A Beginner's Life

Hiring For The Role At Hand

5 min read

I’ve been participating in the hiring of new people for a little while now (~2.5 years), and each time I go through the process I learn a lot and try to improve at least a little. I started out god awful, and while I’m nowhere near expert-level, I hope our recent hires have had a better experience than when I started.

One of the hardest things for me about hiring is the longer feedback loop. It’s still too early and I’m still too close to the situation to know for sure if my current hypotheses are correct. So be sure to take all this with a grain of salt smiley.

I want to talk about one of the early lessons I learned (the tough way, of course).

We were looking for our first Customer Champion. It was late in 2012, and the search had been going for a long time. I was absolutely beat from reading resumes, fitting interviews into a schedule, and meeting candidates. I had interviewed several college kids, who were sweating through their wool suits and had no clue what they wanted to do. I had also interviewed a bunch of folks who had worked for 10+ years at a larger company and were wondering what our vacation policy was.

And then Tom applied (name changed, obvi). Tom was experienced, having worked at a previous startup. His resume was really strong. In his very first interview, we had a really great chat. We talked about the business, and his background, about what we wanted to do in the next five years. We talked about a lot of things at length, except what Customer Champions actually do, which we only talked about a little.

When I did bring up support, I found myself making conciliatory statements. “Don’t worry, you won’t only be working in the inbox. You’ll be involved in discussions about the future of the company, you’ll be on video…” yadda yadda yadda.

I continued to ignore things that should have been clear signs. One of his references went so far as to say, “you know what you should do? Put Tom in a position of power as soon as you can.” Others had questions about him, but I just continued to ignore them. As far as I was concerned, Tom was the guy.

I was excited to make Tom an offer. Now that I’ve reflected on the situation, actually, I was excited to make an offer. Anyone. Tom was beyond qualified.

I told Tom I wanted him to join the team. He smiled, said “thanks”, and then asked me the pay and how much equity he’d be offered. When I told him the salary range, he balked. If this was my first salary negotiation, I wasn’t doing very well.

I locked myself in one of the small rooms in the office with Chris and Ben and we talked it over. At that point in the business, his salary was going to have a huge effect on the bottom line, and going higher was a real sticking point.

I think it was Ben who finally said, “are you sure he’s actual the right fit for the role we’re talking about?”

As usual, he was right.

This post is tough for me to publish – I’m not very comfortable talking about someone else publicly on here. Here’s what I want to make sure I make clear: I made a mistake. If Tom ever reads this and recognizes himself – I’m sorry I dragged you through that experience. I was the one that messed up and put you in a tough position, and to be honest, I think you acted like you should have.

I ended up letting Tom know he wasn’t the right fit. While his salary requests were what made us stop and pause, ultimately it was never the right fit. I’d been too excited to hire someone, instead of trying to find the right person.

Tom is a smart, experienced, and focused guy, and I’m sure wherever he is, he’s making a huge contribution. But he wasn’t the right guy for us at that time. He really liked our business and the people there, but he wasn’t right for the role we needed.


Here’s my takeaway: make damn well sure you are always hiring for the job at hand. Screen, interview, and make offers for the job you spec’d out – not the one you want to offer, or the one you think your candidate wants to hear about, or the one you think they’ll be mostly like to accept.

When I’m interviewing today, I want to be perfectly clear with the applicant what the role actually entails. If anything, I pitch the role very conservatively – I might even try to scare them away just a little. In the end, I’d rather set low expectations, and then blow them away with the fun experiences and learning opportunities that come with this gig, than try to promise them something besides the daily grind of support.

Yes, still look for exceptional people with a multitude of talents. Yes, think about development and growth plans for the folks you work with. But when you are evaluating multiple candidates, look for the right one for the current role. Not what that job might grow to include in the future, or what you’re thinking they want to hear.

Things ended up pretty good for us too, I’m thrilled and so lucky to work with the amazing Jordan, Mercer, and Max every day.

P.S. Every week, I send out a short newsletter with links to my favorite articles. When I write a new essay, that will be included as well. Sign up to get your copy.