Why the Future of Work is About Reskilling Your Current Workforce

Abby Kearns
3 min readSep 10, 2018

I’ve been thinking a lot about the future of work. In fact, if you’ve spent more than 30 minutes with me lately, I’ve invariably mentioned it as a key ingredient to the future success of every company.

As more companies get further along on their journey to automation and digitization, one of the biggest questions they’ll confront is about their workforce. Specifically, do they have the skills necessary to develop the software they need to accelerate their business?

Reskilling is in the future for most of us. Based on a recent report from McKinsey Global Institute, “75 million to 375 million may need to switch occupational categories and learn new skills…” over the course of their career.

What does the workplace of the future look like at the end of this journey? Every organization will encounter hurdles not only around evolving technology, but also around the very culture of their workplace. The technology is the easy part. It’s changing your organization’s culture that’s hard.

Part of this change means embracing a mindset centered around continuously developing new skills in-house and building continuous learning reflexes into the very DNA of your organization. As pointed out in Never Stop Learning, by Bradley R. Staats, “Value is created when we can customize, adapt, and innovate — all of which require learning.”

The Case for Reskilling

Enterprises have adopted a pattern in which they “phase out” existing employees to either hire a whole new team of employees or to outsource those needed skills to another company entirely. But gaining technology skills for the advancement of your organization does not require losing your people. Training should be a cornerstone for any organization’s digitization strategy.

From another McKinsey Global Institute report, “sixty-two percent of executives believe they will need to retrain or replace more than a quarter of their workforce between now and 2023 due to advancing automation and digitization.”

The skills required to develop and iterate on new products and technologies across a large organization are still evolving, particularly in the cloud space. This also means that new skill sets and new technology will develop simultaneously, often side-by-side.

From a practical point of view, there simply aren’t enough developers with the expertise to go around (right now). But I don’t see this as bad news. I think it represents opportunity — for companies to be intentional about how they want their organization to evolve, and how they leverage technology.

I think that companies should emphasize reskilling and retraining. By investing in your existing workforce, you create a healthy work environment based continuous learning and collaboration. Equally important, you hold onto the historic knowledge each of those employees has about your business. To put it simply: people keep their jobs, companies keep institutional knowledge. This value cannot be underestimated.

Of course, not every employee will want to make this shift. But I guarantee many will. If talent feeds talent, organizations who follow a reskilling strategy can see long-term gains in both their business and their culture, as they continue down the path towards becoming a software company.

Continuous learning as a practice

But reskilling can’t just be a one-time tactic. It must be woven into an organization, so it’s baked into the long-term strategy. That means developing continuous learning practices throughout the company.

For an employee that means having the support and resources to continually learn and evolve, either through internal learning and development tools, or access to external training programs. Organizations must provide that framework by embracing strategies that include training, collaboration techniques, as well as an awareness of emerging practices and technologies.

I say awareness because I don’t think it’s necessarily the right move to jump from tech bandwagon to tech bandwagon. What is important is to know what’s in the market, and to have a system flexible enough to assess and incorporate the tools and technologies that are best for your organization — from the IT department to HR.



Abby Kearns

Technology Executive | Board Director | Angel Investor