Upskilling: An 8-step guide to successfully upskill your employees

Upskilling is certainly not a new trend, but the Covid-19 pandemic has ensured it is no longer an option but an imperative.

CEOs and workers alike have been concerned about skills for a few years now. The root of these fears is the rising application of technology such as automation and Artificial Intelligence or AI at the workplace. While CEOs have been worried that the lack of essential skills in their workforce would pose a threat to future business growth, workers are anxious that their skills could become obsolete very soon. So much so that they are keen to upskill or even completely retrain to improve their employability prospects, according to a 2019 survey by PwC.

MuchSkills- upskilling - a 7-step guide to successfully upskill your employees

Upskilling is all the more vital today because of the blow the Covid-19 pandemic has dealt the global economy. Millions of people have lost their jobs across the world after containment measures imposed since March 2020 paralysed entire industries such as hospitality and travel and also led to a sharp contraction in demand in many others. The crisis accelerated the trend of digitization and automation too, which has in turn increased the demand for new (largely digital) skills.

As organisations struggle to emerge from the Covid-19 slump and the changes it has forced at the workplace, upskilling may be the only way forward.

In fact, upskilling and reskilling is the top priority for learning and development (L&D) professionals globally, according to LinkedIn Learning’s 5th Annual Workplace Learning Report (2021). The report added that 62% of CEOs surveyed in the US now prioritise learning in their organisation. This figure is 68% in Canada.

Several CEOs, however, are already aware that upskilling is easier said than done. Before the pandemic struck, upskilling initiatives were not being implemented as fast as CEOs liked, said a 2019 PwC report. The majority of CEOs surveyed for that report agreed that “significant retraining/upskilling was the most important way to close a potential skills gap in their organisation”. Yet, a year later only 18% of them said that their organisation had made “significant progress” in establishing an upskilling programme.

This playbook is intended to be a step-by-step guide for organisations who want to build an upskilling programme. Before we proceed, do remember a hugely important point; we cannot emphasise this enough: Upskilling is not just about hard skills; soft skills are as critical (if not more) to the success of your organisation in the workplace of the future.

Use this playbook to learn…

How to upskill your employees. This playbook covers the following eight steps below:

Step 1: Assess the skills you have today

Step 2: Assess the skills you will need over the next five years

Step 3: Ensure employee buy-in

Step 4: Set upskilling goals

Step 5: Determine what learning format works best for you

Step 6: Design the program in-house or consider partnering with an external training provider

Step 7: Monitor progress

Step 8: Match upskilled employees with new opportunities

A 7-step guide to successfully upskill your employees
What is upskilling?

What is upskilling

The definitions for upskilling range from really simple to complicated.Briefly, upskilling is the process of using education and training to develop higher level or new skills and capabilities in employees to improve work performance, as well to enable them to stay competitive/relevant in the job market.

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.

How is upskilling different from reskilling?

Reskilling is training to learn completely new skills so you can do a different job. An example of reskilling would be an accountant who retrains to become a web developer.

Why upskill - graphic

Why upskill?

Upskilling is certainly not a new trend, but the Covid-19 pandemic has ensured it is no longer an option but an imperative.

Here are just a few reasons why both employers and employees should invest in upskilling.

🔥 Upskill or perish

It is in the best interests of both organisations and employees to upskill to remain relevant in the future.

In October 2020, the World Economic Forum warned in its Future of Jobs report that the “double disruption” of job losses caused by increased automation and the economic impact of the Coronavirus pandemic could displace an estimated 85 million jobs by 2025.

Though 97 million new roles are likely to be created during this period, displaced workers will need to be reskilled and upskilled to take them on, the report said. Skills gaps will continue to be high. To plug skills gaps companies estimate that on average around 40% of workers will need reskilling of six months or less while 94% of business leaders surveyed said they expected employees to pick up new skills on the job, up from 65% in 2018, it added.

“One reality is clear: increases in automation, changes in demographics and new regulations will make it much harder for organisations to attract and retain the skilled talent they need to keep pace with the speed of technological change. They will have to grow their own future workforce,” said PwC’s 23rd Annual global CEO Survey.

Increased automation and the economic impact of the Coronavirus pandemic could displace an estimated 85 million jobs by 2025

Source: Future of Jobs

📈 It's good for business

Companies that invest in upskilling their employees are essentially helping them do their job better. All this has tangible benefits. CEOs with more advanced upskilling programmes cite improved engagement, innovation and ability to attract and retain talent. Companies with high employee engagement have 21% greater profitability, according to Gallup. Similarly, employees who are more motivated and engaged are also less likely to leave, reducing employee turnover, which is also good for business. The Gallup study found that in high-turnover organisations, highly engaged business units achieve 24% less turnover. In low-turnover organisations, highly engaged business units achieve 59% less turnover.

