How To Upskill Correctly

How to Upskill (Correctly)

It would be safe to say that we all daydream of having the corner office from time to time. Yet sometimes when we look around for our next opportunity it feels like the next step is nowhere to be found.

We wonder why we aren’t moving as fast as other employees in the company. We wonder, “Is this all there is?” In my eyes there is only one answer to this existential question: Get better. You must upgrade your ability to deliver more value at work, which leads to the jobs and promotions you want. 

Career self-improvement comes in two flavors. Upskilling is the process of learning new skills and improving your current skills to capture a promotion or a higher position within your current company or a different one. Reskilling is the process of learning new skills to move laterally within your organization or another.

We’ll begin with what the more challenging problem first. 

What is Reskilling?

Reskilling means learning an entirely new set of skills to prepare to take on a different role, within a company or as a job seeker

It’s a common complaint from clients who are working at professional development that they don’t know what to do next. They begin by looking at what industry skills and tools are popular, which is a huge mistake.

Move your focus away from where the “market” is going to where you are going. If the market is infatuated with “big data” today, should you immediately sign up for a course on data science? No. You shouldn’t.

Balancing your career

Your career should not be a series of reactive pivots towards whatever change in technology is peaking at the time. Your career is a delicate balance of passion, proficiency, and market need. If you are not passionate about data science and are not excited to master the skill, you will be a terrible data scientist. You must spread your attention across each characteristic.

If you choose skills that don’t meet all three elements, promotions, and new positions will not appear and aren’t captured. You’re not good enough at it. You’re not excited to learn more, which creates a downward spiral. You can waste years chasing positions that require skills that don’t fit you


If you don’t know what you may like, take an educated guess, and follow it until you see if it’s right for you. Speak with people who are doing it professionally. Don’t speak with hobbyists unless that is your goal.

For example, if you’re curious about machine learning, ask your network if they know anyone actively developing machine learning algorithms. Find that person and ask them how it’s going. If the conversation lasts two hours or so, you may be on to something. 

Understanding market needs

Measuring market need is simple. What openings in your company seem to keep popping up or sticking around? That is a big hint. The company needs those roles.

Ask the right managers the top three skills and tools used in that role. Job descriptions rarely depict a true day in the life of any job. Ask for the real story and you’re more likely to get it. 

Once you’ve chosen a target role, about three target skills and three needed tools used in the role, and simply get to work learning those skills and tools in the time you have available. You probably don’t need another degree. Advanced degrees can be a crutch and delay the difficult task of deciding what work you want to do that exists in the marketplace right now. 

Futureproofing with reskilling 

You can also consider reskilling as a tool to bulletproof your career lifeboat. If for some reason your current job is cut, and you’ve learned skills that make you eligible for other roles within your organization you can shift over with less stress and struggle.

What is Upskilling? 

While both upskilling and reskilling involve learning new skills for your career, context is important. Upskilling is a process of professional learning that focuses on developing new abilities and minimizing skill gaps, while reskilling is focused on making yourself a viable candidate for other jobs.

It’s a good idea to focus on upskilling instead of reskilling (unless you’re unhappy in your career and desire a big change like discussed above). Consider upskilling as your ticket to conquering bigger problems within your organization.


For example, if you’re a marketer and you want to be a marketing director, simply ask yourself, “what does a marketing director do that I don’t have to do?” You may be running a marketing campaign, and you’re responsible for the success of that campaign. The marketing director is responsible for the success of all campaigns, along with training staff, handling incoming requests from other departments, and forming a strategy for what campaigns will meet the needs of the customers buying not only the current company offerings…but next year’s products and services as well. Think I missed something? Eat lunch with your marketing director and hear it straight from the primary source. 

Now that you know what your target role does, isolate the skills and tools used in the role. This is what you must work on. If you’re still wondering how, this is where a coach or career mentor comes in. 

The Value of a Coach

I do not mince words when I explain why my clients should work with a professional. Coaches save you years of empirical trial and error.

A coach helps you overcome barriers to your advancement that seem too confusing, too difficult, or too uncomfortable for you to handle on your own. They could be people, process, or technology. Usually, candidates are interested in learning the ability and confidence to communicate and pitch ideas, lead people, direct employee activity away from efforts that will spin the company’s wheels and into efforts that move the company forward. Employers sometimes lack the intuition to hire the right candidates and place the right staff members onto the right assignments.

So what do you need to work on to get ahead in your own career? A coach will show you. 


A coach takes one look at excuses and throws them in the trash. They understand that you have considerations for why something hasn’t been done or can’t be done. They turn the focus towards “How can we do this”.

Better yet, experienced coaches see the same problems many times over, and immediately shift to being prescriptive instead of investigative. They’ll say, “based on my experience with individuals like yourself, this is what we did, and this is the result we got. If they can do it, so can you.”

Strategies to Upskill Correctly

Now that you have a plan of action to move forward, here are some tips to improve your results.

Make lots of mistakes fast and responsibly

I had a mentor that used to tell me when learning new skills to “mess it up real good.”

Some employees don’t improve because they’re unwilling to make enough mistakes and learn from them. Set up a safe space to study, practice, experiment and fail responsibility. Think of it as playing the stock market with monopoly money. Software developers create a “sandbox environment” to write and test code. Create a process diagram that no one asked for to better understand how an area of the company does things. Give speeches to community groups. These are all safe and responsible environments to earn real experience. 

Go big

You can skip two or three rungs on the corporate ladder at a time. You don’t need to follow a typical path for advancement. Make your own.

You can be a director when your knowledge of the organization, the marketplace, and the people that run a sophisticated machine of a company reaches a breaking point. A few recommendations help too. Once you reach that point, you must have your skills and tools ready. Post for the job and make your case. Play big games, win big prizes. 

Learn fast and bust your chops

If you want a career move or promotion, be ready to post for your target role in 9 months or less. That is plenty of time for tools and training. Remember that you will never be one hundred percent ready. Focus on being eighty percent ready and learn twenty percent on the job.


Don’t Get Ready, Stay Ready

Doctors begin their education by internalizing the statement, “First, do no harm.” I suggest you internalize that as well.

Moving from one job to another can be tricky, and must be done elegantly and with sufficient preparation, otherwise you’re at risk to waste time. The best candidates stay proactive in every role by actively pursuing the skills that will take them to the next level. Upskill well, then climb on your own terms.

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