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 Amazon Google
Cloudflare Complaint Pinpoints Amazon’s Antitrust Weak Spot
Photo by Bloomberg
Today’s blog post from top executives at Cloudflare blasting Amazon Web Services for the “egregious” fees it charges customers who move their data out of AWS’ servers raises an interesting question. Could the most fertile ground for pursuing antitrust action against Amazon lie in its cloud business, not the ecommerce business that gets all the attention from business media and politicians?...
Latest Briefs
 
Electric Truck Maker Rivian Raises $2.5 Billion Round
EU Gearing Up for Lengthy Probe of Facebook’s $1 Billion Kustomer Deal
AWS Accused of Gouging Customers for Networking Bandwidth
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.
Bolt CEO Ryan Breslow. Photo: Bolt
Exclusive
Online Checkout Startup Bolt Valued at $4 Billion
Bolt, a San Francisco-based startup that offers software for online shopping, is raising $333 million in Series D funding at a post-investment valuation of $4 billion, nearly five times its valuation in December, according to three people familiar with the matter.
Exclusive Entertainment
The People With Power at Disney’s Media Distribution Group
Hulu, one of the pioneers of video streaming, has become a training ground for the entire industry as key executives flock to newer rival services.
Rex Woodbury. Photo: Index Ventures
Creator Economy Startups Entertainment
Rebuild America’s Economy for ‘Solopreneurs,’ Says Index’s Woodbury
Rex Woodbury , a 27-year-old principal at venture capital firm Index Ventures in San Francisco, started out as an influencer in college, amassing 236,000 Instagram followers .
TI Comp Survey Startups
The Information’s Tech Pay Survey Shows Power Shift to Employees
The technology-business boom is giving white-collar workers more of what they want. At tech companies, the traditional practice of allowing employees’ shares to vest only after a worker reaches a full year of employment, known as a one-year “cliff,” appears to be eroding.
The Takeaway Amazon Google
What Makes a Good CEO?
Tech CEOs are grabbing their fair share of headlines, per usual. Mark Zuckerberg is in the news again in the wake of a negative new book about Facebook and a controversy over his Fourth of July watersports moment (patriotic or not?).
Vice CEO Nancy Dubuc. Photo: Bloomberg
Exclusive Media/Telecom Entertainment
Vice Media’s SPAC Talks Stall
Vice Media’s plan to go public by merging with a special purpose acquisition company has stalled as the company struggles to raise additional financing for the deal amid questions about Vice’s valuation, according to people familiar with the situation.