How to upskill your team: An 8-step guide

You've been asked to upskill your team, or you know it needs to happen. The first instinct is to find a course, book a trainer or roll out a programme. But before any of that comes a question most organisations skip: What skills does this team have right now?

Without that baseline, upskilling is guesswork. You end up training people in skills they already have, missing the gaps that matter and spending on programmes you can't measure. Employers feel this at scale: In the WEF Future of Jobs Report 2025, 63% name skills gaps as the biggest barrier to changing how their business works. Training is easy to buy. What most organisations lack is a clear view of where their gaps are.

This guide is for HR Directors, L&D leads and people managers who want to build a successful upskilling programme, one that closes the gaps that matter, starting with the ones you can see.

Why most upskilling programmes stall before they start

Most organisations know they need to upskill their people, and most also know that upskilling is easier said than done. In BCG's 2026 Creating People Advantage study of more than 7,000 HR and business leaders, upskilling and reskilling ranked 7th in importance but only 14th in current capability. Part of the reason is that the target keeps moving: In Gartner's 2025 research, 48% of HR leaders said demand for new skills is evolving faster than their talent structures can support. Programmes get announced while the gaps they were meant to close shift underneath them.

The gap between intention and execution usually comes down to one thing: Organisations try to build an upskilling programme without first knowing what skills they have. That is why mapping your team's current skills comes first: Everything else in this guide is built on it.

How is upskilling different from reskilling? Upskilling means developing higher-level or new skills within someone's current field. An example of upskilling could be a software company training all its developers in a new programming language so that they can develop new products and solutions. Reskilling means training someone to do a different job entirely. An example of reskilling would be an accountant who retrains to become a web developer.

8 steps to upskill your team

Step 1: Map the skills your team has today

Before you can identify what your team needs to learn, you need to know what they can already do. This means building a live, accurate picture of the skills, capabilities, and certifications across your workforce, built from what the people themselves report instead of job titles or CVs.

A skills map gives you the baseline against which you'll measure everything: the gaps you need to close, the strengths you can build on, and the hidden expertise that might already exist somewhere in the team. Without it, every subsequent step in your upskilling programme is an estimate.

Most organisations don't have that picture yet. In Gartner's 2024 HR research, only 8% of HR leaders said their organisation has reliable data on its workforce's skills. Everyone else is deciding on training spend, hiring and team make-up with a far hazier view of what their people can do.

MuchSkills gives every employee a skills profile rated on the 1–9 Goldilocks scale, detailed enough to be meaningful and simple enough for everyone to complete. Managers see what their team can do across every skill category. HR and L&D get an organisation-wide skills map they can filter, analyse and act on, and the skills gap analysis tool shows the distance between where people are and where they need to be.

Step 2: Identify the skills your team will need

Once you know what skills you have, map the ones you'll need, usually over the next three to five years. These must be in sync with any changes expected in your industry as well as your long-term business strategy and goals. Perhaps your industry is seeing rapid technological advances that will make some key skills redundant and increase demand for others. Perhaps you intend to expand to another market or develop a new product or solution and need specific skills for this plan. Whatever it is, make sure that your list of future skills takes all this into account.

A practical approach: Ask function heads to name the one or two skills their team members will most certainly need over the next three to five years. Cross-reference against your current skills map. The distance between those two lists is your upskilling agenda. In MuchSkills, the Analysis feature lets you build role and competence lists, draft role requirements with AI and see how well your team covers each one.

Do remember that 100% of your workforce is unlikely to need upskilling all at the same time. Identify the cohorts most at risk and start there: those whose current skills are most likely to become obsolete, or whose development is most directly tied to the organisation's strategic priorities.

Step 3: Get employee buy-in

Upskilling programmes that are done to employees rather than with them rarely stick, so start by communicating clearly what the programme is trying to achieve, why it matters for the organisation and for each person, and what support they'll get: time, resources and backing from leadership. The message from the organisation should be: We are all in this together, to become better together. Make it just as clear that the programme is an investment in each person and has nothing to do with performance management.

It is always rewarding to put employees in charge of their learning wherever you can. Yes, you want them to learn a certain set of skills, but allowing them to choose which critical skill to develop first gives them a say in the process as well as a sense of ownership. And when employees take ownership of their learning, they are more invested in it, more accountable and more likely to put what they learn to use in their job.

Step 4: Set upskilling goals

At a time technology has enabled a mind-numbing amount of personalisation (think hyper-targeted ads on Instagram and YouTube and Netflix movie recommendations), it's quite remarkable that a one-size-fits-all mode of training continues to be popular. It doesn't work for upskilling goals either. Different employees have different starting points, different development priorities and different timeframes, and their goals need to reflect that.

Whatever the goals, they should be SMART: specific, measurable, attainable, relevant and time-bound. A vague goal ("improve data skills") is harder to commit to and harder to measure than a specific one ("move from beginner to intermediate in data visualisation within six months"). A team goal works the same way, for example: Each employee in X department becomes proficient in one critical future skill within six months.

Connect individual development goals to the organisation's skills priorities from Step 2, so people can see where their growth fits. With MuchSkills employee development, employees set goals on specific skills, get AI guidance on the route to each goal and connect with colleagues working on the same skill. Managers see those goals and the progress against them, so a personal goal becomes a shared commitment.

Step 5: Choose the right learning format

How your team learns best, and what your budget and time allow, will shape the learning format. Before you choose, do remember one hugely important point (we cannot emphasise this enough): Upskilling isn't only about hard skills. Soft skills such as communication, leadership, adaptability and collaboration are as critical (if not more so) to your team's success, and they are often harder to build through traditional training. So weigh each option below for both kinds of skill.

