How to Upskill Your Organization: Leveraging Mentorship to Combat the Skills Gap

Written by Santiago Castro
10 mins read
How to Upskill Your Organization Leveraging Mentorship to Combat the Skills Gap_In

Imagine: your organization has the budget to be fully staffed with amazing people who excel at what they do and keep their skills sharp. This allows your organization to thrive, exceeding its quarterly goals and solidifying your value in the market. Collaboration, innovation, and continual education aren’t just “company culture”—these values are practiced every day, by all staff.

This might sound like a pipe dream. After all, an organization’s ability to create such an efficient and impressive team is impeded by certain obstacles. Namely, there is a growing disparity between the skills emerging professionals have and the skills companies actually need. This disparity is typically referred to as the “skills gap” or “skills mismatch.”

According to Boston Consulting Group, a leading global consulting firm, the skills mismatch affects 1.3 billion people globally. And there are financial consequences, too. BCG estimates that 6% of revenue is lost worldwide because of the skills gap’s negative impact on productivity.

This report will cover some of the major factors contributing to the skills gap, how “upskilling” can combat the skills gap’s negative effects, and how upskilling can best be implemented and practiced by organizations in the form of mentorship.

How We Got Here: Contributing Factors to the Skills Gap Crisis

Modern shifts in technology and market demands have contributed massively to the skills gap.

  1. First, the evolution of technology has been rapidly accelerating in recent years, especially in response to the COVID-19 pandemic.Even for workers who can hold onto their jobs in spite of rising automation, 50% of them will need to reskill or upskill in order to remain effective in their roles. As industry tools improve, workers of all stripes will need to stay abreast of recent innovations in useful software, analytic tools, and other resources that can help them perform their work with greater accuracy and impact.For example, an accountant in 1910 would likely have used an IBM punch-card machine, while modern accountants rely on digital spreadsheets to track spending. A transition in technology took place. An accountant employed during the advent of Excel, when such a transition occurred, would need to learn how to use the program in order to stay on top of their work.

  2. Second, it is near impossible to prepare a large number of young people for their future careers. Why?The World Economic Forum estimates that 65% of children currently in primary school will go on to work in jobs that currently do not exist. Consider jobs like SEO Specialist, Social Media Manager, Cloud Architect, or AI Engineer. These roles originated within the last couple of decades. And as technology innovates faster and faster, who can say what jobs will (or won’t) exist in another twenty years? By the time Generation Alpha graduates high school, it’s likely that a significant number of them will not have received an education relevant to their future careers.

These factors contribute to a lack of well trained candidates available for open positions. These factors also create the issue of hiring workers who aren’t effectively trained for their roles prior to starting at a company, thus causing a time/energy drain on the veteran team.

When a worker upskills, they gain new (or revamped) tools that allow them handle their job responsibilities more effectively. This helps their organization have agile, modern responses to their customer base. Organizations need to be proactively upskilling their workforces, but how?

What We Can Do: 3 Methods of Upskilling

There are multiple ways someone can go about upskilling. These options include (1) short-term trainings, seminars, and workshops; (2) formal education; and (3) mentorship programs.

Short Term Trainings

Many companies utilize training resources like online seminars, workshops, and conferences. With the increase in remote learning, it is easier than ever to tap into a virtual session, asynchronous lecture, or live Zoom workshop. Companies like Coursera, LinkedIn, and Reforge offer an abundance of resources and many topics to choose from.

Short-term seminars, lectures, and workshops can be useful, but only to a point. There are two main shortcomings: cost and content relevance.

  • Cost: While there are free resources available, it takes time to sift through all of the Internet’s available content in order to find a high quality webinar, for example. When anyone can post about anything, and you don’t know the instructor’s credentials, you have to dedicate valuable time and energy to finding resources that are well-taught by people with industry experience.If you want access to excellent courses overseen by grade-A instructors, you’ll likely have to pay for it. Some sessions may be held in small groups, so that you can get personal feedback from the instructor and do some guided peer review. These experiences can result in amazing skill development and professional learning. However, not all organizations can afford to spend hundreds or thousands of dollars on training seminars.

  • Relevance: These resources are also sometimes not wholly relevant to the unique circumstances of your organization. Their content is often a bit generalized, not tailored to your team’s specific needs and limitations.This means that when you pay for a course, you might be taught content that is superfluous or irrelevant for your situation. In other words, those sections of the seminar are a waste of your time and money.And on the flipside, there may be sections that are eminently relevant and you want more detail than the instructor provides. While you might be able to ask follow up questions in a live session, this is not always an option. Plus, you can’t guarantee that your question will be addressed, or addressed in a satisfying way.

