This phrase popped out during a conversation with a friend the other night, who was considering leaving a publicly traded technology company to go to a startup. It seems like everyone these days is starting a company or thinking about doing it. One thing we went back and forth on was the decision to go to an early stage startup (e.g. Series A, less than 100 people, etc) or a later stage startup (Series C or later, $100M+ valuation, etc) and what was the more difficult challenge.

A year ago, I was faced with this choice. I left Google to join Square, which would fall into the latter category (at the time I joined, Square was well over 300 employees). I did it because I felt like that size suits me best. I also did it because I think it’s a harder challenge to go to a Square – or a Dropbox, a Pinterest, an Uber or a Palantir – than it is to join one of the seemingly millions of early...

One thing I’ve become increasingly interested in is how qualitative information is gathered, organized and disseminated across groups of people, even in simple settings like giving feedback one to one or with a team reflecting on its performance. I think the choices made in gathering this data are often knee jerk or poorly thought through (“Hey do you have a second”; “Let’s grab everyone for a quick sync”). In contrast to the rigor applied to numbers in spreadsheets, I think leaders treat this exercise too casually and this is probably because it tends to be aggregated through conversations. Seeing one cell wrong in an excel file leads to the whole thing getting discredited, which ratchets the focus of the creators to get it precisely right the first time. Unpredictable group dialogue is just not as easy to structure and synthesize so expectations tend to be lax. (And there are no...

Sometime back in 2010, while hanging around Google Ventures one day, I had a brief conversation with a entrepreneur where I picked up maybe the most useful metaphor I’ve ever come across in assessing leaders for tech companies. It tears me up that I can’t remember who this entrepreneur was to give him credit for it, though he actually was quoting a conversation he once had with Umang Gupta, one of the first 20 employees at Oracle and the current CEO of Keynote Systems. So – blanket statement – this idea did not originate with me, it’s third hand so it’s probably inaccurate and in this day and age everyone is making shit up all over the internet and not giving credit anyway so who cares.

This entrepreneur told me that back in the day he had interviewed with Mr. Gupta. “Before we go any further,” Gupta asked, “I need to know what type of manager you are: a Dirt Road manager, a Gravel...

Late last spring, after seven and a half years in various staffing leadership roles at Google, I moved back to the Bay Area from New York to lead Talent at Square. While letting people in San Francisco know I was coming back, I learned that one of my closest friend’s new roommate worked at my future company as an engineer. It was a bit serendipitous to think that in this apartment I had spent so many years hanging out in and never once met someone who was even good at math, there now lived an iOS developer who worked at my new employer. What were the chances? It turns out – surprisingly high.

In 1973, an American social scientist named Mark Granovetter published a landmark paper called the Strength of Weak Ties. Like anything discovered that ultimately becomes important, its submission to a preeminent research journal was rejected. Eventually published by a competing publication, the...