Peer-to-peer learning is one of the most effective and underused approaches. The default position of many leaders is to bring in outside experts as trainers. But that ignores the fact that every organisation has immense reserves of expertise that can be tapped for the benefit of all. Learning from colleagues builds soft skills in particular, and it reduces the risk of institutional knowledge walking out the door when someone leaves.

It also takes some of the sting out of feedback. Having peers evaluate our work performance feels less stressful than having managers do so because the power dynamic is different. For one, peers do not have control or influence over our salary or career progression, which is why it's easier for us to discuss mistakes made and lessons learnt with them. Similarly, when everyone is being evaluated by each other, all participants make the effort to give valuable and meaningful feedback.

Peer-to-peer learning can take place in several different formats. Here are two:

• Pairs: Pair two colleagues for regular sessions where they discuss the challenges they faced during the past week or month, how they responded, whether their response got the desired outcome and the lessons they learnt from the experience.
• Problem groups: Form groups and assign them to tackle one organisational problem over a few months. At the end of the exercise, ask them to reflect on their learnings, challenges and achievements, and to give each other feedback on what could have been handled better.

Certifications are particularly valuable in technical fields. Data analytics, cloud computing, project management, and AI and machine learning all have well-regarded certification programmes, some of them free. They build credibility as well as capability and are easy to track.

Mentoring, which connects less experienced employees with colleagues who have the skills they're developing, works especially well for leadership, communication and other interpersonal capabilities. Reverse mentoring, where younger employees help more senior colleagues develop digital skills, has become increasingly valuable. A note of caution: You will need to assess if your internal team has the capacity to mentor while also doing their other important work.

Job rotation builds cross-functional skills and relationships between teams, and it is particularly useful for preparing people for broader roles.

Online and self-directed learning gives flexibility: Employees can learn at their own pace, in their own time. Platforms like Coursera, LinkedIn Learning, and Udemy offer structured courses across most skill areas.

Step 6: Build or buy the programme

Whether to build an upskilling programme in-house or work with an external training provider depends on your internal expertise and bandwidth, whether you need one-off or continuous learning, and whether an off-the-shelf course will do or the training has to fit your organisation's context.

In-house programmes offer the highest level of customisation and keep sensitive data internal, but they take time and resources to build. External providers can move faster and bring trainers with both subject-matter expertise and considerable experience in training (yes, there is a difference), but they require investment in finding the right partner and briefing them properly. Many organisations use a hybrid: external providers for technical certification programmes, internal capability for culture, process, and context-specific skills. For continuous or large-scale training, a learning management system (LMS) helps deliver content and track completion. MuchSkills connects to LMS platforms such as Skillsoft Percipio and Udemy, so courses can be linked to the roles, skills and certifications they build, and each gap shows up with a route to close it.

Step 7: Track progress

Once the programme is running, track it. This is where L&D has traditionally struggled, because employee surveys and test scores could never conclusively tell if the training was actually working. Watching how skill levels change gives you a better answer.

Track at two levels: whether each person is moving up in the skills they committed to, and whether the gaps you identified in Step 2 are closing across the team.

MuchSkills gives both views. Employees update their skills profiles as they develop, and the 1–9 scale shows progress step by step instead of a simple completed or not completed. Managers and HR see the overall picture in Analysis, where historical analytics show how skills across the team have shifted since the programme began, and where the next round of investment should go. If you have the resources, sharing progress stories internally, from teams or individuals who have made real headway, helps keep momentum across a longer programme.

Having said that, it is indeed tough to hold a job, handle the demands of any family, AND also upskill. So, be kind to your people if their learning slips because of work or family-related disruptions, or even a dip in motivation. It's ok for them to feel distracted or to struggle to keep up with a course. Let them take a break and breathe, then help them pick up again, ideally by protecting time for learning rather than adding it to an already full week.

Step 8: Match upskilled employees with new opportunities

Many upskilling programmes stop before the last step, matching people with new opportunities, yet it decides whether employees believe the investment was real.

When someone has developed a new skill, they need the opportunity to use it. Without a role, project or responsibility that calls for it, the development stays theoretical and the employee starts wondering whether it was worth the effort.

This is also where upskilling meets internal mobility. With good skills visibility, you can look for internal candidates for hard-to-fill roles before going to the market, and you will often find the capability was already there. In fact, a great way of planning upskilling is to work backwards from those roles. Identify internal candidates who possess some of the skills needed for roles the organisation has had difficulty filling, then give those candidates the opportunity to upskill so that they are able to fill those positions. It's a win-win situation for everyone.

MuchSkills finds people by skill, certification and availability across the whole workforce, so someone who completes a course or moves up a level becomes visible for the next project or role that needs them. Organisations that manage this tend to keep their people longer: In LinkedIn's Workplace Learning Report 2022, companies that excel at internal mobility kept employees for 5.4 years on average, against 2.9 years at companies that struggle with it. Mapping skills, upskilling against the gaps and then offering the next opportunity is a cycle that gives people a reason to stay.

How skills visibility changes upskilling

Every step in this guide is harder without a live picture of what your team can do, and Step 8 is almost impossible without knowing what someone has developed and where the organisation can use it.

The MuchSkills HR and L&D solution is built for this workflow, from skills mapping and gap analysis to development goals and internal mobility. If you want to understand the scale of the skills visibility problem most organisations are working with, the MuchSkills skills statistics playbook pulls together the research in one place.

Build on what your team already knows

Organisations that upskill well start by knowing what their people can do, and only then decide what to teach them.

Book a demo to see how MuchSkills gives HR and L&D teams the skills visibility they need to build upskilling programmes that close the right gaps – and give people somewhere to go when they do.