The Ultimate Guide to Upskilling

Career upskilling is one of the most valuable things you can do with your free time, especially if you’re the kind of person who finds joy in learning new skills. While upskilling at work is commonplace, if you really want to improve your skills at work then it may be worth devoting some of your personal time to the challenge.

That being said, working a nine to five doesn’t leave much time left over for personal development and the idea of spending your precious free hours doing extra work can seem daunting.

In this article, we’d like to break the upskilling process down into simple steps to show how, with the right planning, you can portion out the learning process without ever getting too overwhelmed.

We’ll be splitting the process into distinct, manageable tasks so that you can divide your own work up and keep yourself motivated. We’ll also be talking about ways to integrate upskilling into your regular work hours and persuade your company to invest in you.

Step 1: Lay Out Your Goals

So you’re interested in career upskilling? That’s a great goal and an excellent use of your time but before you go any further it’s important to decide exactly what upskilling means to you.

In its simplest sense, the term upskilling just means learning new skills that will be valuable in a career context. That could be anything from building a site so you can practise your SEO to reading a self help book in order to improve your people skills.

Upskilling can be very specific to your job or industry or it can be very general. It can be something that happens during work hours as professional training from your company or it can be a personal time investment.

And all that is just the what and the how of skilling. The other big question you have to ask is the why.

Put simply, you should have a clear purpose in mind for learning a new skill. Does that skill interest you? Which jobs do you believe that skill will open up to you? Do you think the new skill will make you better at what you’re currently doing?

Goals are vitally important because they’re a fundamental part of how we track progress – a subject we’ll be exploring in more depth further on. For now, suffice it to say that without goals, it’s easy to get stuck in the nebulous area of generic ‘improvement’ without a concrete sense of how and when you’ll have achieved what you’re aiming to achieve.

Step 2: Do Your Research

If the first step towards career upskilling is all about knowing what you want to do, then this second step is about finding out how you’re going to do it.

Although, in practice your research and your goals should be more of a cyclical process – the one informing the other – every time you establish a clear aim it’s important to then find out what the steps you need to take are.

So you want to apply for x job role? Amazing, now find out what employers are looking for and learn those skills.

You want to learn something but you aren’t sure how? Go online and start looking for resources. Don’t be afraid to reach out to people in online communities or on LinkedIn to ask what they did to get where they are.

Most importantly, don’t underestimate the importance of learning how to learn. There’s always more than one way of learning a skill, whether that’s speaking a new language or learning to program.

If you’re struggling to find a way that works for you, then what you need to do is find out how other people are learning, why it works for them, and the lessons you can take away.

Step 3: Talk To Your Boss

Although a lot of upskilling does ultimately happen during personal hours, it’s worth noting that you shouldn’t give up on the prospect of being able to learn while you earn. That said, if you’re looking to improve your skills at work, then it’s important to keep a realistic outlook on what your company will accept.

While some companies are willing to invest in upskilling and reskilling the workforce, the practical reality is that most will only do so when they can see the clear benefit to them. If you want to find great development opportunities in your workplace, then you’ll need to push for those opportunities, persuading your bosses that it really is worth investing in you.

Don’t be afraid to make proposals. For example, if you ever have hours where you’ve finished your work or you’re between jobs, ask your boss if you can spend those hours doing something productive to the skill you want to develop. That could be shadowing another employee or even taking on jobs outside your main role.

Make it clear to them that the hours you spend learning will benefit productivity in the long run. After all, you’ll be able to handle more jobs and be a more versatile employee.

That said, this does come with an important warning: just because you’ve taken on more responsibilities, that doesn’t mean your company will give you a promotion any time soon.

Although it’s far from fair, the reality is that if your company can persuade you to take on extra work outside of your main responsibilities without raising your wage, then they’re probably going to do just that. If you choose to upskill during work hours, know that you’re investing those hours into yourself.

The payoff comes when you find a new job at a higher pay grade but before you reach that payoff, you may have to spend quite some time working extra hard. Either you’ll have to put in those hours outside of work, or else find a way to make more of the hours you’re paid for.

Step 4: Make A Timetable

Whether you’re upskilling at work or in your own time, it’s hard to underestimate the value of a good timetable.

If you’re learning on the job, then you’ll probably want to keep this simple. Instead of laying out exact hours you’ll spend doing tasks, instead give yourself milestones and the date you plan to hit those milestones by. If you’re struggling to meet those milestones, put plans in place to help you get back on track.

For those learning new skills in their own time, timetables are an almost vital component to success – especially if you’re already booked up on your days off.

