Michael Dell on the Simple Way to Tell a Good Mistake From a Bad One

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  • Michael Dell's fortune is estimated at over $50 billion.
  • The computing icon made plenty of mistakes during his career, failing to stay attuned to consumer desires after early success, loading up on way too much debt, and having to restructure the company more than once.
  • It all worked out in the end for Dell. His advice to leaders: Keeping making mistakes, just know the difference between a good one and bad one.

The technology industry is synonymous, for better or worse, with risk-taking and a credo that leans into failure as part of eventual success.

Mark Zuckerberg's "Move fast and break things."

Elon Musk's "If things are not failing, you are not innovating enough."

Michael Dell, from an earlier generation of tech icons, is no exception. He is worth over $50 billion today, but the company's early success in PCs was followed by a period of totally missing where the consumer was headed, botched attempts to catch up, burned relationships with Dell shareholders, and multiple corporate restructurings after business and financial issues, including taking on a lot of debt.

Now Dell Technologies is worth more than three times the value of its 2013 private buyout — a recent success that may not make shareholders in the former company feel that Dell plays quite as "nice" as he claims to be in his new book, called "Play Nice but Win."

Dell gave CNBC's Jon Fortt a few pieces of advice for those seeking leadership success at the recent CNBC @Work Summit, based on his journey from younger tech founder to veteran corporate leader, starting with the simple way he judges mistakes.

1. Make good, new mistakes

If you are a good founder, "you are going to go make some new mistakes nobody else has made," Dell said. "Mistakes are not bad ... so long as you are learning from them. What you don't want to do is make unnecessary mistakes."

Easier said than done, but Dell said it is important to keep the value of mistakes in mind right now when so many things in the world of technology are changing so fast, and as founders chase some of the hardest tech problems ever, which he said he finds to be inspiring.

"There's new things that have never happened before. You are going to fail and you are going to experiment and learn and then ultimately find your way to success as a result of that, so don't be afraid to go make some mistakes," Dell said at the CNBC event. "Just hopefully, you will make some new ones."

2. Think, and plan, in multiple horizons

Successful companies need to plan over multiple horizons, whether it is for talent development, core R&D or customer understanding. Dell knows firsthand from the history of consumer technology how important it is to see the future in multiple time segments. He said an "innovation engine" needs to be focused on the near-term (the next 18 months), the medium-term (out 5 years) and then, finally, beyond.

"We have massive R&D teams focused on delivering products and solutions, but it also requires advanced tech teams and Dell Technologies Capital out on furthest horizon, experimenting and learning about new things that could be in the path of our growth."

Dell won't claim to have any secret to success for innovation beyond saying "it's a combination of deep understanding of unsolved customer problems and deep understanding of all the ingredients that go into technology."

But he does know how important it is.

"When we do that we will be a successful company in the future. If we don't, we go out of business. That's just the way it works."

3. Don't expect to have all the answers about hybrid work

One near-term issue for leaders is hybrid work, and Dell said it is "here to stay," and that is resulting in immediate challenges to innovation, as leaders search for ways to make sure talent is engaged and inspired in a hybrid world, driving collaboration and inculcating culture in new team members.

The answer?

Dell doesn't know, and he said no one really does. "We are finding some solutions, but can't claim we have all the answers. We are all making it up and figuring it out as we go along."

Dell is optimistic the results will lead to a better balance, and life, for people. "Ultimately that's a super-important part of keeping people inspired and engaged and energized about their work. But I don't think anybody has all the answers yet," he said.

4. Be nice. Really, be nice.

There are only nine individuals from the tech sector (including Mackenzie Scott) who have fortunes larger than Dell's $53 billion, according to the Bloomberg Billionaires Index.

Dell insists being "nice" is critical.

"It's who I've been and what I've done and it's the right way to win, and it's something I learned from my parents and it's been a kind of a simple approach."

Channeling his inner-Warren Buffett, Dell said "reputation matters and it takes a long time to build a reputation, and you can destroy it rather rapidly."

"Winning in the right way really does mater over time," he said. "Life is too short to do it any other way. I wouldn't want to live my life on the other side of that."

Missed this year's CNBC's At Work summit? Access the full sessions on demand at

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