In November 2022, ChatGPT came out and traffic on Stack Overflow went up, not down. A huge flow of ChatGPT-generated questions and answers hit the site, and its community decided to ban ChatGPT. What the company had been building for about a decade changed, in his words, "over a moment's notice."

Prashanth Chandrasekar is the CEO of Stack Overflow. He came to the US on a college scholarship to the University of Maine in 1998, worked in consulting and banking, spent seven years at Rackspace, and took his first CEO job at Stack Overflow in 2019, three months before the pandemic. Host Jessica Neal talks with him about leading through the ChatGPT shock, the trust gap in AI, and why the shift ahead is a people problem.

WHAT YOU'LL LEARN

• How a college scholarship to the University of Maine led to his first CEO job at Stack Overflow
• Starting as CEO three months before the pandemic, when people stopped marketing and stopped hiring
• November 2022: why ChatGPT sent traffic up, and why the community banned ChatGPT answers
• The radioactive metal idea: protecting a human-curated corpus from AI slop
• "Chief repeat officer": the email he has sent the company every Friday for seven years
• Why only about 6 to 7% of developers in the Stack Overflow survey would highly trust AI answers in their organization
• How data licensing deals with OpenAI and Google helped replace lost advertising revenue
• Stack Overflow for Agents: launched by two engineers using OpenAI's Codex
• "My agent is my chief of staff": how he works with AI as a CEO
• Why he believes AI creates more jobs, and why you should still learn the fundamentals

CHAPTERS
0:00 Preview
0:32 Truth Works intro
1:20 Welcome to Truth Works
3:00 An immigrant on a scholarship to the University of Maine
5:31 "Go get some operating experience": Rackspace
6:52 First CEO job, three months before the pandemic
7:40 What Stack Overflow is
9:35 November 2022: the ChatGPT moment
11:26 Traffic went up, so the community banned ChatGPT
12:17 Radioactive metal: protecting a human-curated corpus
13:24 "Quite terrifying": how scared was he?
14:16 Leading through the hardest transformation
16:32 Chief repeat officer: an email every Friday for seven years
18:27 Teach it to learn it
19:42 Sponsor: Manifest Law
20:32 The trust gap: only 6 to 7% highly trust AI
22:40 Privacy, security and scattered knowledge
23:41 Stack Internal: decision-grade knowledge
24:09 Licensing deals with OpenAI and Google
25:15 The viral chart: simple questions gone, hard ones growing
27:10 40 to 60% better answers with Stack Overflow data
28:11 Advice for companies: it's a people problem
30:10 From behind average to everyone using AI
30:41 Stack Overflow for Agents: built by two engineers
32:46 How big companies should redesign how they work
33:50 50,000 to 100,000 employees: go big or go home
35:01 Where is the ROI?
35:50 "My agent is my chief of staff"
36:41 A better CEO post-AI?
37:15 Will AI take the jobs?
40:16 Freelancers and new companies as the job engine
41:18 Liberal arts or computer science?
43:01 The calculator lesson: learn the fundamentals
44:44 Something to take into your week

ABOUT THE GUEST
Prashanth Chandrasekar is the CEO of Stack Overflow, the developer question-and-answer site founded in 2008. He came to the US from India on a college scholarship to the University of Maine in 1998 and studied computer engineering, then worked in operations consulting and, after business school, in banking. In 2012 he moved from New York City to Texas to join Rackspace, where he spent seven years building its cloud businesses around AWS, Microsoft Azure and Google Cloud. He became CEO of Stack Overflow in 2019 and has led its move from an ad-supported public site to an enterprise company, including its enterprise product, Stack Internal.

ABOUT THE SHOW
Truth Works is hosted by Jessica Neal. Each episode is an honest conversation about why work is hard and how leaders can make it better.

This episode is sponsored by Manifest Law, Findem and True Search.

#TruthWorks #Leadership #AI #StackOverflow #FutureOfWork #Developers #AIAgents #CEO

Two of Chris Dyer's former senior executives got bonuses, promotions and raises when he sold his company. Over drinks on a rooftop they told him, "We're still really mad at you": they would give up all the money and all the titles to be back working in the old company. What they remembered was not the policies or the perks, but four or five moments.

Chris spent more than two decades building companies and studying culture. After 9/11 he walked away from a safe job and the worst boss to start his own company, rebuilt its culture during the 2009 recession as it grew to thousands of employees, and sold it at the end of 2021. His latest book is Moments That Matter. Host Jessica Neal talks with him about designing culture on purpose, the moments people actually remember, and why AI starts with people.

