22 Executives Reveal The Biggest Mistakes They Ever Made

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Photo: Business Insider / Matthew Lynley

If you take risks — which all successful executives do — you’re bound to make mistakes. In fact, the most successful people also fail the most.But it takes a humble person to admit that they’ve messed up.

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?”

Jamie Dimon, chairman, president and CEO, JPMorgan Chase

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 organisation 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

'I find it very difficult to think of mistakes; not that I don't make any but because I was brought up to look only at the good things in life ... As for what lost the most money, probably Virgin Cola. It is still No 1 in Bangladesh though.'

From a 2006 interview with the Guardian

Mickey Drexler, CEO, J. Crew

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, OK, 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 realisation, 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

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

Lee Iacocca, former chairman, Chrysler

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 30 years of working 18 hours a day, five or six days a week with one crisis after another for 20 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 travelling 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 realised that family does come first.'

From a 2009 interview with Fortune

Max Levchin, co-founder, PayPal

'I am not much given to regret, so I puzzled over this one a while. Should have taken much more statistics in college, I think.'

From a 2009 interview with Fortune

Mark Cuban, chairman, HDNet

'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.

Thomas Stemberg, co-founder and former CEO, Staples

'About two years later than our competitors, we also began to deliver. Probably over time that mistake cost us $100 million in sales and $10 million in profits. Today our delivery business represents $2.5 billion.

That was one of the few times in our corporate history when we made a decision based on cost factors as opposed to customer preferences. It reminded me once again that whenever you plan your business, you're way better off starting first with the customer and moving next to cost rather than the other way around.'

From a 2001 interview with Inc.

Willie Walsh, CEO, International Airlines Group

'Haven't made it yet! People shouldn't be afraid of making mistakes as long as they learn from them and don't make the same mistake twice.'

From a 2011 interview with Marketing Society

Reed Hastings, CEO, Netflix

Hastings said his biggest mistake was trying to phase out Netflix's once-trailblazing DVD-by-mail rental service more quickly than millions of customers wanted. He and his management team concluded a few years ago DVDs that are destined to obsolescence, so they began concentrating on streaming video over high-speed Internet connections.

Ending Netflix's practice of bundling DVD-by-mail and Internet streaming subscriptions together so people are forced to buy them separately was meant to push more households into weaning themselves from discs. Customers instead saw the move as a betrayal by a greedy company and canceled their subscriptions in droves.

From a 2011 interview with the Associated Press

Alan Mulally, president and CEO, Ford

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