So short term trainings and webinars can definitely be useful, but only to a point. As an organization, be thoughtful about how many resources (time and money) your team dedicates to locating and participating in these trainings, and consider if they’re worth the payoff.

Formal Education

Then we have formal education, like college degrees. College degrees (or trade school certificates) are typically used as a form of preskilling—becoming trained in necessary skills prior to entering the workforce. But formal education can also be used as a reskilling option, especially if your organization offers tuition reimbursement.

Formal learning environments can be a fantastic place for professionals to learn alongside their peers and under the guidance of industry experts. Having specific learning benchmarks and being held accountable to formal assignments motivate many students to be proactive about their coursework. But formal education has a big setback.

While it would be fantastic if businesses were able to help tailor the current course offerings of a university, this is typically not the case. University professors, often siloed within academia, can be woefully out of touch with market demands and modern innovations. This ignorance of the “real world” is passed onto college students, who may realize their college education is out of step with the careers they plan to pursue.

According to a 2020 article from BCG on college/career alignment: “Although higher education typically provides a good foundation and mindset for pursuing a future career, it can fall short in providing an up-to-date education that aligns with employers’ needs. In fact, only a third of US college students expect to graduate with the knowledge and skills they will need to be successful in the workplace…”

With this in mind, one might assume there’d be a decrease in university enrollment, since these institutions are primarily viewed as the best path to career preparedness. But given how often job posters require applicants to have university degrees, disillusioned students are left with little choice but to graduate and hope they can supplement the more practical aspects of their training in other ways. This means that professionals seeking to upskill via formal education are likely not getting their money’s worth. And when it comes to organizations providing tuition reimbursement for their staff, that means the org is losing out on money, too.

Mentorship Programs

Mentorship typically works by pairing a more experienced worker (the mentor) with an emerging professional or new hire (the mentee). The mentee is shepherded by the mentor, receiving regular feedback on their work performance, technical skills, and alignment with company culture. Ideally, the mentor acts as the point person for the mentee, providing career advice, support for navigating workplace dynamics, and other feedback on how to thrive in their industry and adapt to the particular nuances of your organization.

An excellent mentorship program is able to sidestep the shortcomings of short-term trainings and formal education. Namely, mentorship provides “content” (i.e. professional support and instruction) that is completely relevant and immediately applicable to your team's unique circumstances, and it tends to be cost-effective. Mentorship also mitigates certain risks associated with bringing new, unfamiliar people into your organization. And to top it off, mentorship accomplishes something that short-term trainings and university education do not: increased retention.

  1. Relevant Content: We’ve discussed how short-term trainings typically feature content that isn’t useful to your organization, and how this equates to a waste of your time and money. Mentorship, on the other hand, is specific to your company's unique circumstances. A veteran employee has a thorough understanding of (1) their own work responsibilities and (2) how these responsibilities play out in the unique context of your organization. This means that veteran employees serving as mentors will provide guidance and knowledge that is immediately, uniquely applicable to your organization. No superfluous “content.”And when a mentee wants greater insight on something, they don’t have to worry about a seminar instructor glossing over the desired topic; the mentor can provide as much information as the mentee needs. The “content” of mentorship is always relevant to the responsibilities and inner workings of your team.

  2. Cost Effectiveness: Mentorship programs also enable companies to hire junior talent, because these newcomers will be guided by a trusted company veteran. This means that your organization doesn’t have to limit itself to job candidates with extensive field experience, whose expertise necessarily comes at a premium.In the United States, the average senior software developer with around five years of experience makes $117,000 in base pay, while a junior developer with about a year of experience makes $71,000. With these figures, hiring the junior talent would allow an organization to save 40% on salary costs.

  3. Lower Risks: Hiring new staff always comes at a risk. There are only so many ways you can vet a candidate’s technical competencies and soft skills (e.g. personality fit, clear communication, a go-getter attitude) prior to extending a job offer. It’s always possible that, once onboarded, someone’s true colors will come out and reveal they’re not a great match for your team, or they aren’t as proficient as you had hoped in a particular skill set.It’s estimated that it takes eight months for an employee to reach peak productivity. That time is best spent honing a new hire’s skills and helping them acclimate to company values via a mentor, rather than leaving the employee’s responsibilities, productivity, and culture fit up to chance.Mentorship allows fledgling staff to be taken under the wing of your veteran staff, learning the ins and outs of their responsibilities, the org’s work culture, and how to best put their talents to use. In other words, the common hiccups and clumsy “bumps in the road” associated with onboarding—waiting for your newcomer to get up to speed and begin working with optimal efficiency—are significantly reduced. When in doubt, the mentee has a point person to turn to for help, thus limiting the amount of time spent floundering on a task. And the mentor observes and guides the newcomer’s workplace behavior, helping shape them to be in line with the company’s values and culture.Mentorship allows for a smoother transition when onboarding new staff, and mitigates the harm a newcomer could accidentally do in the case of a work mistake.

