Upskilling for Job Seekers

By Mike Simpson

Taking your career to the next level takes hard work and dedication. But while it’s easy to assume that advancing is mostly in the hands of employers – as they’re the ones that decide whether you can thrive in a role –job seekers aren’t powerless. By upskilling, professionals can potentially write their own tickets.

But what exactly is upskilling? And, if you’re ready to take the leap, what capabilities should you upskill? And how on earth do you pull upskilling off?

If you want to take your career up a notch, here is what you need to know about the world of upskilling?

What Is Upskilling?

Alright, before we talk about what you should upskill and how to do it, let’s take a quick second to discuss what upskilling actually is in the first place.

In the simplest sense, upskilling involves acquiring new capabilities that relate to your career. Essentially, you’d expand your skillset in a relevant way, making you a stronger performer in your professional niche.

While the need for upskilling has been there for quite some time – particularly in fast-developing sectors with labor shortages, like technology and healthcare – the pandemic has kicked it into high gear.

COVID-19 changed how professionals view their careers and employers. The shift in their priorities caused them to seek out new paths. In some cases, people removed themselves from the workforce, either temporarily or permanently, taking their skills with them. In others, they simply decided to take their careers in a new direction.

While this was happening all throughout the pandemic, the Great Resignation was a culmination of it. People were leaving their jobs in droves, and that made skill gaps in some industries worse. This made the need for upskilling even greater, as it was potentially the only way for some companies to get the capabilities they need.

Alright, you’re probably asking, “Doesn’t that mean that upskilling is an employer thing? How does it affect me?” Well, it’s true that companies do try to upskill their employees to fill gaps. But that doesn’t mean that you can’t, too.

Don’t wait for your employer to create the opportunity to hone your capabilities. By taking ownership of your learning, you can take your career to entirely new heights. With that approach, you’re in control, allowing you to acquire skills that make achieving your goals easier.

How to Choose What Skills to Up

Deciding which skills to target is often easier than you’d expect. You don’t need a crystal ball to see which capabilities bring value to your career, as long as you know where to focus your research. Here’s a step-by-step approach for choosing the skills to up.

Part One: Identify the Right Skills

The first part of the process is identifying skills that represent genuine opportunities. There are several approaches that can work. However, some may be best for specific situations, such as securing a promotion at your current workplace or qualifying for roles at other companies.

Here is an overview of how to identify the right skills to up.

1. Examine Existing Skill Gaps at Work

Approximately 80 percent of Americans believe that there are skill gaps, with 35 percent saying they’re personally affected by it. Additionally, 87 percent of companies state that they’re battling skill gaps now or expect to within the next five years.

If you’re currently working, the first step you should take is examining the skill gaps in your own workplace. Consider what you and coworkers in your department bring to the table. Is there anything missing?

One way to identify opportunities is to reflect on past projects, particularly those that faced hurdles because no one had a particular capability. Exploring job openings in your department may also give you clues. Your manager might include a skill in the requirements list because it isn’t represented in your workgroup, so they’re worth checking.

Any of the approaches above can technically work. Then, by acquiring those skills, you could become more valuable to your employer, putting yourself on the path for a promotion or raise. Plus, you’re more marketable in general, making it easier to access career-boosting opportunities.

2. Talk to Your Manager

Usually, with a bit of brainstorming, you can find gaps in your workplace on your own. However, you could also take a simpler route and just ask about skill gaps.

If you have a good rapport with your manager, let them know you’re looking to bolster your skill set. Then, ask if any capability would be especially valuable to the company, allowing it to close a skill gap. If there is, there’s a decent chance your manager will let you know.

MIKE'S TIP: Asking your manager is an especially great idea if you’re a top performer and the company has a formal training program. By expressing your interest, you might be able to upskill on your employer’s dime. Not only are you increasing your capabilities, but you don’t have to spend your money – or, in some cases, free time – to make it happen.

