Personal History and Trajectory



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.

Considering how a candidate got to where they are gives insight into their abilities. Some people call this “grit,” or “distance traveled,” or “affirmative meritocracy.” Where did this person begin, and where are they now? Have they come further than one might expect? Are there signs they have overcome significant obstacles in life through hard work or creativity? Candidates with a less advantaged background may have had to work very hard to get to the same position another candidate attained more easily. A job at an elite tech company is much easier to land after a Stanford CS degree than for someone from a small community college far from any technology hubs.

story Many years ago, when I was working as a software engineer at a small company, one of the existing engineers referred a close friend of his from high school. Though they had taken many of the same classes and spent a good amount of time building projects together, their paths diverged pretty wildly after graduation. The employee graduated from a top 10 computer science school. His friend, on the other hand, attended a much lower-tier college for a semester before dropping out, and at the time of the referral, he was doing data entry. When we first looked at the referral’s resume, we had no idea what to do with it, and most people on the team wanted to pass on him. But, one thing on his resume stood out—he had spent several seasons teaching programming at a prestigious summer program for gifted high school students. This type of leadership and initiative were largely at odds with what we expected a candidate with his profile, and ultimately that’s what tipped us into hiring him. To this day (close to a decade later), he works at the aforementioned company, and has ownership over much of the application’s backend architecture. —Aline Lerner, co-founder and CEO,

How Did They Learn to Be a Programmer?

While rarely of use for filtering, how a candidate became a programmer can give a lot of insight into their personal journey and technical temperament. There are many ways to become a good engineer, but these backgrounds can cultivate different strengths and styles, and the story can help you get to know someone better. The most common paths to becoming a programmer are:

  • Self-taught at a young age (perhaps they started with an interest in building video games or taking apart and rebuilding computers)

  • Switched course mid-career to become a developer, perhaps going back to school or a coding bootcamp

  • A background in business or finance that led to a focus on programming

  • A role in IT or system administration that led to software engineering

  • Desire to build a product or business (often a young entrepreneur)

  • Formal college or graduate education (in computer science or computer engineering, math, or a field of science where computation was involved).

Strength in Other Domains

In addition to engineering skills, many other areas of drive and skill are relevant for technical roles. If an unusual combination of skills is relevant for the role, these kinds of signals are powerful and excellent for prioritizing resumes. By specifically looking for these signals, you can turn a tedious resume screening process into a huge value add by finding rare candidates with exceptional combinations of skills.

  • Entrepreneurial focus. Has this person started a business before? This can often be seen by project descriptions—does the candidate focus on technical concerns only, or do they include business impact? A purely technical engineering role doesn’t need a proclivity for entrepreneurship or an obsession with revenue, but senior roles or roles at smaller companies can greatly benefit from these qualities.

  • Growth or marketing focus. Does the candidate talk a lot about moving metrics? Are they focused on quantifiable impact? Have they had marketing-affiliated roles?

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