Older Workers and Technology: How They Approach It With a Different Mindset

BY Emily McCrary-Ruiz-Esparza | July 26, 2023

Karen Fleshman is a 54-year-old CEO of a small workshop-facilitation company based in the world’s tech capital, the San Francisco Bay Area. Recently, a potential client approached her about creating some anti-harassment videos, but before they would award her company the contract, they wanted to see a sample. Fleshman’s expertise is content, not tech. To win the job, she would need to deliver both.

“I was like, ‘Oh God, this is not something I can record on my phone,” said Fleshman. “I’m really going to have to work to make this look up to their standards.” 

Video creation and artificial intelligence is new territory for Fleshman—for the project, she’s teaching herself Descript, Loom, StreamYard, and Beautiful.ai—but resourcefulness comes naturally. “I’m not the most technologically proficient person to have walked the planet,” she said. “But I am a very creative person, and I’m also a very strategic person.”

Fleshman is careful to not live down to the stereotypes about people in her age bracket when it comes to technological proficiency. “There is the assumption that I won’t be technologically proficient, so I’m trying to not play into the stereotype that I’m going to ask for help because I’m frustrated,” Fleshman told From Day One. “I try to do what Millennials do and look for a YouTube tutorial.”

Most mid- and late-career workers know the preconceived notions counting against them: bad with tech, slow to learn, resistant to change. A survey by Generation.org found that people 45 and older commonly cite their age as one of the most significant barriers to getting hired. 

If indeed “every company now is a tech company,” like the pundits declare, where does that leave older workers who are especially susceptible to the ageist stereotype that the older you are, the fewer tech skills you have and are capable of learning?

Karen Fleshman, CEO of a workshop-facilitation company in the Bay Area (Photo courtesy of Karen Fleshman; featured photo by Gorodenkoff/iStock by Getty Images)  

In some cases, Gen Zers and Millennials do outperform their older peers when it comes to tech. There’s data to support this. In 2021, the Urban Institute found that, generally, adults aged 50 and older have fewer digital skills than those under age 50, though the gap is not particularly wide. Simple exposure is likely to blame. If Gen Xers wrote their term papers at terminals in the university computer lab, Gen Zers dictated theirs to a phone that autocorrected their spelling and generated perfect MLA citations. 

“People say, ‘I want to hire digital natives because they’re more adaptable and more skilled with tech,’ but I’ve never seen any empirical evidence that that’s true,” said Paul Leonardi, a professor of technology management at UC-Santa Barbara and co-author of The Digital Mindset: What It Really Takes to Thrive in the Age of Data, Algorithms, and AI. Yet in some cases, older workers aren’t given the opportunity to learn new tech skills because it’s assumed they either don’t want to or aren’t capable.  

With the quantity and variety of technology available to the average consumer growing relentlessly, it’s becoming harder for anyone to be a true expert on the innumerable choices at hand. “So many of these technologies are new for everyone, not just the older folks in the workforce,” said Loren Blandon, the global head of learning and development for advertising agency VMLY&R. “We’re all on this learning curve together, so from that perspective, there’s an even playing field.”

If more seasoned workers express resistance to new tools, it’s not on stubborn principle, but because they’ve seen tech trends before, said Heather Tinsley-Fix, a senior advisor at AARP, which offers a multigenerational skill-building platform. How many promising new ideas have been adopted only for them to be made obsolete or replaced just as quickly? “Whereas a younger worker who’s 20 years old, this might be their first or second change of processor platform,” Tinsley-Fix observed.

Older workers pump the brakes out of judicious caution while “young workers charging ahead, and it looks like younger workers are better at this,” said Leonardi.

The distorted notion that older workers look unkindly at change can do a lot of damage to a well-developed career. According to the Generation.org study, hiring managers said that reluctance to learn new technologies is the No. 1 characteristic most likely to limit the success of job seekers 45 and older. No. 2 is the inability to learn new skills. In addition, hiring managers tend to think of workers under age 45 as being more “application-ready,” that they have more relevant experience and are a better culture fit.

But those same managers fail to support their own beliefs. The same survey found that when asked about overall performance, 87% of hiring managers said that their older workers perform as well or better than their younger peers.

Given the penalties for being “old” in the workplace, mid- and late-career workers worry about looking like the stereotype. “There’s this internalized ageism, where they’re afraid that they’re going to be perceived as slow and not able to do it better or fast enough,” said Tinsley-Fix. “If I don’t know how to do something on, say, LinkedIn, I will go to someone and ask them to teach me, but I will never admit it openly because I’m mid-career, and I don’t want people to know that I don’t know.”

