Esther Shein
Contributing writer

9 upskilling tips that pay dividends

Feature
08 May 202310 mins
IT SkillsIT StrategyIT Training 

IT leaders are leaning into training to fill skills gaps and unleash latent tech talent. Here they offer lessons learned about their unique and practical approaches.

Upskilling has moved from what once was viewed as an employment perk to a mandate. Even with tech layoffs and uncertain economic times, the IT labor market remains hypercompetitive and organizations cannot afford not to invest in training existing staff.

Forty-one percent of CIOs reported plans to increase investment in training programs to reskill IT employees, according to Gartner’s 2023 CIO talent planning survey. The most essential skills they need are cybersecurity, cloud, and customer/user experience skills.

In addition, the firm’s 2023 midsize enterprise talent outlook report found that attracting and retaining technology talent have become critical areas of concern for midsize enterprise (MSE) CIOs, with 84% of CIOs reporting more competition for qualified IT talent. Further, 73% of MSE CIOs reported being worried about increased IT attrition rates.


One reason is that digital transformation projects continue, unabated. In the past couple of years, 84% of organizations have started at least two new digital experience initiatives, according to an April report from Enterprise Strategy Group.

So IT leaders are getting creative. Here are nine tips IT leaders have to offer based on their experiences upskilling staff.

Assess skills and personality for training fit

Tim Dickson, CIO of Generac Power Systems, a manufacturer of power products, came to the company over two years ago as the first CIO, and knew immediately he wanted to conduct a skills and personality assessment of his 80-person staff to upskill those who wanted to grow their careers.

It was the height of COVID-19 and Dickson didn’t have a huge pipeline of candidates. Moreover, digital skillsets were lacking in the organization. But digital transformation “is in my blood,’’ and he was hired to lead the initiative at Generac. That meant Dickson needed people with data, AI, automation, RPA, and cloud skills, and he needed them fast.

So, Dickson built a set of artifacts to assess the team’s skillsets and aspirations, complete with various use cases. Then he created templates of use cases he had seen in prior companies related to what he would be asking IT to do. A 30-question digital assessment was part of the artifacts, which Dickson characterizes as “very introspective and subjective” related to personality and skills.

Questions ranged from “Do you understand digital?” and “Do you aspire to do more for the company or do you want to come in from 9-to-5.” From there, Dickson plotted four areas that the team fell into. There was a small group “ready to jump in and very eager.” A second bucket had aspirations but needed tech aptitude. The other two buckets included those who weren’t interested in growing their careers, he says.

Dickson focused most of his upskilling efforts on the group he characterizes as “the crown jewels,” those who aspired to do more, but didn’t know how.

“You’re always going to have people not interested [in growing their careers] and people who are and need upskilling and coaching,’’ he says. It turned out that 40% of Generac’s IT staff fell into the latter bucket.

The personality test was designed to help Dickson understand what makes the IT staff tick and what motivates them. This was helpful in gleaning whether someone has a dominant personality because that is important to know going into a team project, he says.

Hold hackathons for hands-on learning

The last part of Dickson’s three-pronged approach at Generac was to hold a hackathon that included training, incubation, and prototyping aspects, along with public speaking opportunities, with employees selling their ideas. Dickson enlisted eight vendor partners he had worked with previously to co-sponsor the event, selecting them for various types of emerging technologies they offered, such as AI, UX/UI, RPA, and APIs.

The vendors trained Generac IT staff who wanted upskilling for a month leading up to the hackathon. At the day-long event, employees not only showed up with a new skill they learned but also an idea and prototype for how a particular technology could improve something at Generac.

In one example, a team member proposed embedding the Alexa chatbot into Generac’s generators so customers could talk to them. The idea ended up being produced and going live.

There were 16 teams with 70 team members, and over half of those teams’ ideas have been implemented into production, Dickson says.

Hackathons are now conducted on a regular basis. Recently, one was held with a spotlight on OpenAI’s ChatGPT, and a Microsoft reseller came in to demonstrate how the technology has been implemented. “Any time there is a new technology that could be disruptive, we do these hackathons,’’ he says.

One of Generac’s SAP data analysts expressed to Dickson that she wanted to become a UX/UI designer, so he partnered her with a friend who is one and she coached the employee through a hackathon. Now, the employee has become Dickson’s sole UX/UI designer.

