A few more thoughts about hiring

Last week I started hiring again for the first time in almost a year. It felt different this time because I’m now hiring for my own bootstrapped business. It was also different because I was the sole decision-maker.

Here’s a recap on how it went down and what I learned.


It’s been nearly seven months since I was able to officially go full-time on Toofr, my salestech app that finds email addresses for prospecting. In that time I turned the trajectory of the business around. Q1 of this year was on a negative slide and Q2 reversed it. I credit that to a fair bit of product development, more responsive support, and simply being out there, public, about my role with Toofr.

It was a liberating seven months, but I could feel the next plateau approaching. The rate of new customer acquisition was slowing. Churn was growing again. I lost some big, $1K+/mo customers. For a bootstrapped business, those losses are a blow to the gut.

I felt panicked and overwhelmed sometimes because when I thought about what I really needed to be doing (MARKETING TOOFR!) I’d hit a mental wall. I’d start another project. I’d write another Toofr feature. Anything but the one thing that would actually make a difference.

I talked to some people about this and they suggested that I hire someone. Sure, I figured. I should just make a hire. Have someone else do it. That’ll plug the hole.

I wrote up this job description and posted it on Craigslist, LinkedIn, Facebook, and Remoteok.io.

It was amazing. I got inundated with applications. People from all over the world introduced themselves and their work. Between when I posted and when I took it down I probably got 100 applications. I spoke to about 15 of them. I hired one.

And the one I hired was not the one I expected to hire. Here’s why.

Talking to knowledgeable strangers about my business is a terrific exercise

It took the better part of three days and was really distracting, but I enjoyed the phone calls. I looked forward to each one. I was excited to meet someone new, hear their interest in me and Toofr and my other projects. It felt good. I didn’t realize how hungry I was for a teammate.

It was really helpful to pitch Toofr like this and also describe my parallel entrepreneurship hypothesis. These applicants thought it was great. They got fired up and wanted to help. It was validating to hear it. I spoke to programmers, designers, SEO experts, and content marketers. They all wanted to help me grow my businesses.

Over the course of those 15 calls, I could tell my pitch improved, got more succinct, and I could describe what I’m doing with more conviction. That alone was extremely valuable.

And the other insight I got after 15 calls was that I wasn’t ready to hire an SEO expert, or a display marketing expert, or even an email marketing expert. I didn’t want to remove myself from those activities I knew were going to be critical for Toofr to keep growing for the next six months.

After 15 calls I discovered what I really needed. A writer.

Hiring should always be the absolute last resort

I was too quick to hire for the work I didn’t want to do. What I should have done first was been my own boss and forced myself to do it.

“Sit down, read these blog posts, sign up for these tools, and don’t stand up until you’re motivated again.” — Me, talking to me

That was the internal monologue. Don’t give up. Don’t let yourself fall into the same patterns and mistakes I’ve made before. Indeed, although we hired very well at Scripted, I think we hired unnecessarily. If we’d done more with a smaller team we’d have ultimately had a better outcome.

So it was a bit of shock to me when, after a glass of wine and some pointed questions from my wife, I realized I’d fallen into that old trap. I hadn’t exhausted all my options yet.

All I needed to do was stop doing everything else I was doing, essentially using other work to procrastinate, and do the job description myself.

And why not? These are skills I’ve been lacking but they’re critical skills I need. I should know SEO at a very tactical level. If it’s important enough for me to pay for it, it should be important enough for me to learn and try to do myself.

So that’s what I did. Bit by bit, I laid the groundwork for the work that I described in the job post. The one part I allowed myself to neglect, though, was the writing itself. And it just so happened that I interviewed one person with a great attitude and a great writing style.

I asked her if she’d take a more writing-focused job for now while I dove into the other SEO work. She agreed and that was that.

Even part-time or contract employees define your culture in the beginning

The person I hired is great. She’s 100% someone I would have loved to bring into Scripted. I know she would have fit right into that group, and Scripted is still the gold standard to me when it comes to a culture of smart, nice, driven, creative people.

This point weighed heavily on me as I screened and spoke to the applicants for my part-time growth marketing role.

Sure, they’d be remote. Sure, they’re only part-time. But I wanted to plan for the scenario where I’m once again leading a team. I didn’t want to waste time cultivating a relationship with someone I wouldn’t be proud to introduce as my first hire.

It’s a pretty high bar to set for a position like this, but I think it’s still really important. Not just for my own enjoyment right now but for the possibility that future hires will look to this person as a leader. I can’t have that view tainted.

So I screened away some very impressive resumes because I could tell by the tone of the email cover letter that they didn’t pass the culture test. It was also easy for me to dismiss some of my phone interviews this way too.

Culture, in fact, is my easiest filter. It’s also my biggest peeve when it’s off.

I have a harder time judging skills and passion, because I know they’re not so easy to show sometimes. Great skills can emerge only in certain environments, and passion can be hidden by nerves. Cultural fit though, this is a thousand small things and I think I’m pretty tuned into it.

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