Companies with high employee engagement have 21% greater profitability, according to Gallup.

Source: Gallup

🙋🏻 Employees expect it

If the above arguments weren’t convincing enough, here’s one more: employees expect employers to equip them with the skills they need.

87 percent of Americans recognize that they need to continually train and learn new skills if they want to advance in their careers and not be left behind in a rapidly-changing workforce, according to a 2016 survey conducted by the Pew Research Centre. Forty-nine percent of those surveyed said that they believed the employer was responsible for ensuring that they had the right skills to be successful in “today’s economy”.

Employees also report that they’re willing to spend up to two days per month on training to upgrade their digital skills, if offered by their employer.

87 percent of Americans recognize that they need to continually train and learn new skills if they want to advance in their careers.

Source: Markle Foundation

🦄 Attract the best talent

Organisations that commit to their employees’ learning regardless of whether they will stay six months or 10 years, and also allow them to choose the pace of their learning, will more often than not attract dedicated employees who are genuinely committed to their own betterment and that of their organisation. That’s not all. Your organisation will also gain a reputation that will see talent elsewhere keen to work with you.

Upskilling is a global imperative

Recognizing that upskilling and reskilling workers is the key to remaining competitive in a rapidly changing world, the European Union and major economies like the US, India and Singapore have, over the last five years, launched dedicated programmes that are focused on upskilling and reskilling their workforce.

7 steps to start your own upskilling programme

8 steps to start your own upskilling programme

Assess the skills you have today

Step 1: Assess the skills you have today

Map the core competencies and skills you currently have in your organisation. This data will form the baseline against which you can measure progress.

One of the ways you can do this is by asking your employees to create a personal skills profile using the skills visualisation tool MuchSkills. Once all employees enter their skills data, team managers and the organisational leadership will be able to view on a single screen an insightful visualisation of all the hard and soft skills available in the organisation. Users can choose how to visualise skill categories – the options available are a simple bubble chart or a 3x3 expertise scale.

Assess your team's skills illustration

Assess your team's skills

One of the ways you can do this is by asking your employees to create a personal skills profile using the skills visualization tool MuchSkills.

Assess the skills you will need over the next five years

Step 2: Assess the skills you will need over the next five years

Identify the skills you will need in the future. Do remember that these must be in sync with any changes expected to take place 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 other skills. 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 requirement for “future skills” takes all this into account. One way of drawing up this list is to ask all function heads to suggest one skill that their team members will most certainly need over the next five years. 

When you compare the list of current skills against the list of critical future skills, you will be able to ascertain the “skills gap” that will help you plan your upskilling programme.

Do remember that 100% of your workforce is unlikely to need upskilling all at the same time. You need to identify the cohort that is the most at risk of redundancy and start with them.

Ensure employee buy-in

Step 3: Ensure employee buy-in

At the beginning of an upskilling programme, the biggest challenges are to motivate and align resources, according to CEOs surveyed by PwC in 2020. Therefore, to ensure the success of your upskilling programme you must have employee buy-in. The organisation must make sure that it:

Communicate benefits

Communicates both the benefits of the planned initiative to employees.

Be supportive

Makes it clear that the employees will be supported in terms of resources such as time availability and any training material if necessary.

The message from the organisation should be: We are all in this together… to become better together.

Set upskilling goals

Step 4: Set upskilling goals

A one-size-fits all approach to upskilling is impractical. After all, different employees have varying degrees of expertise in certain critical skills or none at all, and employees in some departments are more likely to see technology-related disruptions than those in others. The training plan and goals for each will change accordingly. But do remember, whatever the goals, they should be SMART = Specific, and Measurable, Attainable, Relevant and Timebound.

As an example, a goal could be: Each employee in X department becomes proficient in one critical future skill at the end of six months.

While setting goals, do remember that it is always rewarding to put employees in charge of their learning. Yes, you want the employee 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 and more accountable.

Step 5: Assess what learning format works best for you

How do your employees learn? The learning format you choose depends on your specific requirements, learning objectives and resources. Here are some of the questions you can ask yourself as you mull over the options available: Are you looking at developing specific skills or domain knowledge or both? What is the time frame you are comfortable with? How  much time and money are you willing to spend to enable employees to gain these new skills or knowledge? Where do you plan to get the expertise from? External consultants or internal leadership? How will the training commence? Remote learning, weekly workshops or a classroom in the local college? Will it be accessible to all or to a few?

There are several ways people can learn. The different ways of learning include:

👯 Peer-to-peer learning/coaching

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.

