Get a Sneak Preview of the #1 AI Career Guide

This is a sneak preview of the first two chapters of Career Coach GPT!

Read on to discover how to use AI to get your very own career coach - and find your own perfect career path...


Introduction: Career Coaching for All

What’s the hardest part of the modern job search?

It’s not resumes.

It’s not LinkedIn.

It’s not even interviewing.

It’s the fact that you have to navigate all these obstacles alone.

And so even the best job-seekers often give up or settle for a mediocre job - just so they can end the lonely misery.

Not only have I been there myself as a former kindergarten teacher trying to make the leap to Silicon Valley, but I’ve seen it thousands of times as a leader of LinkedIn’s education team and a career coach to both military veterans and University of Michigan MBAs.

And I hate it. Because it doesn’t have to be this way. Indeed, I’ve seen how a great coach can make all the difference to a struggling job seeker.

There’s only one problem: Great coaching doesn’t come cheap. Whether it’s $500 to rewrite a resume or $100/hour for interview coaching, this pricing puts coaching out of reach for the very people it’s intended to serve - people looking for a job.

Introducing the First Scalable Career Coach

At least this was the state of things in the fall of 2022.

That’s when my boss, Sal Khan, told me about a conversation he had with the team at OpenAI.

“They’re coming out with something huge,” he said. “Something that will change education - and probably the world - forever.”

Now, even working in Silicon Valley, I was skeptical. After all, I had just spent the last decade hearing about the magical Internet of Things, the wizardry of VR/AR, and the supposed power of cryptocurrency. And they had all failed to deliver on their hype, one after another. So it seemed unlikely that a small tech company like OpenAI would be able to really move the needle - let alone change the world.

And then I tried GPT–4.

Within minutes, it was clear that this new technology really would be able to change education (a personal tutor for every student!). And business (a personal copywriter for every professional!). And yes, maybe even the painful and lonely job searches we’ve all endured.

Because just by asking simple questions like “Give me feedback on my resume” or “Generate 5 interview questions for this job,” I could produce better, more personalized feedback than any blog or online course could offer.

It was so eerily good, in fact, that it even rivaled the kind of bespoke advice I gave my individual clients. Which planted the seed of an idea: 

What if I could combine everything I knew about the hidden world of Applicant Tracking Systems, LinkedIn algorithms, and interview evaluations with the power of this incredible new tool?

Introducing Career Coach GPT. 

A complete, step-by-step process to get Jedi-level career coaching. But instead of paying thousands of dollars for it, you can leverage AI to get the coaching - and the job - you deserve for the price of this book.

Here’s How It Works

To fully realize the power of Career Coach GPT, all you need to do is commit to taking action.

Because the beauty of being guided by an AI coach is you don’t have to feel alone. You don’t have to spend hours wading through blogs or getting stuck in your own head.

Instead, just follow each step and prompt in the forthcoming chapters and I guarantee you’ll get farther, faster than you would have on your own.

And the first step is to choose your preferred tool. While I personally love ChatGPT Plus because it gives you access to the most powerful AI without any downtime, I recognize that shelling out money can be a challenge when you’re looking for a new job.

So if you prefer, you’re welcome to use any of the following free alternatives:

  • Bing Chat

  • Google Bard

  • You.com

I’ve tried the prompts in this book with all of those models with similar levels of success. And I’m sure you’ll discover even more after publication, given the incredible rate of change in this new space.

But whichever AI bot you prefer, please go ahead and fire it up now so you can start taking action immediately - and start getting results ASAP.

1) Find Your Path

As tempting as it is to dive right into building resumes and applying online, resist the temptation!

That’s because here’s the secret of all great job searches - whether they’re AI-powered or not: They’re incredibly focused.

While having a clear sense of where you’re headed makes you more likely to actually get there, it’s equally important for your audience: Recruiters.

After all, if you’re a recruiter who’s been tasked with finding a great Product Manager for your company, would you prefer someone whose application is all over the place? Or someone who’s laser-focused?

Which means that if you want to win over this audience - and you definitely do - then you have to start with focus.

How Do I Follow My Passion?

Whether you’re pursuing your 1st job or your 21st, it’s easy to get tripped up at this stage.

There’s so much conflicting advice out there:

  • “Follow your passion!”

  • “Follow the trends!”

  • “Follow the money!!!”

And again, if you’re searching on your own like most job-seekers, you can wind up getting stuck so deeply in your head that you never even get around to applying in the real world.

So to break through that deadlock, let’s turn to AI for some concrete ideas and next steps.

Specifically, plug the following into your preferred chatbot:

Generate 10 specific job titles that could be a good fit for me based on:

My Favorite Skills:

My Interests:

My Major:

My Resume:

Note that you should only include the information that you want the AI to consider. So, for instance, a student who really wants to leverage their Sociology major but definitely doesn’t want to go back to lifeguarding (their most recent job) should include their major but not their resume:

Generate 10 specific job titles that could be a good fit for me based on:

My Favorite Skills: Research, Writing, Interview

My Interests: Animals, Environment

My Major: Sociology

This produces a great list of roles that draw upon what gives the student energy - but doesn’t typecast them as a student worker forever!

