Almost Timely News: 🗞️ How To Find A Job Using AI (2025-08-24)

Use AI to find your next gig

Almost Timely News: 🗞️ How To Find A Job Using AI (2025-08-24) :: View in Browser

The Big Plug

👁️ Pre-register for our new course, the AI-Ready Strategist! Doors open September 2.

👉 My new book, Almost Timeless: 48 Foundation Principles of Generative AI is now available!

Content Authenticity Statement

100% of this week's newsletter was generated by me, the human. You will see bountiful AI outputs in the video. Learn why this kind of disclosure is a good idea and might be required for anyone doing business in any capacity with the EU in the near future.

Watch This Newsletter On YouTube 📺

Click here for the video 📺 version of this newsletter on YouTube »

Click here for an MP3 audio 🎧 only version »

What's On My Mind: How to Find a Job Using AI

I've been fortunate in my life to not have needed to go through the job hunt process in a very, very long time. The last time I did the whole dog and pony show, shopping around resumes, etc. was during the second Bush Administration, more than 20 years ago. Since then, every position I've landed has been through my network, save my current one which I co-created with Katie Robbert.

But what if that wasn't the case? What if I didn't have you (and thank you for being here) to help me? How would I look for a job in 2025 if I had nothing but my work history and the tools at my disposal?

Unsurprisingly, I'd use a heck of a lot of AI. And in fact, I’ve helped friends and loved ones improve their job searches doing exactly that.

As we know, the job market right now is REALLY tough. The impact of AI on jobs and careers is real and it’s now, not in some far off future. In a recent issue of the Trust Insights newsletter, I shared this correlation analysis between Microsoft’s projected future impact of AI on industries with live hiring demand data from Indeed.com.

What we see is stark and clear if you know statistics. The Microsoft study projecting future impacts is projecting current impacts. The impact of AI is real and it’s right now.

A bit more background about me: back in the early 2000s, one of my short lived careers was in technical recruiting. I spent a year as a recruiter, trying to place candidates in jobs just as the dot com bubble burst, which made for an interesting time, but I do have experience in both sourcing jobs and candidates. This is relevant insofar as I have actual work experience helping people get hired. Not like uh an AI person just spouting off from something that chat GPT told them without any actual real world experience.

So with all that preamble, let's do a fresh look at how I'd use AI to help me find work if I had to today. The video version of the newsletter will show me walking through each step.

Part 0: Special Copyright Notice

This issue of the newsletter is released under a special license, the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International
license. This means:

• You are welcome to use it for non-commercial purposes (meaning you are prohibited from reselling it in any way or trying to make money on.)

• You are prohibited from making derivative works from it (i.e. copy pasting it and passing it off as your own)

• If you do share it or redistribute it, you must give attribution by linking to this newsletter

The reason for this special license is that there are a LOT of scammers and predators who are peddling snake oil to people who are increasingly desperate to find work, charging them money and making wild promises that AI can help them find a job if only they fork over money.

My intent is that this newsletter is essentially a public good with the aforementioned restrictions. The last thing anyone should be doing in an employer's market (vs. a job seeker's market) is charging job seekers money they don't have, and I expressly forbid that with this license. Should you happen to see anyone reselling my materials in violation of this license, let me know so I can send my lawyer after them.

Part 1: Mise en Place

Before we begin any kind of job search, we have to know what we want to do. There’s a Japanese cultural concept called ikigai which roughly translated means the things you enjoy, the things you’re good at, the things you can make money at, and the things that make the world a better place.

There are plenty of things that we enjoy that no one's going to pay us to do.

There are plenty of jobs in the world that we won't be good at.

There are plenty of employers that are companies that kinda suck at what they do in terms of making the world a better place. They actively make the world a worse place.

Ideally, any job you work at should be fulfilling along those four axes because… well, you spend most of the waking hours of your prime adult life working.

So your first stop is to grab the beverage of your choice and the voice memos app of your choice and start talking out loud.

• What do you love doing?