Peer-to-peer learning is considered one of the best ways of learning because it covers all four stages of what experts refer to as the “learning loop”: gaining knowledge, practicing through application of that knowledge, getting feedback and reflecting on what has been learned.

It is also an excellent way to learn soft skills such as leadership, active listening, effective feedback, and empathy, all of which are expected to play a key role in the future of work.

It ensures continuity too, by reducing the chances of the organisation losing institutional knowledge with the departure of employees.

Another benefit of peer-to-peer learning is that employees get a 360-degree view of their performance from their peers through informal conversations/formal 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 (peers), all participants make the effort to give valuable and meaningful feedback.

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

  •  Pair two colleagues together for regular one-on-one sessions where they discuss the challenges they faced during the past week/month, how they responded to it, whether their response got the desired outcome and if so (or not) the lessons they learnt from the experience.
  • Hold weekly group sessions with the same format as above. Group reflection, discussion, feedback and learning (hopefully) follows.
  • 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, achievements and give each other feedback if things could have been handled better.

It’s best to appoint a moderator (who is not a manager) during the group sessions to ensure that the group stays on track regarding the topic, and that discussions are positive and meaningful.

Peer-to-peer learning is considered one of the best ways of learning

Source: HBR

📜 Certifications

Certifications are another great way to upskill employees. Besides increasing and updating knowledge and skills, certifications build professional credibility.  In fact, some of the top skills in demand over the past few years – data analytics, Artificial Intelligence and Machine Learning, Cloud Computing, Project Management, Digital Marketing – have professional certifications run by leaders in the field, some of them are free.

The drawback of certifications is that it is largely available only to those in the tech space.

👩🏽‍🏫Mentoring: Connect employees with a mentor

Mentoring is one of the most effective ways to upskill employees which is why organisations have encouraged it for decades. Traditionally, it involves a more experienced person (usually older) sharing their knowledge and skills with a less experienced person (usually younger) in order to help them grow both personally and professionally.

In the digital age, the concept of reverse mentoring has caught on. It usually involves a younger employee helping a mature employee upskill with regard to new technologies and digital tools.

The benefits of mentoring are many. The mentee gains in confidence because of their increased professional competence. The mentor feels a sense of fulfilment because they are recognized for their knowledge, are able to hone their leadership skills, and are also exposed to fresh ideas and different perspectives through the mentee. Both mentor and mentee benefit by being exposed to each other’s professional networks now and long after they cease working together. Organisations benefit because mentoring increases motivation levels, attracts talent and reduces attrition.

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

In this upskilling strategy, employees rotate between different jobs at the same organisation to gain new experience and skills. At the end of this exercise, the employees can return to their original role richer for the experience, or grow into a new role.

The benefits of job rotation for both employer and employee include upgraded knowledge and skills, improved performance and productivity, cross-trained workers who are able to fill in for different roles at short notice, stronger relationships between employees in different departments, and a greater appreciation by all of the challenges everyone faces at work.

👨🏽‍💻Self-learning, online

Online learning resources include formal and informal courses, podcasts, videos and webinars hosted by domain experts.

Several online learning sites offer a wide variety of courses whose levels range from introductory to advanced. While some like Coursera and Open Learn offer more structured courses with lectures and assignments others resources – Udemy or even YouTube videos – are less intense.

Depending on the platform, the courses offered are both free and paid. Coursera has a mix of paid and free courses but learners can also “audit” some paid courses for free. This means that you can take the course without being assessed or being given a certificate of completion. Open Learn has 1000+ courses that are completely free.

Self-learning is often the option of employees whose organisations do not have an upskilling programme in place. If you are an employee, upskilling yourself without your organisation’s support can be quite challenging. However, do remember that it will help you in the long run. Set aside time to learn and be disciplined about it by keeping track of deadlines and ensuring you stick to them.

Having said that, it is indeed tough to hold a job, handle the demands of any family you may have, AND also upskill on your own. So, be kind to yourself if you are unable to proceed with your learning as planned because of work or family-related disruptions or even the lack of motivation. It’s ok to feel distracted and/or find that you are struggling to keep up with the demands of the course/training. Take a break, breathe. Remind yourself that you are investing in your future and that of your loved ones…and lumber on.

Design your upskilling program in-house or consider partnering with an external training vendor

Step 6: Design the program in-house or consider partnering with an external training vendor

Your unique training requirements – if you need continuous or one-off training or whether one department or many need training – are among the factors to consider while determining whether to set up an in-house training team or outsource your entire L&D program.

