made it a priority, to listen to what their teams wanted: flexible schedules, remote work, and real benefits that matter.

Fast forward to today, and flexibility isn’t just a perk—it’s the backbone of potent upskilling. If you want employees to learn, you have to meet them where they are.

That means:

• On-demand options for when they’re ready.
• Just-in-time refreshers that stick.
• Bite-sized microlearning that respects their time.

The fastest way to upskill employees is by using microlearning and on-the-job training that fits into their work. Focus on making learning practical, timely, and accessible—and you’ll see the difference.

How Do You Measure Upskilling?

How do you figure out if your program is working? Let’s break it down:

1. Are They Getting Better at Their Skills?

Start simple: test their skills before and after training. Look at certifications earned, courses completed, or even just higher test scores—these give you a clear picture of growth.

2. Is It Showing in Their Work?

Check performance metrics. Are they closing more sales, delivering projects faster, or making fewer mistakes? Ask managers if they see real improvement in day-to-day tasks.

3. Are They Sticking Around and Staying Engaged?

Upskilling should make employees feel valued. Check if your retention rates are climbing. Check if people are actually completing courses and engaging with the material. Use tools to see how much time they’re spending and where they drop off.

4. What Do They Think About It?

Run quick surveys—did they enjoy the training? Was it useful? Ask them directly! What worked, what didn’t, and what could be better? Collect feedback from both learners and managers.

5. Are They Growing in Their Careers?

Track who’s getting promotions, taking on new roles, or stepping up in projects after training. Upskilling should lead to real opportunities for employees.

6. Is the Business Benefiting?

Link training to business goals. Did it boost revenue, improve customer satisfaction, or cut down project delays? If the business isn’t seeing results, it’s time to tweak the program.

7. Is It Worth the Money?

Compare what you spent on the program to what you got out of it. Did it save you money by avoiding hiring or boosting productivity? Show that it’s not just a cost—it’s an investment.

8. Does It Stick Over Time?

Learning shouldn’t fade away. Check in after 3 or 6 months—are they still using their skills? If not, consider follow-ups or refresher courses.

Make it a habit to ask these questions as a training administrator to track and assess the impact of your upskilling strategies. A strong L&D strategy should always include plans to upskill employees over time.

What About AI Upskilling?

The World Economic Forum's Future of Jobs Report 2023 predicts some major shifts: AI-driven automation could displace 85 million jobs by 2025, and 40% of core skills will undergo a revamp.

Scary? Maybe. But here’s the good news for businesses, especially L&D pros: investing in AI delivers serious ROI—$1 spent on AI brings back $3.50 on average. Only trick here is that your teams should learn how to use it to their & the organisation's benefit. Here are three steps to make it happen.

Step 1: Where Does AI Fit in Your Organization?

Before diving in, figure out where AI can make the most impact. Start with a skill gap analysis (a must-do best practice). Identify what’s missing and where AI could solve real problems or unlock new opportunities.

Step 2: Make AI Part of Everyday Work

The best way to learn AI? Use AI. Embed it into daily tasks. Automating repetitive processes, experimenting with generative tools, or even analyzing data sets will spark a networking effect (as coined by BCG). As more employees adopt AI, your organization’s collective expertise and innovation will snowball.

Step 3: Assess ROI on Learning Investment (ROLI)

Once you have AI involved in daily use, now it is time to assess by gathering feedback and tracking results. Here's how:

1. Level 1: Employee Feedback
   Use quick surveys to gauge how engaging and useful the AI use feels to your team.
2. Level 2: Measure Competency
   Test if employees actually acquired the skills you intended.
3. Level 3: Behavioral Impact
   Watch for shifts in how employees apply AI knowledge to their roles.
4. Level 4: Business Outcomes
   Tie it all back to performance—think productivity boosts, cost savings, or faster innovation cycles.

This framework (also known as the Kirkpatrick Model) makes sure you’re not just throwing money at training but making it count.

AI isn’t the future—it’s happening now. So, start small, learn fast, and watch the returns roll in.

Three Inspiring Upskilling Success Stories

Citi

Citibank isn’t just about staying ahead in finance—it’s about making sure its people do too. As Cameron Hedrick, Head of Learning & Culture, Managing Director and a 21-year Citi veteran, puts it:

“Today, anyone, anywhere, has access to an abundance of free or affordable content to upskill in specific areas. They can climb skill curves independently, regardless of official approval. I've seen this happen within our company, where employees make use of various external resources to develop their skills.”

That mindset says it all – Citi's culture of learning makes it easier to consistently upskill employees and fuel innovation and growth. From tech boot camps and digital courses to leadership programs, employees can grow in coding, AI, management, and more.

The "Reactivate Your Career" program is a prime example, offering tailored roles and development for professionals returning after a break.

