Holloway Guide ToTechnical Recruiting and Hiring

Align your team to avoid expensive hiring mistakes.

A practical, expert-reviewed Guide to growing software engineering teams effectively, written by and for hiring managers, recruiters, interviewers, and candidates.

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Talented people are your strongest asset and your biggest constraint for developing great products and solving challenging problems. This Guide covers everything from understanding the many possible motivations of candidates, to designing interview questions, to helping managers find the best possible fit and ensuring they develop positive, long-term relationships with all the candidates they meet.Aditya Agarwal(former CTO, Dropbox)
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Hiring software engineering talent is a struggle for most companies. The ever-growing demand for software in almost every business leads to extensive searches for the right candidates. Hiring is rated as one of the biggest obstacles to growth by most CEOs. Hiring managers, recruiters, and interviewers all wrestle with how to source candidates, interview fairly and effectively, and ultimately motivate the right candidates to accept offers. The whole process is often costly and frustrating for companies, and all too often stressful or unfair to candidates navigating this high-stakes process.

Anyone who cares about building effective software teams should benefit from the experiences and knowledge of those who have tackled similar challenges, and avoid repeating common and costly mistakes. In this Guide, we’ve assembled know-how from some of the most insightful and experienced leaders and practitioners—senior engineers, recruiters, entrepreneurs, and hiring managers—who’ve built teams from early-stage startups to thousand-person engineering organizations. The lead author of this Guide, Ozzie Osman, previously led product engineering at Quora and teams at Google, and built (and sold) his own startup. Additional contributors include Aditya Agarwal, former CTO of Dropbox; Jennifer Kim, former head of diversity at Lever; veteran recruiters and startup founders Jose Guardado and Aline Lerner; and over a dozen others.

We believe recruiting and hiring can be done well, in a way that has a positive impact on companies, employees, and every candidate. With the right foundations and practice, teams and candidates can approach a stressful and difficult process with knowledge and confidence.

Does this sound like you?

  • We’ve been looking to fill certain roles for ages and can’t find the right engineers, or lose them to other more prominent companies.
  • I’m a new manager and wish I had more support or guidance on building the team.
  • I’m an engineer, not a manager, but I’ve seen bad hiring decisions and care a lot about how hiring is done on my team.
  • How can I and my team level up as interviewers?
  • How can we hire a more diverse team?
  • I can’t connect with the people I most want to hire.

Table of Contents

Read a sample section

Part I
Do You Need to Hire?
Cast of Characters
Overview of the Hiring Funnel
Part II
Diversity and Inclusion
What Is D&I?
D&I in Hiring
D&I Myths and Pitfalls
Improving D&I in the Hiring Process
Part III
Internal Alignment
Defining Roles
Setting Levels and Titles
Hiring Plans
Job Descriptions
Part IV
Connecting With Candidates
How To Read a Resume
Candidate Sources
First Conversations
Part V
Preparing Interviewers
Technical Interview Formats
Technical Interview Questions
Nontechnical Interviewing
Best Practices for Interviewers
Evaluating Interviews
Legal Considerations for Interviewers
Part VI
After the Interviews
Making a Decision
Extending an Offer
Appendix B: Communicating Your Brand
Appendix C: D&I Reading List
Appendix D: Tools and Products
Without a doubt, this Guide is the best resource I’ve read on technical hiring, by a substantial margin.Kellan Elliott-McCrea(formerly Blink Health, Etsy)

Researched, written, and edited by experts.

Written by practitioners. Edited by professionals.