• What are you good at?

• What will other people pay you to do?

• What companies, if they hired you, would at the very least not make the world a worse place?

Spend some time on this. Have a few mocktails over it (I’m partial to seltzer, stevia, lime, and mint). In fact, it’s even better if you just foam at the mouth and talk out loud or talk with a trusted friend over these four topics. Your goal is to have 5-10 minutes of answers for each in raw, honest conversation. Don’t worry about grammar, about correctness, about anything except how you feel and how you express those feelings about work.

Put that through the transcription app of your choice; most voice memos apps these days have transcription built in.

You’ll also want to have a current copy of your CV/resumé (from here on out, I'll refer to this as a CV since most of the planet calls it that) on hand, as well as a current copy of your LinkedIn profile. If they’re not up to date, make sure you have the updates handy somewhere - a voice memo, some notes, etc.

Part 2: Durable Skills Inventory

Katie Robbert recently wrote an excellent piece on “soft” skills, which really are transferable skills, durable skills that endure from job to job, industry to industry, skills like active listening, empathy, critical thinking, etc. In an age of AI, durable skills are more important than ever because they’re the skills AI doesn’t necessarily bring to the table as well.

On top of that, we need to understand ourselves. We might have a sense of self that isn’t in alignment with how we show up in the world, and we especially might have a sense of our personality that isn’t aligned with what we want to do.

The personality analysis framework I use most is the Big 5/OCEAN. This, of all the different personality assessments, is the only one that has passed any kind of peer review, whereas all the others from Myers-Briggs to DISC to... whatever... are essentially business astrology. They're fun, they're entertaining, but they haven't passed peer review, so their reliability as an assessment metric or assessment tools, not so good.

Our first step, then, is to do a personality analysis on ourselves. Here's how. Take all the transcripts of everything you recorded in part 1, plus your CV and your LinkedIn profile, and feed them to the AI of your choice with this prompt.

Special Disclaimer: this newsletter and its prompts are not intended to diagnose, evaluate, or recommend advice for any condition, physical or mental. Always consult your qualified healthcare practitioner for health advice specific to your situation.

Download the PDF of the prompt here, then just drop it into the chat.

What you'll get back is a decent personality analysis based on how much text you provided. If you did a good job of narrating what you want, speaking honestly, and the transcript is accurate, this will tell you a lot about yourself in the specific context of work and the work you want to be doing.

Once that's done, we now take your CV, your personality analysis, and this Durable Skills Mapping Knowledge Block (PDF) and we prompt the AI to analyze and provide a mapping of durable skills:

With this personality analysis and their LinkedIn profile, let's apply the lessons from this research to better understand their durable skills (sometimes known as transferable skills or soft skills) and what lateral professional opportunities might be good fits for them.

What we get back is a solid list of durable skills, the transferable skills we use in every job. Because it's derived from our Big 5 personality analysis, it should be a reaonsable fit - and if it's wildly wrong, verify that your input materials are correct.

Part 3: Tuning Up The CV

Once you've got your durable skills list with your lateral opportunities guide, it's time to start tuning the ol' CV. We want it to reflect not just what we've done, but who we are, and we want it to be comprehensive since it'll be the foundation of future efforts.

We want something in depth. Here's a starting prompt:

With this understanding and the data provided so far, take their existing LinkedIn profile data, CV data, and other data, and provide a rewrite using your recommendations. Merge together conflicting information and deduplicate. There must be no references to previous versions or documents; the LinkedIn profile must be completely self-contained. Produce it with all sections possible; LinkedIn profiles always contain an About statement, experience, education, top skills, contact information. If available, include awards received, publications, causes, and other optional parts of the LinkedIn profile data if the user has provided the information. Remember that we must remain factually correct, truthful, and honest while implementing your changes. When writing personal statements, leverage all the information in our conversation so far, especially about durable skills. If factual information is not available, omit it. Produce the profile in the canvas.

