The anecdote I always share about my 2013 internship at Square involves Bob. It took place during the quarterly Hack Week, when the company allowed everyone to take a break from work and build whatever they liked. Cash App (known as "Square Cash" back then) had just been launched, and the only way to send money was by emailing someone with a dollar amount in the subject line and cc'ing cash@square.com. My fellow interns and I decided to expand this email functionality by building a "pay by Tweet" feature with essentially the same mechanics (https://twitter.com/hackweek9bot).
We downloaded the codebase (I believe it was called "Franklin") and found ourselves struggling to get it up and running. I entered the room where the Cash team was seated and started asking a random guy questions about the dependency injection library (Guice) and various other topics. After about half an hour of answering my questions, he compiled a list of documentation for me to read and sent it to me via email. I returned to my Hack Week team and forwarded the email to them. "Oh, dude, that's our CTO," one of my teammates informed me. At that moment, I was convinced I would be in trouble for bothering an executive. However, instead of that, I ended up receiving a fist bump during our science fair-style project presentation. He was a genuinely cool guy.
Guice was one of my first "aha" moments at Google about how modern Java could be written without a million XML files. I later took Guice to multiple other companies and projects back when I used to sling Java code for a living.
It seems like such a small thing, but it had a huge influence on my career right out of college.
> At that moment, I was convinced I would be in trouble for bothering an executive. However, instead of that, I ended up receiving a fist bump during our science fair-style project presentation.
I suspect many CTOs long for this kind of work. But their time is usually taken up with administrative duties.
I've never found anyone who was punished for asking questions / raising concerns about org problems to leadership.
Most of the times the leadership is clueless about the problems in their orgs because nobody wants to tell them any real problem.
They appreciate that you share your pain points with them even without solutions.
Of course, you should share the pain points in a polite manner where you talk about your perspective only without speculation on other people's intents. But you should do that any way regardless of who the listener is.
Bob interviewed me, and taught me to be a good interviewer. I don't know if other folks remember him for this, but he taught half the company how to interview. This skill proved very helpful in the rest of my career.
We downloaded the codebase (I believe it was called "Franklin") and found ourselves struggling to get it up and running. I entered the room where the Cash team was seated and started asking a random guy questions about the dependency injection library (Guice) and various other topics. After about half an hour of answering my questions, he compiled a list of documentation for me to read and sent it to me via email. I returned to my Hack Week team and forwarded the email to them. "Oh, dude, that's our CTO," one of my teammates informed me. At that moment, I was convinced I would be in trouble for bothering an executive. However, instead of that, I ended up receiving a fist bump during our science fair-style project presentation. He was a genuinely cool guy.