We’ve compiled a list of the best responses from executives who’ve answered the question, “What’s the biggest mistake you’ve ever made?”
22 Executives Reveal Their Biggest Mistakes
By Aimee Groth and Kim Bhasin for www.businessinsider.com
Jamie Dimon, chairman, president and CEO, JPMorgan Chase
Mark Wilson/Getty Images
“My biggest mistake, probably of my whole career, was not closing down our mortgage broker business sooner.”
From a 2009 interview with Bloomberg
Jack Welch, former CEO, GE
“My biggest mistake by far was not moving faster. Pulling off a Band-Aid one hair at a time hurts a lot more than a sudden yank. Of course you want to avoid breaking things or stretching the organization too far — but generally human nature holds you back. You want to be liked, to be thought of as reasonable. So you don’t move as fast as you should. Besides hurting more, it costs you competitiveness. EVERYTHING should have been done in half the time.
When you’re running an institution like this you’re always scared at first. You’re afraid you’ll break it. People don’t think about leaders this way, but it’s true. Everyone who’s running something goes home at night and wrestles with the same fear: Am I going to be the one who blows this place up? In retrospect, I was too cautious and too timid. I wanted too many constituencies on board. Timidity causes mistakes.”
From the 1993 book “Control Your Destiny or Someone Else Will” by Noel M. Tichy and Stratford Sherman
Richard Branson, founder and chairman, Virgin Group
Mickey Drexler, CEO, J. Crew
Financial Times reporter Vanessa Friedman sat down with Mickey Drexler for lunch in 2011:
“After our lunch [Mickey Drexler] had been thinking about the mistake question and reading the news about Gap closing stores in America to expand in China. That had made him realize what his mistake was. So, though he was in California, he called to tell me.
The mistake happened when he was at Gap and the brand was undergoing a “rapid expansion”, increasing its real estate holdings by almost 70 percent, a move he opposed but ultimately oversaw. Now he says, “I didn’t fight the board hard enough to stop it. I should have fought harder.” He isn’t blaming them for a bad decision; he’s blaming himself for caving in.”
Reid Hoffman, co-founder, LinkedIn
“Probably the biggest mistake that I made personally is I knew early on that I wanted to go into start-ups and creating the kind of software that could help change the lives of millions of people.
And basically what I did is I kind of went, okay, I need a set of titles and I need a checklist of skills, and I ran through all that, and that wasn’t a useless thing, but no one gave me the right advice for doing this — is that actually your network, in essentially, is your career. … If I had had that realization, I probably would have gone and begged my way into a job at Netscape.”
From a 2009 interview with Big Think
Larry Fink, chairman and CEO, BlackRock
“Back when I was leaving my job at First Boston, I was going through a lot of turmoil about what I wanted to do and where I wanted to do it. It was pretty clear to me that the buyers of securities didn’t understand the risk of the securities that they were buying … so I came up with this idea that we should start an investment management firm that focused on risk management.”
Brilliant idea, right? Unfortunately, Fink “didn’t have the confidence” in himself to start the company. “It was huge self-doubt,” he said pausing for emphasis. “So I went to see Steve Schwarzman and Pete Peterson at Blackstone and they loved the idea,” because who wouldn’t? Wall Street had never seen anything so awesome. “Within 3 days we came to terms of a partnership. They gave us a 5 million line of credit to start this company and I in turn gave them 40% stake. They believed in me more than I believed in myself. They made the right investment decision. I didn’t.”
From a 2010 interview with Dealbreaker
Carol Bartz, former president and CEO, Yahoo!
“I’ve made a lot of mistakes. There isn’t one that stands out. I make mistakes every week, every month, every year.
“I would say. . . I actually wish I had started having children younger. I was 40 when I had my daughter. And I wish I would have started that younger so I could have had more children.”
From an interview with the Tech Museum
Raul Vazquez, EVP global e-commerce, Walmart
“When I was an engineer at Baxter, we developed a new cap for an iodine bottle that would save hundreds of thousands of dollars. We did a ton of analysis and were confident that the caps would work, so we decided to make the entire change at once.
Then, we started hearing reports that the caps were leaking — it was very stressful. I learned that it can pay to be patient, and do things in a planned, rolled-out fashion.”
