TL;DR: Demands change fast, and upskilling is how you keep your people ready for what’s next. The best way to do this is with a clear upskilling strategy; in this guide, we break down how to build one.
Does your organisation need to upskill its people? The answer is, very likely, a resounding yes. Upskilling is a crucial part of any L&D strategy, helping you sharpen up the knowledge and skills today’s workplace demands.
If you’ve found yourself at an L&D conference or scrolling LinkedIn in the last six months, chances are you’ve heard no end of chatter about upskilling. And it’s not going anywhere; if anything, it’ll only grow more important with AI advancements and changing roles across industries.
Every development effort needs a plan, though, and that’s where an upskilling strategy comes in. Here’s how to put one together.
What is upskilling?
Upskilling means developing knowledge or skills for better performance. Where reskilling teaches people entirely new skills – a big shift away from what they’re already doing – upskilling builds on what someone already knows, refreshing or updating it. It’s often work people are already doing, just done better.
AI is a good example of this, across pretty much every department. Your team are likely already using it day-to-day, but upskilling in it might look like a module on writing effective prompts, or a microlearning nudge on your organisation’s responsible use policy. These are deliberate moments designed to sharpen existing capability, not to teach something new from scratch.
What is an upskilling strategy?
An upskilling strategy is the plan that sits behind it all: a structured, repeatable approach to identifying and closing skills gaps. Specific steps will vary depending on your goals, but an upskilling strategy typically includes the following:
- Goal setting
- Planning (usually backed by a skills gap or learning needs analysis)
- Deploying the right learning solutions
- Monitoring how they perform
- Revisiting the approach as demands evolve
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Why is upskilling important?
Times are changing, and so is the workplace. A few factors are driving that urgency:
AI and tech advancements
As AI progresses, more skills are needed to use it well, or to do the work it simply can’t. A recent BusinessLDN survey of more than 2,000 business leaders found only half of London firms believe their workforce has the skills needed to meet requirements, down from 63% just a year earlier.
Among businesses already using AI, 85% said it had altered the skills needed, with things like “critical thinking” and “decision making” being cited as necessary. In other words, the human skills AI can’t replicate.
The wider skills gap
The skills gap extends beyond just AI too. The World Economic Forum predicts that 59 out of every 100 workers will need upskilling or reskilling by 2030, with 63% of employers already naming skills gaps as the biggest barrier to business transformation. AI is certainly a factor – in fact when grouped with ‘big data’, it’s the fastest-growing skill in demand, according to the report – but other skills are climbing too, including leadership, resilience, curiosity, and environmental stewardship.
Talent retention
Invest in your people, and they’re far more likely to feel valued and stick around. LinkedIn research found that 94% of people are likely to stay at an organisation longer if they feel the business invests in their career. There’s an obvious boost to productivity here, along with a financial one too: developing people often costs far less than replacing them.
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How to create an upskilling strategy: 6 steps for success
Here’s a practical framework to help you put an effective upskilling strategy together.
1. Decide what you’re trying to change
Start by choosing your priorities and link them back to your organisation’s or employees’ goals. There’s little point investing in training that doesn’t make an impact, both for the business and for personal growth, so think carefully about what you want to achieve or improve.
This could be at a company-wide level, or somewhere more granular, such as a team or individual scale. For example:
- AI rollout: You want to get everyone in the company using AI responsibly and effectively.
- Raise in support tickets: The business has had a rise in tickets relating to a particular feature, so the support team need to refresh their knowledge in this area.
- New manager programme: A handful of employees have recently been promoted into management roles, so they need to develop core leadership and people management skills.
2. Find out where the gaps are
Once you know your priority area, you need to find out exactly where you stand now, and map that against the skills you require to succeed. In other words, some form of gap or needs analysis.
When conducting a needs analysis, there’s natural overlap with some of the other steps here (goal setting, rollout, measuring outcomes), but the analysis itself should answer one thing: what do you need to get where you want to be?
A few different models can help, and while there’s crossover between them, they each have nuances:
- Skills gap analysis: compares the skills your people have now against the skills required for a role or goal
- Learning needs analysis: takes a broader view, looking at the full picture of what’s needed, including skills, knowledge, attitudes, and behaviours
- Training needs analysis: narrows in on the specific training needed to close a defined gap
Whichever you use, the goal is the same: pin down exactly which skills need developing, using methods like interviews, surveys, self-assessments, and performance data.
3. Set goals for each initiative
Your goals from step one, at whatever level you set them, determined your priorities; this step is where you turn them into something measurable. Give each initiative its own metric and a timeframe, so there’s a clear health check to run once it’s live.
