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

The top 3 lessons Bill Gates taught this former Microsoft VP

Eleanor Pringle
By
Eleanor Pringle
Eleanor Pringle
Senior Reporter, Economics and Markets
Down Arrow Button Icon
Eleanor Pringle
By
Eleanor Pringle
Eleanor Pringle
Senior Reporter, Economics and Markets
Down Arrow Button Icon
May 2, 2023, 11:55 AM ET
Bill Gates in side profile at the World Leaders' Summit
Bill Gates is “virtually always right,” one of his former Microsoft colleagues has revealed. Jeff J. Mitchell—Pool/Getty Images

It was more than 30 years ago when Chris Williams first found himself in the room with Microsoft founder Bill Gates.

Recommended Video

The man—who a matter of years later was named the richest person on earth—had just purchased Fox Software, a producer of database management systems, for $170 million.

In 1992 Williams, who had worked at Fox Software as a developer and director of marketing, was one of a handful invited to Microsoft’s offices in Redmond, Wash., to meet with Gates and discuss the business he had just bought.

Speaking on LinkedIn, Williams remembered how Gates had little time for pleasantries with the six newcomers in their initial meeting: He wanted to “see what he’d bought.”

The aim of the meeting, Williams said it became apparent, was for Gates to understand how the product he had purchased—Fox Pro—worked faster than existing Microsoft rival, Cirrus.

Gates quickly identified the individual responsible for the speed of Fox Pro, with Williams describing the ensuing back-and-forth as resembling “a Star Trek mind meld.”

Get to the details

Gates fired question after question at the engineer before him, Williams said, getting to such a level of detail that they discussed the movement of single bits and the size of the Intel 80386 instruction cache.

It was only then that Gates seemed satisfied, bringing the meeting to an end.

“In the years that passed, I saw Bill do this same kind of exercise time and again,” Williams said.

“He was always curious, always wanted to understand, always drilling for more detail. As a younger man this drilling was aggressive and harsh. As he got older, his passion for detail never left, just his method for getting there mellowed.”

‘Smell the odor’

According to Williams, Gates isn’t afraid to tell it like it is.

The man worth $125 billion, according to the Bloomberg Billionaires Index, is known for speaking his mind—often sharing his thoughts on his website, Gates Notes.

This year alone the tech titan has shut down a proposal to temporarily ban the development of advanced large language models like ChatGPT, saying the plan wouldn’t solve any of the issues the public is now facing because of the technology.

Similarly, Gates didn’t mince words as the CEO of Microsoft, a position he held from 1972 to 2000.

“It seems that Bill learned early on that pressing for details until failure, resulted in two kinds of responses,” Williams revealed. “There were the people who were strong enough to admit, in the face of the then richest man on the planet…‘I don’t know.’ And there were those who just started making things up. Guessing at answers.”

Gates would apparently swear and call out such answers as the “stupidest thing [he’d] ever heard.”

And this ability—as Williams put it—to “smell the odor of falsehood” only got better with age.

Williams, who is six months older than the famed philanthropist, added: “Later you could tell you were in trouble just from his facial expressions. That look of disappointment that told you, ‘Oops, perhaps I should retreat here.’”

Having been promoted from roles like development manager and director of product development to vice president of human resources, Williams claims he spent a lot of time one-on-one with Gates, and picked up some of his skills by osmosis.

The HR VP turned leadership coach said: “It was hard to be in those rooms many times and not pick up some of that skill. I began to see the same kinds of signs. I learned to watch for the flittering eyes, the unsure tone, or the smell of desperation.”

Get to the point

Having left Microsoft in 2000, Williams said one major lesson still stands out to him: Cut through the noise and get to the crux of the issue.

It was a skill Gates wielded with ease, he said, and at first Williams believed staff agreeing with their boss was merely to placate him.

“A team would bring in a deeply complex set of issues,” Williams explained. “They would have miles of data and dozens of opinions on the correct path. They would say, ‘We’re struggling to decide if we should do X and build this, or head toward Y and build that.’