This should produce a detailed master copy of your LinkedIn profile based on the information so far. You'll want to update your LinkedIn profile and other similar profiles (Indeed.com, etc.) with it. If you have a personal website outside LinkedIn (and you should, ideally), you'll want to update it with this information as well.

Remember that this profile is our master profile. It should have everything and the kitchen sink in it. Don't worry about tailoring it just yet - we'll get to that part later. Right now, completeness is what we care about.

Part 4: Building the Collateral Engine

Our next step is to build the Collateral Engine. What is this? In short, it's a custom app you're going to build that will tailor your profile to specific situations. Here's how. In ChatGPT, we have GPTs. In Google Gemini, they're called Gems. In Claude, they're called Projects. Whatever the platform of your choice calls them, these are AI mini-apps. You don't need to code anything. You just need to provide instructions for how to set them up.

These generally require paid accounts, just so you're aware, the $20/month variety. If you don't have access to the paid version, you can copy paste the prompts instead. It's less convenient, but it's still free.

I'll use ChatGPT as the example, but the process is almost identical on any platform that supports them, and the prompt is just about the same.

• ChatGPT version (PDF)

• Gemini version (PDF)

• Claude version (PDF)

You'll put the appropriate PDF into the system along with your CV, personality analysis, and durable skills inventory. For the Gem/GPT/Project, you'll also provide a basic prompt:

Strictly follow the SYSTEMINSTRUCTIONS in the {system}-systeminstructions.pdf

substituting chatgpt, gemini, or claude for {system} (i.e. strictly follow the SYSTEMINSTRUCTIONS in the chatgpt-systeminstructions.pdf)

What the Collateral Engine does is simple: with any given job description and/or optionally the LinkedIn profile of the hiring manager, it will attempt to tune your existing CV (that you uploaded as cv.pdf), your durable skills inventory (that you uploaded as durable-skills-inventory.pdf), and your personality analysis (uploaded as personality-analysis.pdf) to fit the job description and the hiring manager's profile while remaining truthful and honest, writing in your style.

This will help you tailor revised versions of your documents for any job you're interested in applying to, leveraging ALL the information you've gathered to this point and not making you manually rewrite every single time, which is tedious.

Why am I not providing Gems/GPTs/Projects for you that are pre-built? For one thing, I want you to provide your own CV, personality analysis, and durable skills analysis. And for another, that kind of information is DEEPLY personal, sensitive protected information. I absolutely would not trust a GPT/Gem/Project provided by someone I didn't know well with my detailed employment history and personality information. That's a gold mine for identity theft and fraud.

Don't use other people's AI systems for career stuff unless you trust them, be they a vendor or an individual. Yes, it's convenient if someone else just does it for you, but that convenience always comes at a price.

Part 5: Building the Greatest Hits

Now it's time to hit the bricks. Job hunting, even under the best of circumstances, is never "build it and they will come". It's a full time sales job, and what's for sale is your services. I almost said what's for sale is you, but that's a very different profession. The buyer is the hiring manager and the hiring company, whether you're working in the mail room or the corner office.

The bad news is that job hunting is the worst paying sales job in the world. The good news is that today's AI tools are superb at doing some of the heavy lifting for you.

Before we begin, I'll share some advice from my recruiting days. This is what I told candidates. Set your expectations for job search to follow the rule of 10s:

For every:

• 1 accepted job you will need

• 10 job offers

• 100 interviews (1 interview may have up to 10 rounds btw)

• 1000 screening calls

• 10000 applications/inquiries

Will it actually take this many applications? No. But by setting impossibly high numbers as our expectations, this does two things.

First, it mentally prepares us for the slog that is job seeking. If you knew you had to hit a quota of 10,000 job applications, would you apply for a job a day? No way. You'd be applying to everything you're qualified for, every place you can possibly go, hitting every person in your network, trying to hit that magic 10000 number.

Second, it dramatically reduces the impact of any single rejection. Sales is all about rejection. If you have your heart set on just that one job at that one company, then if you don't land it, your heart is crushed. You're emotionally crashed on the shoals. It sucks.

