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

Trendingnow

1

Microsoft AI chief gives it 18 months—for all white-collar work to be automated by AI

2

Former top Russian official admits the country is over Putin and can 'imagine a future without him' — even elites bail as Kremlin seizes their assets 

3

The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises

1

Microsoft AI chief gives it 18 months—for all white-collar work to be automated by AI

2

Former top Russian official admits the country is over Putin and can 'imagine a future without him' — even elites bail as Kremlin seizes their assets 

3

The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises
NewslettersFortune CHRO

Why AI failures are worth talking about—loudly and publicly

Kristin Stoller
By
Kristin Stoller
Kristin Stoller
Editorial Director, Fortune Live Media
Down Arrow Button Icon
Kristin Stoller
By
Kristin Stoller
Kristin Stoller
Editorial Director, Fortune Live Media
Down Arrow Button Icon
October 20, 2025, 8:41 AM ET
Women panelists at Fortune's Most Powerful Women Summit speak on the "Women Redefining Work in the Age of AI" panel.
When it comes to experimenting with AI, these C-Suite executives advise giving employees permission to fail.Stuart Isett for Fortune

Good morning!

Recommended Video

At Taskrabbit all-company meetings, CEO Ania Smith has taken to instituting what she calls a “Nailed it, Failed it” segment. She asks her executive team—and encourages other employees—to publicly share their biggest flops, particularly when it relates to experimenting with AI. 

“We do stand up very often and say, ‘I tried this, but it didn’t work,’ or ‘I tried that, but it didn’t work,’ to try to normalize a failure,” Smith said.

Smith was one of four C-suite executives I spoke with at the Fortune Most Powerful Women Summit in Washington, D.C. last week on a panel about women redefining work in the age of AI. Encouraging employees to experiment with AI—and giving them permission to fail along the way—was a big theme of our conversation.

When it comes to sharing the stories of things that haven’t gone according to plan, Emma Chalwin, Workday’s chief marketing officer, encouraged business leaders to “get more comfortable being uncomfortable.”

“Vulnerability is a superpower,” she said. “As long as you don’t continue to make the same mistakes over and over again, but you learn from the opportunities and you share what you’re going to do differently moving forward, it makes a huge difference to the team.”

When pilots or trials with AI tools fail, added L’Oréal CHRO Stephanie Kramer, leaders should focus on why humans are needed in order to fix it.

In a time where women are adopting AI tools at a 25% lower rate than men, Pinterest’s Chief People Officer Doniel Sutton advises her female colleagues to lean in. Often, she said, women employees are disproportionately given mundane, administrative tasks. AI can help get that “office house work” done quickly, and free women up for higher-potential swings.

“One of the things that I appreciate about what AI is doing is lessening that invisible work and the burden of it so that it frees you up to have the capacity and bandwidth to focus on more strategic elements of the job, the high-impact work, the things that are going to truly differentiate you in the office,” Sutton said. “I definitely think that’s an advantage.”

Kristin Stoller
Editorial Director, Fortune Live Media
kristin.stoller@fortune.com

Around the Table

A round-up of the most important HR headlines.

The secret to building teams that thrive? “Glue employees”—the quiet team players who exhibit high emotional intelligence and hold everything together. Wall Street Journal

China’s sharp population decline means that it will soon run out of workers, potentially affecting supply chains. Washington Post

Some 76% of U.S. employees say they’d look for a new job if they were forced to return to the office. CNBC

Watercooler

Everything you need to know from Fortune.

The humanity approach. Author and researcher Brené Brown said that fear-based, tough-minded leadership doesn’t fit the needs of a younger workforce. —Sydney Lake

Balance backlash. Billionaire bosses like Jeff Bezos and Reid Hoffman have denounced the term “work-life balance.” Here’s why. —Emma Burleigh

Volunteer vision. As millions of young grads face unemployment, Verizon’s talent chief says that unpaid experience can set candidates apart.—Orianna Rosa Royle

This is the web version of Fortune CHRO, 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
Kristin Stoller
By Kristin StollerEditorial Director, Fortune Live Media
Instagram iconLinkedIn iconTwitter icon

Kristin Stoller is an editorial director at Fortune focused on expanding Fortune's C-suite communities.

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
  • World's Most Admired Companies
  • See All Rankings
  • Lists Calendar
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
  • Group Subscriptions
About Us
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in Newsletters

Jenn Hyman reflects on the highs and lows of running Rent the Runway for almost two decades
NewslettersMPW Daily
Jenn Hyman reflects on the highs and lows of running Rent the Runway for almost two decades
By Emma HinchliffeMay 15, 2026
2 days ago
Andrew Feldman, co-founder of Cerebras
NewslettersTerm Sheet
Cerebras soars almost 70% by market close in a true blockbuster IPO
By Allie GarfinkleMay 15, 2026
2 days ago
OpenAI CEO Sam Altman (left) and Apple CEO Tim Cook in Washington, D.C., on Sept. 4, 2025. (Photo: Will Oliver/EPA/Bloomberg/Getty Images)
NewslettersFortune Tech
OpenAI may take legal action against Apple over Siri’s ChatGPT integration
By Andrew NuscaMay 15, 2026
3 days ago
State Farm CEO is betting big on AI—and contemplating the company’s future in California
NewslettersCEO Daily
State Farm CEO is betting big on AI—and contemplating the company’s future in California
By Diane BradyMay 15, 2026
3 days ago
The AI boom sidelined sustainability. Two researchers want to change that
NewslettersEye on AI
The AI boom sidelined sustainability. Two researchers want to change that
By Sharon GoldmanMay 14, 2026
3 days ago
‘Be delusional enough to call yourself something the world hasn’t called you yet’: What powerful women told the class of 2026
NewslettersMPW Daily
‘Be delusional enough to call yourself something the world hasn’t called you yet’: What powerful women told the class of 2026
By Sydney LakeMay 14, 2026
3 days ago

Most Popular

Microsoft AI chief gives it 18 months—for all white-collar work to be automated by AI
AI
Microsoft AI chief gives it 18 months—for all white-collar work to be automated by AI
By Jake AngeloMay 16, 2026
1 day ago
Former top Russian official admits the country is over Putin and can 'imagine a future without him' — even elites bail as Kremlin seizes their assets 
Politics
Former top Russian official admits the country is over Putin and can 'imagine a future without him' — even elites bail as Kremlin seizes their assets 
By Jason MaMay 16, 2026
1 day ago
The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises
Politics
The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises
By Jake AngeloMay 12, 2026
5 days ago
SpaceX heads into a record-shattering IPO with the 'deepest moat that exists today' as investors vow to 'never bet against Elon'
Innovation
SpaceX heads into a record-shattering IPO with the 'deepest moat that exists today' as investors vow to 'never bet against Elon'
By Jason MaMay 16, 2026
1 day ago
Oil markets could be a month away from the moment of truth. Brace for a 'non-linear' price spike and panic buying, analysts warn
Energy
Oil markets could be a month away from the moment of truth. Brace for a 'non-linear' price spike and panic buying, analysts warn
By Jason MaMay 16, 2026
1 day ago
'No one was coming to save me': How Reese Witherspoon built a $900 million company from a problem Hollywood wouldn't fix
Success
'No one was coming to save me': How Reese Witherspoon built a $900 million company from a problem Hollywood wouldn't fix
By Sydney LakeMay 17, 2026
12 hours 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.