The complete 8-step guide on how to upskill your employees successfully

As organizations struggle to emerge from the Covid-19 slump and the changes it has forced at the workplace, upskilling is a crucial way forward.

The complete 8-step guide on how to upskill your employees successfully

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.

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 paralyzed 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 organizations struggle to emerge from the Covid-19 slump and the changes it has forced at the workplace, upskilling is a crucial 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 prioritize learning in their organization. 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 organization”. Yet, a year later only 18% of them said that their organization had made “significant progress” in establishing an upskilling program.

This playbook is intended to be a step-by-step guide for organizations who want to build an upskilling program. 

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 prioritize learning in their organization. This figure is 68% in Canada.

Use this playbook to learn…


Assess the skills you have today


Assess the skills you will need over the next five years


Ensure employee buy-in


Set upskilling goals


Determine what learning format is most suitable for you


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


Monitor progress


Match upskilled employees with new opportunities

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 as 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.

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Why upskilling?

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 organizations 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, the report added.

“One reality is clear: increases in automation, changes in demographics and new regulations will make it much harder for organizations 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.

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 programs 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 organizations, highly engaged business units achieve 24% less turnover. In low-turnover organizations, highly engaged business units achieve 59% less turnover.

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. 

Attract the best talent

Organizations 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 organization. That’s not all. Your organization 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 programs that are focused on upskilling and reskilling their workforce.

8 steps to start your own upskilling program

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Step 1:

Assess the skills you have today

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

Organizations have traditionally used a skills matrix or a competency matrix to map the skills they need for each role as well as the existing skills available to them in different teams and departments.

Today, leading training providers offer assessment plans where they, in collaboration with their customers, map employee skills, identify skills gaps and training needs and offer training solutions to bridge these gaps. These assessments take into account each employee’s role and department and are designed to fulfill each organization’s specific needs.

Another way to assess skills in your organization is to ask your employees to create a personal skills profile using the skills visualization tool MuchSkills. Once all employees enter their skills data, team managers and the organizational leadership will be able to view on a single screen an insightful visualization of all the hard and soft skills available to them.

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. You could ask yourself the following questions: Is my industry seeing rapid technological advances that will make some key skills redundant and increase demand for other skills? Do we intend to expand to another market? Do we intend to develop a new product or solution? What skills will we need for these plans? Answers to these questions will help you ascertain all your skills needs for the future.

If you are designing your training program inhouse, 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. 

Organizations that partner with training providers can work with them to map their future skills needs so that any training programs are designed around these needs.

When you compare the list of current skills against the list of critical future skills, you ascertain the “skills gap” of the future and can use this knowledge to design your training program to make it more effective.

It is very unlikely that 100% of your workforce will need to be upskilled all at the same time. We recommend starting with a selected cohort that is the most at risk of redundancy.

Step 3:

Ensure employee buy-in

At the beginning of an upskilling program, 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 program you must have employee buy-in. The organization must make sure that it:

Communicates the benefits of the planned initiative to employees.

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 organization should be: We are all in this together… to become better together.

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. Any goals set for your employees should be specific, challenging, and time-bound. As an example, a goal could be: Each employee in X department becomes proficient in two critical future skills at the end of six months.

While setting goals, it is crucial 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.

Set upskilling goals

Step 5:

Assess what learning format is most suitable 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? Will the training be accessible to all or to a few?

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

Live Instructor-led training – virtual or in-person 

Instructor-led training is the kind of learning most of us are familiar with. In this format, an instructor conducts face-to-face training with a group or an individual in a classroom setting using a combination of lectures, presentations, group discussions, workshops etc.

Instructor-led training is one of the most traditional forms of teaching. It has several advantages, including the ability of the instructor to customize their delivery according to the skill levels or experience of the learners. Teams learn well with instructors because they are able to ask questions and get immediate feedback, collaborate with their colleagues, discuss the skills, ideas and concepts they have learned and put them to use during discussions or workshops. All this reinforces what they have learned, which boosts learning retention.

Instructor-led learning has better outcomes, according to research. Courses where human interaction was present (learner-facilitator, learner-learner and learner-colleague) was reported to be linked with more active behavioral engagement, higher cognitive engagement and stronger and more positive emotional engagement than where human interaction was absent, according to a 2019 academic study that looked at the use of blended learning at the workplace.

Instructor-led training has evolved in recent years to include a virtual aspect. Virtual instructor-led learning combines the advantages of face-to-face training with the economies, convenience and flexibility of virtual learning.

Given the shift to remote working forced by the Covid pandemic and predictions that the future of work will be hybrid it is not surprising that LinkedIn Learning’s 5th Annual Workplace Learning Report (2021) has said that going forward “learning experiences with a mix of virtual instructor-led training (VILT) and online learning — will remain the status quo”.

It is important to remember that instructors who are experts in their field and great at in-person training do not necessarily become good virtual trainers automatically. The dynamics of a virtual platform require an additional set of skills and in-person instructors may need to be upskilled themselves if they want to become efficient virtual trainers.

Essentially, if organizations opt for virtual instructor-led training, it may be best if you work with instructors who have experience in virtual training than instructors who happen to train virtually because global circumstances have forced them to.

Peer-to-peer learning

Peer-to-peer learning – where peers support each other with the learning process by transferring their own unique skills or knowledge –  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 organization 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 learned 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:

  1. 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.
  2. Hold weekly group sessions with the same format as above. Group reflection, discussion, feedback and learning (hopefully) follows.
  3. Form groups and assign them to tackle one organizational 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.

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

Mentoring: Connect employees with a mentor

Mentoring is one of the most effective ways to upskill employees which is why organizations 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. Organizations 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 organization 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

Employees whose organizations do not have an upskilling program in place often choose to educate themselves online to help themselves grow professionally.

Online learning resources include formal and informal courses, podcasts, YouTube channels 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 offer structured courses with proper instructor-led lectures and assignments, others are less intense and may be as simple as watching a training video online. 

Upskilling yourself without your organization’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.

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, organizations 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.



Customization: People working within the organization know its needs and processes best. An in-house L&D team can achieve a high level of customization and also tweak programs faster to ensure that they stay relevant to the changing needs of your employees as well as the organization.

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.


High cost: Though organizations 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.

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 organizations may find this easier to pull off than smaller organizations because they have the resources for this. Smaller organizations might find themselves and their resources stretched.



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.

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.

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.


Time taken to find and implement: With so many L&D platforms in the market, organizations 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.

Is it worth the trouble: Some organizations have unique policies/processes that they want their employees to get acquainted with. Though many training providers offer customised solutions, these organizations will need to evaluate whether it is worth their time to educate external trainers about all these processes or just get someone from the organization to hold training sessions instead.

Step 7:

Monitor progress

At this stage, organizations 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.

Organizations 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 organizations may need a Learning Management System to track progress while smaller organizations 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. 

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

Step 8:

Match upskilled employees with new opportunities

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

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

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

It’s a win-win situation for everyone.

Portions of this playbook were first published on MuchSkills, a smart skills visualization software. It has been republished here in collaboration with them.

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