Original Author
Osman (Ozzie) Osman (Monarch Money, formerly Quora and Google)
Contributing Authors
Aditya Agarwal (formerly CTO, Dropbox)
Alex Allain (Dropbox)
Jose Guardado (Alpha Talent)
Jennifer Kim (Inclusion at Work, formerly Lever)
Aline Lerner (Interviewing.io)
Joshua Levy (Holloway)
Viraj Mody (Convoy)
Kevin Morrill (formerly Mattermark)
Jason Wong (JWong Works)
Scott Woody (formerly Dropbox)
Contribution and Review
Laurie Barth (Gatsby)
Juan Pablo Buriticá (Splice)
Joe Cheung (Craft Ventures)
David Connors (Sequoia Capital)
Ryn Daniels (HashiCorp)
Tammy Han (Emergence Capital)
Robert Hatta (Drive Capital)
Zack Isaacson (Sweat Equity Ventures)
Kellan Elliott-McCrea (Dropbox)
Pradeep Muthukrishnan (TrustedFor)
Benjamin Reitzammer (Freelance CTO)
Aaron Saray (More Better Faster)
Dave Story (Next Level Leadership)
James Turnbull (Glitch)
Jon Volk (Unusual VC)
Sam Wholley (Riviera Partners)
Haley AndersonResearch, definitions
Jennifer DurrantDesign
Rachel JepsenEditor
Joshua LevyEditor, design
Sakhi MacmillanProofreader
Courtney NashEditor
J. Marlow SchmauderCopyeditor
Nick StoverGraphics
Titus WormerPrint engineering
And 13 more

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Over 130 definitions of key terms

Definition A job requisition (or job requisition form) is an internal company document a manager uses to formally request permission to fill a role or position. These documents are particularly useful for coordination and wider alignment at larger companies. For instance, the requisition might require approval (often from finance, HR, and upper management) to ensure sufficient space and funding are available for a new hire. Once the requisition receives the necessary approvals, it can serve as the starting point for a discussion between the hiring manager and their designated recruiter (for instance, at a role intake meeting).

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Pitfalls and confusions highlighted

danger️️ Wording in your job description can have unintended consequences in determining who applies. Attempts to make your roles sound more enticing can actually discourage people from applying. Researchers have found evidence that using gendered language contributes to an imbalanced pipeline of candidates; certain language can also discourage older candidates or candidates from marginalized communities from applying.

confusionPeople often confuse percentiles and percents, with serious consequences. When someone recommends compensating at the 75th percentile, they are talking about percentile rank, or paying at a rate that is greater than what 75% of companies pay for a role (in a given market, stage, et cetera). This is very different from paying 75% of what a fair market salary would be.

controversyThe “best” interview format for coding questions is a notoriously controversial topic. While many companies rely primarily on onsite, face-to-face coding interviews, a significant fraction of engineers consider “whiteboard coding” to be intimidating, stressful, and not predictive of job performance. On the other hand, alternatives like take-home tasks have drawbacks as well.

Visual presentations

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)

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We believe you, the reader, know the difference. It’s 2020. You recognize sites riddled with ads and clickbait headlines. Deep and comprehensive resources take expertise, time, and money to build. By buying access to a Guide, you’re supporting a place online that makes longform reading a pleasure—and allowing us to pay authors, contributors, engineers, and editors who build and improve them. We see Holloway as a new and powerful way to publish. We hope you’ll join us on the journey.


People are the lifeblood of your company, because without them, there is no company. This Guide is mandatory reading for anyone who is in a hiring manager or interviewing role and wants a practical, step-by-step playbook to set up technical recruiting and hiring processes for success. Holloway has curated actionable advice, resources, and battle-tested approaches from the best hiring managers and veteran recruiters in the tech community—honest advice you won't find anywhere else, that can be implemented by your team tomorrow.Tammy Han(Head of Talent at Emergence Capital)
As a candidate, sometimes recruiting processes can feel like they’re designed by someone trying to recount the series of incantations that summoned new hires at their previous organization. This Guide walks back the magic, building the foundation for an equitable, effective recruiting system that works for your candidates and your company.Will Larson (Author of An Elegant Puzzle)
The Holloway Guide to Technical Recruiting and Hiring is invaluable—it gives you the kind of insight and wisdom that is usually only found through hard earned experience, right at your fingertips. Save yourself, your company, and your future employees the trouble of learning it the hard way, and read this Guide instead.Adam Jacob(Co-Founder and former CTO, Chef)
Holloway Guide ToTechnical Recruiting and Hiring
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