How to be Userful

August 2012

##a System for Superstars

TechStars’ Katie Rae is in full flow at Boston Startup School in front of seventy wannabe entrepreneurs. We’re sitting in the Harvard iLab, and over the course of about three minutes she’s mapped out this incredible system of thought for interns and new employees at early-stage firms. If only I’d known this at my first gig. Or my second.

It goes like this. Startups operate by turning problems into tasks. There are two ways to rank tasks: by difficulty and by familiarity. So any potential job fits into a 2x2 matrix:

y: task familiarity x: task difficulty


Simple enough. In the ( + , + ) quadrant are tasks that keep the CEO up at night - difficult problems with no apparent solution. Below them in the ( + , - ) quadrant are tasks that everyone knows are a pain in the ass. They’re difficult, but at least they’ve been done before. The upper left ( - , + ) contains tasks that are straightforward, but haven’t yet been attempted. And the ( - , - ) quadrant is grunt work.

A new employee who’s not a strategic hire is tackling jobs in the ( - , - ) quadrant. They’re easily explained by the core team and not very difficult to complete. The newbie feels pretty good at their job.

But lining up tasks for the new guy to complete is yet another item for a busy entrepreneur to worry about. To be better than good, a new employee needs to seek out a problem, hunt it down, and drag its skin back to camp. A fresh hire wants to get out of the bottom left and move, like the company itself, up and to the right.


It’s 2010. My summer internship at True Ventures has placed me with, pre-launch. I arrive at the ill-fated Pier 38 office to meet the team, and I receive my first task: assemble a list of the top 1,000 Twitter users, by followers, in case we need them later for promotional purposes.


I don’t know what I expected. I have no work experience, no coding skills, and no clue how a startup operates. I am, objectively, pretty useless. But I know I don’t want to be stuck doing work nobody cares about for the duration of my internship.

The web scraper is my first-ever python script (I had recently read the ‘import antigravity’ XKCD and wanted to try it). I’m completely ignorant of the word API and the libraries that should allow me to avoid the hours I will spend debugging. The next, day, I report back with a .csv of one thousand Twitter celebrities.

You’re done already? That was the job we had for you this week.

We sit down and think about the set of problems that actually need solving, and the set of tasks that my fledgling skills allow me to complete, and try to figure out where they intersect. By the end of the day I’ve got a new assignment for the summer. Product quality will be ensured - and our developers’ lives made easier - by a set of test suites covering every possible use case on every page of the site. I just have to learn how to build it.

And that’s excellent, even though I have no idea how to build tests. I’ve unwittingly made my first step up and to the right in a new environment. I could be spending my summer excelling at Twitter lists, but in the end I wouldn’t learn anything and I wouldn’t contribute anything. I’ll end up learning more in the next two months than I have in the previous two years.


What are some tough jobs that everybody knows how to do, but nobody likes to do? Maybe they’re difficult, maybe they’re just obnoxious. Do them. What quick and easy fixes can you bring for problems your boss hasn’t even noticed? Implement them. These are the paths to getting the really juicy stuff - the land of opportunity in the upper-right quadrant. And that’s where you really add value as a startup employee.