Hiring Opportunistically

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Updated August 24, 2022
Technical Recruiting and Hiring

You’re reading an excerpt of The Holloway Guide to Technical Recruiting and Hiring, a book by Osman (Ozzie) Osman and over 45 other contributors. It is the most authoritative resource on growing software engineering teams effectively, written by and for hiring managers, recruiters, interviewers, and candidates. Purchase the book to support the author and the ad-free Holloway reading experience. You get instant digital access, over 800 links and references, commentary and future updates, and a high-quality PDF download.

I always have a role for talented people.Mark Suster, Managing Partner, Upfront Ventures*

Say you come across a fantastic candidate, but they just don’t fit into any of the open roles you have right now. Should you try to hire them? Exceptional talent is rare; exceptional talent that is attracted to your company is even scarcer; exceptional talent that is attracted to your company and at a serendipitous moment where they would make a move requires the stars to all align. Can you miss that opportunity?

Stripe CTO Greg Brockman had a philosophy of hiring for people, not roles. He suggests that “If you can think of one thing this person can do, then there’s probably ten more you’re not thinking of that he/she can do two months from now.”*

I encourage entrepreneurs and CEOs to create positions for strong candidates—even if that position doesn’t exist.Vinod Khosla, founder, Khosla Ventures*

On the other hand, adding people to a team has immediate cost and overhead. Hiring someone talented and driven without a clear role can result in a frustrating experience for you and for them if things don’t work out. For instance, they might feel underutilized and underchallenged. In an interview with forEntrepreneurs, Jordan Burton notes that turnover increases when companies try too hard to fit a role to a candidate, especially if that means they end up joining without a specific mandate.


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