  4. Increased Retention: Turnover is costly. For each employee an organization replaces, it tends to result in paying an additional 33%, compared to the previous employee’s salary. Increasing retention by keeping employees satisfied in their roles is a cost saving measure. How does mentorship help with this?

When a company provides a new worker with professionalization resources, this can foster a sense of loyalty. And when one of those professionalization resources is a mentor dedicated to the newcomer’s growth, this means a professional relationship is developed, giving the newcomer a sense of belonging within the company. They feel like part of the team! And when a worker feels like part of a team, with whom they have emotional bonds, this can lead to increased retention. Robert Gabsa, a senior consultant at Gallup, writes:

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“Employees yearn to feel connected to their roles, colleagues, managers, and companies. The higher the emotional connection, the higher the likelihood they will remain loyal to the brand. By creating better experiences in the onboarding phase, companies can build these emotional connections early in the employee journey.”

Robert Gabsa Senior Consultant, Gallup

Mentorship helps create a positive, personal onboarding process, which helps the new hires feel invested in their company.

Consider how often Millenialls and Gen-Zers are characterized as “mercenaries,” job hopping for better employment opportunities at an unprecedented rate compared to previous generations. About 25% of Millennials and Gen-Zers report that they are hoping to leave their current employer within the next six months.

A significant contributor to this “job hopper” trend is the belief that companies aren’t loyal to their employees, so workers don’t owe companies loyalty in return. When a company invests in an emerging professional’s career development and provides personal support in the form of a mentor, this helps combat the message that “companies don’t care about their staff.” And in turn, this can help employees feel uniquely valued, like their work situation is healthier and more supportive compared to other companies that don’t provide such resources.

Mentorship is a unique option for upskilling. It offers greater relevance/applicability, cost savings, lower onboarding risks, and increased retention. While short term trainings and higher education can help companies upskill their staff, these options pale in comparison to mentorship.

How We Can Do It: Direct Mentorship Programs

If you want your organization to pursue mentorship as an upskilling method, what’s the best way to do it? Let’s discuss some pitfalls to avoid and how to set your mentors and mentees up for success.

Getting Everyone Onboard

First, if you decide to use mentorship at your organization, you may encounter some resistance. It’s possible that some company members will be opposed to hiring anyone other than senior level candidates. In these moments, it’s important to remember that senior staff only exist because they were once beginners in their industry. They are where they’re at today because an organization took the chance of hiring them at the start of their careers. Strong mentorship will allow you to take a chance on emerging professionals while mitigating common risks and increasing benefits.

Incentivizing Mentor Participation

You can't assume that all veteran staff will be willing to serve as mentors without some kind of incentive. Make being a mentor worth their time. Otherwise, mentoring or helping onboard a new employee could be seen as a waste, something that pulls staff away from more pressing responsibilities.

To that end, consider providing the senior staffer/mentor with some form of extra compensation, like a bonus or stipend, to recognize and incentivise their wholehearted participation in mentorship. If extra compensation isn’t an option, consider what other perks you could offer in order to help senior staff get involved in this important program.

Providing Adequate Support

In addition to incentivizing senior staff to mentor juniors, you also need to provide them with support and guidance throughout the program. After all, mentorship is a skill, and not everyone will be naturally gifted at it. To make sure that all junior staff are receiving a high quality mentorship experience, you need to equip your senior staff to be great mentors.

Be sure to clearly communicate expectations, benchmarks, and best practices for mentorship before mentors make contact with their mentees. What signs will your organization use to determine if a mentorship relationship is succeeding? Maybe there are specific technical skills, company insider knowledge, or particular habits that you expect mentors to pass on to their mentees. And how will you evaluate the quality of a mentor? You might survey mentees at regular intervals throughout the program, to assess if they’re gaining valuable experience and knowledge from their mentor.

