A Dozen Things I’ve Learned from Sheryl Sandberg about Management, Careers & Business

1. “I sat down with Eric Schmidt, who had just become the CEO [of Google], and I showed him the spread sheet and I said, this job meets none of my criteria. He put his hand on my spreadsheet and he looked at me and said, ‘Don’t be an idiot.’ Excellent career advice. And then he said, ‘get on a rocket ship. When companies are growing quickly and they are having a lot of impact, careers take care of themselves.’ ”

This quote above extends on the importance of getting involved in situations that create positive optionality. For example, when companies grow there is a need to do new things – workers become managers, people who do X are trained to do Y and Z, and everyone learns new skills. There tends to be more opportunity and less politics in a growing company since it is more than a zero sum game. Companies that are shrinking tend to be the reverse.

A less than zero sum game at your place of work is problematic when it comes to your career. Startups can be particularly attractive sources of optionality. In the early days of a growing company (when there are just a few people working at the company) there was no shortage of opportunity. Startups tend to make for more battlefield promotions and people are more often allowed to learn new things and grow as employees.  


2. “The reason I don’t have a plan is because if I have a plan I’m limited to today’s options.”

Positive optionality is very valuable. If you are not open to opportunity as it arises, you can’t harvest optionality. My friend Craig McCaw likes to say flexibility is heaven. If he can delay a decision somehow, he will do it because he knows a better option might arise in the meantime. Sheryl Sandberg is a protégé of Larry Summers who is close to Robert Rubin. So to understand Sheryl it is useful to understand Rubin. In a New York Times article Summers describes Rubin’s approach: “Rubin ends half the meetings with – ‘So we don’t have to make a decision on this today, do we?’ Summers says. New information will evolve.”

“What so many people have a tendency to do is to lock into a scenario,” Summers says. “What Rubin will say, at times to the frustration of others, is that some questions don’t have answers – which is to say that just because a problem is terrible, we don’t have to act. It may not be the right time.” In a Fortune magazine article Carol Loomis wrote about Rubin: “Part of Rubin’s approach to decisions at the Treasury was to put them off as long as possible. Some people might call that procrastination; Rubin called it getting that one last fact or well-judged opinion, from whoever at the table might offer it, that might make a decision the right one. Geithner says the young members of the Treasury staff would on occasion rush into Rubin’s office, imploring him for a decision about something consequential. Rubin’s first question would often be,How much time do we have before we have to decide? Summers calls this Rubin’s habit of “preserving his optionality.”


3. “There is no straight path from your seat today to where you are going. Don’t try to draw that line.”  

Life is not linear. Opportunity usually arrives in life in strange and unexpected ways.  Opportunity also tends to arrive in a lumpy fashion. This nonlinearity and lumpiness means that it is wise to be both patient and ready to be very aggressive when opportunity presents itself. One odd thing that I like to do (there are many) is read obituaries. When you read a good obituary it often reinforces how nonlinear life can be. The line “life is one damn thing after another” is variously attributed to Edna St Vincent Millay and to Elbert Hubbard, but whoever said it was speaking to a fundamental truth. You can see the nonlinear path life takes in many obituaries.


4. “The traditional metaphor for careers is a ladder, but I no longer think that metaphor holds. It doesn’t make sense in a less hierarchical world. … Build your skills, not your resume. Evaluate what you can do, not the title they’re going to give you. Do real work. Take a sales quota, a line role, an ops job, don’t plan too much, and don’t expect a direct climb. If I had mapped out my career when I was sitting where you are, I would have missed my career.”

Sheryl Sandberg is saying that the traditional career path is history. And that you must sometimes move horizontally into positions where you acquire new skills to advance in life.

Reid Hoffman has a similar view: “The notion of a career has changed. Whereas we used to have a career ladder, now we have a career jungle gym. Success in a career is no longer a simple ascension on a path of steps. You need to climb sideways and sometimes down; sometimes you need to swing and jump from one set of bars to the next. And, to extend the metaphor, sometimes you need to spring from the jungle gym and establish your own turf somewhere else on the playground. And, if we really want the playground metaphor to accurately describe the modern world, neither the playground nor the jungle gym are fixed. They are constantly changing—new structures emerge, old structures are in constant change and sometimes collapse, and the playground constantly moves the structure around.”


5. “All of us, and especially leaders, need to speak and hear the truth. The workplace is an especially difficult place for anyone to tell the truth, because no matter how flat we want our organizations to be, all organizations have some form of hierarchy. What that means is that one person’s performance is assessed by someone else’s perception. This is not a setup for honesty.”  

Genuine listening is hard. People in senior management tend to get surrounded by people who tell them what they want to hear. In his famous speech The Psychology of Human Misjudgment Charlie Munger pointed out: Now you’ve got Persian messenger syndrome. The Persians really did kill the messenger who brought the bad news. You think that is dead? I mean you should’ve seen Bill Paley in his last 20 years. [Paley was the former owner, chairman and CEO of CBS]. He didn’t hear one damn thing he didn’t want to hear. People knew that it was bad for the messenger to bring Bill Paley things he didn’t want to hear. Well that means that the leader gets in a cocoon of unreality, and this is a great big enterprise, and boy, did he make some dumb decisions in the last 20 years.”


6. “Leadership is about making others better as a result of your presence and making sure that impact lasts in your absence.”

Here I think Sandberg shares the view that Marissa Mayer and others have, which is that at a top level in management the job is less about making many decisions but rather making a few very important decisions – then doing what it takes to enable other people to get things done that matter. An effective leader needs to articulate a set of priorities that enables the team to make decisions in the absence of a leader, which is necessary most of the time. Effective leaders find ways to amplify their impact whether they are present or not.


