The Holloway Guide to Technical Recruiting and Hiring

Courtney Nash
▪︎ 6 minutes read time

Talented people are your strongest asset and your biggest constraint for developing great products and solving challenging problems. The costs of hiring poorly, or too slowly, can be enormous for both companies and candidates. Everything from company branding to designing interview questions to understanding the many possible motivations of candidates will help managers find the best possible fit, and ensure they develop positive, long-term relationships with all the candidates they meet.Aditya Agarwal, investor and former CTO of Dropbox

We’ve all either heard it, or said it while swearing under our breath: “Hiring is broken.” Recruiting and hiring software engineers is a significant part of nearly every technical team’s daily work, and is an enduring responsibility for engineering managers. Nearly every company now has to figure out, often by trial and error, how to source, interview, and hire technical talent. Engineers interviewing at those companies don’t have it any easier, as they get caught in opaque and sometimes highly imperfect hiring processes.

So we decided to make ourselves useful. Today, we’re pleased to announce our third Guide, the Holloway Guide to Technical Recruiting and Hiring.

The costs of recruiting—emotional, temporal, and financial—can be immense and overwhelming. The stakes are high for candidates and for companies. It’s informally taught, difficult and painful to execute well, and filled with numerous pitfalls. The status quo perpetuates an endless cycle of new managers and their teams repeating their peers’ mistakes. Searching Google, they get their on-the-job training from blog posts, Glassdoor, Blind, HackerNews, and Reddit, hoping the advice they choose is the advice that will work.

That advice often focuses on narrow components of recruiting and hiring—such as interviewing, or closing a candidate—and is typically written by a single author, reflecting only their perspective. It’s entirely possible to take the singular opinion of a respected person and put it into practice only to discover it was incomplete, inaccurate, or doesn’t work for your organization’s size or your team’s specific needs.

It’s your responsibility to move beyond reciting popular opinions, and put the time in to understand hiring as a system. Even if you work with a team of sourcers and recruiters, anyone in charge of hiring still needs to know the details and how they fit together in context to make good decisions. We’ve built this Guide to get you there much sooner than the collective decades it took everyone writing it to figure these things out. That’s time, money, and pain saved for you and your team, so you don’t need to reinvent the wheel.

At Holloway, we believe everyone should be able to learn from people who have been in the hiring trenches and figured out how to do it better. This Guide began as a series of conversations between Ozzie Osman (former head of Product Engineering at Quora), Aditya Agarwal (former CTO at Dropbox and early member of Facebook’s engineering team), and Josh Levy (co-founder of Holloway, who brings more than 10 years of experience building and scaling engineering teams at startups).

From there, we sought out contradictory opinions and differing perspectives from engineering leaders and recruiters from leading companies like Y Combinator, Lyft,, Microsoft, Netflix, Twitter, Facebook, Slack, and more. This Guide gives readers the opportunity to learn from more than 25 of the best minds in technical recruiting and hiring, who together have made thousands of hires and conducted countless more interviews.

Hiring has been the hardest part of every single job I’ve had as an engineering leader. I wanted to write this Guide because I think we all can and should get better at hiring. It’s not the zero-sum game many think it is—if every company in the world suddenly gets better at hiring, the industry would be a better place for both companies and candidates.Ozzie Osman, lead author

At Holloway, our mission is to consolidate the practical wisdom of experts for all to learn from and build upon. Our Guides will help you orient yourself in a complex landscape. We’ll help you solve specific problems, and you’ll avoid looking silly for not knowing some industry jargon. You’ll get a leg up from the experience of other dedicated learners who happened to show up a few years or decades before you. You shouldn’t have to climb the same mountain they did—their knowledge should be your foundation.

We create every Guide by corralling experienced and proven experts—the best, most knowledgeable folks we can find on a topic—along with professional editors, and the feedback of those actively engaged in navigating these challenges in the wild. We pour over sources (articles, books, papers, interviews, and more), reconcile differing opinions, showcase disagreements, integrate feedback, and publish with the goal of updating the work over time. And we know you’re busy, so we’ve made sure to break each one down into sections you can read over your lunch break or in between putting the kids to bed and passing out.

Access to this Guide (along with updates) will be available for purchase starting this summer. If you’re interested in reading drafts, giving feedback, or being the first to know when the Guide is available, make sure to get on the waitlist.

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