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Creating a personal skill development plan that works

By David Davis

Few industries change as fast as technology, and no set of professionals are tasked with keeping up with changes to the way they work like engineers, developers and other technology professionals. No matter if your role is in web or software development, IT or DevOps, data, cybersecurity, machine learning or cloud computing, mastering new technologies is critical to your career development, job security and company’s growth. 

While you’ll naturally learn new skills on the job by virtue of your tasks or advancement within a given company, a proactive approach to upskilling allows you to steer your career and progress more deliberately, regardless of external factors and changes to your role. 

The core of a proactive approach to gaining new skills is a technology skill development plan, which gives you a framework to follow and measure your progress against. And for technology leaders, helping your team design skills development plans will ensure you’re on the forefront of new advancements in your industry.

How to know what skills to develop

A meaningful plan depends on knowing what skill to work on as much as it does gaining that new skill. Figuring out the “right” thing to focus on is wildly relative and may have more than one suitable answer, so two of the best places to start is 1) identifying your own skills gaps and 2) evaluating what the market is looking for. 


Do a self-assessment to determine where you stand

A simple way to evaluate yourself is to bucket your tangible knowledge into three categories: tools, skills and tasks.

  • Tools: These are the resources at your disposal to do your job. Tools include programming languages, SaaS platforms, systems and certifications you’re proficient in, like VMware, C++, Wordpress, R, Tableau and so on.

  • Skills: This is how you apply and use your tools. Within a single tool, you may excel at analysis, architecture, data manipulation, troubleshooting, architecture, QA or any number of relevant skills. Consider your tool (be it Google Analytics, Angular, Linux, AWS, Kubernetes or Cloudflare) and ask yourself, “What do I actually know how to do with this?”

  • Tasks: Tasks cover broader responsibilities at your job. What does your company rely on you for? What are some projects where you played an integral role? Are you expected to regularly do things outside your job description? An example of a task (compared to a skill) would be performing a cloud migration, undertaking a security assessment or building a CI/CD pipeline.

Each of these categories blends into each other, and will provide you a jumping-off point to begin mapping out skill adjacencies and areas for improvement.


Identify what skills are in demand, both in the market and within your company

Gaining new tech skills just for the sake of gaining new skills can have value, but at work, your manager will want to see how your skill development helps drives toward business needs. A good way to find what to focus on is by simply talking to your manager and asking for open feedback. 

To cast a wider net and get a sense of how you can “future-proof” your skills, search job listings for roles you’d want to advance to over the next five years, or jobs at innovative companies who do the type of work you aspire to do. Look at the tools, skills and tasks involved. What minimum technical skills do they require? What software programs and platforms do they utilize? What tasks would expect you to take responsibility for? You may even want to look at the ads within your own company as you make a broader career development plan for yourself.


Consult your colleagues

The best sources of information are often sitting right next to you. Ask the high performers on your team what skills they can share with you — and what resources they tapped in order to develop those skills. Offer your availability to help them with tasks outside of your day-to-day so you can get hands-on experience with tools you might otherwise never use.

Focus on learning activities that move the needle

Once you have a good idea of the skill you want to develop, it’s time to go to work. Above all, your skills development goal should be S.M.A.R.T.:

  • Specific: “Get better at Javascript” isn’t a specific goal; outline exactly which elements of the language you want to get better at.

  • Measurable: Your goal should have some sort of soft or hard metric that lets you clearly know if you’re improving. For example, a developer could focus on personal efficiency at completing requests, or a data professional could focus on increasing adoption and use of the data they provide to the marketing org.

  • Actionable: Stretch yourself to hit your measurable goals, but make sure your plan doesn’t overstep others’ authority or ownership on your team. You want to people to support you in your skill development plan, and that requires keeping their trust.

  • Realistic: Learning an entire new framework or language in a few months may not be realistic. Start small and concrete, then move from there.

  • Timely: Do you have the time to fit your skill development in without draining yourself? If you can’t perform your day-to-day tasks while learning new skills, you probably need to rebalance.


Once your goal meets those criteria, these three ideas will help you reach them:

Set a daily/weekly/monthly cadence

To keep your plan timely, break your skill development plan into days, weeks and months. If you work best on a time-structured basis, set a goal to work a set amount of minutes a day on your goal. Others may want to benchmark by progress. If you’re working through a Pluralsight course or path, for example, set of goal of where you want to get each week (which you could measure using Skill IQ).


Carve out time on your calendar to learn

Since the skills you are gaining will help you on the job, don’t hesitate to set aside time on your calendar as part of your development plan. Blocking out the time is crucial. If you don’t, something more important will always come up, or a meeting could get scheduled over the time you had set aside in your mind.

It’s a good idea to include your manager in your plan, especially when it comes to devoting work hours to skill development. Good leaders should understand and respect your desire and commitment to learn and help provide you with opportunities to do so. Make sure you follow through on your plan and report back to them on your progress so you can keep their trust and show them your time isn’t going to waste.


Teach others what you’ve learned

The best way to help your skills stick is to teach someone else. As Albert Einstein said, “If you can't explain it simply, you don't understand it well enough.”

Walk a coworker through a new program or process you learned, or offer to take a few minutes in team meeting to share a new concept. If they have questions you don’t know the answers to, incorporate researching the answers to the questions into your plan.

If you work remote and don’t have people around you to teach hands-on, you can always jump online write a blog post, film a tutorial or post in a developer forum. 


Don’t wait to develop your skills

This is arguably the most important tip I can provide: Get started today! The fact that you’re reading an article like this means you have the itch to grow, so capitalize on that by devoting even just 15 minutes a day, and you’ll give your skill development journey the momentum boost it needs.

Need a little more help on your skill development journey? Keep your technology skills in-demand, learn new skills quickly and measure your team’s workflow efficiency with a free Pluralsight trial.

About the author

David Davis has authored over 50 courses for Pluralsight around enterprise data center technologies such as cloud computing, virtualization, and (especially) VMware vSphere. He is a partner at where he creates compelling enterprise technology content, moderates online events, and helps to connect some of the best-known technology companies in the industry with the end user community. With over 20 years in enterprise technology, he has served as an IT Manager, administrator, and instructor. David is an 11x VMWare vExpert, VCP, VCAP, & CCIE# 9369.