EXCLUSIVE: Microsoft Cloud Computing System Suffering From Global Shortage Read Now

The Advice Founders Really Need to Hear

It has been the season of graduation speeches, virtual graduation speeches, essays pondering graduation speeches one would have given if asked—and more.

And reading all that advice prompted me to reflect on the good and bad counsel I’ve received over the years.

One piece of bad advice immediately jumped out—and it is pretty ubiquitous. Indeed, many workplace performance cultures are centered around it. Over time, I’ve come to believe that it is the opposite of what many leaders—particularly young and inexperienced ones—need to hear.

The bad advice is to “focus on your strengths.” It’s what your investors and advisers tell you when you are starting a company. It’s what, even before that, your teachers and managers emphasize in your performance reviews to make you feel good. I’d guess that there are very few successful people, in any field or role, who do not deeply understand their strengths—because they’ve been reminded of them again, again and again, in many cases since they were very young. 

But what about their weaknesses? Maybe a few people pointed out some areas in need of improvement along the way. If you are a high achiever, though, people don’t usually bombard you with a list of things you are bad at. And the higher you rise in an organization, the less likely you are to get honest feedback about areas where you perform poorly—both because people are afraid to share them and also because individual direct reports, or even board members, may not have a full enough picture of the company and its challenges to accurately assess you. 

The trouble is, it’s pretty clear that compensating for your weaknesses by hiring other excellent people to fill the gap basically marks the difference between a good leader and a great one. In other words, if you can’t identify and build around your weaknesses, you are doomed in the long term.

That puts a huge burden on leaders to be self-aware enough to identify their own weaknesses, take whatever feedback they do get, assess it and act upon it.

This is, of course, personal for me. I spent most of my career listening to positive feedback. Now, I get plenty of critical feedback from all corners of the world along with the good, and I’m grateful for it. But distilling that all down to a very honest picture of my weaknesses, and figuring out how to compensate for them while predicting how they will affect my company years down the line—that’s a challenge, and one I wish I had prepared for earlier. I can rely on many trusted advisers and people I work with. But assessing what I’m not good at comes far less naturally than doing what everyone has been telling me to do for decades: focus on my strengths. 

I was lamenting about this recently to a friend, who had a different view. He said my weaknesses weren’t weaknesses—just “things I hadn’t focused on being good at yet.” If that isn’t Silicon Valley optimism in a bottle! 

I guess in some ways I agree with that point of view. There are so many things about running a company I now find easy and straightforward that I found so difficult in the early days. Experience helps a lot. But so does knowing oneself—the good and the bad—as early as possible.

Let’s spread that advice to all the young people who need to hear it. 

Jessica Lessin founded The Information in 2013 after reporting on Silicon Valley for eight years for the Wall Street Journal. She writes a weekly column about all things tech, media and the wild ride both industries are in for. She can be found on Twitter at @jessicalessin.
Get access to exclusive coverage
Read deeply reported stories from the largest newsroom in tech.
Latest Articles
The Briefing Crypto Facebook
How Netflix Can Regain Momentum
Netflix co-CEO Reed Hastings. Photo by Bloomberg.
We’re now just a couple of weeks away from the second-quarter earnings reporting season. And if history is any guide, first out of the gate will be Netflix’s report on July 19, which is likely to be one of the most closely watched tech earnings updates of the quarter. Netflix’s first-quarter report, revealing a tiny drop in subscribers and forecasting a bigger one for the second quarter,...
Latest Briefs
Klarna to Raise Cash at $6.5 Billion Valuation in Dramatic Down Round
Amazon Secures UK Broadcast Rights for Lucrative European Soccer Games
China’s Tencent, ByteDance Implement New Round of Layoffs
Stay in the know
Receive a summary of the day's top tech news—distilled into one email.
Access on the go
View stories on our mobile app and tune into our weekly podcast.
Join live video Q&A’s
Deep-dive into topics like startups and autonomous vehicles with our top reporters and other executives.
Enjoy a clutter-free experience
Read without any banner ads.
Microsoft CEO Satya Nadella in 2019
Exclusive Cloud Microsoft
Microsoft Cloud Computing System Suffering From Global Shortage
In March 2020, Microsoft’s Azure cloud buckled under the strain of companies around the world shifting to remote work, causing service outages and forcing some customers to wait to launch and update applications.
Tesla's Fremont factory, in a photo taken in May 2020.
Exclusive Autonomous Vehicles
At Tesla, Returning to the Office Creates New Problems
On the evening of June 8, speaking from Tesla’s factory in Fremont, Calif., Elon Musk addressed a few dozen of the electric car maker’s employees in person, and thousands more in a livestream.
From left: Brooke Hainey & Keith George, co-founders of Cortina; Bennett Carroccio, co-founder of Canal; Conner Sherline, founder of Disco.
Startups to Watch Startups E-commerce
Three Startups That Help Online Retailers Cut Out Facebook Ads
Direct-to-consumer brands that rely heavily on Facebook and Instagram ads have been reeling ever since Apple’s 2021 privacy changes made it harder and more expensive to land new customers.
Art by Haejin Park
A Girl Killed Herself. It Took TikTok Six Months to Remove Her Account.
Nina is the name I’ll use for the girl who loved my 16-year-old son. Until recently, when he wanted to think about her, he could still find her videos on TikTok, including the ones she posted under a false name while she was a patient in a psychiatric hospital.
Coinbase CEO Brian Armstrong. Photo: Bloomberg
Coinbase Pulls Back Its Startup Investing as Others Weigh Options
Investors are fleeing crypto as the markets collapse. So will big crypto companies keep pumping money into startups to help the fledgling industry stay afloat?
Nate CEO Albert Saniger. Art by Mike Sullivan
Exclusive Venture Capital E-commerce
Coatue-Backed Shopping Startup Lays Off 20% of Staff After Exaggerating Tech Capabilities to Potential Investors
Shopping startup Nate, which touted its use of artificial intelligence–powered checkout technology while it was actually relying on overseas workers to power transactions , has laid off at least 30 of its nearly 150 employees, according to an employee who was at an internal meeting to inform the laid-off workers.