Aside from the hackathons, Dickson also organizes lunch-and-learns with vendors, which he says have been effective. “The best way to get someone to a generic meeting is to give them food,’’ he says.

The downside of upskilling? “The [daily] work still has to get done,” Dickson notes. “So if I’m moving people into new roles, that’s leaving holes, so that’s where I leverage contractors to keep the ship running.”

Personalize the approach

CIO Taren Rodabaugh says much of Bridgestone Americas’ recent focus has been on “eternal” skills that build “well-rounded technology professionals.” This includes business acumen, financial literacy, problem-solving, agile ways of working, and wellness programs to support mental and emotional well-being.

“We continually evaluate and refine the upskilling strategy based on our overall business strategy — which likely includes more than just technology,” she says. “We work to personalize the approach based on your team.”

The issue leaders ran into with required learning was that people would sign up to say they took a course, but they didn’t actually engage with the training, Rodabaugh says. “We changed our approach and instead of requiring it, we made it available for them to enlist and learn on their own. This was a lesson learned for us.”

For example, she has instituted Gemba walks, which take teammates out from behind their desks to where work is happening.

“This gives them a breadth of knowledge that makes them well-rounded and allows them to move around IT,’’ Rodabaugh says. “Gemba walks allow our teammates to put themselves in their customers’ shoes. They see in real-time what processes or tools are working and what isn’t.”

Leaders should not be afraid to adjust personalized learning if they aren’t seeing the impact they desire, she adds.

Lean into aspirations

Desperate times call for desperate measures. With “a significant amount of turnover,” and difficulty finding IT candidates to work at the University of Montana, Zachary Rossmiller, associate vice president and CIO, turned inward. Rossmiller identified students and non-IT staff who had an interest in technology and found mentors for them to work with along with providing training modules on what they needed to do to get a job in the department.

Higher education doesn’t pay as well as the private sector, he notes. Rossmiller also has to compete with a number of tech companies that have moved into Missoula, Mont. He has about 15 to 20 student employees and he zeroed in on seniors who were working part-time and told them, “We’ll get you kick-started with your career.’’

“It was mostly out of necessity to stop the bleeding of our staff,” Rossmiller adds, noting that 16 people left IT within a six-month span.

He also upskilled two of the university’s HVAC technicians, one of whom expressed an interest in network engineering and the other in project management.

Now Rossmiller is contending with moving the university’s ERP system to the cloud and upskilling other staff, some of whom have been there 20 years and are only accustomed to on-prem server administration.

“One person said, ‘OK, you’re basically telling me I won’t have a job after’” the move to the cloud, Rossmiller recalls. “I said, ‘No, we need managing in the cloud. We’re here to retool you and add more skills to your existing resume so you can learn more and take on more.’”

He set up a training portal after looking at classroom-led training, which didn’t work for people who didn’t want to travel and be away from their families for one to two weeks. But there were other employees who didn’t want to train in the office because they felt they couldn’t concentrate.

Like Bridgestone America’s Rodabaugh, Rossmiller customized learning based on the individual, because he found that a lot of the younger staff wanted to move into Linux administration while senior staff wanted to learn how to manage databases in the cloud.

He wrote a playbook that looked at traditional 12-week courses offered at the university that people could enroll in, but also included self-taught training because, in some cases, Rossmiller needed people to ramp up more quickly.

Pair people up

Rossmiller also did what he calls a “triangle of mentorship,’’ by pairing people with cyber mentors, for example, and when one of those mentors needed further skills expertise, “they would go to the infosecurity team and grab someone from that team” to train the employee, he says.

Then Rossmiller looked at where any potential gaps were and whether an individual needed a certification. Rossmiller says he got lucky hiring some very good students with an aptitude for learning.

“What hasn’t gone well is we tried moving way too fast and sometimes we forget these are 20- and 21-year-olds trying to get an idea of life, and we moved at a pace faster than most of them are used to,” he says.

Jose Ramirez, a senior principal analyst at Gartner, says pairing two employees is a great way for employees to learn from each other. “It’s a mode for social learning,’’ he says. “You’re not necessarily using a formal training approach like classroom-style training or a conference or taking a course online.”

Build digital academies and talent marketplaces

Another approach is to find non-IT talent with “high potential and upskilling them into IT roles’’ by creating digital academies, which tap tech talent and help non-IT employees upskill and become future IT employees, Ramirez says. “We’re seeing that more and more.” Twenty-two percent of non-IT employees have some foundational untapped talent, according to Gartner research.