If the job is just one of thousands you've applied for, and you get a rejection, you'll still be disappointed but you'll know it's just one more rejection on the pile.

And as a side benefit, if you treat it like a numbers game, if you treat it as a B2B sales process at scale, then when it comes time to make a decision, if you've hit those absurd numbers, you'll likely have more than one opportunity to choose from.

With that in mind, one of your greatest allies is AI deep research agents, the ones built into tools like ChatGPT, Gemini, Claude, etc. usually on the paid program, but some places like Perplexity will give you a couple reports a day for free. That's more than enough.

Here's how you'll use them. With this Deep Research prompt, plus the header text, you'll kick off a research project every day.

Download the Jobs research prompt here, in PDF format.

You'll prompt it with this information. Copy and paste this, with the PDF, and edit the prompt with your specifics like location, keywords, etc.

Conduct a Deep Research report with the Jobs Deep Research Prompt.

## VARIABLES

* `USER_CV_TEXT`: attached as a PDF
* `USER_GEOGRAPHY`: [Enter your desired job location, e.g., "Boston, MA", "Austin, Texas", "United Kingdom", or "Anywhere (Remote)".]
* `USER_DESIRED_ROLES_KEYWORDS`: [List the job titles, keywords, or industries you are targeting, e.g., "Senior Project Manager, Agile, Scrum Master, PMP", "Digital Marketing, SEO, Content Strategy", "Registered Nurse, ICU, Emergency Room".]
* `MAX_POSTING_AGE_DAYS`: [Enter the maximum age of job postings in days. The default is 30.]
* `CONSIDER_REMOTE_OPTIONS`: [Enter "Yes" or "No". If "Yes", the search will include remote roles in addition to your specified geography.]

Then kick off a deep research report.

What should come back is a curated list of 15-20 jobs you can apply to. The next day, you'll prompt for the same thing, but provide the previous day's listings as jobs the Deep Research agent should exclude.

Rinse and repeat.

Once you've got your jobs list, then start grabbing each job description and optionally the hiring manager if you've got it, and feed it into your Collateral Generator from the previous step. Format your CV and cover letter in whatever format the portal requires, and go through as many as you can per day.

Part 6: Wrapping Up

The process I've outlined here is what I use for my friends who are looking for work. There's a more technically sophisticated version that uses AI agents and some code to make things like PDFs automatically, but the core is all the same, and anyone who can copy/paste or drag and drop can use this.

As I said in Part 4, be very cautious when using anyone else's systems that you did not build when it comes to career stuff, because that is sensitive, protected information. It's everything a malicious actor would need to commit identity fraud with your data, so be careful who you give your data to.

As a reminder, if you're using a free AI tool, it is not free, you are paying with your data. So make sure that you are using a tool that has a good privacy policy, a clear terms of service. Read the terms of service, read the privacy policy, make sure that your data is safe before you build a GPT or a gem or an artifact, whatever, in the system of your choice, because you want to protect this very sensitive data.

Finally, I have to put in the obligatory legal disclaimer that I provide absolutely no warranty or service or any kind of support for these materials. Use them at your own risk; if ChatGPT lights your career on fire, it's not my fault. If my prompts make you unemployable, it's not my fault, etc. I have done my best to create reasonably effective tools and I'm giving them to you for free with the understanding that after this, it is entirely up to you. The results you get good or bad are entirely up to you.

How Was This Issue?

Rate this week's newsletter issue with a single click/tap. Your feedback over time helps me figure out what content to create for you.

• 😄 Good

• 😐 Neutral

• 😦 Bad

Here's The Unsubscribe

It took me a while to find a convenient way to link it up, but here's how to get to the unsubscribe.

If you don't see anything, here's the text link to copy and paste:

https://almosttimely.substack.com/action/disable_email

Share With a Friend or Colleague

If you enjoy this newsletter and want to share it with a friend/colleague, please do. Send this URL to your friend/colleague:

https://www.christopherspenn.com/newsletter

For enrolled subscribers on Substack, there are referral rewards if you refer 100, 200, or 300 other readers. Visit the Leaderboard here.