From a 2009 interview with Fortune
Jennifer Hyman, CEO, Rent The Runway
“One issue was on technology. We always knew we wanted to have an in-house technology team but we also wanted to get the site up very quickly and in order to do so we used an outsourced team based in India. This meant that our site got up in time for the holiday season, which was great in terms of sales, but at the end of the day, there was a lot of work to clean up on the back end of our site. Another mistake is that I wish we had ordered more inventory. We never predicted this much demand, which is a good problem to have.”
From an April 2010 interview with Kembrel.com.
Warren Buffett, CEO, Berkshire Hathaway
“I started out to buy Fannie Mae, for example, back in 1988 or so. And for what reason or another, I just didn’t follow through. We’d have made about a billion and a half dollars on that. I think we made about 5 million. Those are the mistakes you don’t see. The mistakes you don’t see are way bigger.”
From a video on the WarrenBuffettBlog YouTube channel
Bill Gates, chairman, Microsoft
Victor Cheng wrote a column about a PBS special starring Gates:
Gates had one of his infamous “Think Weeks” where we locked himself in a retreat for 1 – 2 weeks — no telephone calls, no email – with nothing but time to think.
He realized he totally missed the Internet opportunity.
The next day, he issued a company wide memo that pretty much said EVERY project and product in Microsoft had to incorporate the Internet.
Lee Iacocca, former chairman, Chrysler
“I think it was the biggest mistake of my business career,” he says of hiring Bob Eaton fromCorp. in 1992 as Chrysler’s president and chairman-in-waiting.
Eaton was chairman of GM Europe at the time. “I got the wrong guy. I wanted Hughes or Smith (Louis Hughes or John F. Smith Jr., then both high-ranking GM executives).” Iacocca blames himself. “I didn’t do my due diligence,” he says. “Eaton was always a staff guy. He never ran a division.”
From a 2003 interview with WardsAuto
Alexis Maybank, co-founder, Gilt Groupe
“When you scale so quickly, you inevitably make some hiring mistakes. And every part of your business is going to break at one point or another. In 2009, we launched a business that took a more mass market approach to brands. But our customers wanted luxury.”
From an interview with Business Insider
Ted Turner, founder, TBS and CNN
“The biggest mistake I ever made, really, and Malone told me not to do it, was bringing Time Warner into the consortium of cable operators for that five hundred and something million that we needed to pay down the debt that we incurred when we acquired MGM. I shouldn’t have done that, I shouldn’t have let them have the veto, but I was tired too. That was the other thing. I was tired. After thirty years of working 18 hours a day, five or six days a week with one crisis after another for twenty years, I was tired. And when you’re tired you don’t make the best decisions and I knew we were selling out. I didn’t know what the consequences would be.
“I never thought in my wildest dreams that I would actually lose my job. I just couldn’t believe that, but it happened. It happened. So my advice to any younger people in the room is be real careful who you sell to if you sell your company. Be prepared to leave it.”
From a 2001 interview with the Hauser Project
Marc Andreessen, co-founder, Netscape
“The biggest one that we’re still kicking ourselves over is probably Square. I think Jack Dorsey is one of the most phenomenal founder-CEO’s in the industry and we probably made a huge mistake on that one when he first came in.
“We overthought the deal and we probably just should have said Jack Dorsey, check. And write the check. That’s probably the big one.”
From a 2012 interview with Bloomberg TV
Rio Caraeff, president and CEO, VEVO
“When I was much younger, I was traveling on a business trip when a close family member passed away at home and I decided to not travel home for the funeral as I had made the decision that my work was more important at the time. I look back in regret at that decision frequently and have now since realized that family does come first.”
From a 2009 interview with Fortune
Max Levchin, co-founder, PayPal
Mark Cuban, chairman, HDNet
Business Insider / Matthew Lynley
“Professionally, it was not aggressively going after the MPAA (Motion Picture Association of America) and RIAA (Recording Industry Association of America) in negotiations for the DMCA (Digital Millennium Copyright Act). Another mistake was not applying for patents. I personally think patents are for the most part worthless and don’t protect your business, but at Broadcast.com we did so many original and unique things in streaming, multicasting, uploading of content that now that the climate of litigation has changed, that portfolio would be worth a ton of money.”
From a 2011 interview with TechCrunch.