WHAT YOU'LL LEARN

• How 9/11 pushed him out of a safe job and into starting his own company
• Why the 2009 recession showed him the culture problem was his fault
• The electricity lesson: new technology only pays off when you redesign the system around it
• The ostrich meeting: delete your whole inbox in front of your team after vacation
• "If you're wired, you're fired": how to make time off real
• What happened when every employee got the monthly P&L
• Why we remember only about 1% of what happens to us, and the seven moment types
• Why not all moments are created equal, and the one a leader cannot miss
• AI: start with people, then process, then the tool

CHAPTERS
0:00 Preview
0:24 Truth Works intro
1:12 Welcome to Truth Works
3:06 9/11, the worst boss and a job that squashed his soul
6:41 2009: "It was totally my fault"
7:53 The electricity lesson: redesign the whole system
9:48 No email on vacation and the ostrich meeting
16:33 If you're wired, you're fired
18:29 Sponsor: Manifest Law
19:19 Divorces down, marriages up: measuring culture
21:55 Every employee gets the P&L
24:02 Culture gets designed whether you design it or not
25:05 One North Star: the best place people will ever work
26:43 Moments That Matter: "We're still really mad at you"
31:59 Seven moment types
33:25 Firsts: show up when it happens for the first time
37:30 Not all moments are created equal
38:48 The client who dropped the F-bomb 50 times
43:10 Overdoing moments: the on and off switch
45:27 Culmination moments
47:12 AI and thriving through relentless change
49:17 Start with people, then process, then the tool
51:27 Connecting AI to your email, calendar and bank
54:04 Something to think about this week
55:56 Where to find Chris (the non-dread one)

ABOUT THE GUEST
Chris Dyer is a former CEO, entrepreneur and keynote speaker who has spent more than two decades building companies and studying culture. He started his company weeks after 9/11, grew it to thousands of employees, and sold it at the end of 2021. His latest book, Moments That Matter, is about recognizing the moments that have an outsized impact on people, leadership and organizations. His keynotes include Thriving Through Relentless Change. Keynotes and booking: chrisdyer.com

ABOUT THE SHOW
Truth Works is hosted by Jessica Neal. Each episode is an honest conversation about why work is hard and how leaders can make it better.

This episode is sponsored by Manifest Law, the AI-native immigration law firm.

#TruthWorks #Leadership #CompanyCulture #MomentsThatMatter #EmployeeEngagement #FutureOfWork #AI #Management

Why do so many people do everything right, finish the course, earn the certificate, and still end up exactly where they started? Connor Diemand-Yauman was one of Coursera's early employees, where he and Jessica worked together, until an Uber ride changed his path: the driver had completed a Coursera course, earned the certificate, and was still driving.

Connor and his Coursera colleague Rebecca Taber Staehelin went on to co-found Merit America, the nonprofit that trains low-wage working adults for better-paid careers. Fast Company named it the #1 most innovative education company of 2026, and a University of Virginia analysis of its first 3,000 graduates found an average raise of $22,500. Host Jessica Neal, former Chief Talent Officer at Netflix, talks with him about founding, leading, taking feedback, and why humor belongs at work.

WHAT YOU'LL LEARN

• The Uber ride that turned two Coursera employees into nonprofit founders
• Why access does not equal opportunity
• Why growing from 15 people to 500 feels like "constantly birthing a new organization"
• The founder's ripple: why a passing idea in a meeting can land as a tsunami
• How to take your co-CEO hat off so your team can push back
• "I am never as clear as I think I am": clarity as a leader's job
• The Netflix feedback that changed how Jessica leads: "It's not about you"
• How to take hard feedback without getting defensive
• Why humor builds trust, and the trait Navy SEALs value alongside stoicism

CHAPTERS
0:00 Cold open
0:40 Welcome to Truth Works
1:17 Introducing Connor Diemand-Yauman
3:32 Catching up: a baby on the way
9:14 The Uber ride that started Merit America
11:16 Access does not equal opportunity
13:15 Constantly birthing a new organization
14:45 Work you'd do for free, with people you'd hang out with
15:54 Sponsor: Manifest Law
16:44 Founders are always being watched
18:17 Small ripples, big tsunamis
21:12 Name the hat you're wearing
23:31 Clear is kind: "I'm never as clear as I think I am"
25:07 Netflix: "That is your job. It's not about you."
29:26 Taking feedback: "Thank you, I'll think about it"
33:47 David Inc.: banking negative feedback
34:45 Is This Working?: his podcast and Katie Couric
37:46 Humor: Serious Business, his Stanford class
39:51 Why humor at work builds trust
43:15 Your joke can fail and still work
46:10 It's just work: we make it too serious
47:09 SEAL Team Six: stoicism and levity
48:03 Something to think about this week
48:19 Purpose is a state, not a destination
49:48 Thank you, Connor

ABOUT THE GUEST
Connor Diemand-Yauman is co-founder and co-CEO of Merit America, a nonprofit that helps low-wage working adults train for and move into better-paid careers. He was an early employee at Coursera, where he helped build the company's business with organizations, teaches Humor: Serious Business at the Stanford Graduate School of Business, and hosts the podcast Is This Working?

ABOUT THE SHOW
Truth Works is hosted by Jessica Neal. Each episode is an honest conversation about why work is hard and how leaders can make it better.

This episode is sponsored by Manifest Law, the AI-native immigration law firm.

#TruthWorks #Leadership #MeritAmerica #Coursera #Stanford #Humor #FutureOfWork #Nonprofit