Kyra Sutton, who teaches at the Rutgers School of Management and Labor Relations, said the ability to use or learn new skills isn’t usually what divides the generations, it’s the format. Sutton is currently surveying her students about their learning preferences, and the unofficial results indicate that “those under 25 prefer mechanisms like TikTok and YouTube. People that are 45 and older still want technology, but they want it consumed in a different way. TED Talks or podcasts are very popular among that group.” 

Blandon at VMLY&R flagged something similar. “I think learning styles are more personality-based than age-based, but if I had to say where age differences emerge, it would be in attention span. For our entry-level folks, we need to come at them with short-form video.”

Leonardi notes that motivation can also vary across generations. Older workers, he’s found, have less patience for learning things they aren’t interested in. Employers may be wise to have senior team members take on new tech that corresponds to a totally new skill they’re interested in learning. “Let your older workers surprise you,” Leonardi said. “Give them the opportunity to use a new tool not for the sake of using a new tool, but to expand their own knowledge, and they will have the motivation.”

For many, interest is self-generated. “There have been times in this when I’ve become incredibly frustrated,” said Fleshman, the Bay Area entrepreneur. The video tools she’s teaching herself don’t integrate with each other, and the standards for video production are exceedingly high. “Because we have all these tools at our disposal, the standards of what things should look and feel like are so high. And then it’s me and my laptop.”

Why, then, didn’t she just hire out the work? Wouldn’t it be easier to write the content herself and hire experts to do the video production? Because it’s new, she said. It could land her this new client, and now she’s considering recording other sessions and gating them behind a paywall. “I wanted to develop a new skill, and I wanted to see what these different things are capable of doing. I’m doing this on contract for another company, but I can apply this to my own. I’m excited about that possibility.” 

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 Washington Post, Quartz at Work, Fast Company, Digiday’s Worklife, and Food Technology, among others.

 

 

 

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One resource to help spot misinformation is Rumor Guard from the News Literacy Project, a nonprofit dedicated to teaching Americans how to discern fact from fiction and dispelling viral rumors.Take Ten—and Commend It to Your Team“Most of us are working with tired brains,” says Amit Sood, M.D., author of The Mayo Clinic Guide to Stress-Free Living. If you're getting caught up in the rapidly changing political rhetoric, take ten-minute breaks during your workday. Treat yourself to micro naps, mini nature walks, or a sound bath on Spotify—anything that will give your tired mind some time to rest and recharge. And please, don’t scrimp on sleep. This is no time to be running on empty. You need to be in good mental shape for yourself and your workers.Model Self-compassion and CuriosityWhile this might sound self-indulgent, research proves that workers who treat themselves with grace rather than punishment perform at a higher level, have less workplace stress, and are better team players. 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It certainly seems like a bleak moment to be a worker in America. Scroll the news or social media and a picture forms of an uncaring, turbulent, and miserly workplace.Why is this so striking? Empathy, or the ability to understand and be sensitive to others’ feelings and experiences, became a fashionable trait in business just a few years ago. For a while, employers were getting really good at responding to the needs of the workforce. Some companies even traded on it. Empathy, as well as its more active cousin, compassion, took many forms. As more attention focused on how some demographic groups were often left on the sidelines, employers said OK, let’s find ways to level the playing field, and they set hiring goals and stood up mentorship programs. When Covid lockdown closed schools and day-care centers and quarantined babysitters, companies told workers to take care of their families and welcomed Zoom cameos from kids. 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Emily McCrary-Ruiz-Esparza March 19, 2025

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Companies have long used leadership assessments for succession planning to find people who are capable of climbing the ladder, but it’s expensive to interpret the results, present them to leadership, then work with HR to write development plans. “That’s human time that I think will be able to be taken over by AI,” he said.AI is still relatively new to HR professionals. This is due, in part, to privacy concerns. Companies can’t just throw employee data into a gen-AI chatbot, even if it is a closed system. And HR is not historically a tech-forward department, but that’s changing. For now, HR is primarily using AI for time-saving, says Farner, but that will expand over time. Organizations are beginning to move past tapping AI as an assistant completing admin tasks to tapping AI as a consultant that operates like a colleague.Emily McCrary-Ruiz-Esparza is an independent journalist and From Day One contributing editor who writes about business and the world of work. Her work has appeared in the Economist, the BBC, The Washington Post, Inc., and Business Insider, among others. She is the recipient of a Virginia Press Association award for business and financial journalism.(Featured illustration by Photoman/iStock by Getty Images) 

Emily McCrary-Ruiz-Esparza March 19, 2025