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Applying vs Defining

A case for automating forms for role-seekers


tdlr; applications suck and so many people’s time is wasted on them

Nowadays the flood of applications, cold-emails and other personalized expressions of interest is at monsoon-levels.

Any application, no matter how specific or selective it is, has turned into LinkedIn’s “Easy apply” where with a click of a button, you have all the necessary fields you need to submit it.

People don’t want to read AI slop, and the new flood of submissions doesn’t help those who are seeking roles either. AI detectors aren’t correctly sorting signal from noise, and so it’s very possible for someone whose dream is to land a certain role to be drowned out by dozens of AI-generated job applications.

However, I think we can all agree that we’d rather not be spending our time on job applications.

I have been reflecting on how much time I spend applying to roles, and how much time I spend defining my interests and skills. There’s an endless cycle: deadline for application comes up, drop a few hours on an application, submit, and repeat. For example, SPAR and MATS, two AI safety research fellowships, both have applications that recur several times a year with new cohorts and refreshed projects. And there are many other AI research programs out there. Last year, I felt like there was always something I should be working on an application for.

If you get an offer - congrats! Your time might now be devoted to an intense project that you were under pressure to apply to asap because of the deadline and growing number of applicants, but you actually didn’t feel that excited about?

Taking a break from applying and using that energy on personal projects, reading, and writing felt so much more productive to me.

If what you read, learn, and do is all driven by the qualifications listed under a job posting, what happens when the job description changes or you realize there’s another job you want more?

I remember once receiving career advice that was to read the Required Skills section of job descriptions you’re interested in and study those skills. That may work, but it also feels a bit backwards to me. Since job descriptions are fluid and the possibilities are endless for what new jobs become available, I feel it’s important not to skip the step of define what skills you want to develop based on your strengths and interests, and then try to find roles based on that.

If what you read, learn, and do is all driven by the qualifications listed under a job posting, what happens when the job description changes or you realize there’s another job you want more? I worry that people will end up training hard to be X only to realize that it wasn’t what they enjoyed all along. I now only put effort into applying for opportunities I really care about because I learned the hard way that you might waste a lot of time and energy on things that aren’t a good fit for you if you just want to “keep doors open”.

Just some thoughts on potential solutions to the competing demands of job-seekers wanting to spend less time on job apps and hirers wanting to spend less effort finding the best applicants:

Hirers + Applicants

1. Ease the pressure. The status quo is that people need well-recognized names and a lot of experiences on their resume to be considered for some roles. However, independent projects can result in just as much if not more learning. What if those are weighed equally, would people feel less application-frenzy and spend more time building the skills that really matter to them?

2. Value “unproductive” time. Time well spent doesn’t have to produce a credential. Hirers should be understanding of resume gaps. Applicants should feel like they can take time to explore their interests more deeply without needing to output something.

3. Use channels that AI can’t flood as easily. For job-seekers, one response is to create your own next opportunity rather than waiting for a posting to appear. Start a project. Organize a reading group. Reach out to someone because you have a specific idea you want to discuss, rather than because you want them to refer you for a job. Make something that gives another person a reason to seek you out. For hirers, I’m still trying to think about ways that the application process can feel more human while being scalable.

4. Lean into AI agents. If someone has spent adequate time defining themselves and their skillsets, why not let AI use that context to fill out a job application for them? Applications are mostly repetitive administrative work—entering the same information, adapting a résumé, answering routine questions, scheduling interviews—there is little reason for humans to spend hours doing that work manually. Agents could eventually handle much of the mechanical process on both sides. An AI agent could identify opportunities that genuinely match someone’s interests, prepare the administrative materials, and keep track of deadlines. On the other side, an agent could help a hiring team organize candidates and surface relevant evidence.

Applicants

How to spend time in a way that helps you define your skills and interests:

  • Talk to people
  • Keep a record of what catches your attention
  • Read. Write. Experiment. Work on side projects
  • Keep a digital record of all this that others can find
  • Try a class
  • Instead of asking, “What does the world want, and how can I become qualified for it?”, you can start with, “What do I want to become an expert at, and where could that be useful?”

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Kaitlyn Hennacy

Currently @ Stanford & Kraken

I've spent the past 6 years improving how information flows between operations, management, and AI.

In addition, I'm obsessed with how we can use data & AI in our daily routines to deepen understanding and make aligned decisions.