Advertisement: Bring Me In To Speak At Your Event

Elevate your next conference or corporate retreat with a customized keynote on the practical applications of AI. I deliver fresh insights tailored to your audience's industry and challenges, equipping your attendees with actionable resources and real-world knowledge to navigate the evolving AI landscape.

👉 If this sounds good to you, click/tap here to grab 15 minutes with the team to talk over your event's specific needs.

If you'd like to see more, here are:

• My speaker preview reel (YouTube)

• A full-length keynote you can enjoy

ICYMI: In Case You Missed It

This week, Katie and I did some benchmark testing for bias (specifically gender bias) on the livestream. Find out who won among Gemini, ChatGPT, and Deepseek.

• So What? AI Bias Benchmark Testing

• How Generative AI Is Making Recruiters More Valuable Than Ever

• Unlock the Full Power of AI for B2B Marketing: 3 Advanced Strategies Beyond Basic Content Generation

• Is Your Website Invisible to ChatGPT Search? The Hidden Cost of Blocking AI Crawlers

• AI Doesn’t Know It’s Lying—Here’s Why You Must Verify Its Answers

• Senate Slams Big Tech: 99-1 Vote Blocks AI Regulation Ban, Paving Way for State-Led Controls

• Almost Timely News: 🗞️ The Ethics of AI (2025-08-24)

• In-Ear Insights: Reviewing AI Data Privacy Basics

Skill Up With Classes

These are just a few of the classes I have available over at the Trust Insights website that you can take.

Premium

• 🧭 New! The AI-Ready Strategist

• 💥 Generative AI Use Cases for Marketers

• 👉 Mastering Prompt Engineering for Marketers

• 🦾 Generative AI for Marketers

• 👉 Google Analytics 4 for Marketers

• 👉 Google Search Console for Marketers (🚨 just updated with AI SEO stuff! 🚨)

Free

• New! Never Think Alone: How AI Has Changed Marketing Forever (AMA 2025)

• Generative AI for Tourism and Destination Marketing

• Powering Up Your LinkedIn Profile (For Job Hunters) 2023 Edition

• Building the Data-Driven, AI-Powered Customer Journey for Retail and Ecommerce, 2024 Edition

• The Marketing Singularity: How Generative AI Means the End of Marketing As We Knew It

Advertisement: New AI Book!

In Almost Timeless, generative AI expert Christopher Penn provides the definitive playbook. Drawing on 18 months of in-the-trenches work and insights from thousands of real-world questions, Penn distills the noise into 48 foundational principles—durable mental models that give you a more permanent, strategic understanding of this transformative technology.

In this book, you will learn to:

• Master the Machine: Finally understand why AI acts like a "brilliant but forgetful intern" and turn its quirks into your greatest strength.

• Deploy the Playbook: Move from theory to practice with frameworks for driving real, measurable business value with AI.

• Secure Your Human Advantage: Discover why your creativity, judgment, and ethics are more valuable than ever—and how to leverage them to win.

Stop feeling overwhelmed. Start leading with confidence. By the time you finish Almost Timeless, you won’t just know what to do; you will understand why you are doing it. And in an age of constant change, that understanding is the only real competitive advantage.

👉 Order your copy of Almost Timeless: 48 Foundation Principles of Generative AI today!

Get Back to Work

Folks who post jobs in the free Analytics for Marketers Slack community may have those jobs shared here, too. If you're looking for work, check out these recent open positions, and check out the Slack group for the comprehensive list.