This is how it may look, from the examples in step one:
- AI rollout: 80% of the team confidently using AI tools within the policy inside six months, verified through a short self-assessment skills check or manager feedback.
- Support tickets: a measurable drop in resolution times for that issue area within a set number of weeks.
- New manager programme: All new managers complete the programme within three months, with improvements measured through pre- and post-programme business simulation assessments.
4. Design your learning content
With your gaps and goals defined, it’s time to design the learning itself. Start from the behaviour you want to change and link the learning directly to the job. For example, if you’re designing a module on an AI platform, don’t just focus on how to use it, focus on the thinking behind it too. That way, you’re building understanding people can carry into their day-to-day work.
Designing learning is its own meaty topic, worthy of thousands of dedicated blog posts, but here are some core principles to think about:
- Learning methods: eLearning, workshops, coaching, on-the-job practice, and peer learning each suit different skills, and a blended mix of these often works well. Where it fits, blend in AI-supported tools too, like an agent for in-the-flow learning and practice.
- Reinforcement: Knowledge fades quickly without follow-up, so build in refreshers along the way, whether that’s a quick quiz, a manager check-in, or a microlearning nudge a few weeks later.
- Engagement: The format matters as much as the content. Short-form video, infographics, visual walkthroughs, audio, and microlearning bursts tend to work better than long, static modules, especially when paired with scenario-based examples.
- Room for practice: People build confidence by doing. Give them a low-stakes way to apply the skill before it counts on the job, such as a business simulation.
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5. Map out learning pathways
Not everyone starts from the same place or wants the same thing out of their career, so this is where personalisation makes a big difference.
Rather than one set course, build pathways that guide people through the right content, in the right order, based on where they are now and where they want or need to be. For individuals, this can tie into a personal development plan, turning long-term career goals into clear learning actions.
A few things can determine the route, including:
- Role
- Team
- Skill level
- Career goals
- Future skills needed
Many LMS solutions support this through learning paths, and AI-powered platforms, like CYPHER Learning, can go even further, recommending content and adjusting the route as people progress. Either way, pair it with regular check-ins, tying progress back to the goals from step three.
6. Measure impact and keep improving
Circle back to the goals you set in step three. Are people hitting the marks you defined? Has behaviour changed on the job, not just in a course completion report? This is where you find out whether the initiative has delivered.
Treat the results as a way to refine your approach, too. Where the initiative has fallen short, dig into why: was it the wrong method, the wrong timing, or a gap that wasn’t fully understood in step two? Feed what you learn back into the next cycle, so your upskilling strategy keeps sharpening rather than staying fixed once it’s built.
Upskilling strategy FAQs
What’s the best way to upskill?
There’s no single best method; it entirely depends on the skill and the person. Blended approaches tend to work well for most skills: pairing structured learning (a course or module) with hands-on practice, coaching, or on-the-job application. Upskilling also works best when it’s connected directly to real tasks, rather than sitting separate from the day-to-day.
What are the benefits of upskilling?
There are many benefits to upskilling, including:
- Stronger performance
- Better employee retention
- A more adaptable, resilient workforce
- Futureproofing against industry and tech shifts
- Lower reliance on costly external hiring
How do I know if my company needs upskilling?
Common signs include performance dipping in a specific area, a new tool or process rolling out faster than skills can keep up, rising errors or customer complaints tied to a particular task, or employees expressing they feel underprepared for parts of their role. That said, upskilling shouldn’t necessarily stem from a problem. Look for opportunities to grow your people consistently, not just when something’s gone wrong.
Is reskilling different from upskilling?
Yes, upskilling builds on a person’s existing role, sharpening or expanding what they already do. Reskilling prepares someone for a different role altogether, often because their current one is changing significantly or disappearing. Both are important in the workplace, but they solve different problems.
What are the top skills to improve in the workplace?
According to the World Economic Forum’s Future of Jobs Report 2025, employers rank analytical thinking as the most essential core skill, with 7 in 10 citing it as a must-have. Resilience, flexibility, and agility also rank highly.
Separately, AI and big data are named the fastest-growing skills businesses expect to need going forward.
How can I measure the impact of an upskilling programme?
Go beyond completion rates, which tend to only show participation, rather than actual change. Measure against the specific goals set before launch: changes in performance data, behaviour on the job, manager feedback, or relevant business KPIs. Comparing before-and-after data against your defined success metric is the clearest way to know if it worked.
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