My Biggest Takeaway on 37Signals’s New Book on Remote Work (Hint: It’s Not Technology)

REMOTE: The new book from 37signals 2013-11-08 07-41-46I just finished reading Remote: Office Not Required, by Jason Fried and David Heinemeier Hansson, partners at 37Signals.

It’s a great read and here’s the  basic premise:

  • In today’s economy, the quest for talent is so great that organizations can no longer afford to merely look at individuals co-located in their physical presence (their metro area)
  • It is easier than ever to coordinate the work of individuals from around the world with just a good internet connection and a few pieces of web-based software (including 37Signal’s own products)
  • There are many drawbacks to forcing people to work in an office and many perks to allowing them to work (even a few days a week) at home / at a cafe or coworking space that benefit both the remote worker and the organizations that employ them
  • There are simple ways to address many of the concerns people have with remote working (review the work, not time in seat; put relevant information where it can be seen by all, overlap working hours, etc)
  • There is a tipping point coming with remote work. Many organizations large and small, from across many industries, are using remote workers and it’s time you (the reader) became an early adopter.

They actually went out and interviewed a bunch of companies that do remote work as well so REMOTE is not just “the edgy opinions of Fried and DHH”. The book has useful tips for making the case for remote work to your boss (or to your team, if you are the boss). There’s a lot of value in learning how to structure a good remote work environment.

But personally, I got a bigger shift in perspective from something else.

My biggest takeaway from REMOTE:

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Sarah Allen’s Little Rules For Working Life

SONY DSCI’ve learned a lot of stuff working with the fellows in my program, particularly Sarah Allen, who’s paired with me on the Smithsonian Transcription Center. I noticed that she’d often mention a policy she had on doing (or not doing) certain things. I remarked that there seemed to be a lot of them and has she ever put them in one place?

Well luckily for us she has. Here are some my favorite policies of Sarah Allen, an incredibly accomplished software developer, manager, and entrepreneur, and my comment on it.

I never take a job where I don’t know at least one team member very well. The most important indicator of success for any group is the quality of the people. VCs invest in the team, rather than the idea, since it is easier for a great team to change their idea, but impossible for a great idea to find a new team. Where you choose to work is an investment.

Most people would say it’s good to get along with your future coworkers when evaluating new jobs, but this policy takes it a lot farther. It essentially means companies where you’re applying cold, or who are pursuing you with no prior connection, is completely off limits. I think you need to be at a certain stage in your career to be able to pull this off, but that time frame is probably sooner than you think (5 years?)

Write stuff down. I take meeting notes and send them out afterwards. I don’t work without a contract. It’s not an issue of trust. There are a thousand small decisions about the work that go unsaid in a meeting. This applies to any collaborative work. Anytime I need to say to you “I will do this” or “I expect you to do that,” a follow-up email will solidify alignment or catch misunderstandings — saving time and forging stronger relationships.

Sarah and I have become known as the note taking fellows. We have a Google Doc pulled up for almost every meeting we’ve been in. A rough count of our Google Drive has around ~170 meeting notes, planning docs, spreadsheets and talking points in just three months.

Iterate. Celebrate. Iterate. Celebrate. I wish I knew where I read this. Celebrate the little things. You can’t really control the big win. It’s the small series of little wins that we can make happen. We need to celebrate these.

One thing I wish we did more at Ridejoy was celebrate the small wins. There was a feeling from some of my other cofounders that we should only celebrate when we hit a really big milestone, but it often felt too far away, and then the celebration was a huge endeavor in itself, which was not ideal. I like this policy.

Tell someone’s boss, in writing, when they do a great job, especially if they are far away in an organization.

This is like a karma thing – we all hope that if other people work with us and find it an awesome experience, that they’d tell our boss (if we had one) how awesome we were doing.

The #1 job of a good manager is hiring and retaining great people. When I’m in a management role and things get crazy, as they often do, I tell this to myself every morning and twice during the day. It takes discipline to spend time writing an excellent job description or having individual meetings with staff when there are urgent, pressing, seemingly more important issues to deal with.

This is exactly the difference between individual contributors and leaders of teams. Your effort as a manager is multiplied when you find the right people, invest in them, and prune when necessary.

Never hire until you’ve interviewed at least three great candidates. Hiring should be a tough decision. We should have to ask ourselves what is really important so we can decide between these amazing people. We should have cause to wonder if we should stretch our budget to hire more than one.

This is such a great rule for preventing a “He/She is the the one” situations where you fall in love with a candidate. I’ll admit that at Ridejoy, we definitely hired someone we fell in love with, but I think Sarah’s policy is the right one. If you can’t do this, you aren’t recruiting hard enough.

Read them all at: little rules for working life.

