Interview with Allen Cheung, Senior Director of Engineering at Affirm

Location: San Francisco Bay Area
Current Role: Senior Director of Engineering at Affirm

What’s your background and how did you get into management?

Before I became a manager, I was a software engineer for about 8–9 years in Silicon Valley. I had a BA of Computer Science from Cal, worked for a number of mid-sized companies and startups, and eventually, during my 4-year stint at Square, eased into a management role after acting as my team’s tech lead for over a year. I’ve since taken on management roles at 2 more startups, and find myself enjoying the challenge and the impact that a manager has within their organization. I’m currently a Senior Director of Engineering at Affirm.

What are the biggest challenges you face?

I think that for a lot of managers, hiring good software engineers remains a huge challenge. It’s a competitive market for engineers, and both the recruiting and interview processes are imperfect at best. I do what I can to get people excited about our opportunities.

Other than that, I’d say that the next biggest challenge is good communications both within and across teams. It’s a prerequisite to further collaboration and teamwork, and most engineers either under-appreciate its importance or understand it well enough but don’t do a good job regardless.

What is your approach to hiring?

I like to hire what I term to be “intellectually curious” candidates. As I mentioned above, the hiring process is itself imperfect and tends to create a lot of false positive and negative signals, but what I look for are signals that a candidate is hungry for more knowledge, that they can think fast on their feet and adapt to uncertain/unknown situations. Whether they’re still in school or have 20+ years of experience, I’ve found that people who are always curious about new things and *also* apply their past knowledge to these new areas are the ones that perform excellently and I can rely on to tackle tough problems.

What’s your advice for managers who are just starting out?

One piece of advice given to me when I first started: “Stop coding.” The idea is not only to try to avoid being both an IC and a manager (and most people, even after hearing this advice, will try to do both anyway), but to also force yourself to exercise/learn the management skillset without falling back into familiar IC territory. If you follow the spirit of this advice, you’ll work hard to stop using coding as a crutch for tough deadlines and decisions.

Whats your work day like and how do you manage your time, emails, etc.?

My workday nowadays is fully on the manager’s schedule, with plenty of meetings and a bucket list of emails to process on any given day.

To make the schedule work, I try to be rigorous about the meetings that I attend vs. opt out of attending, and provide enough time for the important 1:1s I have on a weekly/biweekly basis. I block out time when I can to have some quiet alone time, but admittedly it’s hard; schedules have a tendency to fill up whatever gaps I leave open. Again, since I find 1:1s high bandwidth, I tend to bias myself towards making time for those, sometimes at the expense of other team and group meetings.

For email, I’ve adapted Inbox Zero for some time now, and that + power Gmail usage has kept my email under control for years. I rarely miss an email, I tend to read most of the important mail sent to mailing lists or my inbox, and I get to respond to important emails in a timely manner. I’d be curious to see if this scales to even higher levels of management and more communication channels.

What’s a personal habit that contributes to your success?

I’d say that one habit I’ve kept since college is to read a lot, and when I come across something that’s particularly resonant with me, I tend to copy it as a “best practice”. I’m not smart enough to come up with my own processes and philosophies and ways to work and be effective, but others are and they’re usually very happy to share their experiences and techniques. Over the years, having an open mind to read and understand that advice, and then selectively applying them to my own set of tools has provided direction and orientation to a rather fuzzy and usually inefficient area of my life.

Share an internet resource or tool that you can’t live without.

I’m going to cheat and provide two.

1. is my RSS reader. I use the Reeder iOS/macOS app, with the backend served by Feedly. As I mentioned above, I like reading and consuming good content, and I still like RSS feeds for that purpose.
2. is my todo list app, which is the Things iOS/macOS app. Specifically, it implements a version of Getting Things Done, a system that I’ve adapted (though I’ve picked and chosen which parts) a decade ago which really helps my head above water on daily tasks both for work and life.

If you could recommend one book to managers, what would it be and why?

It’s a somewhat boring choice, but I’d say that High Output Management is a singular book worth reading. Not only does it provide some tactics on how to be an effective manager, it’s one of the rare management books that will explain strategies, philosophies and guiding principles, coming from someone who has been executing at the highest levels of one of the most important companies in the world (at that time). It’s a classic for a reason: lots of people have found the advice useful across its decades of publication, which should indicate both the weight of its advice as well as its timelessness.

Where can we go to learn more about you? (LinkedIn, Twitter, GitHub, etc.)

You can find me on my blog at http://allenc.com, and Twitter at @allenmhc.

This series asks engineering managers to share their experiences with the intent of helping other engineering managers learn and improve. Have someone you want to see featured or questions you think we should ask? Contact me.