For instance, companies often want to start a training program but they simply do not have the bandwidth to start one from scratch themselves. They would rather spend their time doing what they are good at: developing their product/solution and keeping their customers happy. In other cases, organisations may require rigorous and continuous training across multiple departments like sales, marketing, legal and IT. With each of these departments having their own unique needs, an internal learning and development (L&D) team may struggle to develop training modules tailored to each department and deliver them on time.

In all these cases, outsourcing the program to an external training provider is a great option.

On average, 28% of companies surveyed for the Training Industry Report 2019 said that they mostly or completely outsourced Learning Management System (LMS) operations/hosting (up from 26% in 2018), while LMS administration and learner support largely were handled in-house (78%). Instruction/facilitation was handled about equally in-house (47%) and outsourced (53%), it added.

Below, we talk about a few advantages and disadvantages of both in-house training and outsourced training.



  1. Customisation: People working within the organisation know its needs and processes best. An in-house L&D team can achieve a high level of customisation and also tweak programs faster to ensure that they stay relevant to the changing needs of your employees as well as the organisation. 
  2. Confidentiality: All your data stays with you. When you design your own training program with an in-house team you ensure that you don’t have to share employee data or other confidential business data with an external entity. Having said that, most agreements with training providers usually have a built-in confidentiality clause.


  1. High cost: Though organisations will save on the cost of hiring trainers, they will have to bear the cost of setting up an L&D team, buying or licensing any training-related hardware and software or other tools they need for their program. On the other hand, many L&D platforms come with their own training management systems that your employees can simply login to use.
  2. Time taken to implement: Setting up an L&D program – hiring a team, brainstorming, designing and then implementing a training program – will take time and effort. Larger organisations may find this easier to pull off than smaller organisations because they have the resources for this. Smaller organisations might find themselves and their resources stretched.



  1. Faster development and execution: The process from conceptualisation to training is substantially shorter if you outsource your L&D. The best training providers will not only work with you to define the goals and outcomes of what you want to achieve and identify the stakeholders that will benefit, but also help you design a course that contains the right blend of learning options mentioned in the step above.
  2. Access to subject-matter experts + expert trainers: Training platforms have a number of well-qualified trainers on board; you don’t have to hunt for them. These people have both subject-matter expertise and considerable experience in training (yes, there is a difference). They will also be acquainted with the latest training and learning methodologies.
  3. No long-term commitment or flexibility: If you aren’t happy with your external L&D team you don’t have to continue with them. Even if you love their work, you can downscale or upscale training depending on your business needs at each point in time, ensuring that you save costs. It’s not easy to do the same thing when you have hired people and spent time and resources to set up your own in-house L&D team.


  1. Time taken to find and implement: With so many L&D platforms in the market, organisations will need to thoroughly assess them all and pick the one most suitable to their needs. Working with them to deliver customised solutions to fulfil your specific training requirements will also take time.
  2. Is it worth the trouble: Some organisations have unique policies/processes that they want their employees to get acquainted with. Though many training providers offer customised solutions, these organisations will need to evaluate whether it is worth their time to educate external trainers about all these processes or just get someone from the organisation to hold training sessions instead.

Step 7: Monitor progress

At this stage, organisations will have their list of critical skills for the future and their upskilling plan and have either hired a professional training provider or designed their own training program.

Once the training starts, it’s time to monitor progress.

Organisations that engage training providers will be able to use the platform to track progress over time. Among those that have chosen the in-house option, larger organisations may need a Learning Management System to track progress while smaller organisations can appoint managers or team leaders to create a chart or dashboard to monitor each individual’s progress towards their upskilling goals.

Skills visualisation tools such as MuchSkills gives its users a 3x3 expertise scale that helps them track their skills growth over time. In its next release, users will be able to plan their upskilling by scrolling forward to set their skills goals for the future. They can monitor their progress on MuchSkills as they work towards those goals.

If the organisation has the resources for it, the HR team can showcase any success stories internally to motivate other employees.

The MuchSkills 3x3 expertise scale


The MuchSkills tool has a 3x3 expertise scale that helps users keep track of their skills growth over time.

What to do after a one-on-one

Step 8: Match upskilled employees with new opportunities

Once the first phase of your upskilling programme is over and employees have gained new skills or built on existing ones, organisations must give the newly upskilled employees the opportunity to apply for internal positions that require these skills. This doesn’t only demonstrate the organisation’s commitment to upskilling but further builds employee engagement and organisational resilience to the changes that are inevitably hitting businesses globally this decade.

In fact, a great way of planning upskilling is to:

  • Identify internal candidates who possess some of the skills needed for roles the organisation has had difficulty filling.
  • Give those candidates the opportunity to upskill so that they are able to fill those positions.

It’s a win-win situation for everyone.

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