“Within seconds Bill had absorbed it all. Somehow, someway, he found the two or three variables that mattered. He would blurt out, ‘Don’t you see, this and that are what matters, it’s so clear you should do X.’”

The whole room would fall silent, Williams said, while people realized Gates was right.

Having seen the phenomenon a few times, and after seeing more of Microsoft’s culture, Williams said he realized that other senior managers would call Gates out if they disagreed with his thinking.

This rarely happened, Williams points out, as Gates was “virtually always right.”

At the Fortune Workplace Innovation Summit, Fortune 500 leaders will convene to explore the defining questions shaping the workforce of the future—delivering bold ideas, powerful connections, and actionable insights for building resilient organizations for the decade ahead. Join Fortune May 19–20 in Atlanta. Register now.
About the Author
Eleanor Pringle
By Eleanor PringleSenior Reporter, Economics and Markets
LinkedIn icon

Eleanor Pringle is an award-winning senior reporter at Fortune covering news, the economy, and personal finance. Eleanor previously worked as a business correspondent and news editor in regional news in the U.K. She completed her journalism training with the Press Association after earning a degree from the University of East Anglia.

See full bioRight Arrow Button Icon

Latest in Success

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 Success

Jon Gray, Blackstone
SuccessCareers
Blackstone COO Jon Gray predicts ‘huge boom’ in blue-collar jobs—his own data center company is hiring 30,000 new roles
By Preston ForeMay 14, 2026
16 hours ago
fulfilled
Healthaging
Half of older Americans are unfulfilled. Their doctors can’t see it
By Nick LichtenbergMay 14, 2026
19 hours ago
newman
Commentaryphilanthropy
Newman’s Own Foundation CEO on steward ownership: succession when you don’t want to sell
By Alex AmouyelMay 14, 2026
19 hours ago
Young woman walking dogs and using smartphone in urban neighborhood
EconomyInflation
Business formations hit all-time high as ‘under-employed’ Americans turn to side hustles to make ends meet
By Eleanor PringleMay 14, 2026
20 hours ago
Male CEO looking out a window in a large office.
C-SuiteJobs
Job-hopping is now the fastest path to becoming a CEO—and company loyalty may actually hold you back
By Tristan BoveMay 14, 2026
1 day ago
Steve Jobs had a ‘beer test’ he used for interviews at Apple—if he didn’t want to drink with you, you didn’t get the job
SuccessThe Interview Playbook
Steve Jobs had a ‘beer test’ he used for interviews at Apple—if he didn’t want to drink with you, you didn’t get the job
By Orianna Rosa RoyleMay 14, 2026
1 day ago

Most Popular

Despite having a $165 million net worth, Scarlett Johansson says work-life balance doesn’t exist—and the first step to success is admitting that
Success
Despite having a $165 million net worth, Scarlett Johansson says work-life balance doesn’t exist—and the first step to success is admitting that
By Preston ForeMay 13, 2026
2 days 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
2 days ago
Nearly 50,000 Lake Tahoe residents have to find a new power source after their energy source looks to redirect lines to data centers
Travel & Leisure
Nearly 50,000 Lake Tahoe residents have to find a new power source after their energy source looks to redirect lines to data centers
By Catherina GioinoMay 12, 2026
3 days ago
The airplane fuel shortage is a myth propagated by airlines who want to cancel unprofitable flights, says private jet CEO
Energy
The airplane fuel shortage is a myth propagated by airlines who want to cancel unprofitable flights, says private jet CEO
By Jim EdwardsMay 14, 2026
1 day ago
Steve Jobs had a 'beer test' he used for interviews at Apple—if he didn’t want to drink with you, you didn’t get the job
Success
Steve Jobs had a 'beer test' he used for interviews at Apple—if he didn’t want to drink with you, you didn’t get the job
By Orianna Rosa RoyleMay 14, 2026
1 day ago
Current price of oil as of May 14, 2026
Personal Finance
Current price of oil as of May 14, 2026
By Joseph HostetlerMay 14, 2026
19 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.