On the other hand, an experienced professional may want to double-down on their existing career by including their Sales resume but not lead the AI astray by mentioning their long irrelevant Philosophy major:

Generate 10 specific job titles that could be a good fit for me based on:

My Favorite Skills: Sales, Presentations, Negotiations

My Interests: Education, Healthcare

My Resume: XXX

Now they get a hyper sales-relevant list that builds upon their existing experience without taking a detour to long-defunct parts of their CV:

Either way, the goal is to immediately break through the analysis paralysis and start thinking about concrete job titles. Especially since, as mentioned, that’s the exact way recruiters see the world. So there’s no point in focusing on abstract job categories (“I want to work in tech!”) when you can immediately hone in on the language of your target audience.

How Can I Possibly Choose?

The next step where solo job-seekers tend to get stuck is the FOMO Phase. Once you’ve developed a list of potential jobs, it can be excruciating to choose a specific path - after all, they all seem so tempting.

But again, your trusty AI sidekick is here to help you break through.

Start by feeding it all the job titles that seem intriguing to you and ask the following:

Please tell me about a typical day for each of these job titles and the kinds of people who tend to enjoy them: INSERT TITLES

This test tackles the first underlying element of FOMO: Ignorance. Specifically, the lack of insider knowledge that makes every job look glamorous from the outside.

Because once you know what a job is really like, it can be easier to rule out if the work doesn’t sound appealing or if it’s not a good fit for your personality.

And then, to help break ties for any jobs that still seem like a good fit, try the following prompt:

Rank these jobs - INSERT TITLES - based on my:

Career Goals: INSERT GOALS

Qualifications: INSERT SKILLS + CREDENTIALS

Moving one step beyond personal preference, we now get down to the crucial questions of whether the job is right for your goals and whether you’re actually right for the job.

So, for example, a new grad who has to pay off massive student loans and only has a BA may prove to be a poor fit for a professorship. But they could be an excellent fit for a well-paid Social Media Manager role that leverages their expertise in this space.

Alternatively, an experienced marketer who’s looking for work-life balance may not connect with a COO role at a big company but could be a great CMO at a small nonprofit.

By now, you should have narrowed down your list of potential titles to a relatively small list. To get all the way to a singular focus, there’s two strategies left - one online and one off.

The first technique involves returning to AI to get some homework. It turns out that ChatGPT and its brethren are great at making assignments - if you let them.

So feed your AI bot a prompt like the following:

What are three specific ways I can test my fit with each of the following roles: INSERT ROLES

This will often give you homework that’s highly actionable - whether it’s reading specific resources or trying out specific experiences.

Alternatively, you can take on two birds with a single stone by turning to LinkedIn. That’s because one of the most powerful techniques for applying to jobs is to get someone on the inside to refer you.

And so if you want to both learn about roles today and get ready to earn referrals tomorrow, reaching out to alumni from your alma mater can be a great place to start.

Here’s how it works:

  1. Start by searching for your university on LinkedIn

  2. Click the Alumni tab on the university’s page (this is the Alumni Tool I used to work on there!)

  3. Now filter for alumni who work in your field of interest - and maybe companies and locations that interest you, too

  4. Send a personalized connection request to the resulting alumni along the following lines:

Hi NAME,

I’m a fellow Wolverine/Spartan/etc. and I’m at a career crossroads. Specifically, I’m trying to decide whether to pursue your path. Would you be open to a 10-minute Zoom chat so I could learn from your journey?

Then, once you have a chat, you can ask them some of the questions we’ve already asked the AI (“What’s a typical day like for you? What kind of person tends to be really happy in this role? Does it give you a chance to leverage X skills or achieve Y goals?”). But this time, instead of just getting a generic AI answer, you can get specific insider info to better shape your decision.

But What If I Just Can’t Choose???

Ideally, you now have just a single job title to focus on. This not only will come in handy with your LinkedIn profile (since you only have one version to customize), but will also make your job search much easier because you won’t have to constantly switch back-and-forth between different stories and skills as you make resumes and prepare for interviews.

That said, it’s totally understandable if you just can’t choose between a handful of fascinating opportunities. In that case, just remember your poor recruiter on the other side of the screen.

They’re looking through thousands of resumes to find the handful of candidates who actually match the specific role they’re looking to fill. And so getting generic, one-size-fits-all resumes actually makes their lives easier - by making it easier to reject you!

So to avoid that fate, be sure to generate customized resumes, cover letters, and interview stories for each role in the next few chapters.

While it might seem like a pain in the butt to do so, in the age of AI-powered job searching, it’s actually more painful to settle for mediocre outcomes when you could have generated tailored applications in mere minutes.

Read on to learn how!


Want to get all my best AI-powered techniques, including:

  • Full prompts for every step of the hiring process - from finding your path to negotiating the offer

  • An interactive workbook - including a keyword scanner to measure the quality of your resume

  • My very own resume and cover letter templates - the exact same ones that earned me a job at Google

  • Free access to my own CareerCoachBot - an automated coach to help you find and win the best jobs

Then just grab Career Coach GPT on Amazon today!