You Got Past the Algorithm. Now What?

The Seven Pillars - Issue 11

Hi everyone and welcome to the eleventh issue of The Seven Pillars.

This one started as a reporting project and turned into a reckoning. I reached out to recruiters and career coaches who work specifically in the humanitarian and development space, asked them what they actually look for, and then sat with the gap between their answers and how I'd been approaching my own 250-plus job applications. This issue is about that gap.

Imagine you see a job opening that feels like it was written just for you. The ideal candidate matches your background and experience in an almost eerie way. This seems like the job you’ve long been waiting for and all you have to do is craft the perfect application package.

You’ve been applying for jobs for most of your career and you feel like you know all the secrets to getting your application pulled from the bottom of the pile. You know how to write a good CV. You can craft a cover letter that cleverly drops the key words mentioned in the job description. You’re able to describe your experience with all the necessary action words: executed, delivered, managed, aligned. You have a deep bench of contacts that are ready to sing your praises. You even run the whole thing through AI so you can be sure you haven’t missed anything.

You submit the application. How could they possibly choose anyone but you? And how could you fail with your meticulous approach? But then you get the form email that starts “Dear candidate…”

I’ve been through this a lot lately. It’s not the rejection that hurts. I’ve applied to at least 250 different jobs over the last year and who knows how many more in the past 15 of my career. It’s the anonymity and opacity of the whole process that creates the most frustration.

I’ve heard the words “abyss,” “dark hole,” and “black box” thrown around a lot to describe both the process of applying for jobs in the humanitarian and development sectors and the emotions the whole thing conjures.

We know that there is some methodology, though hidden behind the curtain, that is being used to identify good job candidates and hire them, but what is it?

We have learned to tailor each cover letter in excruciating detail to the job description. We have learned to use AI tools to evaluate our resumes, and sometimes even to write them for us to make them as relevant as possible. But when everyone else is doing the same thing, putting the same amount of effort into their application as we are putting into ours, what separates one from another?

That’s what I set out to investigate in this edition of The Seven Pillars. I reached out to several people in the recruiting and coaching industry to get their insights and to try to shine a little bit more light into the abyss.

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To be honest, I have no idea how it all works. Or maybe that it’s just very different across organizations. I’ve been on the inside and participated in CV reviews and sat on technical interviews, but I feel like the larger process—from when the hundreds of applications are submitted to when they get shortlisted for interviews—is a complete mystery.

I think this was the part that is hardest to understand. And because it was hard to understand, I thought that’s where I needed to build knowledge.

There’s that phrase in e-commerce about the “last 10 feet” and how that’s the part of the whole logistics process that makes or breaks a relationship with a customer. In the job search, I had always felt like it was the first 10 feet that were most important. The part when those algorithms or ATS systems are scanning my documents for key words.

But now I see this line of reasoning for the trap that it was. The opacity and mystery of the algorithm distracted me. The result has been that I invested my time and effort in only one half of the equation.

Over the past few weeks, I spoke with hiring managers and recruiters who helped me understand something profound. Many of us are putting too much effort into getting past the algorithm and not nearly enough into impressing the human reader waiting on the other side. And it is that failure to connect with the human that is quietly eliminating good candidates from the running.

AI tools have certainly made it easier to generate a polished application and for employers to quickly screen it. We are also investing a ton of money into special CV templates to make us look polished. But at some point, a human steps in. And most applicants, it turns out, are not prepared for that moment.

It’s almost as if they have built a Trojan Horse that gets them past the gatekeepers, but then once they’re inside the walls, they’ve forgotten to bring their swords.

Kirsten Visman, a career coach with Clarity Compass and recruiter with over a decade of experience in the humanitarian sector, described exactly what she’s looking for in those first sixty seconds: what she calls a “red thread,” a clear career story that connects expertise, experience, and purpose into something a human reader can follow without having to work for it. “If it sounds too confusing and I have to read it multiple times to understand, you’ve lost me,” she says. “If it’s a clear, value-driven story, I keep reading.” 

The irony she identifies is sharp: candidates spend hours fine-tuning their CVs with AI, only to sound like a robot and blend in perfectly with their competitors. You can pass the algorithmic screening and still lose the room.

Lisa Wilds-Garland, a leadership coach at Wild Cedar Consulting who works closely with humanitarian organizations and job seekers, makes a similar observation from a different angle. What makes someone memorable, she says, is rarely the credentials. It’s the human story. It’s the narrative thread that connects the experiences on the page and makes it obvious why this particular person is the right fit for this particular role. She recalls one candidate who stood out not because her qualifications were superior, but because she proactively addressed a long gap in her employment history. She told a human story–not a collection of dates and buzz words.

This is what AI, for all its utility in keyword matching and formatting, cannot do. It cannot tell your story.

What many recruiters I spoke with converged on is that the thing separating memorable candidates from the pile is not a more perfectly optimized and polished CV. It is specificity. The kind of specificity that only comes from a real person who has done genuine background work and is writing directly to an organization’s actual situation.

Stephanie Mansueto, a career coach with 10+ years in the sector, puts it plainly: the candidates who genuinely impress her are the ones who “name drop specific projects, partners, conferences, networks, and leaders worked with that are directly aligned to the employer. They are talking the same language and clearly demonstrate they know the stakeholder ecosystem of the company they’re applying to.”

Kirsten frames it as a question every applicant should be asking themselves before submitting: have you written this application in the language of your past employers, or in the language of the organization you’re trying to join? “There cannot be a ‘lost in translation’ moment throughout your CV,” she says. The cover letter, if you write one, should not be a history of your career. It should be, in her words, “a high-impact, value-first pitch that proves you understand my current challenges and you can provide practical solutions from the first day I hire you.”

Robert Simpson, who has spent nearly a decade as a human resources director in the humanitarian field, said that when he’s reviewing applications, what stands out are the “[n]on-linear career paths, interesting diversions and loops,” he looks for a “compelling career narrative,” and wants to “get a sense of why a person chose to do this thing in this place with this organisation at this time.”

That is a fundamentally different task than matching keywords. It requires you to understand the organization well enough to speak to problems they haven’t explicitly named in the job posting. It requires research, and it requires genuine thought about what you would actually bring to this specific team at this specific moment. AI can help you structure that thinking, but it cannot do the thinking for you.

Writing this piece, I have been forced to reckon with something uncomfortable about my own 250 applications. I was playing a numbers game, and it didn’t really work.

My focus was on getting the highest number of applications out the door in as short a time as possible. I put the majority of my effort into the half of the equation I could see and measure: resume, cover letter, and keyword density. It felt like this part was controllable. First, I thought the ATS was the biggest obstacle and, second, I could easily beat it with available AI tools and resume templates.

What I didn’t fully appreciate was that getting through the algorithmic filter is just the “buy in,” as they say in poker. The real game hadn’t started yet. A human was still going to pick up the application, scan it in under a minute, and make a (sometimes biased or emotional) judgment. 

That human is not going to be asking whether my CV matched the job description or checking how many key words I covered. They’re asking whether they can picture me solving their problems, whether my story makes sense, whether something about the application signals that I actually understand what they’re dealing with.

For a long time, I’ve been building Trojan Horses and forgetting my sword.

The application process doesn’t need a shortcut or a better AI tool. It needs a rebalancing. Get the CV in shape: that part still matters. But then ask yourself the harder questions. Have I told a story here, or just listed a career? Does this application speak to what this organization actually needs, or to what a generic job posting asked for? 

If the answer is the latter, the algorithm may let you through. The human on the other side probably won’t.