Why We Did It: Creating the Guide to Technical Recruiting and Hiring

Hear from the lead author and senior editor on what makes the latest Holloway Guide special.
Ozzie Osman (Monarch Money)
Rachel Jepsen (Holloway)
▪︎ 8 minutes read time

Photo by Natalie Pedigo on Unsplash

In this post, the lead author and senior editor of the Holloway Guide to Technical Recruiting and Hiring share their thoughts on what it was like to work on the Guide, why they wanted to build this resource, and what they learned. The comprehensive Guide assembles the work of over 40 contributors and insights from dozens of interviews with experts.

I want every employee at my company and every company I’ve ever invested in or advised to read this Guide. It’ll make every one of them better interviewers, better recruiters, better co-workers, and better members of our startup ecosystem. I’ve never seen a Guide on technical recruiting that is as comprehensive or practical as this one.Ankit Jain (CEO, Infinitus Systems, former Founding Partner, Google’s Gradient Ventures)

Note from the Author

Hiring has been the most important part of almost every job I’ve had. When it’s gone poorly for me, it has usually been a sign that something was very wrong. In some cases, my heart wasn’t in my work, and I struggled to get people excited about joining my team. At other times, I’d fallen victim to Silicon Valley-style “grow-at-all-costs” mentality, not realizing how painful the costs of hiring too quickly could be. I would watch companies that were really successful at hiring with admiration and envy, and wonder what I could learn from them. When I did something well in the hiring process, the outcomes were amazing. I wanted to get better. And I did get better over time, through experience and my own mistakes and failures. This Guide was the opportunity to make sure others don’t have to struggle for years like I did to understand what makes a good hiring process work.

This Guide was also an opportunity for me to learn even more, to share experiences and debate ideas with some of the most talented engineers and managers out there. While best practices differ company to company and stage to stage, a pattern pretty quickly emerged as I began having these conversations: the people and companies most successful at hiring were thoughtful about every step of their process, and looked at the process holistically. They did not focus solely on assessing candidates via hazing-style interviews. Nor did they swing the other way by desperately trying to sell candidates on why joining their team was the opportunity of a lifetime, regardless of whether the candidate was right for the opportunity. Instead, the most successful recruiters, hiring managers, and interviewers never lose sight of the fact that good hiring is about finding a two-sided fit. And we’ve done our best to show everyone involved in hiring how to do exactly that.

This Guide wouldn’t have been possible without the help of over forty contributors who agreed to share stories, learnings, and ideas, nor without the Holloway team. Rachel: thank you for your editorial guidance, and for helping me (and the rest of the contributing team) find our voice and express our ideas. Josh: for giving me this opportunity and helping me overcome my impostor syndrome. Courtney: for pushing me and the team forward anytime we seemed stuck or distracted. Aditya: for the initial inspiration for this Guide, and for providing the initial seeds and direction for many of the ideas we cover. And finally, for my lovely wife Dina, for showing me, in practice, the harmony of finding two-sided fit.

Ozzie Osman is Co-Founder and Head of Engineering at Monarch Money. Ozzie successfully sold his last startup to Quora, where he was later Head of Product Engineering. He is a former tech lead at Google, and a graduate of both MIT and Harvard. He is the lead author of the Holloway Guide to Technical Recruiting and Hiring.

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Note from the Editor

We have optimized hiring to death. All the metrics, tests, and numbers we’ve thrown at the hiring process haven’t helped companies make good decisions consistently, and certainly haven’t helped candidates succeed in the process or in the roles they eventually take. These things can be helpful—we all want a fast, efficient process—but they are not a replacement for being human.

As I got started researching for this Guide, I had trouble with the question of whether that optimization obsession was somehow worse in software. I didn’t believe it, or rather, I tried hard to fight against the stereotype that engineers only cared about optimizing whatever was in front of them. But early on I was told repeatedly by hiring managers, recruiters, and interviewers that engineering candidates did face unique challenges when trying to join companies. They were judged on resume factors that didn’t reflect their abilities, had to tackle assessments that didn’t translate to the skills needed on the job, they were ghosted by companies and recruiters, and subject to interview formats that privileged specific groups. All of this in service of processes that replicate those of large companies with powerful brands, and move as quickly as possible. There’s a lot of conversation and writing these days about how tech hasn’t met its own expectations, that we’re breaking some of our promises about making the world a better place for everyone. Bringing the human back to tech starts with bringing the human back to technical hiring.

So that’s what we focused on with this Guide, ensuring that hiring be recognized as a human process, and as difficult to successfully navigate as any human relationship can be. That recognition is the only way to help push against the outcome that the process be dependent on any one person’s biases, weaknesses, or circumstantial fallibility. The goal of this Guide is to give humans the tools to run a fair, efficient process. Treating people with respect doesn’t have to come at the expense of efficiency, and in fact, focusing only on metrics that optimize how quickly people can be moved through the pipeline can drastically hurt hiring teams and companies, not to mention candidates. The Guide demonstrates how a candidate-focused hiring process can serve companies better than a process that devalues candidate’ experience. What Ozzie and our contributors have done is prioritize the human and make it possible for anyone to get better at this extremely difficult thing, so long as they participate in a way that demonstrates respect for everyone else involved.

I am extremely proud to have helped make this Holloway Guide possible. I’m grateful for the help of all of our contributors, and our lead author, Ozzie Osman, who was the first engineer I’ve known to teach me that being better usually just means being good—that doing better means doing good.

Rachel Jepsen is Senior Editor at Holloway. She has worked with nonfiction writers from many different fields, as well as poets, essayists, and, in her spare time, dogs and musicians. She lives in Iowa.

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