Product Thinking for Job Hunters

I think the hiring process is broken, but instead of looking at it from the perspective of a job seeker, I think we should look at it as if the hiring teams were our users/customers.  

• Recruiters are given job descriptions and high-level checklists with criteria that would likely signal a good fit for the role.

• They are incentivized to fill the roles as quickly as possible and to bring in qualified candidates to the next step of the process.

• The whole hiring team (and process) revolves around a fairly antiquated standard for applications, requiring them to identify the best candidates based on how well they package all of their skills and experience into:

  • Single page resume

  • Single page cover letter

Pain Point: Recruiters have no incentive to think outside of the box or consider non-traditional candidates, taking some of the creativity out of their work.

Pain Point: Hiring managers struggle to keep up with DMs, screened candidates, interviews AND all of the work they are trying to get done. Leavin them with little to no time to consider non-standard candidates - or even the candidates that are near perfect fits.

I know this isn’t just a “me problem”, as I’ve heard this echoed from senior execs at companies like Google, Atlassian, and Typeform. Recruiters are functioning as screeners and are incentivized to find people who fit a specific mold. Even when the hiring manager says they are interested in finding “non-standard” candidates or open to people who have deeper experience with specific skills, the recruiters focus on finding the people who check the most boxes.

Hiring managers are too busy to allocate time towards initial screening and are bombarded by candidates who reach out directly via Linkedin and/or email (if they can find it). The number of candidates who do this assuming they can skip a step or that the hiring manager will pursue them is mind-blowing, and generally creates an automatic adverse reaction to anyone reaching out in this way.

So instead of giving you the same tired advice on tweaking your resume fonts, let’s think about how we can improve the experience and solve problems for hiring teams.

Prologue - Full-time vs Contract/Part Time

Before we dive into the tactical, I would encourage you to forget all of the preconceived notions about a “good job” coming with a swath of perks and benefits, and consider the requirements you need to meet: If you make enough money, you can buy your own insurance, retirement plan, equipment, snacks, entertainment, etc.

Consider benefits as part of the overall compensation, but be open to any and all opportunities. The market is tough and any opportunity to get your foot in the door and/or establish some stable income is worth pondering.

I spotted a really relevant post when looking up something the other day, but I wasn’t able to find it again. It said something along the lines of:

My Go-To Tactics

1. Use Video to Show Who You Are

Recording a video does more than just make you stand out—it makes you human. It’s an opportunity to share your personality and your passion in a way that words on a page just can’t convey. I had a former manager who would request video submissions from candidates on LinkedIn. It let them self-screen: those truly interested took the time to record a video. And if they did? He would watch it, provide feedback, and refer them directly to the hiring team.

- In Product? Record a Loom and walk through the product you love or are applying to. Point out what grabbed your attention, but do not turn it into a critique on how you could "do it better."

- Not in Product? No worries. Research the company, learn its values, and explain in your video why those values resonate with you.

I lean on Loom for its ease of use, editing features, and AI tools, but if you want a free option, OBS does the job too.

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2. Build a Custom GPT That Knows Your Career

This one’s a game-changer. Imagine having a personal assistant who knows all your accomplishments, the praise you’ve received, and the skills you’ve honed, etc. (Checkout mine here).

- How It Helps You: Feed it job descriptions and ask if you’re a good fit. Instruct it to be critical and help identify any gaps a recruiter might see—and more importantly, ask it how to address those gaps.

- How It Helps the Hiring Team: If they’re on board, they can ask things like, “Does this candidate have experience in [skill]?” or “What feedback has their team given them?”

You can even set up conversation starters for them to make engagement easier. This isn’t about having AI write your resume for you—it’s about refining your story in ways that make sense.

Check out the video below to see how to create a custom GPT and some of the things I did to personalize it that have made a big difference in the quality of its responses.

3. Curate Your Story with NotebookLM

NotebookLM offers a great way to put your story together, complete with audio summaries formatted like a podcast-style discussion. It’s something that helps you stand out by giving hiring teams a break from the monotony of reading and scanning pdfs.

You can create notes that specifically answer common questions about your skills, experience, or accomplishments, making it easier for hiring teams to find answers to the questions they will have — but haven’t thought of yet. I included things like:

• How have Mike’s skills and expertise evolved throughout his career?

• What do Mike’s direct reports say it’s like to work with him?

• What do Mike’s direct managers say about working with him?

• What are some quantifiable results Mike has produced?

• What are some of the most difficult challenges Mike has had to overcome?

Unfortunately, NotebookLM doesn’t let you publish so it’s open and available to anyone with a link. They did just roll out public links for audio summaries, but I made this Notebook before that launched so you can check out my audio below and you can see some of the output on this FAQ page I started putting together.

Since my goal is to help you actually do these things, I recorded another video to walk you through the process with some tips I found to improve the responses and output.

4. Tap Into Professional Communities

I’ve found more hidden opportunities in Slack communities than on any job board. From alumni workspaces of previous roles to communities like Lenny’s Slack, these spaces are packed with high-priority job postings, and people are often willing to help you get a foot in the door.

I don’t spend a ton of time in the job boards, but when I hit a wall, this is where I look. As with anything, if you’re going to get value from the community, you should put something into it so remember to share opportunities that you come across, encourage others, and participate in conversations where you can add useful perspective and helpful insights.

5. Get Intros on LinkedIn (And Then Get More Intros)

Before you go off on a DM marathon, read this. Understand that hiring teams are bombarded and that you can make their lives easier or harder based on how you engage.

Use it to map out shared connections. Once I spot someone with a higher concentration of mutual contacts, I dig in. I look for who I’ve got the strongest relationship with, then reach out to ask for an intro.

Here’s the trick: I don’t ask for the referral straight away. I take the opportunity to learn about the company’s culture, the team, and the role. If the conversation goes well, they’re usually happy to refer you. If they aren’t up for a call, I ask them to answer a few specific questions — that show I’ve done my homework

Even if I don’t get anywhere for myself, I look for opportunities to add value. Maybe they are hiring other roles and I know some great people on the market I can introduce them to. Maybe they are looking for partners and I happen to have connections in that space. Just find a way to add value, and you’ll get past the initial walls of a company.

Now what?

The bottom line? Connect with people at a human level, find a way to add value, and use tools that help you tell your story in a real, human way. Whether it’s video, AI, or good old-fashioned networking, these strategies have worked for me to start great conversations, get interviews scheduled, open new business and partnership opportunities, and even

get my friends and former colleagues hired.