The Hard Questions: thoughts after 3 years at Zumper

Justin Pollard
Jul 22, 2017 · 3 min read

This is a speech I delivered to my colleagues on July 21st, 2017, my 3-year anniversary at Zumper, Inc.

Wow! It’s been three years since I started at Zumper. A couple fun facts: 1) I’ve been employed here longer than any company before this (second place comes in at under two years), and 2) Zumper is the largest company I’ve ever worked for by almost two times. It’s astonishing to think that when I started here, the entire company was just 12 people: three founders and nine employees.

While it’s been three years since my first day at this job, it’s been three years, one month, and 19 days since my former company, another startup, gathered the last of its employees in a conference room and let us know it was all coming to an end. Recalling this fact has caused me to reflect on why I’m standing in this office today and not that cavernous, former wine cellar in the Mission District where I once worked.

I think there are a lot of answers to that question, all of which hold some truth: we had a rather inexperienced team, we didn’t have the funding that we needed, our technology didn’t meet expectations, we had tried to disrupt an industry protected by staunch barriers to entry. I’m sure my former colleagues could name dozens more.

Still, I see these issues more as symptoms of a systemic and important problem: as a group, we didn’t ask the hard questions. I’m wearing this shirt today to remind me of that (I was wearing my former company’s t-shirt). And I hope it will remind all of us that Zumper is still alive right now, because up until this point, we’ve done a relatively better job at asking hard questions.

Sometimes these questions are hard because discovering the answers to them is hard. Everyday, our growth team asks “How do we set our organization on the path to doubling traffic year-over-year?” Everyday, our backend engineers ask “How do we build our platform to scale elegantly and fail gracefully?” Everyday, our Select team asks “How do we develop processes that will enable us to achieve what now look like imposing lease goals?” Answering each of these questions, and those that the rest of us ask day in and day out, is crucial to building Zumper into the impactful and valuable company that we all hope it will become.

Beyond these job-related puzzles, though, is another category. These are the questions that are hard not because answering them is hard, but because we’re fearful of what the answers may be. These are the nagging inquiries that cause us to wake up in a cold sweat wondering if we’ve set the right course; the questions and decisions that try our integrity, test our morality, and strain our courage. They define who we are as individuals and define our culture as a company.

These questions are sometimes hard to pinpoint beforehand because most of the time they’re situational in nature. Still, you know when one’s been asked of you because you’ll think to yourself “What is the right thing to do?” And the difficulty often lies in that the right thing to do, the answer to that question, is much harder than simply not asking it in the first place. Don’t be mistaken, though; asking these questions of yourself, and of your colleagues, is paramount as Zumper grows from a startup into a company that makes a real impact on our industry.

So, as I embark on a new year at Zumper, I encourage all of you, whether CEO, team lead, or most importantly, individual contributor, to remind yourselves to ask the hard questions and to be prepared when hard questions are asked of you. Don’t cower at the challenge, but embrace the opportunity to lead. While the tests will only continue to get more challenging, it’s crucial to Zumper’s success that we continue to ask, and answer, the hard questions when called upon.

Justin Pollard

Written by

Interested in software experimentation and company building. Android @ Zumper.

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