Once you add the skill, you may be able to leverage your growing skill set to secure a pay bump or promotion. Just make sure to note how the skill improved your performance or led to a critical achievement, allowing you to build the strongest case possible.

3. Research Emerging Trends

Learning about what’s on the horizon in your industry is another great way to find upskilling opportunities. Essentially, this approach allows you to prepare for the job requirements of tomorrow. You’ll be adding skills that may not be in high demand right now but will be once other companies in the industry catch up, embracing the latest and greatest advancements.

For this approach, staying in the know is the most important part. Subscribing to trade publications, attending industry conferences, following thought leaders on social media, and similar approaches help you learn about upcoming shifts in your sector or profession.

Along the way, you can identify emerging skills that go along with those trends, acquiring the ones that will likely be in demand in the near future. Then, you’ll be more marketable when that skill becomes a must-have capability, making it easier to secure promotions or find lucrative job opportunities.

4. Check Out Job Postings at Industry-Leading Companies

Industry-leading companies tend to be ahead of the competition when it comes to operations and technology. By reviewing their job ads to see what skills are on the required and preferred lists, you can learn more about what all companies in your industry might be looking for shortly.

As with the options above, you could identify capabilities that are prime targets for upskilling. Since some of the leaders in your niche are already after those skills, there’s a good chance it’ll become widely desired in the coming years, making you more marketable. Plus, it allows you to qualify for those roles, potentially letting you secure a position at one of the bastions in your industry if you so choose.

5. Review College Degree Programs

Most college degree programs aim to give graduates the right skills to secure specific jobs. By looking over the required courses at cutting-edge schools, you can learn a ton about the future of your field. If a new skill is part of a mandatory class, that’s a sign of potential value.

Similarly, if a university begins offering a one-off course, major-related class (that isn’t a full-blown requirement yet), or a certificate program that wasn’t there before, that’s worth noting. It could be a sign of an emerging skill that might be a smart one to add to your resume.

Just be aware that not all colleges are at the forefront of every field. It takes time to develop coursework, so many schools are actually a bit behind the curve when it comes to in-demand capabilities. However, some colleges are known for keeping pace reasonably well, making them potentially strong resources for this kind of research.

Part Two: Estimate the Value of a Skill

Once you have some potential skills, you’ll want to estimate their value. This is especially true if you’re going to have to dedicate your personal time and cash to acquire them.

Here’s how you can estimate if a skill is worth adding to your resume.

1. Explore Options for Learning the Skill

How you learn a skill plays a big role in the equation. For example, if you have access to employer-provided training programs, you might be able to acquire the capability for free and tackle coursework during work hours. If you don’t (or the skill isn’t available that way), you might have to explore other options, like paid classes or self-directed online learning.

Consider which learning pathways are available. Then, compare their financial costs, time commitments, and impacts on work-life balance. That way, you can learn more about what you’ll have to do to get that skill.

2. Assess Demand for the Skill

Assessing demand for a skill might seem tricky. However, you can usually get a solid idea with a bit of research.

For example, you can head to a major job board and run a search where the only criterion is the name of that skill. Then, you can see how many listings include it as a required or preferred capability.

You could also go a web search for the skill coupled with the phrase “skill gap.” While this option isn’t foolproof, it lets you know if anyone is talking about the lack of candidates with that capability, which can give you insight into demand.

Now, is low demand an automatic dealbreaker? No, it isn’t.

Skills relating to emerging trends might not be in many job ads today but could be in the next few years. If you’re looking at an up-and-coming capability, you need to factor that into the equation.

However, if a skill has been part of your industry for several years (or longer), and there aren’t a ton of requests for it, that’s different. In that case, it can be a sign that employers may not see that capability as a necessity, decreasing its value.

3. Determine What Companies Pay for the Skill

This step requires a bit of effort, but it’s worth doing. Here, you want to compare the salaries for highly similar jobs, where the main difference between the positions is whether the skill you’re considering is required or not. That way, you can see the approximate dollar value of that capability.

