The 1 Mistake that Absolutely Crushes Career-Changers

Pop Quiz!

Quick - what’s the #1 mistake that job-seekers make when trying to break into an industry? 

Typos on their resumes, right?


Grammar mistakes on their cover letter?


An unprofessional photo on their LinkedIn profile???

Not even close.

Believe it or not, the biggest mistake is way worse than this...

Believe it or not, the biggest mistake is way worse than this...

The #1 Career-Changer Mistake

No, after spending the last three years hiring and coaching candidates, I’ve come to realize that the absolute killer mistake nearly every career-switcher makes has nothing to do with their application. In fact, this critical error is made before a single drop of ink is spilled. Because it comes at the precise moment they forget who they’re writing for.

Let me explain:

When I reviewed applications in the tech world, first at LinkedIn and later at a VC-backed startup, it wasn’t the glamorous experience you might expect. I wasn’t wining-and-dining candidates, I wasn’t jet-setting around the world. Instead, I was sitting in a tiny conference room at the end of a long day with hundreds of applications to get through before I could even think about dinner.

The "glamorous" life of a hiring manager...

The "glamorous" life of a hiring manager...


So you can imagine how frustrating it was to read application after application that began like this:


Dear Sir or Madam, I would like to apply for a job at your firm. With five years of experience in X industry and a positive attitude, blah, blah, blah...


Bam. Right when I desperately needed a strong shot of caffeine, they gave me a wallop of Ambien.

The cover letter equivalent of a tranquilizer!

The cover letter equivalent of a tranquilizer!


But why? I mean, it goes without saying that these prospective career-changers should be working at least twice as hard to break into an industry as someone who's already there. So, what could possibly compel them to sabotage their own slim chances???


The answer is that, too often, candidates end up writing for themselves, not the recruiter or hiring manager. In other words, they focus on what seems right to them - not to the person on the other side. Which is a totally understandable mistake because:


1) It’s easier.

Having a single, generic resume and cover letter lets you quickly copy-and-paste one application after another.


2) It feels safer.

Everyone else is doing the same thing and using the same template, so why stick your neck out?


3) It’s what you’ve been taught.

When you learn about job applications in school, you’re taught to play by the rules - action verbs, past tense, CAR format - as if you were programming a computer, not communicating with another human.


Unfortunately, these rules and this approach obscure the fact that there is, indeed, another living, breathing person on the other side of the application “Submit” button. And when you ignore that person, you do so at your peril. Because he or she isn’t some resume-grading robot, but a tired, cranky human who just wants to find the perfect candidate and go home. And so you can be sure that when your weak-sauce application pops up at 7 PM on an empty stomach, it's definitely not appreciated!

Dream on: "Analyzing. Resumes. Beep Boop Beep."

Dream on: "Analyzing. Resumes. Beep Boop Beep."


On the other hand, this daunting challenge is also an opportunity. Because intrepid candidates who resist the siren song of the easy way out have a real chance to stand out - not through fancy templates or action verbs - but by putting themselves in the hiring manager’s shoes. Because it turns out that empathy is the the true application superpower.


To understand why, let’s examine The 3 “C" Commandments of successful career-changers:


1) Make it Clear

Empathy begins with a deep understanding of your audience. So start by imagining what it’s like to be a member of your application's audience - for example, a tech hiring manager. In this case, how likely is it that you'll have deep expertise in nonprofit fundraising? And yet, a candidate with an initial job in that world might send in a resume bullet like this:

Analyzed Raiser’s Edge data to increase life income pooled trusts by 75% and enhance donor recognition.

Huh? Raiser’s Edge? Donor recognition? Life income pooled trusts???

If you're spending 10-15 seconds on this resume - which is exactly how fast you need to read to get through all 200 and still get home for supper - you don’t have time to guess what this jargon means, let alone consult your English-Klingon dictionary. Whereas, 1-2 minutes of the applicant's time could have turned that bullet into the perfectly clear:

Analyzed fundraising database to increase retirement gifts by 75% and enhanced our process for thanking donors.

Maybe not the most inspiring bullet in history - but at least you get it now.

And so remember this: No matter how convenient it is to slap down your accomplishments the way you talk about them with your colleagues, the most important evaluator of those accomplishments - the hiring manager - might not speak that language. So have a little empathy and translate them first!

The power of translation!

The power of translation!

2) Make it Count

So now our applicant's got a bullet that’s comprehensible. But is it the right bullet? Because again, with 10-15 seconds to read, you don’t have the time to consider her fundraising database skills. Instead, you want to quickly check the mental boxes:


So let’s say our applicant is shooting for a Product Marketing role. In that case, you basically need someone who can do these four things:


  • Understand her audience

  • Develop a strategy to engage them

  • Design creative campaigns that compel the audience to take action

  • Measure her results and optimize campaigns based on this data


Unfortunately for our applicant, fundraising expertise isn’t on the list. So just like she translated the original bullet from NGO-ese to English, she’s got to invest a couple of minutes to find the relevant angle. In this case, let’s hone in on the last point - measurement and optimization - because it seems similarly analytical to what she’s already done.