Supportworks

At Supportworks, exceptional home service professionals were ready to step into leadership roles – they just needed the right training. With teams spread across offices and field locations, the company faced a challenge: how to deliver consistent leadership development that works for everyone?

The answer was ManagementU, a hybrid leadership program built from the ground up by Supportworks' own experts. Instead of generic management training, they created something uniquely tailored to the home services industry.

The program combines virtual sessions, self-paced learning, and in-person workshops to teach both practical and leadership skills. Participants learn everything from recruiting and onboarding to communication and culture-building, all while continuing their daily work.

"Before ManagementU, I was great at fixing foundations," shares one participant. "Now I'm building and leading teams that can handle any challenge."

Participants emerge with a strong foundation in leadership, ready to take on advanced training and new career opportunities. More importantly, Supportworks is building a pipeline of leaders who understand both the technical and human sides of the business – making a stronger future for the company.

KPIT

KPIT Technologies, a global partner in the automotive and mobility ecosystem, were managing around 80 internal applications—from travel management to reimbursements. These apps, including critical tools like project management software and HRMS, were central to employee productivity.

The challenge? Digital upskilling for employees on all the main tools. Employees needed to:

• Master relevant features for their roles.
• Make sure to input accurate data to avoid workflow hiccups.
• Meet deadlines without getting bogged down by tool navigation.

This often led to stress, delays, and countless queries flooding the IT team.

Their L&D team zeroed in on each software and listed skills such as task prioritization, collaboration, and reporting and started using Gyde to upskill employees by integrating learning into their daily workflows.

Here’s how they made it happen:

• Employees got daily doses of bite-sized walkthroughs and videos, served directly inside the tool. No fluff, just actionable learning that stuck.

• For employees who knew their way around but hit occasional roadblocks, Gyde’s Assist Mode stepped in without interrupting their workflow.
• Training content was tailored to each role. Different teams saw only the help articles and walkthroughs relevant to their work.
• Every time the project management tool rolled out updates, Gyde delivered quick nudges for the new features—assuring instant adoption.
• With their team spread globally, Gyde’s multilingual support helped every team receive guidance in their language of preference.

For Training Admins:
Gyde simplified content creation. Admins only had to click through a process, and the AI-generated a walkthrough draft that could be polished and published in no time. The same content was easily repurposed into videos or guides, eliminating extra work.

Plus, by analyzing how employees interacted with the help content through Gyde analytics, KPIT spotted skill gaps and rolled out tailored training.

With Gyde in their corner, KPIT turned a digital upskilling challenge into a game-changing advantage.

The Upskilling Advantage: Where To From Here?

Throughout this blog, we've explored all about upskilling – from foundational principles to real-world success stories.

We've seen how organizations transformed their workplace by creating supportive learning cultures, embracing digital tools, and developing tomorrow's leaders.

But perhaps the most crucial insight is this: while we often say learning is lifelong, making it a reality requires more than just providing training programs.

The magic happens when organizations tap into their employees' natural curiosity and ambitions. The most successful upskilling initiatives don't just push knowledge – they create an environment where employees actively seek growth opportunities.

As we've seen through numerous examples, upskilling isn't just another corporate initiative – it's the bridge to your organization's future. In today's rapidly evolving workplace, staying still means falling behind. The question isn't whether to upskill, but how to make it an integral part of your organization's DNA.

Remember: The best time to plant a tree was twenty years ago. The second best time is now. The same goes for upskilling. Your next success story begins with the skill you choose to develop today.

The future belongs to organizations that embrace continuous learning. What skill will you and your team master next?

FAQs

• What is the meaning of digital upskilling?

Digital upskilling means learning new digital skills or improving the ones you already have to keep up with today’s technology. It’s about gaining the knowledge and tools to use modern software, apps, and platforms, whether for work or personal growth. Think of it as upgrading your tech skills to stay relevant and confident in a digital-first world.

• Which platform is best for upskilling?

If you’re planning to design a digital upskilling program, a platform like Gyde could be a game-changer. It provides real-time guidance through walkthroughs and in-app videos, helping users navigate and master software easily. Plus, with its AI-powered capabilities, Gyde simplifies content creation for training admins, making it easier to develop great training materials in no time.

• What skills should you prioritize when upskilling your workforce for emerging technologies?

Just like learning a new language, building comfort with tech tools, data analytics, and AI isn't about becoming experts overnight – it's about helping your people confidently navigate their digital world. After all, these aren't just fancy buzzwords; they're tools that can make work smoother and more interesting.

But here's the thing: while tech skills matter, it's the human touch that makes all the difference. Your team's ability to communicate clearly, work together seamlessly, and roll with the changes – that's what turns good tech adoption into great transformation.