If You Don’t Have Time for a Side Project, You Are Probably Just Lying to Yourself


side projectsHaving a side project to work on is a tremendously powerful way to develop new skills, improve your career capital and recharge from the repetitive tasks you do at work. In a couple of months (or less) you could learn how to code, or train to run a marathon, improve your social skills or write a novel.

Despite these advantages, most people never even get started with their side projects.

They make excuses, saying how they don’t have time, how next month will be less busy or how they’re more dedicated to their job or their families to embark on such extracurriculars. Look, I know it can be tough to find the energy to embark on a side project. But unless you are working 100 hours a week (and you’re probably exaggerating) or the parent of a newborn child, you are probably just lying to yourself.

Stop Watching So Much TV

Most Americans watch around THREE HOURS of television per day. Sure, there are probably a few people watching like 10 hours a day, but that’s still a lot of people vegging out for over an hour a day. For a lot of folks, TV can be swapped with social media or video games to the same effect.

You really only need average 35 mins a day on your side project to net 4 hours a week on your side project. That’s 200+ hours over a year – which would allow you to do a tremendous number of things.


The Mayor of Newark Has a Side Project

Cory Booker is the well-known mayor of Newark, NJ and unofficial Senatorial candidate, has also co-founded a video sharing startup called Waywire. Now, I don’t care what your political stance is, being the mayor is a lot of work. And if you believe even half the stories that make him one of the “hardest working mayors in America” you’ll understand that Booker is not just punching the clock on his public service duties.

Yet that has NOT stopped him from creating something new from scratch – on the side.

Paul Graham Spends 3-4 Hours a Day on Hacker News

Paul Graham is the cofounder of Y Combinator, which funded my startup Ridejoy and other, far more successful startups like Airbnb, Heroku and Dropbox. In addition to running Y Combinator as a partner and being a husband and father, he also spends a lot of time working on Hacker News, the Reddit-like community he created that gets 1.6M pageviews daily.

How much time? Three to four hours per day, according to a recent article on TechCrunch. Sure, Hacker News is tangentially related to his job running Y Combinator, but most side projects do provide real tangible benefits to your main work responsibilities.

Start Slow

Swayed? Thinking about buckling down to really take on that side project? Cool. But don’t start too hard.

From my research on human behavior change, I think one of the big missteps of human psychology is that we’re overly optimistic about our own abilities to change. We bite off more than we can chew.

Instead of diving in for hours one day, try spending 10 minutes a day on the project for a week. Consistency is great than intensity. You’ll make more progress in the long run if you keep at it a little bit each day, than if you immerse yourself once every few weeks.

I estimate it took me about 100 hours over many months to learn enough programing to build the first version of RewardBox, but there’s no way I would been able to do it over 50 hrs/wk for 2 weeks.

What’s a side project you’ve wanted to start? Let me know what’s holding you back in the comments.

Startup Founders: Don’t Forget to Sell the Dream

I’ve been speaking with some Y Combinator hopefuls as they prepare to interview for this coming batch. As usual, there are some really enthusiastic and super smart folks working to solve really interesting and important problems.

I love taking these meetings because I get to get back to the community that has supported me plus I learn a ton in the process. For instance, it was from all these meetings last time around where I wrote my most popular post of 2012: 11 compelling startup pitch archetypes.

This post addresses a very specific piece of the startup pitch: selling the dream.

The Final 10%

The vast majority of your pitch should be around the mechanics of your business: your customers, your product, your team, your distribution strategy. This is what’s going to make you successful: competent people who really understand the needs of their users and who have the ability to create the right product to address those needs and get it into the hands of their users.

But, there is a final 10% of your pitch which should be more aspirational. It’s about the vision, the dream, the magic. It’s the answer to the question “How is this going to be a billion-dollar business?” [1]

Two of the companies that I’ve spoken to were missing that part of their pitch. They had identified a market segment which had a burning problem, and their products all that problem, and they had good specific strategies to acquire those customers. This is a great start. [2]

But they were missing that aspirational story.
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Ignore the critics: Lean In should be required reading for everyone, including men

Disclaimer: as a man writing about gender inequality, I acknowledge my privileged (and biased) viewpoint in this discussion. I’ve run this post by several smart, awesome women and incorporated their feedback, but I know I still run the risk of getting things wrong. Still, this topic is so important that I felt I had to try to add to the conversation.


I recently finished Sheryl Sandberg’s new book, Lean In: Women, Work and the Will to Lead. [1] Everyone from the New York Times, Slate, TIME and a host of bloggers has weighed in on Lean In — and many of the reviews are quite critical.

Among other things, people have said it blames women, offers unrealistic advice from a wealthy elite, and dismisses stay-at-home moms.

