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.

  • 440-page online book
  • 838+links and references
  • Digital access to this title in the Holloway Reader
  • Downloadable PDF for personal offline use
Length: 440 pages
Edition: e1.0.6
Last Updated: 2021-03-05
Language: English
ISBN (Holloway.com):
978-1-952120-06-0
ISBN (print):
978-1-952120-00-8
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)

Everyone should have access to expert knowledge.

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.

What People Are Saying

IneedmoretimeinmylifesoIcanreadallof@hollowayguides
avatar
Will Larson
Author of An Elegant Puzzle
“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.”
Lookingforwardtoreadthe“GuidetoTechnicalRecruitingandHiring”by@Holloway-ifitisasgoodastheothersonequitycompensationandraisingventurecapital,itshouldbeamazingandmuchneededhttp://sco.lt/7OLcP2
IcouldreadonlineforeverifitwereUX’dlike@holloway.
avatar
Tammy Han
Head of Talent at Emergence Capital
“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.”
Oneofmyfavoritesonthetopicis@holloway’sdigitalbook“TechnicalRecruitingandHiring”.Reallyhigh-qualitycontent!
Holyhell.HowamIJUSTstumblingacross@hollowayrightnow?ThisiswhatcuratedexpertpapersshouldbeforEVERYTHING.
CanwegetyourteamtoreformattheentirewebintothispleasantUXexperienceplease?:)
avatar
Adam Jacob
Co-Founder of Chef
“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.”
IamashamedtoadmitthatIonlylearnedabout@hollowaythisweek.HOWISTHISPOSSIBLE?Theirmaterialis✨fantastic✨BoughtseveralbooksalreadyandsharedafewexcerptswithcolleaguesfromtheGuidetoTechnicalRecruitingandHiring
Reallyenjoyinghowwell-writtenandinformativethe@hollowayguidesare.Finishedthe“GuidetoTechnicalRecruitingandHiring”and“EquityCompensation”andIcantotallyrecommendthem.

Table of Contents

Part I
Foundations
Do You Need to Hire?
Principles
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
Compensation
Hiring Plans
Job Descriptions
Part IV
Connecting With Candidates
How To Read a Resume
Candidate Sources
First Conversations
Part V
Interviewing
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
Appendices
Appendix B: Communicating Your Brand
Appendix C: D&I Reading List
Appendix D: Tools and Products
Disclaimer
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)

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)
Production
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

Get lifetime access now.

The full book, interactive and searchable. Plus a download that’s yours to keep.
Instant lifetime access$75
  • The 440+ page Guide
  • Curated commentary from experts
  • Ongoing updates to the content
  • PDF copy for offline reading that’s yours to keep
  • Access to advanced search, bookmarking, and other features on the Holloway Reader

Read with Holloway.

More than words on a page.

We believe the reading experience for book-length resources can go beyond paper or e-books. Reading on Holloway means a distraction-free, interactive format to help you find what you need, when you need it, in your browser. Digital access to a Guide also means access to ongoing new content, curated commentary from experts and readers, and features like search and bookmarks.

Screenshot of the guide on phone and laptop

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).

Find what you want, when you need it

Screenshot of the search window

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

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)

Why pay for an online book?

At Holloway, we imagine a place on the web where depth, quality, and high-value writing are the norm. A place where experts’ ideas are accessible to anyone. Where thoughtful, inclusive, and well-written resources win over quick takes, self-promoting blog posts, and content marketing.

We believe you, the reader, know the difference. It’s 2021. You recognize sites riddled with ads and clickbait headlines. Deep and comprehensive resources take expertise, time, and money to build. By buying access to this title, 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. Holloway is a new and powerful way to publish. We hope you’ll join us on the journey.

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.

Learn more.

Enter your email for more details, updates from the authors, and free samples from the book.

Frequently Asked Questions

  • What exactly am I buying?

    Every title sold on Holloway.com is a one-time purchase for full digital access. That means you get lifetime access online for that title on the web, using the Holloway Reader. That also includes future updates from the author or editors. Finally, you get a PDF download for offline use.

  • What is the Holloway Reader?

    The Holloway Reader lets you read and engage with books bought on Holloway. It is the most advanced reading experience for books on the web—you use it right in your browser, on desktop or mobile. In contrast to ebooks and paper books, online content in the Holloway Reader is always up to date, including updates when changes to the content are made, like responses to reader questions, new data, or new developments. It includes expert commentary in the margins and offers bookmarks and highlights, instant definitions of technical terms from a glossary, instant previews of links and footnotes, and a powerful search capability only available on Holloway titles—and we have a lot more on the way.

  • Do you sell print books?

    For a few titles, yes, you can buy paperback editions directly on Amazon. We believe the web is the most flexible interface for reading—but we know it won’t replace the satisfaction or practicality of print for some people. Current paperback titles include Art for Money: Up Your Freelance Game and Get Paid What You’re Worth, Ask Me This Instead, The Holloway Guide to Technical Recruiting and Hiring, and Angel Investing: Start to Finish and more are on the way. (Stay on our mailing list to get notified when new ones are out!)

  • Can I get a Holloway title as a download?

    Yes. A majority of our readers take advantage of the Holloway Reader because of its power and convenience, but you have other options as well. If you buy a title, you get a PDF that you can download and keep to use on any of your own devices—or even print it if that’s your thing. If you care about design, you’ll be pleased that it’s formatted using the same quality of typography you’ll find in books. (Just please don’t share or republish downloads.*)

  • Do I have to be online to read?

    To access the Holloway Reader, you need a connected browser. It works for desktop and mobile (iOS and Android) browsers. If you’ll be offline to read, you can save and use the PDF download on your device or laptop. PDFs also work on Kindle.

  • Are there any discounts?

    Before a book is released, it may be available for pre-order. By pre-ordering a title, you’re supporting us and our authors in their work. Pre-ordering also gets you early access to authors, a discount, and other perks. We also offer student discounts to individuals with a valid .edu email address.* And stay on our mailing list! We send updates about our titles, as well as seasonal discounts and other special deals.

  • I have more questions!

    Don’t we all. We’d love to hear from you at hello@holloway.com.

HollowayTechnical Recruiting and Hiring
Instant lifetime access$75

The Holloway Startup Bundle

Five essential guides for early-stage startups

✨New!✨ Unparalleled resources for startup teams and founders that bring you instant, lifetime access to decades of experience. Now available as a digital bundle at a special price.

Other Titles

Readers of this book also purchased these titles

Holloway
Equity Compensation
by Joshua LevyJoe Wallin
$25
Stock options, RSUs, job offers, and taxes—a detailed reference, including hundreds of resources, explained from the ground up, for both employees and managers.
Holloway
Remote Work
by Katie WildeJuan Pablo Buriticá
$35
A comprehensive guide to building, managing, and working with distributed teams.
Founding Sales
by Pete Kazanjy
$40
A detailed and tactical guide to accelerate learning and success on the early-stage sales journey, from founder to early salesperson to sales leadership. Written by a sales expert for startup founders and first-time sales staff.
Keep in touch.
We’ll send early announcements of new books from Holloway, free excerpts, and offers available only on our email list.