17 Essential Best Practices for Making Things Happen

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After reading through Sarah’s little rules of working life, which I thought was pretty useful stuff, I decided to think through some of my own rules, or as I’m calling them, “Best Practices for Making Things Happen”.

The idea is that these are all maxims that I live and work by, that I’ve learned over time and that I believe have made me more effective in accomplishing meaningful things.

The list is neither complete nor fully elucidated, but that’s totally in line with BP #2 and #7. =)

Would love to hear what you think: questions, feedback, etc.

Jason’s 17 Essential Best Practices for Making Things Happen

  1. Keep the promises you make to yourself. I learned this one from Stephen Covey – we make little promises to ourselves all the time (“I’m going to stop working on weekends.” or “I’ll definitely get a workout in tonight.”) These promises are in fact more important to keep than the ones you make to your customers, your boss or your family. Because private victories come before public ones.
  2. If you’ve got a good idea, try to take some kind of action on it right away. Too often good ideas slip away, either due to momentum (it was exciting at the moment, but less so now) or just through forgetfulness. So when you have a good idea, send an email to a potential collaborator, sketch out some designs, or at the very least, make an Evernote note for the idea. Continue reading…

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.

Great Training Beats Great Equipment and Other Thoughts

A friend recently emailed me an old compilation video of myself as a high school gymnast. It includes clips from both training and competition and sparked a few thoughts for me that I thought I might share. Watching the video isn’t really necessary but I’ve included it below for context.

(Click through to watch the video if you’re reading this as an email)

  • Great training > great equipment:
    I switched to a new gym and a new coach in fall of 2001-02. It was my sophomore year in high school and I was working under a young Armenian coach named Levon (who I interviewed earlier this year). He really understood great gymnastics technique and extremely enthusiastic about making sure you made corrections every turn. Despite the fact that the gym was small and the equipment was old and rickety, but I improved tremendously – making the junior national team. Even after moving to a better facility the next year, and even better equipment at Stanford, I never experienced a greater improvement in my skill as a gymnast in a single year, than I did that year.
  • You rarely see the long road to excellence
    We often see other people only when they are at their best. Presenting at a meeting, pushing a finished feature, showcasing a portfolio. Rarely do we see the struggle, the mistakes, and the preparation that came before that performance. In the video, I repeat one move on the parallel bar, where I swing up, release and land with two arms on one bar. I do it over and over again – usually with an error. But if you just watched me in competition, you’d rarely see me miss it.
  • Nothing beats the thrill of performing at a high level
    Watching myself compete at the USA National Championships (the clips where I’m wearing a silver, red and blue uniform) bring me back to the excitement of competition and high level performance. Psychologist Mihaly Csikszentmihalyi coined the concept of “flow” which he says is triggered by a “high challenge, high skill” endeavor. I think many athletes would find that a good descriptor for their experience when competing/performing. And I think this idea applies to careers as well. Finding work that you enjoy, fulfills a market need and that you can get really good at is so important – because it feels so good to succeed at something that is hard and that you are good at.

PS – The friend who sent me the video is Jamie Northrup, a professional stuntman and a former teammate of mine. You can see his stunt reel here.

What’s Your Big Decision? (My 27th Birthday Giveaway)


So I turned 27 about a week ago.

Last year, for my 26th birthday, I had a giveaway where I asked you, readers, to share your biggest lesson you wish you learned when you turned 26 — or who you hope to be by then if you were younger than me.

That was a lot of fun, so let’s do it again!

The giveaway: Decisive by Chip and Dan Heath – a phenomenal book about making better decisions, not through a soulless spreadsheet, but with sound and proven psychological principles. One lucky commenter gets a free copy (closes June 6th)

The request: Leave a comment about an important decision you made in life and what you learned from it.

Here is mine:

Choosing to work at the Stanford Daily

When I was getting ready to graduate Stanford, I interviewed for and was offered the job as the Chief Operating Officer of the Stanford Daily. It would be a full-time, one year paid position for a recent grad to run business operations for our student newspaper. I was also in final round interviews with Teach For America and the Coro Fellowship in Public Service.

The role at the Daily was less prestigious and I had no particular experience working at the newspaper. It would be local. TFA and Coro could potentially take me far away from the Bay Area and would take me down the road of public service.

I spoke with a mentor of mine, Dan Gill of Huddler, and he told me something I’ll never forget: “It’s rare to get P&L (profit and loss) experience so early in your career, and that’s a really valuable experience. Since newspapers are struggling, if you fail, no one will blame you. And if you succeed, you’ll look like a hero. It’s a no lose proposition.”

Now I’m not saying you should always think about decisions in this way, but that advice made a lot of sense to me and I took the Daily job. It was tough and we did struggle, but I think I did make some lasting contributions to the organization. And I’m really glad I took the job – it put me down the path of business, lead me to working at isocket, and well, the rest is still being written. =)

Alright, well, that’s my story. What’s yours?

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.”