How To Overcome Any Obstacle In Your Skills Development Journey

Skills Development Obstacles And How To Overcome Them
Diki Prayogo/
Summary: Are you starting your upskilling journey? Here are some common skills development hurdles to look out for along with some solutions.

Obstacles To Avoid In Your Skills Development Journey

Today's workforce is seeking to fuse cross-functional and diverse skill sets that help them adjust to and leverage advancements and shifts in their niche and market. Hungry and ever-searching for continuous learning and upskilling opportunities, professionals and leaders are more interested in Learning and Development than ever. Hence, if you're a leader planning your next L&D initiative for upskilling and reskilling your team or a professional on a solo path to developing your own skill set, beware of falling prey to some common obstacles associated with skills development. The secret to overcoming said obstacles may require some soul-searching, expert advice, and plenty of research. So, let us accompany you on your skills development journey. In this article, we'll list some of the most common obstacles of skills development and show you how you can overcome them.

Common L&D Obstacles Companies Face

Skills development initiatives allow companies to build future-proofing safeguards to protect their business and corporate culture. As the concept of Learning and Development becomes more vital to avoid stagnation on an individual and a collective level, creating innovative upskilling solutions for the contemporary workforce is a must. Yet, companies continue to face obstacles when it comes to designing and delivering effective skills development strategies to their staff.

A common obstacle faced by L&D leaders is addressing skill gaps from an individual viewpoint; meaning, while detecting areas for improvement is usually clear-cut, approaching an employee's skill gap according to their decided career pathway is definitely more challenging. Usually, people either are unsure of where the future will take them, or their 5-year plans are so strict and inflexible that they give no room for unplanned growth. L&D professionals need to target learner profiles with versatility, adaptability, and personalization in mind. Sure, some may be more reluctant to accept change, and that is a whole other can of worms. Lastly, ensuring engagement throughout the skills development journey is another great challenge. Yet, every obstacle mentioned can easily be remedied with one ace up your sleeve: personalization.

Skills Development Obstacles When Solo Upskilling

Similarly to company-wide obstacles in skills development initiatives, individual upskilling comes with its own set of challenges that may cause setbacks. Though, in contrast, when on a solo journey, finding ways to personalize a trial approach to upskilling is much easier. When a professional sets out on an upskilling journey, they have identified a good amount of their training needs. With specific goals in mind, they know their targets. But do they know how to reach them? A partnership between the individual and their organization is encouraged in this context. Through close collaboration, L&D departments and employees can team up and co-create an effective upskilling strategy.

The employee's personal upskilling agenda contains valuable information for the L&D leader, as your employees know what they need in order to receive personalized training, and you know how to deliver it to them. Combine your knowledge to get the desired results and overcome any obstacle in your skills development journey.

How To Overcome Any Skills Development Obstacle On Your Way To Betterment

1. Personalize The Material

To start, the goal is to provide an upskilling initiative that targets each employee's pain points and areas they want to improve with precision. Personalizing your skills development efforts will go a long way. Begin by identifying training needs. Usually, companies that launch upskilling initiatives wish to prioritize cultivating specific, company-valued skills and assets. While that's a valid approach, consider consulting your employees to determine what skills they wish to nurture that fit their desired career pathway. Essentially, personalizing the material will save you a good deal of unused or outdated content, ineffective training modes, and other common obstacles in skills development.

2. Analyze Previous Upskilling Initiatives

If you have compiled data on previous upskilling initiatives, you have a goldmine. Older training programs can give you the answers you are looking for in order to avoid the most common obstacles to skills development. Learn what worked in the past, what didn't, and what you can improve in your new strategy. Your employees don't want a repeat of an outdated workshop. They need fresh material specifically targeted to their current needs. Since the previous step involved deploying a Training Needs Analysis, this step involves looking back at previous TNAs and databases that contain what your older programs missed.

3. Collect Feedback

Based on your employees' individual recounts of their training needs, their identified skill gaps, as well as the data from previous training or upskilling initiatives, you can start collecting feedback. What can your company do to further support employees' Learning and Development? Your people can answer that question better than any data. Employ questionnaires or one-on-one sessions with your team and find out what they wish to see in your new initiative. This helps keep up with your staff's needs and personal aspirations and also aids in further personalizing their upskilling journey.

5. Launch Mentorship Sessions

Implementing mentorship opportunities in your skills development project allows for a constant reevaluation of the program's objectives and methods employed. By regularly touching base through mentoring sessions, L&D departments can provide an extra kick in their upskilling and reskilling initiatives. These mentoring sessions can provide opportunities to discuss issues surrounding the employee's personal growth, any obstacles found during their skills development journey, or any experiences that are of note. Through mentorship, companies and L&D departments can further optimize their upskilling efforts by providing extra support, lived testimonials, and expertise to those on their journey to growth. Not to mention, both mentor and mentee can utilize these sessions to cultivate their interpersonal skill set and reach their own targets.

6. Aim For A Continuous-Growth Mindset

Always remember that upskilling needs to be a company-wide initiative. Not only does it help L&D leaders focus on organization-specific goals and targets, but it also proves highly effective in cultivating a collective continuous-growth mindset. Business-wide initiatives draw from and give back to the company and its culture. They are, first and foremost, created to reinforce company values. And what company that values employee growth doesn't have the drive to overcome any obstacle on their skills development path?

7. Revisit Your Successes

As your skills development program progresses, you may discover that, along with unexpected obstacles, there are some unexpected successes as well. Make sure to catalog the process so that you can revisit your success in future endeavors. This will also allow for longer-term documentation of skills and talent retention rates, ROI, and other vital metrics that showcase every win against the obstacles in your skills development journey.


The demand for versatile and diversified skill sets is more pressing than ever. As companies continue to devise L&D programs and initiatives to keep their staff upskilled through thick and thin, they may come to find unexpected challenges along the way. Well-rounded and well-developed upskilling L&D strategies leverage the obstacles of skills development to utilize them as lessons learned. To find allies in this journey, locate the right expert from our list of Top Content Providers For Upskilling And Reskilling Employees and get started.