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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 regularly writes about all things tech, media and the wild ride both industries are in for. She can be found on Twitter at @jessicalessin.
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