I recently hired an assistant—someone to work remotely with me on projects, social media and client management. Even though this person won’t be working out of my office in Portland, Oregon, I decided to advertise the position locally. I know that there’s a lot of talent in this city, and given the flexible hours and OK-ish pay, I thought I’d have a pretty good chance at finding a fit. I was blown away by the quality of candidates—it was ah-mazing.

And then I was on the other side of the hiring table.

It’s extraordinarily hard to evaluate fit, experience and even talent based on a piece of paper. Duh, right? No, seriously. It’s really, really hard. Maybe more so for someone like me, who finds it pretty easy to figure out someone’s unique “career capital,” even on paper, by noticing their special career threads. With almost every applicant, there was one differentiator that was appealing to me.

I planned ahead. I knew I might have a number of qualified candidates to choose from, so I asked each applicant to answer three additional questions (see my ad here) to give me some insight about “fit” and interests. Now, I know this isn’t the most scientific way to assess fit and personality, but I needed something other than just a resume. I’m glad I did: the 42 applicants (Oh yes! I took down the ad after 72 hours) were mostly qualified and skilled for the job.

I debated whether to include these questions.

Why? I know, from my clients, that jumping through additional application hoops is a frustrating and demoralizing activity. And I wanted the process to be easy. This job, after all, isn’t with Google or Microsoft. I didn’t want to add too much pressure. It’s also no longer an employer’s job market, and who better to recognize that in her hiring process than this career coach?  But seeing as I was only asking for a resume and cover letter, it didn’t seem like a huge burden to ask a few unique questions.

Did I have an ulterior motive for asking the questions? Yes. Was it to see if they would follow instructions? Nope. That felt a little too adversarial for me—like a “trap”: Job Seeker versus Hiring Company. My motive was more about the message behind the questions. “Hey job seeker, we’re in this together—I know you’re looking for a cool gig. And you appreciate that I’m trying to find someone who fits my needs.” Plus, this would give me a sense of their writing style and insight into their personality and interests. I was also looking for authenticity. How genuine was their response to “why this job?”

Now I had to find the right one.

I narrowed it down to a short list of 10 who I wanted to interview. I worked through my criteria again and narrowed it down to 5. I invited each to interview (via Google hangout) with me. I decided to do a virtual interview because I wanted to see how comfortable they were with technology in a practical, real sort of way. One of the candidates had a problem with the video component, and how she handled it told me a lot about what it might be like working with her.

I tried to make the interview as casual and informal as possible, more of a conversation than a barrage of questions. When a candidate had done some research on me, I wasn’t creeped out at all (this is for those of you who think that looking at your interviewer’s LinkedIn profile prior to an interview is like stalking). They asked better questions and shared relevant examples from their experience that weren’t always obvious on their resume.

Bridget’s cover letter and resume caught my attention because she was direct and clear about how considering her would be a win-win for us both. She’s a graduate student. She’s studying publishing and has journalism and marketing experience. The bottom line: She was confident in how she presented her skills and experience. Not “I can do anything” but “this is what I do well and where I’ve had success.” That impressed the heck out me. Bridget knows what her career capital is!

And then I broke the rule.

So, I did what any good business owner does (and what experts caution against)—I  trusted my intuition. I also heard my business coach whispering in my ear “Hire for where you’re going, not where your business is at this very moment.”

And that’s how I broke the number one rule of hiring: I made a subjective decision that went outside the boundaries of objective assessment of experience, skills and abilities. It’s impossible to make any hiring decision in a completely objective way. Trust that you’re a great candidate and put it down on paper. Be like Bridget.