Anatomy of a Successful Job Hunt: What Emails Subconsciously Reveal

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Every year, college grads go through the ritual of finding their first corporate job. If you focus on what the pundits or online articles suggest, you’d think the job hunt were a series of high profile interviews and intense negotiations. I certainly thought so during my first job hunt.

Yet, in reality, most of the action happens in the most mundane of places: our email inbox. From initial outreaches to talking with recruiters, a lot of the job hunt takes place in the inbox. Instead of wholly trusting the job hunt experts, we wanted to delve deeper; we asked ourselves, “What did our emails reveal about us at a subconscious level?”

As someone who’s been on both ends of the spectrum, hiring and pleading for a job, I thought this would be a fascinating place to start an experiment.

Ariella’s Story

When Ariella graduated college, she was like most graduates: eager to get employed. She took the first job she was offered and ended up in the marketing world, working in supply chain management.

Like Ariella, plenty of people jump at the first opportunity to be employed. But for our experiment, we focused on the emails of people who were looking to start their “real” career — people who had found something they truly loved doing.

“Top performers know that 80% of the work in an interview is done before you ever set foot in the room.”
 —Ramit Sethi

We analyzed Ariella’s and several other people’s email inboxes to look at patterns successful people have in their inbox, how they handle their outreach, and how their sentiments change throughout the process.

If top performers separated themselves from typical applicants early on, we wanted to see how.

The Story Behind The Data

Before I could appreciate what the data and analytics showed, we had to look at the stories behind these job hunters who were following their passion. Talking with Ariella, I noticed a certain drive that came through immediately.

Her positive attitude paralleled that of the other millennials we talked to: they wanted to succeed early on in their careers. But with Ariella, I could sense the follow through. We talked at length about her days before she became a developer.

Ariella described how unfulfilling her job in supply chain management was and found herself wandering over to the developers, poking them with questions and slowly learning how to develop. After taking herself as far she could with self-teaching and felt prepared, she moved back home to Detroit to enroll in a bootcamp.

Illustrations by Haruka Aoki
“I wanted to isolate myself and be in my parents basement [to learn to code]”
 — Ariella

The Other Side Of The Table

Most of my involvement in the job hunt these days is from the other side of the table. Whether it’s hiring for a startup, a side project or even in finance, the applicants seem to have similar characteristics across all levels.

The most noticeable similarity is the initial email, an interesting area of exploration for our data engine. We looked at the average length of the initial outreach email. We were looking for patterns: was it the short response or the well thought out analysis that led to further conversation?

In my experience, I came across extremes. I remember several cases where I’d be eager to meet a candidate in person, and then receive a three-page essay or a few words giving me nothing to go off of.

Shockingly, this person didn’t get an interview.

I’d gladly delete the poorly formatted essays I’d receive. But for the applicants who’d put in the time, I was guilt laden enough to skim the first few paragraphs. Almost always I would skip over these candidates as they just didn’t seem to “get it.”

There were a few candidates who really understood though, and it was an instant relief. The sense is that this is someone I can trust. What did these people do that the others didn’t understand?

To start they didn’t write short snippets or novels that would take up my day. It was all geared towards how it would help me. Rather than rambling on their accomplishments, they geared their successes to actionable things that would make a difference for the business.

Diving Deeper


We found that a vast majority of the emails we studied were within a strict range. The 50th percentile for the emails were around 277 characters and only 3 sentences. We saw that at the extreme end, 90% of the emails were less than 500 characters.

To put that in perspective, the poorly written editorial intern email above is around 150 characters. These successful candidates were brief and to the point. They didn’t write one word emails but they erred on the side of brevity. Talking with multiple recruiters, I was surprised to find that they often regarded essays as generic instead of personal.

Smart candidates wrote short and focused emails. This was certainly a good start to understanding the top performers, but we knew email length and first response weren’t enough data.

Typical Storylines From School

As Ariella and I continued to talk, I wanted to know what her experience was like as she finished up her bootcamp and prepared for the job hunt. As someone who’d gone through a similar experience I wanted to see if similar storylines had been told to her of the job hunt.

The storyline I’m sure sounds familiar that its a number’s game. Perhaps the worst advice I’ve received is that getting a job is about hitting a certain magical number.

But Ariella described in detail how focused and almost linear her process was when searching for a job. While most of her career counselors emphasized being open to experience and trying anything, Ariella had a more disciplined and direct approach.

She described how many of the instructors advised her to try out for any programming language and to be open and honest about your weaknesses. But as we discussed earlier, there’s a few shortcomings in that. Does being completely forthcoming about your faults truly alleviate the fears of a hiring manager? We’d have to do more research to have a definite answer but it doesn’t seem likely.

Burst vs Scattered

Ariella took a different path and emphasized the Photoshop and front-end skills she already had. She quickly went through her network to gain exposure to interviews and whiteboard exercises. Ariella and the other participants in our study showed us something very different. 

They weren’t playing a numbers game it was a much more targeted approach. They averaged 10–12 different outreach campaigns with many being people they already knew. Very few candidates went above 20. 

They didn’t send out hundreds of emails or go through tons of job portals. It was a few focused bursts of effort. The timing of the emails were also within a month or two. Successful people don’t spend months sending out resumes hoping someone will respond. Energy is a finite reserve, and stretching the job hunt over months as your enthusiasm and energy drop is a recipe for failure.

Ariella and the other successful applicants were more aware of the need to use their networks and create a direct connection. Knowing this, I wanted to see if they avoided perhaps the most damaging mistake negative trigger words.

The Trigger Words: Like, Maybe and Sort of

We’ve all been told the importance of using assertive language. But what’s often missed is how damaging even subtle slip ups, or trigger words, can be. Words like “sorry”, “perhaps”, “maybe” send a trigger even if only used once to the employer subconsciously of your uncertainty. 

We created an engine that allowed us to scan every email for these trigger words to see how often these subtle mistakes popped up. We ignored instances where like was being used to describe similarity between objects and other similar use cases.

Unsurprisingly, Ariella and the other candidates had a very low frequency. For every one hundred emails, we saw that words like “maybe,” “sorry,” and other similar words came up at 2.40 trigger words per one hundred emails. Running my own emails against the engine, I saw a bit of a higher ratio, but that’s a topic for another day.

In an email, a few words can mean the difference between an interview and an empty inbox. Avoiding these trigger words puts you in the rarified group of people who aren’t subconsciously self-defeating.

After The Emails:

Ariella found her home in the front end

Ariella is now working in advertising as a front-end developer. Talking to her, I could see she was already planning her next move. While she had originally been attracted to the design elements of the front-end role, the more she dove into engineering, the more the logic and puzzles of back-end development enticed her.

Arielle sidestepped most of the damaging mistakes like writing generic templates, mass emailing, and spreading the job process out over a long period time. 

These mistakes are where most candidates’ problems start, as they unconsciously set the narrative as an inexperienced candidate interested in any job they can get. Craft your narrative and your emails to put yourself into a unique group.

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