CIOs shouldn’t feel they have a responsibility to upskill only their own employees — they should upskill any employee with some degree of technical skills, Ramirez stresses. This is because “we’re shifting toward skills-based staffing to help close the talent gap. It’s the idea that great talent can come from anywhere.”

This can be done by utilizing learning platforms and talent marketplaces, where IT employees share their strengths. One way of doing this is by IT posting small projects that employees can work on together, which they find out about through a talent marketplace.

But Ramirez cautions that “if people haven’t bought into it, they won’t learn. Culture plays a huge part.” He adds that talent marketplaces are not that prevalent.

Foster employee ownership

Mark Long, CTO of platform provider Vytalize Health, calls himself a big believer in instilling a culture of learning and says he expects “every employee to keep up with the state-of-the-art in their particular skill set.”

“The second thing I tell people is my job is not to have all the answers. If your job is senior anything, you should bang your fist on my desk once a quarter” and let him know about conferences they attended or videos they watched, Long says. “This is a learning organization, and we obsess about learning about what our professions are and our external internal customers. If you’re not a curious person, this isn’t the place for you.”

The speed with which technology changes requires every employee who cares about their job to upskill and train, and Long wants to make that a shared responsibility.

“We as a company want to improve skills, but I remind employees they’re the custodian of their career.” Employees have an annual meeting with their manager to set goals in terms of jobs and skills, and Long says he and other leaders are there to help and provide mentorship.

From there, it is incumbent upon the employee to schedule a meeting with their manager once a month or quarter to update them on what they’ve done on their development plan, he says.

“At the end of the day, I want to create ownership on the employee that they’re pushing their career forward in a way that meets not only meets the company’s needs but their long-term needs,” he says.

The idea of employees taking ownership of their careers is a “conceptual shift,’’ so “everything’s on the table” for upskilling. This also includes lunch and learns, reading and discussion groups, shadowing, and certificate programs, says Long, adding that he genuinely wants everyone to be successful so there may be a conversation about looking for something different.

“I had a software architect 20 years ago and he wasn’t great,’’ he says. “I said, ‘It’s time to move you into a different role.’ He pushed back in the beginning but then found joy in something new” as a project manager.

Upskilling doesn’t have to be a top-down process, Long says. It’s important to involve employees and all the different stakeholders in bringing a program and methodology together.

Explore rotational programs

Like University of Montana’s Rossmiller, Vytalize Health’s Long says peer pairing and real-time coaching have been successful in his software engineering group. He also rotates whom people are paired with.

Ramirez says rotational programs are one of the most unique ways to upskill. Unlike apprenticeship programs or early career development programs, it is faster and easier to invest in junior IT talent and put them in a six- to eight-month rotational program where they learn critical skills for weeks at a time in areas such as cybersecurity, cloud, and AI/machine learning, he says.

Rotational programs provide “a culture of experiential learning and sharing that is much more powerful than reading a book or taking a class in abstraction’’ because it is putting work into practice, Long says.

At Vytalize Health, the feedback on rotations and pairing hasn’t always been positive. In the peer pairing example, Long recalls an employee telling him they felt “uncomfortable and upset” that he made them try this. He chalks this up to some people not being as up to speed as others.

But other employees told Long that while they were skeptical going into it, they were glad he paired them with more senior IT members.

Upskill for skills, not jobs

CIOs should embrace and foster a culture of agile learning, where upskilling is integrated into the flow of work rather than outside or in addition to work, Ramirez says.

Gartner research on agile learning has found that organizations are 4.3 times as likely to achieve business outcomes when learning is done as a collective. There is also a significant correlation between upskilling and retention, Ramirez says. Nearly 21% of employees have reported leaving an organization because of a lack of development opportunities.

Vytalize Health’s Long pushes back a little on the word ‘upskilling,’ saying that, “I actually don’t think that’s the right way of thinking about it. This is the work of your career — it’s not something you do from time to time when tech changes.”

Part of being in IT means you need to think about upskilling every day, he says.“The world we’re in is moving so fast … and I went to school to learn how to learn.” People need to get out of the mode of thinking upskilling is an occasional event, Long says. “It’s as important as security and everything else you do with employees.”

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