7. “Your life’s course will not be determined by doing the things that you are certain you can do. Those are the easy things. It will be determined by whether you try the things that are hard.” 

“Ask yourself: What would I do if I weren’t afraid? And then go do it.”

This again is thinking about your life as if you were a venture capitalist. As I pointed out in my post on Chris Dixon, it is in the areas where people are not looking that you can find mispriced opportunities. The “price” you pay in a career when trying to capitalize on an opportunity is not just money, but time and energy.  If you aren’t failing sometimes you are not learning. Try not to repeat the same mistakes and instead make new mistakes. Good judgment is often acquired by a progress that often involves bad judgment.


8. “The most important thing I can tell you is to open yourselves to honesty. So often the truth is sacrificed to conflict avoidance. You know your closest friends’ strengths and weaknesses, and what cliff they might drive off. Ask them for honest feedback.”

No one has perspective on themselves. We all need people who can tell us when we are off course. Charlie Munger puts it this way: “This first really hit me between the eyes when a friend of our family had a super-athlete, super-student son who flew off a carrier in the north Atlantic and never came back, and his mother, who was a very sane woman, just never believed that he was dead. And, of course, if you turn on the television, you’ll find the mothers of the most obvious criminals that man could ever diagnose, and they all think their sons are innocent. That’s simple psychological denial. The reality is too painful to bear, so you just distort it until it’s bearable. We all do that to some extent, and it’s a common psychological misjudgment that causes terrible problems.”


9. “Google is fundamentally about algorithms and machine learning. And that that has been very important and continues to be very important. They’re doing a great job. [At Facebook] we start from a totally different place. We start from an individual. Who are you? You know, what do you want to do? What do you want to share?….There’s one thing that I think is most important that’s to Facebook, which is that we are focused on doing one thing incredibly well. We only really want to do one thing.”  

Focus matters. For a company to be a master of one thing can be very valuable, whereas an attempt to be a jack of all trades can be problematic. One thing that is tremendously clarifying for a business is a single principle around which a company can optimize decisions (that one thing). This allows people, even in a large business, to know how to optimize daily decisions. At Google, people know that the “one thing” is selling more targeted advertising. Everything is optimized to achieve that objective.


10.  “No one can have it all.”

“Life and business inevitably involves tradeoffs. Family, work, personal life all potentially create conflicts. Some people have a great ability to balance things in life, but no one can have everything. Operational effectiveness is about things that you really shouldn’t have to make choices on; it’s about what’s good for everybody and about what every business should be doing.”

Tradeoffs are inevitable in business and in one’s personal life. There is work, personal life and family. Getting the mix right between these three things is neither simple or easy. Often the tradeoffs are caused by limitations created by laws of physics. Business must also make tradeoffs. I have always found this quote from Michael Porter to be useful: “Strategy is about making choices, trade-offs; it’s about deliberately choosing to be different.”


11. “Done is better than perfect.”

The people who succeed in life are people who get things done. Not just getting anything done, but the things that matter. They don’t necessarily clear their screens or desks every day, they clear their screens or desks of the things that matter most. Here’s an example of done being better than perfect: Every weekend I write 5,000 words or so. The post aren’t perfect, but I get them done. The perfect blog post is the one that has never been written. The perfect life is the life that has never been lived. Mark Zuckerberg wrote in the letter that accompanied Facebook’s S-1 filing with the SEC:

“Hackers try to build the best services over the long term by quickly releasing and learning from smaller iterations rather than trying to get everything right all at once. To support this, we have built a testing framework that at any given time can try out thousands of versions of Facebook. We have the words “Done is better than perfect” painted on our walls to remind ourselves to always keep shipping.”

Facebook has created a system where everything they ship is an experiment that is rigorously tested and improved through nearly constant iteration. Hundreds or even thousands of experiments are conducted at a software company like Facebook every day.  Most things fail, but the experimentation process discovers improvements via what Nassim Taleb Calls via negativa.


12. “Work hard, stick with what you like, and don’t let go.” 

Being relentless and working hard often pays big dividends, financially and otherwise. Staying relentless in pursuit of your goals and working hard is far easier and more likely to be successful if you are doing what you like. Sheryl Sandberg’s statement is not always true, since life is often unfair, but not working hard, doing what you hate and letting go, almost certainly won’t get you anywhere. What Sheryl Sandberg is saying here is quite simple. Someone might even complain that it is too simple or even obvious. Business is often made too complex and at its core is simple. Being a great manager like Jim Barksdale or Tom Murphy requires the daily equivalent of blocking and tackling in football.  Building a business brick-by-brick is what great managers do.




New Yorker – A Woman’s Place

HBS Speech – Sheryl Sandberg: Get On A Rocketship Whenever You Get The Chance


Harvard Magazine – Harvard College Class Day 2014

McKinsey Interview – Facebook’s Sandberg: No one can have it all


Amazon – Lean In

Harvard Commencement – Sheryl Sandberg Graduation Wisdom (video)


NY Times – Keeping the Boom From Busting

Fortune – Robert Rubin on the job he never wanted

6 thoughts on “A Dozen Things I’ve Learned from Sheryl Sandberg about Management, Careers & Business

  1. Pingback: A Dozen Things I’ve Learned from Sheryl Sandberg about Management, Careers & Business | PaulJustice – Invest in U

  2. This is one of the best blog posts I have read recently. It encompasses so many of the essences of management and leadership. It’s pleasure reading your blog overall but had to let you know that I especially enjoyed this post. Thanks!



  3. Pingback: A Dozen Things I’ve Learned From Arthur Rock about Business & Venture Capital | 25iq

  4. Pingback: A Dozen Things I’ve Learned from Seneca The Younger About Venture Capital, Startups, Business and Life | 25iq

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