• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
NewslettersFortune CHRO

You might be upskilling all wrong—Here’s how to actually get workers to retrain for the future

Emma Burleigh
By
Emma Burleigh
Emma Burleigh
Reporter, Success
Down Arrow Button Icon
Emma Burleigh
By
Emma Burleigh
Emma Burleigh
Reporter, Success
Down Arrow Button Icon
March 6, 2024, 8:15 AM ET
Business woman teaches lesson to colleagues on a whiteboard.
Companies should think more about career paths for individual workers rather than large-scale upskilling initiatives.Getty Images

Good morning!

Recommended Video

The AI revolution has begun, and businesses are rapidly integrating the technology into their daily operations. Some companies have openly admitted that those changes have led to hiring freezes, and many employees have been left wondering how they can gain the skills of the future to avoid getting left behind. 

That anxiety has helped give rise to a new corporate obsession: upskilling, the idea that companies should teach their staff new skills outside their current capabilities. A majority of workers want learning opportunities from their employers, and bosses want reskilling, too—it creates a modernized workforce. 

But companies are struggling to figure out how to retrain their workers. Only around 50% of companies attempting to implement large-scale upskilling programs in 2024 had activated those initiatives, according to a new report from LinkedIn. Around 41% were still in the planning stage, and just 4% were at a point where they could measure any progress. 

One-size-fits-all programs designed to train thousands of employees at once are ambitious, but slow-moving and non-specific to individual needs, Stephanie Conway, director of talent development at LinkedIn, tells Fortune. Instead of solely funneling efforts into rolling out these big endeavors, she says that companies should also focus on the specific potential career paths of individual workers. 

Conway says that when it comes to upskilling, employers should take a two-pronged strategy. Companies should give employees specific ways that they can obtain technical skills, which could include internal training sessions or outsourcing through external learning platforms. They also need to develop a skills-based infrastructure within the organization at large—valuing and redefining talent based on skills instead of just resumes or education level. That clarity about which skills apply to which jobs offers a path for a worker to travel from one role to another.

“You know what is expected and what you need to learn, because the skills have been mapped,” Conway says. 

With a solid idea of what training is needed, it’s then up to workers to create a game plan with their bosses on how they want to educate themselves, and which skills they should focus on. That, says Conway, comes down to “a conversation with your manager.”

Emma Burleigh
emma.burleigh@fortune.com
@EmmaBurleigh1

Around the Table

A round-up of the most important HR headlines.

DEI lawyers have experienced a surge of audit requests amid the backlash against diversity initiatives. Bloomberg

Employers are pulling on back weight loss drugs as an employee benefit, saying they can’t keep up with high costs. Wall Street Journal

The global gender gap is very real—and there isn’t a single country in the world that gives equal opportunity to both men and women. Guardian

U.S. businesses are suing over President Biden’s gig worker protections as they attempt to stop independent contractors from being treated as employees. Washington Post

Watercooler

Everything you need to know from Fortune.

Feeling low. Young millennial and Gen Z employees are growing increasingly detached from their jobs and employers. But their boomer coworkers are more engaged than ever. —Jane Thier

Clothes for change. North Face is offering customers 20% off their purchase if they attend a racial inclusion class, in an effort to bring awareness to racial privilege in accessing outdoor activities. —Orianna Rosa Royle 

Elon’s crusade. The National Labor Relations Board hearing for SpaceX began yesterday. The company is fighting accusations that it wrongfully terminated employees who criticized owner Elon Musk. —Jessica Mathews

This is the web version of CHRO Daily, a newsletter focusing on helping HR executives navigate the needs of the workplace. Sign up to get it delivered free to your inbox.

About the Author
Emma Burleigh
By Emma BurleighReporter, Success

Emma Burleigh is a reporter at Fortune, covering success, careers, entrepreneurship, and personal finance. Before joining the Success desk, she co-authored Fortune’s CHRO Daily newsletter, extensively covering the workplace and the future of jobs. Emma has also written for publications including the Observer and The China Project, publishing long-form stories on culture, entertainment, and geopolitics. She has a joint-master’s degree from New York University in Global Journalism and East Asian Studies.

See full bioRight Arrow Button Icon

Latest in Newsletters

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
About Us
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map
Fortune Secondary Logo
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in Newsletters

AIEye on AI
After months of quiet, Perplexity’s CEO steps into the OpenClaw moment
By Sharon GoldmanFebruary 26, 2026
15 hours ago
NewslettersMPW Daily
Hillary Clinton’s Epstein testimony underscores a familiar burden for powerful women
By Emma HinchliffeFebruary 26, 2026
15 hours ago
The NVIDIA logo is displayed on a mobile phone screen.
NewslettersCFO Daily
Nvidia’s record quarter and what it signals for CFOs: ‘Compute equals revenue’
By Sheryl EstradaFebruary 26, 2026
19 hours ago
NewslettersTerm Sheet
Senator opens inquiry into Binance over allegations it fired investigators who flagged that more than $1 billion flowed to Iranian entities
By Ben WeissFebruary 26, 2026
21 hours ago
NewslettersCEO Daily
Bilt’s new AI ‘Neighborhood Concierge’ goes head-to-head with Amazon as the battle for home-based commerce heats up
By Diane Brady and Claire ZillmanFebruary 26, 2026
22 hours ago
NewslettersFortune Tech
Wall Street’s beef with Nvidia’s blowout earnings
By Alexei OreskovicFebruary 26, 2026
23 hours ago

Most Popular

placeholder alt text
Innovation
An MIT roboticist who cofounded bankrupt robot vacuum maker iRobot says Elon Musk’s vision of humanoid robot assistants is ‘pure fantasy thinking’
By Marco Quiroz-GutierrezFebruary 25, 2026
2 days ago
placeholder alt text
Success
Jeff Bezos says being lazy, not working hard, is the root of anxiety: ‘The stress goes away the second I take that first step’
By Sydney LakeFebruary 25, 2026
2 days ago
placeholder alt text
Economy
Trump claims America is ‘winning so much.’ The IMF agrees, adding that Trump’s trade policies are the only thing holding it back from even more
By Tristan BoveFebruary 26, 2026
14 hours ago
placeholder alt text
Success
Gen Z Olympic champion Eileen Gu says she rewires her brain daily to be more successful—and multimillionaire founder Arianna Huffington says it really does work
By Orianna Rosa RoyleFebruary 25, 2026
2 days ago
placeholder alt text
AI
Jamie Dimon says society should start preparing for AI job displacement: ‘Now’s the time to start thinking about’ it
By Marco Quiroz-GutierrezFebruary 25, 2026
2 days ago
placeholder alt text
Success
Ex–presidential candidate Andrew Yang warns that millions of white-collar workers will lose their jobs within 18 months: ‘The AI jobpocalypse is here’
By Preston ForeFebruary 25, 2026
2 days ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.