One Audacious Request Per Week — Asking for what you want in Software Engineering

Recently I arrived at my gate three hours early for my flight to Toronto. Interestingly enough, an earlier flight to Toronto was on final boarding at the very same gate. After about 2 minutes of pondering, I decided to make my audacious request of the week; ask if it would be possible to get on the earlier flight.

In my career and everyday life I try to strive to make one audacious request per week. Of course, there are weeks where I make many more, and weeks where I don’t make any at all — but the one-a-week is a good reminder for me to take more risks, and speak up for what I want.

Speaking to the gate agents, I learned that even though the earlier flight had some free seats, there was a fee equal to almost half the cost of the ticket. Having spent enough money in San Francisco, I thanked the agents for their time, and asked for recommendations to their favourite places to eat in the airport. Not more than 30 seconds after walking away from the desk, another agent chased me down and let me know Air Canada would put me on the flight and waive the fee. Delighted, I grabbed by bags, boarded the plane, and started writing this very post.

While a lot of this was luck, politeness, and being in the right place at the right time, there is a moral to this story. Audacious requests won’t happen by themselves — they need to be acted upon. In these situations I remind myself the worst someone can say to my request is “no” (which happens quite often).

A good manager is there to help you grow your career, gain new experience, and achieve your personal and professional goals — but they’re not mind readers. A software engineering manager won’t know what you want unless you ask for it. Want those two weeks off to go to Burning Man? A desk by the window so you can stare at the ice cream truck across the street? Google Cloud Platform for your next project? Ask for it — the worst that can be said is no. When you get denied (which will happen) don’t let it dissuade you from making these requests in the future; signed by a guy who no longer has to take the redeye.