Of course, mentorship also takes time. It isn’t fair to assume that senior staff will be able to add mentorship to their existing workloads. How can you temporarily scale back someone’s responsibilities to make room for quality mentorship? If that’s not possible for some senior staff, then those people might not be in a great position to serve as mentors.

Selecting Mentees

How do you decide who to include in your mentorship program? Some companies may choose to mentor every new hire, as part of the onboarding process. However, your organization may not have the resources to do this. If you aren't in a position to offer mentoring to each new employee, there is one thing you should avoid: prioritizing mentees who self-select or volunteer for the program.

This may sound strange. After all, don't we want the people being mentored to feel enthusiastic about the mentorship program? The short answer is yes, we do want our teams to be made up of go-getters eager to grow their skills and learn from seasoned experts. However, studies show that the benefits of mentorship are most felt by the type of staff who would typically not volunteer to be mentored.

The staff who tend to sign up for courses, professionalization resources, and mentorship programs are already likely to be top performers who show initiative, critical thinking, and high workplace engagement. Mentorship offers the greatest benefit for people who struggle in these areas—in other words, people who aren't likely to volunteer to be mentored.

So when it comes to finding a pool of staff to mentor, consider having leadership select staff themselves and require mentorship as part of your company’s expectations for professionalization. We recommend using a metric that will make selection as objective as possible, like “all staff who have been at the company for less than three years,” or “all staff not yet trained in X skill or tool.”

Setting Mentee Expectations

When a junior team member begins the mentorship program, the mentor should set their expectations about regular activities and responsibilities. What will the mentee’s work look like on a day to day basis? For example, junior staff might observe meetings that the mentor attends. And for hands-on practice, trainee software developers, for example, can do peer programming each week alongside their mentor. Once a certain level of trust has been established, the mentor can delegate lower risk tasks, like debugging, to the mentee, and then provide feedback on their work. When a mentee has clear, accurate expectations of what they’ll be expected to do during the program, this will help them assess how helpful the program is and what gaps in experience they’d like to have addressed.

Partnering with a Mentorship Firm

Implementing a mentorship system that is purposeful and well organized takes time. Your organization may not have the time or know-how to build such a program internally. If this is the case, you can partner with a third party who specializes in mentorship programs.

When it comes to third parties who run mentorship programs, look for companies who…

  • Can connect you directly with junior staff, if you’re looking to hire.
  • Have a clear process of continual assessment (i.e. check-ins) throughout the duration of the program, so that course correction can take place when problems arise.
  • Manage trainee staff through a variety of avenues, including their People Experience Partners, who can assess how the trainee feels about the program, what they’re learning, and if they're connecting well with their mentor.
  • May provide bonus compensation to mentors. For example, with Jobsity’s Nex Gen program, client’s mentors are usually already Jobsity staffers, so Jobsity provides them with the extra compensation directly; the client doesn’t have to cover the extra pay.
  • Provide access to continued training via courses and certifications for mentees, which mentees can learn from under the guidance of their mentor. This way, your organization doesn’t have to cover training costs or worry about irrelevant content being a waste of money. The mentor can serve as an instructor, answering the mentee’s questions and reframing the content in ways that are relevant to your organizatio


With the growing skills gap, companies are having a harder time finding job candidates whose talents align with their needs. Options like short term trainings and formal education can help “upskill” an organization’s workers, but these options have notable pitfalls. Mentorship, on the other hand, allows organizations to upskill their staff in a more effective, lower risk way.

Mentorship programs provide a way to upskill trainee talent effectively, while reducing turnover and saving on training funds. Mentorship programs are also applicable to just about any industry, as opposed to certification programs that are limited to certain sectors. This means that once an organization finds a mentorship program that works well for them, they can easily replicate it across different departments, for different teams.

While strong mentorship programs can take time to implement, the benefit of a junior staffer being shaped to an organization’s needs and culture cannot be understated. Their skills will more closely align with your company’s unique goals and limitations, and the bonds formed between a junior staffer and their teammates will create better circumstances for retention. Partnering with firms who specialize in mentorship programs can reduce the challenges organizations face when trying to launch their own internal program.

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Written by Santiago Castro

With over +16 years of experience in the technology and software industry and +12 of those years at Jobsity, Santi has performed a variety of roles including UX/UI web designer, senior front-end developer, technical project manager, and account manager. Wearing all of these hats has provided him with a wide range of expertise and the ability to manage teams, create solutions, and understand industry needs. At present, he runs the Operations Department at Jobsity, creating a high-level strategy for the company's success and leading a team of more than 400 professionals in their work on major projects. 

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