“Should I leave Google Legal?”

Advice for lawyers thinking about leaving the best legal department in tech

Two years ago, I left Google Legal to join the team at Pinterest. Since then, from time to time I’ve spoken with former colleagues asking for advice on whether they should move on as well. While every conversation has been unique to each person’s circumstances, there are certain questions or points I find myself repeating often enough that I thought it might be useful to post them. Because startup life doesn’t exactly provide a lot of free time, I hope you’ll forgive a certain brusqueness or lack of polish.

“Why are you thinking about leaving?”

It’s a pretty obvious question, but the answer tells me a lot about whether a person is actually serious about leaving (in which case I will try and help them as best I can) or if I’m going to be providing therapy for their Google angst (which I am also happy to do). My experience has been that people whose answers emphasize what they want next are far more likely to leave than those who emphasize what’s making them unhappy at Google. And to the extent I form my own opinion on whether someone should leave, it’s the forward-looking folks where I feel much more strongly that it might be good for them.

I also would suggest that you have a focused, thoughtful, and sincere answer to this question before you start talking to people about specific job opportunities — people outside of Google joke about being able to spot a mile away a Googler that isn’t actually going to leave. It’s like asking to borrow someone else’s car because “I might be sick of my Tesla”. Maybe you are, but deal with that on your own time.

“Are you learning what you want to be learning?”

There is no other legal department that provides the opportunity to learn as much as you can in Google Legal.

First, there’s the sheer scope and impact of the company’s products, the immediately global nature of most issues, the level of scrutiny applied to the company, the willingness to stake out a position on what the law should be (and power to influence it), and the risk tolerance. There’s internet law, of course. Hardware? Yep. German/Brazilian/Korean/Indian/Pakistani/[insert country here] law? All of the above. Cars, planes, satellites, robots, thermostats, microbes? Got those too. Multi-billion dollar acquisition with one week’s notice? Every month. Want to help manage an international incident? It’s just a matter of time. If you can’t find something to learn at Google, you just aren’t looking.

It’s not just the substance. Yes, Google Legal is huge and sometimes that’s a bummer. But if you want to learn how to manage a legal team operating globally at the highest level, there’s nowhere else with as many opportunities.

Finally, you’re surrounded by the smartest and most experienced lawyers in the business, working for clients who create technologies that raise brand new legal issues on a regular basis. All of which is a long way of saying, you should only leave Google Legal if what it’s teaching you isn’t what you’re optimizing for anymore. There’s a lot you don’t learn as well, but what you do is pretty damned amazing and is likely to be a huge part of the rest of your career. Don’t throw that away prematurely.

“If you’re going to look, you should actually look”

Some conversations I’ve had start with “I have an offer from [AmazeCo.], do you think I should take it?” My response is usually, “what other options have you considered?”. The answer is often “I haven’t considered anything else, I just happened to get recruited by [AmazeCo.] and I was intrigued, and here I am.”

First, congratulations — another team believes you can do a lot for them, and that’s a credit to you. But fundamentally, your decision is not “[AmazeCo.]” vs. “stay at Google”. If you took the time and effort to do an in-depth search, you’d probably find that there are all sorts of other opportunities out there, whether at more established companies, as general counsel at a small startup doing something really cool, or even within Google. Looking lets you learn about yourself and what might be a good next step for you. Until you’ve talked to a few companies, it’s hard to really grasp just how different founders, teams, and cultures can be. Also, not all great things that are happening in tech are known to Google or worthy of respect in the Google worldview. But if you make the rounds, you may stumble across a team doing something amazing, or discover an idea that really speaks to you.

This advice is driven largely by my own personal experience. Pinterest wasn’t on my radar when I started thinking about life after Google. And my first impression was that the product wasn’t a great match for my skills and interests. But after speaking with Ben about what he wanted Pinterest to be and how he wanted to do it, I came away with a completely different view. And more importantly, the process of talking to Pinterest and others helped me realize that my happiness was as much about helping to build a team from early on as it was about the legal issues I’d be working on (I’ve done a lot of corporate, contracts, and employment work at Pinterest). It turned out that what I wanted was something very different than Google, not another Google circa 2005. I wouldn’t have known that if I hadn’t looked.

