Upskilling your people for digital transformation

Annee Bayeux, Chief Learning Strategist at Degreed, discusses why having the right skills is fundamental to your digital transformation strategy.
Annee Bayeux, Chief Learning Strategist at Degreed, discusses why having the right skills is fundamental to your digital transformation strategy.

Digital transformation is as much about people as it is technology. Yet, people are often overlooked in the rush to go digital — and this can significantly hinder a transformation strategy’s success. By upskilling people ready to implement new technologies and processes, business leaders can ensure that their digital transformation won’t fail due to a lack of the right skills. The following article offers some quick and cost-effective ways to do this.

Our whole lives are going digital. Everything we do is, in some way, touched by technology and none more so than our work. Yet, although workplaces are quickly adopting digital tools, many are failing to equip their people with the skills needed to use such technologies effectively. This is hindering digital transformation strategies in over half of organisations (53%).


Digital transformation is less about technology and more about the people using it. With technology, it’s just a matter of knowing what to buy and when. But your people need to adapt to an increasingly digital environment. Your organization’s success hinges on developing the next generation of skills ready to embrace automation, the Internet of Things, smart cities, the blockchain, and artificial intelligence, to name but a few.

Equipping everyone with a baseline knowledge of digital technologies will create greater opportunities to innovate with emerging solutions. People can collaborate on pilots and proof-on-concepts in their teams and add to your overall digital transformation strategy. It also empowers employees with greater visibility and ownership of the transformation occurring in their workplace.

The skills needed for digital transformation

Beyond digital skills, there are a number of ‘power’ skills that support company-wide transformation. According to CIOs, the top skills needed for digital transformation are strategy building, project management, business relationship management, user support, success measurement, and risk management. Product management, cost management and vendor management are also helpful.

Luckily, all of these skills can be built through a range of upskilling activities. Many of them don’t suit traditional classroom and instructor-led learning either, which makes them extremely cost-effective to teach your workforce.

Prioritising who to upskill first

As for who to teach, well, ideally it would be your entire workforce as everyone will be impacted by digitisation. However, if you have to prioritise, start with the groups who will be interacting with new technology and processes day in and day out. Writing for HBR, Becky Frankiewicz and Tomas Chamorro-Premuzic also recommend that you focus on the employees who “are most adaptable, curious, and flexible in the first place.” As these workers are better placed to navigate the many changes that arise through transformation programmes. They add, “Technical competence is temporary, but intellectual curiosity must be permanent.”

Learning agility

Indeed, learning agility is another useful skill that will enable your workforce to quickly upskill to new needs and technologies. It will make it much easier to introduce a new AI-driven process, for example. Learning agility isn’t something that’s easily taught through formal training. Instead, it’s developed over time by stoking people’s curiosity, motivation to learn, and making it easy for them to find upskilling resources.

Building relationship skills

As for the other skills, areas like relationship and vendor management are best taught through experiences. On the job learning opportunities can help someone develop the communication and negotiation skills needed to manage vendors and stakeholders effectively. This can take the form of a stretch assignment or shadowing a senior team member who regularly carries out this activity. Likewise, strategy building can be taught in this way, or through a senior leader mentoring employees and showing them what an effective strategy consists of.

Technical and user support skills

For user support, there will be a degree of technical and product knowledge needed that can come through practising tasks with a new tool, or through dedicated training in the new technology. Many vendors will offer this as part of their product onboarding process. A temporary redeployment into a support function will enable someone to build specific skills in understanding a user’s pain points and troubleshooting.

Product management

There are many short courses available to build product management skills and offering this kind of modular, bite-sized learning makes it easier for employees to engage with learning throughout their day. It’s less of a time commitment compared to, say, taking a day off for a seminar.

Additional learning options

Beyond this, a plethora of online content is available for people to learn from. This includes blogs, articles, whitepapers, podcasts and videos. For more technical upskilling, resources like GitHub can help people connect with a network of experts who can teach them as they work on a project. Offline, books by industry leaders can provide insights into product management, project management, cost management, overall leadership skills, and more.

Meeting every learning style

Offering a range of different learning options means people can pick the ones that best suit their learning style. Whereas some people are visual learners and may prefer a YouTube video or infographic, others find it better to take in information by reading about it. This makes it more likely that people will proactively build the skills you need — it becomes much more engaging.

Reinforcing new skills

Newly learned skills will have to be reinforced quickly. The Forgetting Curve shows that people forget 90% of what they’ve just learned within one month if it’s not put into practice. So the timing of your upskilling efforts needs to be well aligned with your strategy’s implementation. If you upskill people too early, they’ll have forgotten by the time a new technology rolls out. If your digital transformation will take a long time to implement, an alternative is to find experiential learning opportunities that can stretch newly learned skills. These can include secondments or temporary deployments in other business areas, volunteering and mentoring.

Aligning with individual interests

Upskilling involves a lot of personal effort — and sometimes a time sacrifice if the learning is happening outside of work hours. If you’re encouraging your workforce to upskill, make sure it’s in skills that align with their interests and career goals. People will be much more likely to engage with your upskilling plans if they have a vested interest in it. Of course, the entire organisation shifting to a digital process will be a good incentive in the first place, as there’s a direct impact on someone’s daily work. But an employee may also upskill ready for a future career move, whether that’s a promotion or lateral career move into another department. By knowing their career goals and interests, you can find the common ground where their skill-building and your organisation both benefit.

Ensuring you’re on track

Finally, when embarking on an organisation-wide upskilling strategy, you need a way to track all of the skills being built. This will enable you to quickly see if your skills are on track ready for your digital transformation or proactively spot and address any skills gaps that threaten progress.


A huge change

Your organisation is going through a huge change as it transforms itself for the future. Your people’s skills must also adapt. As you plan your digital transformation, don’t overlook the integral role that your workforce will play in its success. Upskill your people ready for the change now and your digital transformation won’t be waylaid by missing skills.

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Amber Donovan-Stevens

Amber is a Content Editor at Top Business Tech