6 Benefits of “Upskilling” or “Reskilling” in Your Job Search

By:   |   Updated: 2023-03-27   |   Comments   |   Related: More > Professional Development Job Search


Technology professionals understand the importance of continuously developing and strengthening their skill sets. Still, many people don't value or prioritize upskilling throughout the year and their job search. There's already so much to do when looking for a new opportunity; training usually falls to the bottom of most job seekers' to-do lists. Yet there are more benefits than most people realize to investing time weekly or monthly towards keeping key skills current and learning new skills that are in demand and highly sought after.


There's certainly no shortage of free and low-cost technical and soft skill training resources out there. There seem to be endless online communities and threads, a growing number of conferences, a plethora of courses on online training sites, more and more companies pushing out content via their websites, blogs, and YouTube channels, and a variety of Meetup groups and other groups for all your technology skills development needs.

But how does investing even two hours a week or month in learning key skills and technologies in demand HELP you (especially during a job search)? Here are six benefits and how to take advantage of them.

6 Benefits of Upskilling


"Hang out where your target audience hangs out." That's a common phrase I frequently spout to job seekers. Especially because the biggest hurdle and frustration job seekers experience is applying for jobs and getting radio silence, i.e., no response to their application. Getting involved in the right technology/SQL Server/data Meetup groups in your area can be the secret sauce to your job search. Making this time investment has a ton of benefits, as it gives you more relevant content for your resume, LinkedIn content (you can share that you are going to events, pictures from attending events, event recaps, and more!), helps you learn and strengthen skills, and gives you an avenue to learn about companies that are hiring, new Recruiters who are engaged in the group, and likely will help you meet and network with "ultra-connectors" in your community.

Adding involvement in a group to your resume is easy. We typically recommend including your participation after you join the group, attend at least one meeting, and plan to attend them periodically going forward (even one every three to six months). Here's how:

  • Section Title: Technical Community Groups, Community Involvement, or Meetup Groups
  • Have a row for each group you're active in, such as 'Member, Tampa Power BI Meetup Group'

2-Increases Confidence

What gets in the way of many job seekers being successful in their job search is themselves and, often, a lack of confidence in their skills and abilities. Technologists regularly feel they simply aren't strong enough in a specific area or technology, especially if they haven't worked with it in a year+. Other times, they feel their skills are outdated or obsolete. Yet, when you spend the time to take training courses, attend tech Meetups/events and/or play around with a technology in your home environment, your knowledge base, comfort level, and confidence all go up!


There's a lot you can't control, especially in a job search. However, investing in yourself and your skills development is something you can control. During any job search, you should balance the rollercoaster ride that most people experience. Incorporate incentives for yourself along the way, especially as you achieve things on your task list. Also, build in time for continuous development.

4-Increases Qualifications

Have you ever skipped over applying for a job you were interested in because you didn't have every requirement on their list? When you engage in training around a specific skill or technology, you can add it to your resume, making you more qualified for that job.

EX. Resume Addition: If your goal is to learn Power BI, you could take courses, build your own dashboard or reports, join a local Power BI group, and/or attend a conference that offers a track that includes Power BI sessions. You could then add this content to your resume:

  • Section Category: Technical Courses - add names of the specific courses and the provider where you took them.
  • Section Category: Technical Community Involvement – add 'Member, Tampa Bay Power BI Meetup Group'
  • Section Category: Conferences or Technical Community Involvement – add 'Attended local SQL Saturday and Code Camps, attending sessions on Power BI, building custom dashboards, etc.'
  • Section Category: Pet Projects – add any personal dashboards you developed.

5-Optimizes Resume and Profile

I recently received a LinkedIn message from a Sys Admin who said, "I need your advice. I've applied for at least 100 jobs I'm qualified for, and I haven't heard a peep back. What is going on?" One of the most common reasons a resume or profile might not get viewed is that it doesn't "rank highly enough" against the job description and list of requirements/buzzwords.

One of the biggest game changers to your job search and anxiety level is figuring out how to optimize your resume/applications so your resume lands in the top 5-10% of applications. How do you do this? Make sure you include the right skills, technologies, and other "buzz words" found in the job description and list of requirements. First, you must identify the buzzwords to build into your resume, LinkedIn Profile, and cover letter. Then you need to determine how you'll learn or re-develop any of those skills (that make sense for you and your target jobs!) so you can add them honestly.


I've supported hundreds of managers over the years, and a good portion of them like to ask some interview question that helps them understand if the interviewee is continuously learning and/or has a passion for bettering themselves. Recruiters and managers may ask, "How have you been keeping skills fresh?" "What are you learning right now?" "What are your favorite resources for growing your skills?" "Who is your favorite technology thought leader(s)?" "What do you do when you don't know an answer?" You get the idea; there's a variety of ways an interviewer might ask you this. But they're looking for and evaluating one primary thing: do you invest in yourself and continue developing your skills?

Leverage the Benefits

At this point, we hope you're excited about the prospect of continuing to or working towards further developing your skill set and seeing more of the benefits to yourself, your overall career, career satisfaction, and your job search. Here's a recommended plan to pursue upskilling and leverage the benefits.

Step 1

Determine skills, technologies, etc., you want to learn or strengthen. This can include soft skills and technical skills. Be strategic about what you want to focus on. Get input from others (such as technical community leaders/members, your boss, and/or recruiters who specialize in supporting your skill set. Be realistic, and maybe limit your 'Need to Learn/Grow' list to 2-4 skills/technology.

Step 2

Outline HOW you'll go about your upskilling. How many hours a week/month can you devote? When will you dedicate this time? Which channels/resources exist that can best support your goals? Are there relevant groups, technical training sites, local or virtual conferences, GitHub projects, etc.? What projects could you initiate at home?

Optional: Does anyone in your network share your upskilling goals? Reach out and see if they'd be interested in doing any of these or different actions with you, and you can sync up monthly to review progress, share favorite resources, talk through challenges, etc.

Step 3

Put your plan in motion, block off at least 15 minutes a month to review progress, identify a new upskilling channel/approach you want to try, and plan for the next month. Use planning best practices such as time blocking to ensure you're prioritizing your skills development goals.

Step 4

As you're completing your upskilling, document it. When you complete a relevant course, are you adding the course to your resume and adding that skill to your LinkedIn profile? When you sign up for a technical group/Meetup meeting, could you share that you're going on your LinkedIn feed? When you attend conferences/Meetup group events, are you adding that involvement to a 'Tech Groups/Community Involvement' section of your resume? When you get a certification, could you upload a visual to your LinkedIn or portfolio?

Step 5

Share proactively during your job search. Whether it's communicating what you're doing to strengthen key skills in demand to the recruiting partners you're working with or highlighting them in a cover letter or during an interview, there should be rare instances when you have no answer to an interview question of "Tell me about your experience in ____" for an in-demand skill!

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About the author
MSSQLTips author Erica Woods Erica Woods has nearly a decade in the IT staffing world, an MBA, and is a member of the Professional Association of Resume Writers and Career Coaches.

This author pledges the content of this article is based on professional experience and not AI generated.

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Article Last Updated: 2023-03-27

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