Up-Skilling: Convincing Your Boss to Pay for It

Up-skilling is popular among certain companies at the moment. For example, Amazon recently announced that it would spend $700 million to retrain 100,000 employees, including the transition of “non-technical” employees to software-engineering roles.  

But technologists don’t need to wait around for their company to announce some kind of up-skilling program. Many managers and executives are open to a conversation about continuing education on the company’s dime—but for technologists who want to go this route, it’s important to first consider the relationship between employee and employer.

That’s the point of view of Sean Chou, CEO of digital automation platform provider Catalytic, who is convinced that employees have an incredible amount of domain knowledge and can help with companies’ overall digital transformation. Up-skilling, in other words, will align with broader company and industry goals.

“If you think about what are the good conditions that create an environment for an employee to say, ‘Hey, up-skill me’, that usually stands under the auspices of process engineering or digitalization, reexamining the way work gets done,” he said. “When you look at things like process automation, you’re looking to change who is going to do the work, and that means doing more rewarding work more often.”  

The employer is excited because they can get more production out of their newly up-skilled people, while the employee now has the opportunity to do more interesting stuff. But employees should be willing to reach out and ask their employers to help them learn how to use platforms and products that help them do better work.

“This isn’t turning non-coders into mega programmers, but with the right tools, they can be not just the passenger on the digital transformation ride, but they can be the driver,” Chou said. “Employers should want their employees to be the ones guiding the process.”

Up-Skilling and Automation

When Chou hears executives say “digital transformation,” he often wonders if, at the end of the journey, they know about the company-boosting skills that their employees can potentially unlock: “’Transformation’ at the end of the day means your employees should have more skills and more capabilities—if they don’t, you haven’t transformed.”

Last year, in a report titled (rather dramatically) “The Upskilling Crisis,” West Monroe Partners noted that 60 percent of employees believe their existing skillset will be outdated within five years. Moreover, 55 percent said they needed up-skilling in order to remain relevant.

But which skills? Several recent studies suggest that automation is at the forefront of many company roadmaps. That’s a bit worrisome for technologists, as it means that some jobs currently done by flesh-and-blood humans will eventually end up taken over by machines and/or code. However, it also presents something of an opportunity; those technologists who “upskill” themselves to manage automation could unlock a whole new career level.

“We’re of course focused on work that can be automated—if they map out their process, they’ll see how much is automatable, and they can make the pitch to take the initiative and learn the skills on their own,” Chou said. “You need to make that pitch, and good executives should listen to that.”

Of course, it’s not just automation—as demonstrated by Amazon and other firms, there’s a generalized hunger for technologists of all types and skill-sets, from app-building to project management. Although the “average” technologist made $94,000 in 2019 (according to the just-released Dice Salary Report), up-skilling can radically boost that compensation—and sometimes result in additional benefits, such as equity.

Show You’re a Team Player

Showing that you can work on a team, on more strategic tasks, can also help highlight that your company needs to invest in you. “Seeing a person rise to that level creates a lot of confidence in those executives,” Chou noted. “Instead of me saying, ‘I spent all my time doing data entry and this is a waste of my time,’ take a step back and think about how this leads to the sales process and look at the people who are doing comparable tasks.”

You can show off your aptitude for skills and bigger projects by sitting down with colleagues and going over processes that may need to be rethought, or are redundant in some way. Once you’ve done that, the skills you might need to learn in order to advance the company’s goals (and your own) may become clear. And from that point, you can successfully argue that the company should pay for your up-skilling in order to advance its own interests. 

“If you can understand inefficiencies, if I can have the same team doing twice the work, you can make the argument that you’re going to be much more productive,” Chou explained. “A lot of organizations will automate a process, go from 10 employees to six, but the four get put onto higher value work, essentially getting a promotion.”

Most companies are growing, and what you’re arguing is: Instead of hiring more people, train and invest in your current workers—boosting everyone’s productivity. “Employers should love that, because their employees have that domain knowledge and contribute to the culture of the company,” Chou noted.

The employee has to be at the heart of any successful up-skilling plan. “A lot of times I feel like employees are not empowered to make these changes, but I bet a lot of employers would be excited by being asked to help make their transformation,” he added.

Even before you ask your boss about the possibility of the company paying for classes and other opportunities, seek to expand your skillset by any means necessary. For developers, there are a variety of channels for doing so; as revealed by HackerRank’s latest Developer Skills Report, younger technologists have an affinity for YouTube, while their older colleagues prefer books and on-the-job training; all ages are affectionate about GitHub.