• Business Analytics Manager at Virtual Business Office Associates

• Customer Data And Insights Manager at Prosum

• Data Analyst (Adobe) - Part-Time at NMQ Digital

• Data Analyst at Brooksource

• Data Analyst at Insight Global

• Director Of Business Intelligence & Analytics at Integra Connect

• Ecommerce Manager at LookOurWay

• Manager, Managerial Consulting V at Kaiser Permanente

• Paid Social Strategist at Blue Wheel

• Performance Marketing Manager at Headlight

• Sales And Marketing Specialist at RUBIN FINANCIAL GROUP

• Senior Manager, Product Marketing at SimplePractice

• Senior Marketing Analyst, Member at Carrot

• Senior Product Manager Prm, Reporting & Insights at Muck Rack

• Social Media Strategies at Fast Supplements LLC

Advertisement: New AI Strategy Course

Almost every AI course is the same, conceptually. They show you how to prompt, how to set things up - the cooking equivalents of how to use a blender or how to cook a dish. These are foundation skills, and while they're good and important, you know what’s missing from all of them? How to run a restaurant successfully. That's the big miss. We're so focused on the how that we completely lose sight of the why and the what.

This is why our new course, the AI-Ready Strategist, is different. It's not a collection of prompting techniques or a set of recipes; it's about why we do things with AI. AI strategy has nothing to do with prompting or the shiny object of the day — it has everything to do with extracting value from AI and avoiding preventable disasters. This course is for everyone in a decision-making capacity because it answers the questions almost every AI hype artist ignores: Why are you even considering AI in the first place? What will you do with it? If your AI strategy is the equivalent of obsessing over blenders while your steakhouse goes out of business, this is the course to get you back on course.

👉 Pre-register today! The course begins September 2.

How to Stay in Touch

Let's make sure we're connected in the places it suits you best. Here's where you can find different content:

• My blog - daily videos, blog posts, and podcast episodes

• My YouTube channel - daily videos, conference talks, and all things video

• My company, Trust Insights - marketing analytics help

• My podcast, Marketing over Coffee - weekly episodes of what's worth noting in marketing

• My second podcast, In-Ear Insights - the Trust Insights weekly podcast focused on data and analytics

• On Bluesky - random personal stuff and chaos

• On LinkedIn - daily videos and news

• On Instagram - personal photos and travels

• My free Slack discussion forum, Analytics for Marketers - open conversations about marketing and analytics

Listen to my theme song as a new single:

• Apple Music

• Spotify

• YouTube

Advertisement: Ukraine 🇺🇦 Humanitarian Fund

The war to free Ukraine continues. If you'd like to support humanitarian efforts in Ukraine, the Ukrainian government has set up a special portal, United24, to help make contributing easy. The effort to free Ukraine from Russia's illegal invasion needs your ongoing support.

👉 Donate today to the Ukraine Humanitarian Relief Fund »

Events I'll Be At

Here are the public events where I'm speaking and attending. Say hi if you're at an event also:

• Marketing Profs Working Webinar Series, September 2025

• SMPS, Denver, October 2025

• Marketing AI Conference, Cleveland, October 2025

• MarketingProfs B2B Forum, Boston, November 2025

There are also private events that aren't open to the public.

If you're an event organizer, let me help your event shine. Visit my speaking page for more details.

Can't be at an event? Stop by my private Slack group instead, Analytics for Marketers.

Required Disclosures

Events with links have purchased sponsorships in this newsletter and as a result, I receive direct financial compensation for promoting them.

Advertisements in this newsletter have paid to be promoted, and as a result, I receive direct financial compensation for promoting them.

My company, Trust Insights, maintains business partnerships with companies including, but not limited to, IBM, Cisco Systems, Amazon, Talkwalker, MarketingProfs, MarketMuse, Agorapulse, Hubspot, Informa, Demandbase, The Marketing AI Institute, and others. While links shared from partners are not explicit endorsements, nor do they directly financially benefit Trust Insights, a commercial relationship exists for which Trust Insights may receive indirect financial benefit, and thus I may receive indirect financial benefit from them as well.

Thank You

Thanks for subscribing and reading this far. I appreciate it. As always, thank you for your support, your attention, and your kindness.

See you next week,

Christopher S. Penn