Essentially, the difference between the salaries gives you an idea of what that skill is worth to employers. You’ll want to gather several examples of jobs that say the skill is a must and positions that don’t. That way, you get a broader picture of what the capability is worth in the marketplace.

Just make sure that you focus on companies in the same geographic area when you make the comparison. Why? Because rates can vary from city to city even when job requirements are identical. By limiting the comparison by location, you end up with a more accurate picture of the skill’s value.

4. Analyze What You Find

After you’ve done the research above, it’s time for some analysis. Ideally, you want to see a skill where the cost of earning that skill is low compared to its value. Additionally, you want to choose capabilities where demand is either strong or poised to rise. If you can find all of that, it’s a good target for upskilling.

How to Highlight Upskills for Your Job Search

If you’re upskilling, highlighting your efforts during your job search is wise. For one, employers prefer candidates with a willingness to learn and who actively try to stay current in their fields. For another, it means you’re open to skill expansion, so you aren’t stuck in your ways.

Finally, highlighting your upskilling lets you showcase skills in development, even if you don’t have them fully yet. This can be ideal if there’s a requirement for the role that you’re working on, but you’re not quite finished learning it.

When you highlight upskills, you can use several approaches. Your cover letter is an ideal spot to showcase skills you’re actively acquiring, allowing you to touch on requirements that you’ll have covered soon.

In your resume, you can showcase newly acquired capabilities in the “Skills” and “Education” sections, depending on how you earned them. Plus, you discuss your efforts as an achievement, allowing you to mention it in your “Work History” or “Professional Summary.”

During the interview, you can tap into your efforts when answering several questions. For example, if the hiring manager asks, “How do you stay current in your field?” you’ll have an outstanding answer ready.

As with all parts of the job search process, you’ll want to embrace the Tailoring Method. With the Tailoring Method, it’s all about relevancy, ensuring you address a hiring manager’s specific needs. That way, you’ll be the strongest candidate possible.

Upskill Examples

Expanding in a Direct Way

One of the most common upskilling approaches is expanding capabilities in a way that relates directly and wholly to your current role.

For instance adding a programming language to their repertoire is one of the most popular forms of upskilling for software developers and coders. It allows them to work on more projects or use different approaches for specific needs, so it’s a logical choice.

By expanding your skills in a direct way, you’re becoming more capable in the role you have now. It may also put you on the path for a promotion or a raise, which is beneficial. However, a promotion isn’t guaranteed if the new capability doesn’t align with the next role up.

Cross-Training into a Related Area

Cross-training into a related area is another widely used approach. It allows professionals to tap into roles that are effectively adjacent to their own, broadening their capabilities.

Usually, the biggest drawback here is that it may not provide a ton of value in your current role. As a result, getting employers to cover the cost is harder. However, if you plan to move up into management and oversee a wide variety of professionals in your larger niche, this could make you a stronger candidate.

Boosting Soft Skills

You don’t have to limit yourself to hard skills when you upskill. Instead, soft skills can make excellent targets, too, particularly universally desirable ones like leadership.

With leadership skills, you can guide projects, supervise others, and manage teams more effectively. In most cases, there’s little to no downside for honing this capability, too, making it an excellent option.

Communication and collaboration skills are excellent choices, as well as tech-savviness. They’re universally valued, making you a stronger candidate. However, they don’t always come with clear financial gain, so keep that in mind.

Putting It All Together

Ultimately, upskilling is a great way to keep your career on target. Just make sure to pick capabilities that provide you with genuine value. That way, you can achieve new levels of success.

Good luck!

About The Author

Mike Simpson

Co-Founder and CEO of Mike is a job interview and career expert and the head writer at His advice and insights have been shared and featured by publications such as Forbes, Entrepreneur, CNBC and more as well as educational institutions such as the University of Michigan, Penn State, Northeastern and others. Learn more about The Interview Guys on our About Us page.