“Don’t romanticize startup life”

It’s not always evident from the tech press, but working at a startup is really hard and stressful. At Google, failure is a learning opportunity. At a startup, failure means everyone goes home with their professional hopes and dreams temporarily dashed. A $1,000,000 mistake at Google draws a chuckle. At a startup, it puts you one step closer to corporate death.

Even the most successful startups go through periods where from an internal point of view the business might be failing. There’s constant churn and chaos, and sometimes the people you like the most are suddenly gone from the company. New colleagues are arriving by the dozens, and not everyone will get along. Some of them came from companies where the lawyers were clowns, or the enemy. Strategies change. Re-orgs happen and people get upset (if you thought this was something that only happened at big companies, it actually happens more often at small ones). You have forehead-smacking moments where you can’t believe what someone did. Or that no one actually did that thing that obviously needed to be done. In short, all startups are screwed up in their own way.

If you have the right attitude and circumstances, you can do something about some of these problems. But you can’t help with them all, and on a bad day, there you are working on the catering contract while THE COMPANY IS GOING DOWN IN FLAMES. You’re the violinist on the Titanic (except you’re a lawyer which is so much less cool than being a musician).

The above is, of course, a bit dramatic. One of the great things about being at a startup is the opportunity to contribute beyond your legal skills. But do not for a second think that it’s frolicking in green fields under blue skies where money rains from the sky after four years. That’s not a startup, that’s actually where you are now (except that you don’t even need to wait for the money to rain).

Speaking of money….

“Assume you will make less money”

You are paid a ridiculous amount of money. You will make even more the longer you stay at Google. Among other things, this money makes opportunities available to your loved ones and can be used as a force for good in the world.

It’s possible you might make more money at a startup, but the odds are not good. If making anywhere close to as much as you make at Google is important to you, you will be miserable and stressed out during those inevitable stretches where the startup’s success is in doubt.

Ask if you can honestly tell yourself: “Even if this company flames out, I may be disappointed but I will have no regrets”. That may be because of the mission, the learning opportunity, the camaraderie, the career building, the fact that you already have a nest egg, or something else. People who can say that put a big smile on my face because I know they are likely to be happy making a change, and that’s really exciting.

“Should I stay at Google until I reach [title]?”

No. No one gives a ____ about your title at Google. Your experience, your skills, and your responsibilities are what matters.

Also, while we’re so lucky to work in a time of many opportunities, they are fleeting. *If* you are ready to leave Google and have found an opportunity that appeals to you, take it. The Venn diagram of companies with good prospects, doing something you believe in, with the culture that’s right for you, that needs lawyers, and where you beat out the other candidates, is really small. In addition, as a general rule the earlier you join a company the more opportunity for impact there will be.

“Realize you are making a commitment”

It’s tempting to emotionally compare the excitement of a new opportunity vs. the downsides of spending another year at Google. Try to remember that you’re making a meaningful commitment to your next job(especially if it’s an earlier stage company, in which case you’re looking at probably five years or more). As with any long-term relationship, there will be ups and downs and eventually the novelty bonus wears off.

You should also assess your emotional commitment. Are you really excited about what the company might be able to do for the world? Will you embrace your new teammates as your new family and go to bat for them? Are you ready to question Google’s motives? Are you comfortable with the prospect that your former colleagues at Google might be trying to snuff out your company, and are you excited to compete tooth and nail with them?

I don’t think you need to answer all these questions emphatically yes to make the leap. But I do think you should explore how they make you feel, because your happiness depends on your ability to embrace the fact that you are leaving one of the most iconic and impactful companies in modern history. That’s not something to be done lightly. But know also that there are many of us “out here” who are very happy, and if you make a good decision, you might be one of us too.

With affection, nostalgia, and respect,