Ignore the critics. They’re wrong and they’ve missed the fact that Sandberg has produced a powerful book that should be required reading. [2]

Incidents like the disastrous PyCon/Adria Richards debacle underline the fact that some men have little understanding of the unique difficulties professional women face, and some female professionals have struggled to find effective ways of dealing with these challenges. We need to bring more constructive voices to the table discussion. Lean In is a nuanced and highly relevant read for anyone who cares about building a more equitable world in tech and beyond.

A short summary

Sandberg is a total badass, and yet she has struggled with significant hurdles to achieve professional success. Many of these struggles were with confidence, advocating for herself and balancing competence with likability, as well as overt sexism. I was forced to reconsider how to evaluate outward appearances of confidence between men and women and recognize there are no simple answers for ensuring a meritocratic workplace.

Sandberg cowrote Lean In with Nell Scovell, a professional writer, and acknowledges the help of many experts in refining her arguments. The collaboration made for writing that’s leaps and bounds above your typical business-buzz-book fare: paragraphs flow well, stories contain appropriate detail, research is cited and explained.

In the rest of this post, I’ll share some highlights, but I seriously encourage you to read the book for yourself.

More women in power

Sandberg makes the mission of her book very clear. She wants to see women in board rooms and the halls of Parliament, running companies and nations.

In the first chapter, she recounts hosting a dinner party for Leymah Gwobee, the winner of the 2011 Nobel Prize winning activist. Gwobee had helped lead women’s protests that toppled the dictatorship in Liberia and was asked what the best way to help her people and fight the mistreatment of women.

Her answer: “More women in power.”

Sandberg writes this book from a moral imperative. She wants to help ambitious women succeed, not just for their own sake, but to bolster the conditions of women across the globe.

Sitting at the Table

A phrase that frequently appears in Lean In is “sitting at the table.” Sandberg recounts a story of hosting a number of Silicon Valley executives along with Tim Geithnier, the Secretary Treasurer, and his staff at Facebook. While all the executives sat at the main table, Geithnier’s all-female staff seated themselves in chairs along the side of the room.

Sandberg was surprised and waved them over. They demurred and refused to “sit at the table”. Women often are unwilling to jump into the action, Sandberg claims, and this holds them back from moving their career forward and making their voices heard.

She says this not disparagingly from up high, but from the perspective of a woman who has sat on the sidelines herself more than once, and often feels doubts about her position as one of “the most powerful women in the world.”

Confidence versus Caution

There seems to be a disparity in how men and women value their abilities and approach job hunting. According to data from recent graduates at Northwestern, males were 8x more likely to negotiate their salary than women. At Hewlett-Packard, an internal report found that while men apply for open jobs if they think they meet about 60 percent of requirements, while women are more cautious and won’t apply unless they think they meet 100 percent of the criteria.

In the book, Sandberg shared her thoughts on negotiating once she received her COO offer from Facebook:

“My husband, Dave, kept telling me to negotiate, but I was afraid of doing anything that might botch the deal. I could play hardball, but then maybe Mark would not want to work with me. Was it worth it when I knew that ultimately I was going to accept the offer? I concluded it was not.” [3]

In discussing this post with a former female coworker, she told me how one time, after receiving a generous offer from a new employer, she made the decision to negotiate. However, her own mother actually tried to dissuade her from negotiating, saying “It’s already a such a high offer! Don’t push it!”

Ultimately she negotiated a better offer and accepted the position (woot!), but I thought this was a poignant example of how women are often discouraged from negotiating — a message rarely given to men.

Competent women lose points on likability

Sandberg cites a tremendous wealth of research around gender bias: the most memorable example is involved a real-life business case study about a take-charge entrepreneur/venture capitalist named Heidi Roizen. In 2003, some Columbia business school professors had their class read the case study, but half the students got a version of the case with “Howard” switched for “Heidi.”

When polled, students found both Heidi and Howard equally competent, but Howard appeared to be a more appealing colleague. Both men and women felt that Heidi was more selfish and “not the type of person you would want to hire or work for.” This is a very clear example of gender bias: the students read the exact same case!

“When a woman excels at her job, both male and female coworkers will remark that she may be accomplishing a lot but is “not as well-liked by her peers.” She is probably also “too aggressive,” “not a team player,” “a bit political,” “can’t be trusted,” or “difficult.” At least, those are all things that have been said about me and almost every senior woman I know.”

When you want to become C-level executive, having the support of your peers is crucial, and we must be aware of how competent women lose points for likability. This is the double whammy that makes it hard for women to advocate for themselves: because they’ll be docked points for seeming “too aggressive”.

