Upskilling and Reskilling the Workforce: How to Prepare Your Team for the Future

Being agile and adaptable has quickly become a necessity over the last handful of years, and even more so as we navigate the challenges and opportunities ahead in 2025. According to your fellow HR and L&D professionals, that’s why upskilling and reskilling will be one of their top priorities next year—and it’s the top priority for organizations with 20,000+ employees.

For enterprise companies, there’s been a lot of buzz around upskilling and reskilling initiatives over the past couple of years, so let’s explore what that looks like and how you can create your own reskilling and upskilling initiatives.

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What is reskilling and upskilling?

Reskilling means training employees to do a different job within your company, while upskilling aims to update and improve the skills of your employees in their current or similar roles. Both will be essential strategies to stay flexible and future-ready as we look ahead to 2025.

Why is upskilling and reskilling important?

Upskilling and reskilling the workforce is the second highest 2025 priority for a reason. Recruitment and turnover are costly and drain a lot of other resources, too. And employees are hungry to grow, with 86% of professionals saying that they would change jobs if a new company offered them more opportunities for professional development. Retention is only one of the reasons why upskilling and reskilling are important.

So, instead of looking for fresh talent, reskilling and upskilling help you nurture your employees to reach their full potential—whether it’s in their current role or something completely different. You already have great people on your team that want to succeed; upskilling and reskilling help put the right people in the right seats while updating skills and knowledge to match latest technologies and best practices.

Benefits of upskilling and reskilling

Training programs need a pretty significant investment of time and resources, so understanding how they will benefit your company overall is key to getting buy-in. Here are a few benefits of upskilling and reskilling initiatives:

• Better employee retention: Investing in your employees’ growth through reskilling and upskilling is shown to build loyalty and satisfaction and improve retention rates.
• Increased productivity: A workforce that stays up to date with industry trends and skills is more efficient, innovative, and productive.
• Cost savings: Training current employees is often more cost-effective than recruiting, hiring, and onboarding new talent.
• Improved flexibility: A team that’s capable of adapting to new roles and skill requirements helps your company remain agile in times of change.
• Stronger organizational culture: A commitment to employee development goes a long way to making your workforce feel valued, building a positive company culture.
• Competitive advantage: When your company prioritizes reskilling and upskilling, you can better anticipate and respond to new technologies, industry trends, and regulations—giving your organization a competitive edge.

Upskilling and reskilling examples: In-demand skills

Understanding which skills are in demand is key for shaping effective reskilling and upskilling programs. So, let’s dive into some upskilling and reskilling examples and in-demand skills:

• Data analysis and interpretation: With the rise of big data, being able to sift through complex datasets and pull out actionable insights is gold across many industries. Professionals who can do this are essential in driving strategic decisions.
• Digital literacy and technology proficiency: As tech becomes a staple in every workplace, a solid grasp of digital tools and software is a must. Skills in areas like cybersecurity, cloud computing, and artificial intelligence are particularly sought after.
• Project management: Skills in planning, executing, and overseeing projects efficiently are incredibly valuable, and knowing methodologies like agile and scrum can really give employees a leg up.
• Emotional intelligence: Being able to manage emotions and empathize with others boosts leadership and teamwork. It helps build stronger workplace relationships and smoothens communication.
• Creativity and innovation: Creativity is crucial for problem-solving and generating fresh ideas. By nurturing an innovative mindset, teams can come up with creative solutions and meaningful improvements.

By focusing on these in-demand skills, your company can keep your workforce competitive and in tune with industry demands.

How to develop an upskilling and reskilling strategy

Creating an upskilling and reskilling strategy is about aligning your company goals with the skill demands of today’s technologies and best practices. It’s more than just spotting skills gaps; it’s capturing the potential of your team and investing in them to take your company forward. 

1. Assess current skills and identify gaps: First off, get a clear picture of the skills you already have in-house. Do a skills gap analysis to highlight where development is needed.
2. Align training with business goals: Make sure your reskilling and upskilling efforts align with your company's bigger picture. This ensures your workforce development initiatives are hitting the mark for organizational success.
3. Leverage technology for upskilling and reskilling initiatives: Tap into e-learning platforms, mentorship software, and other digital tools to deliver engaging, accessible, personalized learning. These tech solutions can adapt to different learning styles and keep employees engaged.
4. Create a culture of continuous learning: Encourage everyone to embrace lifelong learning. Cultivate a team culture where people feel pushed and supported to take on development opportunities regularly.

💡Tip: Personalization is key! Many professional development programs fail to launch and most fail to reach the measurement stage. But, most programs that fail are described as “expensive, one-size-fits-all programs that aim to reskill hundreds or thousands of employees at once.” Leverage technology to personalize learning experiences and empower employees to drive their own growth.

How to measure the impact of upskilling and reskilling initiatives

To make sure you see the benefits of upskilling and reskilling, set clear metrics and benchmarks right from the start. Regularly check in on these programs to see if they're meeting those goals and tweak strategies as needed.

• Employee feedback surveys: Keep in touch with those participating in the training. Regular feedback helps in understanding how satisfied they are with the program and gets you fresh ideas for improvement.
• Performance metrics: Take a closer look at pre- and post-training performance indicators to see if there's a boost in productivity and efficiency.
• Skill assessments: Test out skills before and after training to directly measure what employees have learned and how they've improved.
• Business outcomes: Dive into key business outcomes like revenue growth, customer satisfaction, and innovation rates that could get a lift from your team's newfound skills.
• Retention rates: Keep an eye on employee retention and engagement to figure out if training is helping with job satisfaction and loyalty.
• Internal promotions: Track how often people are moving up within the company as a sign of successful skill development.

Walmart: Seeing the benefits of upskilling and reskilling

Anticipating huge changes in available talent due to retirements, Walmart is looking to its 2.1 million global employees to fill over 100,000 in-demand roles within the next three years. The retail giant wants to give employees the opportunity to shape their own career paths within the company, often moving to higher paying, more specialized roles. To make this happen, Walmart has ramped up and rolled out several reskilling and upskilling initiatives.

Here are just a few examples of how Walmart is taking reskilling and upskilling seriously:

• Associate to Driver: A 12-week program that helps supply chain employees earn their commercial driver’s license to join Walmart’s private fleet of drivers.
• Career Explorer: One cool part of this story is how they leverage AI in learning and development. Their AI-powered “career explorer” tool helps match employees’ interests and ambitions with fitting roles and upskilling opportunities.
• Live Better U: This program makes GED classes, college degrees, and certification courses available to their employees free of charge.
• Walmart Academy: Their upskilling program that offers in-person and virtual training courses to any of their employees across the globe.

How Together supports upskilling and reskilling initiatives

The need for upskilling and reskilling is more evident than ever. By pushing for ongoing learning and development, your company can keep up with the competition and the ever-evolving factors that affect how your company serves its customers. Your employees are your most valuable resource and investing in their skill development—like Walmart has—not only opens doors for better careers but addresses talent shortages in many skilled positions.

But, you don’t need to be a part of a multi-trillion-dollar retail giant to see success from your upskilling and reskilling initiatives. No matter the size of your company, you can jump on strategies that promote growth and development. Tools like Together's mentoring platform, peer learning software, and employee engagement activities offer flexible solutions that fit to your company’s needs. These tools help build an encouraging atmosphere where employees can learn and flourish, setting the stage for a more agile, capable workforce that's ready to meet whatever the future throws your way.

Get started with Together today! Book a demo with one of our experts.