This is part of the SaaS series. Any connection to reality will be strictly denied.
I started in Windows Azure in 2007. Back then, the name “Azure” wasn't invented, and Azure was still called “Reddog.” I started on the OS team, drawn in by my dream of changing the world, and getting to be Dave Cutler's lackey. I didn't get to work with Cutler, but I still may change the world - now that I’ve learned it’s OK to wake sleeping giants. My giant was named Jay.
See, when you join a team at Microsoft, you're assigned a mentor and I was assigned Jay. Jay is a technical wiz. He knows nine flavors of assembly, and has every machine type back to the PDP-11. Jay's also a little odd.
For example, my first day on the team, I wanted to make a good impression, so I sent a mail to the team calling out something clever with the intention of impressing. Four hours later, Jay replied with a 22-page analysis. I started reading, but by page two, I was sweating bullets and scared. Luckily, as I was starting the third page, a new mail arrived. It was another member of the OS team replying with a translation: "Jay means – Yes, good thinking."
Another interesting thing about Jay was he kept a sleeping bag at work and often slept under his desk. I was intimidated by Jay's technical brilliance, so I decided to ask Colin, a fast-tracked junior executive, what to make of Jay sleeping under his desk. Specifically, could I wake Jay up and ask him questions? After all, Jay was MY mentor.
"Dude, imagine if you were sleeping at home, would you want to be woken up? Of course not, let Jay sleep!" – Colin scolded. Armed with Colin's advice, I let Jay sleep in peace.
Several weeks later, I was 12 consecutive hours into fixing a tough bug and needing a break. I grabbed an IPA and decided to shoot the shit with Jay, who was wide awake with me at 2 a.m. We talked for a while about cloud computing and esoteric coding convention when Jay paused a few moments longer than usual. He tried to start his sentence a couple times, but was unable to find the right words or the right tone. Eventually, he looked down at the label he had been peeling off of his beer and in a more withdrawn tone than usual, began to answer the question I should have asked HIM directly weeks ago.
"Hey, I take my mentorship responsibilities very seriously, and I noticed you've never woken me up. You know if I wasn't your mentor, I'd be at home sleeping in my comfortable bed."
I guess the only thing worse than waking your mentor up night after night is letting them sleep under their desk in untapped anticipation.