Technical Coach and Professional Interviewer

Technical Coach, Professional Interviewer

My first interviewing experience came in 2008 at a startup, 12 years into my career. It was a very casual experience at the time, because our startup was very casual. The next startup I joined had me conduct just a single interview.

The main interviewing experience of my career would happen in 2011 when I joined the team at SendGrid. My VP of Engineering’s first task for me was to build a team, that I would lead. I started screening hundreds of resumes, dozens of cover letters, and conducting phone screens. I was also remembering every interview I had ever attended as a candidate. What was good about them? What was bad about them? Would I want someone to sit through a similar process?

Conducting an interview which is a mirror copy of interviews you have attended as a candidate is usually a recipe for failure.

As a team, we started changing the internal rules about what interviewing meant. We developed ideas around conducting on-site interviews, and I argued my choices to my VP of Engineering. We would later refine our approach, add more people to the process, and build more strategies on how we would interview. In two years I had helped hire dozens of engineers, from interns to VP of Engineering candidates, in California, Colorado, and Romania. To hire dozens, you must interview many dozens. To interview many dozens you must phone screen many more dozens. To phone screen that many people you need to screen thousands of resumes and cover letters.

My next role was a Director of Engineering role, where I tripled the size of a small team. I left there to work at another startup where I helped hire several others.

At Turing, I conducted interviews for almost 400 students to prepare them to get jobs as software developers.

I’m also a paid, professional interviewer at in San Francisco where I have conducted several hundred more interviews.

Between 2011 and mid-2019, I estimate I’ve conducted over 2,000 in-person or remote technical interviews, and many hundreds of phone screens. I’ve also reviewed more than 10,000 resumes in that time, and have quite a few thoughts on how to build a great resume.

Also a prolific writer of interview topics

I write a lot of content at Quora about interviewing topics, anecdotes of my experiences, and bits of advice. Some of that text will appear in this book as well.

Early Technical Coaching

I used to run a weekly Monday night Google Hangout, open to anyone who wanted to attend, on technical interview processes and open Q&A. I discussed common preparation areas for being on the “candidate” side of a technical interview. The content took 60-90 minutes to review, and decided to start writing it down in a Google Document and added a lot more notes for those who have attended the Hangout the past, others who were unable to attend due to the day/time I conducted the class, and for people to whom a spoken class is otherwise inaccessible to them in some way.