What an Effective Cross-skilling and Upskilling Strategy Looks Like

Like Janice from human resources after her second morning coffee, nothing stands still for long in the workplace. We live in times of constant change, driven by technological development and a whole host of external factors that are completely out of our control. 

With all this in mind, how are you supposed to ensure that your workforce is equipped to handle the demands of today, let alone the demands of tomorrow? One of the best ways is to implement an effective cross-skilling and upskilling strategy. 

Job done? Not quite. Despite being a bit of a mouthful, cross-skilling and upskilling are easier said than done. Building an effective strategy requires a good deal of thought and expertise to get it right — and that’s where we can help. 

All this being said, putting the time into cross- and upskilling pays off. Not only does it benefit managers by providing a more skilled workforce, it also helps employees develop their skills (and their career prospects while they’re at it).

In this article, we’ll break down exactly what an effective strategy looks like — and how you can put it into practice in your business.

Pro tip: Check out our webinar on how to upskill leaders into coaches. It’s a cracker, we promise (and we most definitely aren’t biased).


What’s the difference?

What skilling? Up-whating? Good questions. Allow us to explain.


Sometimes known as cross-training, this is the process of developing transferable skills and knowledge that are applicable across roles and functions. Cross-skilling provides employees with a broader skill set, allowing them to adapt to changing roles and requirements more easily.

Cross-skilling also makes organisations more flexible and adaptable to change, maximising the talent potential currently at their disposal rather than dipping into the job market.

For example: to help improve cross-departmental collaboration, an HR director might learn the basics of L&D management — and vice versa.


This is the process of improving existing skills or acquiring complementary skills. Upskilling basically makes employees more confident in their current roles and closes skills gaps for the organisation. In an ever-changing world, upskilling helps ensure that employees’ skills remain relevant and effective.

For example: when a promising young talent is promoted to their first managerial role, they might need some help improving their managerial soft skills such as active listening, mentoring, and leadership. You know, those soft skills every bad manager in history definitely has…right?

This is backed up by the brains over at the CIPD. They say that communication, team building and collaboration are some of the skills managers need to develop as we settle into a hybrid working system.¹

Together, these two approaches allow your business — and employees — to future-proof itself against an ever-shifting business landscape through continuous learning. Now that we’ve cleared that up, let’s look at what an effective skilling strategy might look like. 

Suggested reading: Read our guide on the best ways to upskill your employees.

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Tailored to your employees’ needs

When it comes to learning, one size most certainly doesn’t fit all. In fact, one size might not even fit anyone. That’s because learning is a personal process, not a bumbag with adjustable straps. 

Everyone has their own unique needs, preferences, and goals. Rigid learning pathways have little-to-no positive effect on your employees. If anything, they might do more harm than good — especially in a world where remote work is the standard.

That said, businesses must tread carefully. Personalising skilling strategies can also lead to problems. How do you design potentially hundreds or thousands of individual learning pathways while constantly updating them to ensure that they are relevant? 

So what’s the best way forward? In our experience — and without wanting to sound too smug, we do have a fair bit of it — the best way to find a sense of balance is to have access to learning content that is engaging, flexible, and evergreen. This way, it seamlessly fits into the strategies you develop, allowing it to become part of the natural flow of work. Accessing this learning content can be done one of two ways:

  1. You throw all your money, time and energy into trying to curate fun, flexible content with zero plan, bankrupting your business and sending your CEO fleeing to Mauritius.
  2. You invest wisely in digital learning material designed by experts to break complex topics down into digestible chunks, delivered by a hilarious bunch of British comedians.

Doesn’t stretch anyone too thin

While cross-skilling, in particular, is a powerful way to harness employee skills and make your workforce more adaptable and capable, piling too much on your employees’ plates can soon backfire. 

First of all, asking employees to acquire new skill after new skill without any kind of reward for their hard work can lead to disengagement and burnout. They may feel like you are asking too much of them without giving anything in return. They may simply want to focus on building on their existing knowledge instead.

Secondly, you may find that some people are resistant to learning new skills that they see as irrelevant to their job role or ambitions — and they may have a point. I mean, how excited would Malcolm from Accounts really be about learning how to write snappy Instagram posts? And how much sense would it make from a business perspective?

Here are some tips to head these potential issues off: 

  • Cross-skill people in areas that make sense from a professional, personal, and organisational perspective. Cross-skilling is about broadening people’s skill sets, not ripping them up and starting again. 
  • Make sure that your strategy and learning content is engaging and entertaining. This will help people buy into the process and make it worth their while. 
  • Emphasise to employees why they are being asked to develop this skill. What purpose does it serve? How will it help them improve as employees and/or people? 

Covers a variety of crucial skill sets

When talking about upskilling and cross-skilling, there’s a temptation to think only in terms of hard skills — those process-related, quantifiable, often-technical skills like coding, writing, or accounting — and ignore soft skills altogether. 

That’s because soft skills — those hard-to-measure capabilities such as communication skills, teamwork, and emotional intelligence — have historically been left to the wayside. But as you’ve probably guessed by the way this paragraph is going, that is a huge mistake. 

Soft skills are important not just in terms of bridging communication gaps, improving time management, and articulating ideas — they effectively champion hard skills as well. 

For example, you might have someone who’s an absolute legend at data analytics. However, if they aren’t able to effectively communicate their ideas and the importance of their work, all those meaty insights they uncover may slip under the radar. 

This can be improved by:

  1. Identifying the soft skills your team is lacking.
  2. Investing in the training your team needs to really develop those soft skills.
  3. Regularly checking in with your team to ensure they feel supported and listened to. 

Pro tip: You can learn all about why soft skills are more crucial than ever in this blog.

Video Arts is here to help

Despite the complexities and challenges that come with upskilling and cross-skilling, it is critical to be proactive. Doing nothing means standing still in a world that is constantly changing. 

If you’re feeling daunted, fear not. Video Arts is here to help. As a pioneer in the workplace learning game, we’re well-versed in anything and everything to do with upskilling, reskilling, and cross-skilling — pretty much all of the skillings. 

With decades of experience producing video learning content that is genuinely entertaining, fun, and informative, we’ve got the stuff you need to deliver a truly engaging learning and development strategy that drives long-term success. 

If you’re just a little bit tempted to find out more, why not get in touch with one of our learning experts today?  

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¹ Planning for hybrid working | CIPD 

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