When Sandberg finally did negotiate with Zuckerberg around her offer, she did it in a friendly manner, emphasizing that as COO, she would be doing Facebook’s deals and of course needed to demonstrate her ability to be a good negotiator.

Forming truly equal partnerships

“I truly believe that the single most important career decision that a woman makes is whether she will have a life partner and who that partner is. I don’t know of one woman in a leadership position whose life partner is not fully— and I mean fully— supportive of her career.”

To get more women into power, they shouldn’t have to decide between raising families or advancing careers. [4] There has to be a way to do both.

On this point, Sandberg wants women to ask for truly equal partnerships (if they have a partner) and for men to respond and deliver on an equal partnership. In households where both men and women work full-time, women still do 30% more housework and and 40% more childcare than men. It is unsurprising then that women might feel more burdened by their jobs and struggle more professionally, as they just have a higher total workload than men.

And just in case you feel annoyed by Sandberg’s wealth and ability to hire nannies, note this anecdote:

“When I went back to my job after giving birth, other working mothers told me to prepare for the day that my son would cry for his nanny. Sure enough, when he was about eleven months old, he was crawling on the floor of his room and put his knee down on a toy. He looked up for help, crying, and reached for her instead of me. It pierced my heart…”

Being a working mom is hard, no matter who you are and while Sandberg has lots of money, it does not buy her unlimited maternal bliss.

Closing Thoughts

This book covers a lot of ground: Sandberg also discusses mentorship, taking initiative, seeking growth opportunities, stay at home dads, and a host of other topics. I’ve just scratched the surface with this blog post. I especially encourage men to read it because even if you think you’re “gender-neutral” [4] , I bet this book will led you to change the way you do things.

Here are some very unflattering examples of how Lean In has been relevant for me:

  • When discussing the business career prospects of a girl I knew growing up, I made an offhand remark that “it probably doesn’t hurt that she is an attractive Asian female.” I’m mortified those words escaped by lips, but even more disappointed that this line of reasoning made any sense even in my head.
  • When having a coffee meeting (not a date!) with a female I had previously only talked with online, I found myself wondering if the meeting was going well because she wasn’t smiling or sharing very much. Then I wondered if I would have the same concerns if I was meeting with a man. Probably not.
  • When I’m in conversation with any group that includes women, I am much more cognizant of how often I interrupt/talk over men vs women.

Lean In is an important book that should be read by men and women, in tech and beyond. Having more women in power will help unlock the abilities and contributions of a significant proportion of society that is often under appreciated. And making sure that talent surfaces and worthy ideas are heard is good news for all of us.

Thanks to Winnie Kao, Christine Yen, Margot Leong and Kat Li for reading drafts of this and Christine Lan for helping shape my thinking on this subject.


[1] This is an affiliate link. If you buy this book on Amazon, I’ll get a few cents. [2] To address those claims directly:
  • Blaming women: Sandberg acknowledges there is a chicken-and-egg issue with gender inequality, with external barriers and internal ones. As a woman who’s struggled with these internal barriers and an executive who’s seen hundreds of women struggle as well, she’s chosen to focus this book on the internal ones, without denying there are significant societal problems that prevent gender equality.
  • Unrealistic advice from a wealthy elite: while it’s true that Sandberg has more money, power and connections than your typical working woman, she routinely discusses her own struggles before she became one of the most powerful women in the world, and she also shares stories from younger, “more typical” women she’s mentored and how they’ve leaned in. Additionally, she shares some of her more recent struggles of being a professional and a mom. In my opinion, the fact that Sheryl-fucking-Sandberg, the TED-talking COO of Facebook, still sometimes cries at work over issues that probably relate to her gender go a long way in underscoring the far greater difficulties that “regular” working women must overcome.
  • Dismisses working moms: simply not true. First she says she’s grateful to the many volunteers, who are mostly mothers, that sustain our schools, nonprofits and communities, and calls for working mothers to “regard mothers who work inside the home as real workers.” She describes many of the painful the trade-offs she’s made as a mother in order to work full-time and recognizes it’s not a path everyone would want to choose.
[3] Sandberg ultimately decided to negotiate only after her brother-in-law made a striking point about how no man at this level would ever accept the first offer. [4] Sandberg makes it clear that not every woman wants to be a working mom, and that some people find full-time motherhood deeply fulfilling and she honors that. She does point out though that the more you can achieve before stepping away to bear your child, the more likely you’ll want to return to the workforce because you could have an exciting career lined up. [4] Actually, people who claim to have no bias are actually more likely to be biased, according to research Sandberg cites in Lean In. So people who think they’re gender-blind may need this book the most.

“When evaluating identically described male and female candidates for the job of police chief, respondents who claimed to be the most impartial actually exhibited more bias in favor of male candidates. This is not just counterproductive but deeply dangerous.”