On a work day, it can be really hard to motivate yourself to squeeze those extra hours in. In the morning you’re tired and you just want to get through the day as fast as possible. By the evening you’re ready to relax and the thought of booting up the computer and getting some more work done isn’t likely to be appealing.

All the same, if you’re determined to squeeze that extra work out of your day, then a timetable is great for establishing a routine. You know it’s coming and you’re prepared for it.

Most importantly of all, a timetable helps you measure the time you’ll be putting into a task. Whether two hours a week or ten, this is the best possible indicator of how long it will take you to learn that new skill, helping you to set reasonable expectations for yourself.

Step 5: Request Feedback

Learning is hard. Learning in a vacuum can be almost impossible.

When you start learning something new, there’s always the temptation to put off showing your work to someone else. Just one more week, you tell yourself. Just one project.

It’s true that most of the best learning you do will be on your own and it can feel like there’s no use asking for help when you already know the areas you need to improve in.

The problem with this thinking is twofold. Firstly, you can’t know for certain that the problems you’ve assessed are the real issue with your current skill level or just a symptom. Secondly, it’s easy to get stuck in a loop, struggling to improve because you’re not bringing anything new to the table.

Getting feedback on what you’re doing not only keeps you grounded but it encourages you to always try your hardest, knowing that the work you do doesn’t exist in isolation.

With all that in mind, do make sure to be careful who you get feedback from and how. Receiving feedback is a skill and one that you’ll want to practise. In general, try to only solicit feedback from people with experience of the skill you’re learning and enough knowledge that they can explain a problem in your work rather than just pointing to it.

If you’re not sure where to find feedback because the skill you’re learning isn’t related to your current job, then you’ll have to seek feedback online via communities dedicated to said skill. These spaces can be useful, although always take this feedback with a pinch of salt as it’s a lot harder to know exactly who you’re getting feedback from.

At the end of the day however, almost any feedback is better than none so don’t let these concerns get in the way of an otherwise valuable learning resource.

Step 6: Track Your Progress

We’ve talked already about the value of milestones and goals in tracking your progress but now we’d like to take a moment to discuss why it’s so important to monitor how far you’ve come.

First of all, there’s motivation. This might seem minor, but motivation is absolutely vital to career upskilling. When all’s said and done, improving your skills is all about the energy you put in, and finding ways to reinforce the value of what you’re doing is a great way to keep that energy up.

Tracking your process is also particularly valuable for upskilling at work as it helps demonstrate to your company that you are worth investing the time and effort into. Being able to show how you’ve improved and how your improvements have directly translated into increased productivity is one of the best ways of encouraging your boss to keep putting their faith in you.

And that’s just the start. If you can clearly talk about how you’ve improved your skills, the steps you’ve taken, and the further steps you intend to take, then you’ll have a much better chance in job interviews. Being able to talk about your progress helps you show how ambitious and hardworking you really are – that you’re just the kind of proactive employee every company is looking for.

Not that it’s all about success. Sometimes tracking your progress is just as important for flagging places where you could be doing better. If you spend two months working on a skill and you’re not seeing much improvement, then that’s a sign that something needs to change.

That said – and this is really important – remember that a lack of progress isn’t the same as a complete failure. Many people find a lack of progress deeply demotivating, often deciding that they’re simply not capable of learning the skill they’ve been working on.

This mindset is pretty defeatist, not to mention misleading. As we noted earlier, there are many ways of learning something and sometimes a lack of progress just indicates that your learning approach isn’t working. Now’s your chance to shift gears and try something new.

Although you might feel as though you’ve wasted time, remember that a large part of learning is about experimenting. Sometimes you have to try something to know it’s not going to work. Try to see it as ticking off one approach on a list and moving on to see what works best for you.

Step 7: Keep It Sustainable

One of the reasons some companies are reluctant to upskill their workforce is sustainability. Put simply, you just can’t expect a person to work two jobs at the same time.

What’s true for a company is also true for an individual. If you try to push yourself too far and too fast, you’re likely to burn out and this can spiral into larger problems both at work and at home.

Of course, finding that line of what is and isn’t sustainable is deeply personal. Some people love what they do and are willing to pour countless hours into it. Others need to split their focus, giving them the chance to break from one thing and focus on another.

A lot of the time this is also very connected to your other responsibilities outside of work – whether or not you have a partner or a family. The truth is that your capacity to sustainably upskill is something only you can figure out and even that can take some trial and error.

If you’re struggling to sustainably learn or you’re worried about hitting that line of burnout, then the best thing you can do is build things up slowly. We chose to present this guide in the form of steps to help you split the task up. Hopefully, this shows how, even if you can only spare an hour a week, by taking clear steps and staying organised both about what you’ve done and what you plan to do, you can keep a handle on your progress and keep pushing forwards.