How to Hire Like an HR Pro (When You’re Definitely Not One)

6 min read

Interview with Jonah Phillips, Founder & Owner of Crossword Hobbyist and My Word Search

Five years ago, Jonah was your ordinary analytics guy working at a small-to-mid sized tech company.

The company was doing pretty well and Jonah was doing pretty well. But something wasn’t quite right. “Things were good and bad. The environment was challenging and there were lots of smart people, but it was very competitive,” says Jonah. (How competitive? Like, Amazon competitive. Yeesh. 😬)

As an analytics and programmer guru, Jonah wanted to try his hand at making a crossword puzzle, but the software he needed to make it was painfully outdated. “I thought, ‘What the hell?’. I’ll make my own.”

jonah philips

Programmer gone rogue

One month later Jonah’s crossword-builder went live. “The goal was NY Times style puzzles but then we found out all these teachers were using it.” But it’s not just teachers who love Crossword Hobbyist and My Word Search.

Word puzzle lovers from all walks of life use Jonah’s tools to build their own crosswords and word searches, often to give away as super-personalized birthday or anniversary gifts, unique family reunion favors, corporate training games and more. Unlike the free puzzle-builders, Jonah’s tools let you customize your word puzzle as much as you want, without being bothered by endless ads.

We sat down with Jonah to figure out how he made the move from employee to entrepreneur and leader of a rockstar remote team. And exactly how in the world he manages to hire like a talent pro, despite having zero HR experience.

Tell us a little bit about your biggest hiring challenges and how Breezy helps you solve them.

Because I’m not an HR person, there’s a lot that I don’t know that Breezy knows for me.

When I was at the company I worked for years ago, I was part of the hiring team for analytics team hires. Looking back, I can see what we did well and what we did poorly. In terms of remote hiring, Breezy does it all.

For me, one of the biggest things is the sourcing. I just hired two remote programmers and the job post integrated so perfectly with We Work Remotely. I pressed a button and it was up and it looked great, plus we even got a $50 discount! When you’re new to hiring, it’s hard to know what the good job boards are. We want to be everywhere but which ones are really worth it?

Breezy makes this easy. You see a full list of all the free and paid job boards and can compare all your options right there. This is especially important with remote recruiting because it’s all online.

Were there any other big hiring headaches Breezy helped you out with?

The other big thing for me is all the amazing customization you can do on your applicant pipeline.

Instead of being bombarded by thousands of applications, when the applications come in they’re all in a nice concise list. If I want to decline a person who’s not a good fit, all I have to do is drop the application into the ‘Declined’ folder and Breezy tells me they’ll send the applicant a nice friendly email to let them know it didn’t work out this time. Breezy even time-delays the email by 4 hours so the person doesn’t think I’m just trashing them.

crossword hobbyist

And for the great candidates, I get a different drop down and I have it set up to send them my customized questionnaire to make sure they’re actually interested in the job, give them more info on what the job is and a bit about why I think they’re a great fit.

In a glance I can make a yes/no decision and give a fully customized response as if that applicant is the only applicant I looked at, when actually they were 200th applicant I looked at.

How much of your day is focused on creating an awesome candidate experience?

I just finished bringing on two developers so right now it’s 0%, but before it was 100%.

My tip for candidate experience is to always be aware that if whoever I’m evaluating passes the hiring process, I need to sell them on working for the company and make them excited to work with us so that they do a fantastic job.

I wanted the interview process to be very positive and collaborative. I know a lot of places like to make it an interrogation. They throw their candidates all these curveballs and it might result in a good hire, but in the end, will that person be excited to work there?

All of the people I’ve hired through Breezy were my first choice and they all accepted immediately when I called to make the offer. If I want to hire them, I want to be their first choice. That’s what it’s all about.

What are your favorite insider tricks and tips for engaging potential candidates?

One thing I do is track why the person wants the job from the initial screening so I can use that to sell them on the company at the end of the screening process. At my last company, it was HR who always did the initial screening to make sure the applicant could communicate ok. The HR person would ask the basic question, ‘Why are you interested in this job?’ just to make sure they really are interested.

The applicant’s always going to say something that indicates what they really want, whether that’s security, a new challenge, etc. There are a lot of reasons and they’re all valid. So just write it down.

my word search

I also think it’s important to explain the full interview process from the beginning. Don’t keep your second round skills test a secret. They’re gonna be uncomfortable about it and you don’t benefit from them being uncomfortable.

Moving them from one stage to the next is something that Breezy makes it easy to do. You can easily let them know you’re excited and make them feel good about the fact that they passed a skills test or hiring round. It’s nicer when you feel like you’re celebrating together as they go from point to point in the process.

How does Breezy help you hire better and faster?

I would be cutting a corner if I didn’t have Breezy.

In terms of the automated systems for managing who’s at what stage of the process, it’s incredibly helpful. Especially for remote teams when there’s no geographical limitation, because any human being in the world can go to the job board and apply. All the names kind of run together, so to be able to view them all in the pipeline all next to each other is huge.

I think it took me an hour, or maybe two the first time, to set up my pipeline for exactly how I wanted my hiring process to go and get my templates ready. After that, there was zero time spent on process. It was just about what makes the hiring process good, evaluating and connecting with people.

Do you have any personal passions or side projects most people might not know about?

I’m collaborating with a 97 year-old woman who lives in California and who I’ve never met before. We’re writing a puzzle book together!

I met her when I was still doing customer support and she reached out for help. She makes one puzzle per day to stay sharp. It takes a smart person 8 hours to make a puzzle the first time, and three to four hours after that. She has all these great grids but she doesn’t like the clues so I’m writing and editing the clues for her and we’re making a puzzle book that will hopefully come out this summer.

Want to see what Breezy can do for you? Try it for free today!


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