With that in mind, our clear but irrelevant bullet becomes clear AND relevant:


Analyzed fundraising database to measure the success of our retirement gift campaign and optimized the campaign to increase those gifts 75%.


Again, starting with empathy, our applicant has found a way to understand her audience. She knows that you’re time-pressed and relevance-starved, so she’s given you exactly what you need.


Or has she…?


3) Make it Compelling

I mean, sure, our applicant’s new bullet fits the textbook definition of a good resume point - she’s given you the context, action, and result (i.e., the classic CAR format). But would you actually read it? Especially with just 10 seconds on the clock???


Here’s how to find out: Go back to the top of this article and scroll down five lines per second while counting “One Mississippi, Two Mississippi…” until you get to 10 (it turns out there are about 50 lines on a regular page with 1-inch margins and 11-pt font).


Now ask yourself: What did I actually read when I was scanning that fast?


Chances are, unless you’re the proud graduate of one those late-night TV speed reading courses, you don’t remember a whole lot. Most likely just the pictures and some of the more interesting copy: “Killer mistakes,” “Ambien,” "superpower.”


The reason for this, of course, is that our brains are finely-tuned to filter out noise and focus only on areas of intrigue. And while that might have been a great survival strategy back on the Serengeti with lions stalking us from the brush, it’s not a great recipe for retaining resume information. Which means that our job-seeker is going to have to play by Neanderthal rules if she actually wants you to notice her accomplishment.

"Sorry I keep getting distracted - it's just hard to focus on your resume with HIM staring at me..."

"Sorry I keep getting distracted - it's just hard to focus on your resume with HIM staring at me..."


Now, when one communicates with a caveman, one must think like a caveman (uh oh - it’s empathy time again!). And if you know anything about cavemen, you know they love stories. In fact, the earliest cave drawings we’ve discovered aren’t just random scribbles - they’re stories about adventure, danger, even spirituality.


So rather than just focus on C-A-R, our candidate would do best to focus on B-H-H:


  • Bad guy

  • Heroic action

  • Happy ending


Because those three elements are present in just about every great story, from the earliest religious texts all the way through Star Wars. In fact, if you had to boil the first Star Wars movie (OK, "Episode IV" you nerds! :) down to its most basic elements, you could do worse than: Darth Vader destroys planets -> Luke Skywalker blows up the Death Star -> Freedom is restored to the galaxy. Bad guy -> Heroic action -> Happy ending.

Let's just say the plot has about as many key points as Tatooine has suns...

Let's just say the plot has about as many key points as Tatooine has suns...


So what does that mean for our candidate’s story? Is there some way she can apply this classic story format to get her bullet point read? How about this:


After the 2008 stock market crash, analyzed fundraising data and found a golden opportunity - retirees looking for social impact + guaranteed returns; optimized campaign to boost annuity donations 75% in the middle of the Great Recession.


All of a sudden, a nice but quiet bullet becomes a hero’s journey:


Bad guy

Up against a fundraiser’s worst nightmare… (AKA a deep recession)


Heroic action

…Our plucky hero boldly uncovers the perfect antidote... (AKA donors who want to help out but also need their own financial security)


Happy ending

…And her decisive action saves the day! (AKA keeping the nonprofit afloat in the midst of crisis)


And if you don’t believe that this story format makes the bullet more compelling, try quickly scanning the new version. While our candidate still has all the important keywords (analyzed, data, optimized), she also now has several phrases that your eye can’t help but notice: “stock market crash,” “golden opportunity,” and “Great Recession."


Which means that you’re more likely to read it. And when you do, you’re more likely to think: “Woah. Who is this fundraiser who turns crisis into opportunity? And how can I get her to do the same for my team?"


The Bottom Line

So there you go - the most costly applicant mistake has nothing to do with fonts or formats. But everything to do with feeling, with understanding that person on the other side of the table, with empathy. Or the lack thereof.


And so as you boldly venture into the wild blue yonder of career change, don’t just do the convenient thing. Instead, think of that poor hiring manager guy, hunched over the conference room table, searching for a talent needle in a resume haystack. Give him a clear point that his sleep-deprived brain can comprehend, make it count by focusing on what he’s looking for, and make it compelling by turning it into a story.


Because then he just might return the favor by giving you a chance to share your story in-person. And maybe, just maybe, he’ll finally make it home for dinner...

Good applicants don't make hiring managers resort to this...

Good applicants don't make hiring managers resort to this...


Worried about other potential applicant pitfalls? Get a complete list in my free guide, The 7 Essential Secrets of Tech Recruiting.

And one last thing...

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