How to Make Upskilling and Reskilling Part of a Corporate Culture of Learning

BY Emily McCrary-Ruiz-Esparza | June 03, 2024

When there’s a problem at Fortive Corporation–maybe it’s a recurring operational hiccup, high employee turnover, or a slow production process, for instance–the company invites the best and brightest to put their heads together and come up with a solution. And by best and brightest, they mean anyone willing to come with an open mind and think creatively.

“It’s good to have a few experts who know exactly what the process is and why, what the critical steps are, and things like that. But it is even more important to have people who know nothing about the process,” said Shannon Flynn, VP of corporate HR at the industrial technology holding company. Anyone is encouraged to participate in the problem solving, from individual contributors to the C-suite, but, to join one of these Kaizen sessions, “you park your title at the door.” This, Flynn says, is a culture-creator.

How employers can create a culture of corporate learning was the topic of discussion among a panel of HR experts during From Day One’s May virtual conference. The events of the day addressed employee retention, coaching, and advancement.

“Shifting a culture really is different than just implementing a program,” said Erica Ishida, the CEO of executive coaching firm Yellow Cedar Group. She participated in the panel along with Flynn and their long-tenured colleagues in human resources. “It requires a shift of minds and hearts across the organization. I suggest that you think about it organically, leading by example.”

How to Lead by Example

“The best advice I can give is to start at the very top,” said Yonata Rubin, head of talent at entertainment and hospitality company MGM Resorts International. “We are very fortunate that our CEO and board is incredibly invested in leadership development. They actually came to us, rather than us going to them,” she said, but not everyone will be able to start from that position. Make sure you have the agreement at the top of the organization that learning is a priority, then move on to strategy. “What is it that you are trying to build? Where is the biggest need? What do your employees want?” she said.

Meredith Haberfeld, the founder and CEO of leadership development platform ThinkHuman, said it’s worthwhile to have executives talk candidly about what they’re learning, and what they’re grappling with. “Those with power and authority create influence,” she said. “We found it super useful to get CEOs to share learnings from the last quarter. It’s just a small action — what did they learn that they can share with the company?”

The panelists discussed the topic, "How to Make Upskilling and Reskilling Part of a Corporate Culture of Learning" at From Day One's May virtual conference (photo by From Day One)

When business leaders are forthcoming, lower-level employees are encouraged to do the same. “Leaders need to pay attention to the environment that their people are working in,” said Ishida of Yellow Cedar Group. “People can only learn in an environment where they feel psychologically safe–do they feel free to learn and try new things, and maybe fail?”

Structured Learning or Free Exploration?

What about the mode of delivery? Maybe your staff feels comfortable trying new things and making mistakes, but, practically, where and how are they learning those new skills?

Will Campbell is the VP of learning and leadership development at commercial real estate firm JLL. He says that an exhaustive menu of new skills or training programs isn’t likely to generate much engagement. Instead, he recommended making it easier for employees to jump in by narrowing the options. For instance, perhaps frontline managers pick from one tailored list of courses, junior leaders pick from another, and senior leaders from a third list.

This limits the number of choices, prevents analysis paralysis, and helps workers stay on track. “Structured doesn’t mean rigid,” said Campbell. “You have to have structure. Otherwise, it will be a free-for-all. But you can be flexible. You can make it fun, you can make it exciting.”

Formal structures may facilitate long-term upskilling and reskilling across an organization, but small habits build a learning culture at the team level. For quick hits, Haberfeld recommended beginning meetings with five to ten minutes of “microlearning.” For instance, an individual contributor might bring back ideas from an industry conference and prepare a short lesson. “We rotate who is teaching so people from all different parts of the organization get to show their expertise, and the organization gets to learn,” she said.

MGM International takes a similar tack. “We have ‘odd shifts’ or ‘pre-shifts,’ where you gather small groups of employees and do a quick huddle and then debrief,” said Rubin. She’s found this to be a time-efficient way to deliver upskilling to frontline workers, who don’t have the luxury of sitting down for a thirty-minute learning session.

Getting Workers Excited About Learning

Sometimes being made to learn new skills can feel like punishment, said Campbell of JLL, especially when the training is for compliance purposes. But “people have an interest in things that aren’t their daily responsibilities,” he said. When people get to pursue new skills because they want to, “that fire has been lit, that groundswell now takes hold, and the whole thing takes a life of its own.”

If workers don’t see the connection between what they’re being asked to learn and how it will benefit them personally, you’ll struggle to engage them, said Ishida of Yellow Cedar. Managers can be the ones to make that connection for their direct reports. “One of the key ingredients is having supportive relationships. Connect [the new skills] to the individual’s wishes and desires, and make sure they have people around them to support them in the change.”

Emily McCrary-Ruiz-Esparza is a freelance journalist and From Day One contributing editor who writes about work, the job market, and women’s experiences in the workplace. Her work has appeared in the Economist, the BBC, The Washington Post, Quartz, Fast Company, and Digiday’s Worklife.


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