Almost Timely News: 🗞️ How to Demonstrate Your AI Chops in Job Hunting (2026-07-26)

Almost Timely News: 🗞️ How to Demonstrate Your AI Chops in Job Hunting (2026-07-26) :: View in Browser

The Big Plug

👉 New book! 21 Use Cases of Generative AI For Marketers

Content Authenticity Statement

90% of this week’s newsletter was made by me, the human. You’ll see multiple outputs from Claude Opus 5 including a demo that I recorded with Claude’s speaking script. 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 Demonstrate Your AI Chops in Job Hunting

This week, an interesting question from Margie in our Analytics for Marketers Slack group that I thought I’d tackle: how would you demonstrate, to a prospective employer, your AI capabilities and skills?

It’s a given at this point that basic AI skills are nearly mandatory for knowledge work jobs, so in some ways it’s expected that you have them, in the same way you know how to use a web browser, a search engine, and a word processor.

So what would set you apart as a candidate, or at least reassure a hiring manager that you’ve got skills that are competitive with other candidates? This is a crowded marketplace where every candidate sounds the same, polished to a meaningless shine by AI tools to sound identical to everyone else. Every candidate is like a painting in a hotel room - polished, professional, inoffensive, fits in nicely, and completely unmemorable.

How do we solve this? With the one thing AI struggles with: specificity. Let’s dig in. As always, a disclaimer: while I’m using myself as the example in this issue, I’m in no way looking for employment - though Trust Insights is always looking for qualified clients! So I guess I am for hire in a sense, just not as a regular employee.

Part 1: Motivations

Following Katie Robbert’s 5P Framework by Trust Insights™, the most important of the 5Ps is Purpose: why are we doing something? In the case of the hiring manager, why are they hiring?

In the current workforce environment, you only make a hire for a critical need that you can’t fill with the staff you have or the agencies/contractors you work with. Hiring is costly, time intensive, and the consequences of a bad hire are far reaching, which is why the hiring process takes so long these days. It is genuinely the last resort of a manager a lot of the time.

Take a look not only at the job description of the position a company is hiring for, but all the other positions (if any) in the same department. Is there a pattern that you or your favorite AI can see? Is there a trend? Some websites are friendly enough that you can check an open jobs page in the Wayback Machine to see what past open jobs might have been listed.

If you’ve ever bought or sold a house, you know that listings often get taken down and relisted to appear new; the same thinking can apply to a role. If a company is having a hard time filling a role, there’s probably a good reason why.

And listings contain tons of information, some of it implicit, that becomes harder and harder for us to find as we stare at more and more listings that all start to read the same. How do we overcome this? With AI, of course.

Here’s how to think about this, as a candidate. Copy and paste all the job listings that are relevant and adjacent to the job you’re interested in - same department, same location, etc. - and paste to a plain text file, nothing fancy. Then go to your smart AI of choice and add the file plus a starter prompt like this (refine and revise it):

You’re a management consulting expert in the style of McKinsey/Bain/BCG. Included in this conversation are open jobs listings for {Company} that are a snapshot of what’s on their hiring portal right now. I’m a candidate for {Open Position} and I’ve attached my LinkedIn profile as a PDF {attachement}. My goal is to approach them with a novel, different perspective in my application by identifying not only what I’m qualified to bring to the role, but what genuine business problems I see adjacent to the role. Examine the job listings; what patterns, if any, do you see? What appear to be the real priorities, the real pain points that perhaps they’ve disguised in soft language to avoid tipping their hand to competitors? What are the upstream and downstream pain points here? What are the likely pain points and motivations of the hiring manager for this role? Draw whatever conclusions the data support, plus feel free to use your web search tools to investigate other parts of the company’s website or key competitors’ websites and job listings, to do this strategic analysis. If appropriate, consider common frameworks like SWOT, PESTLE, Porter’s Five Forces, BCG Growth Matrix, 5P Framework by Trust Insights™, and other common management consulting frameworks that could help shape a strategic lens around the role. Provide your analysis in Markdown format with URL citations as an endnote to all sources you used.

Now, obviously this might be overkill for a role. If you’re applying for front end cashier at your local grocery store, this is completely unnecessary. If, on the other hand, you’re applying for a knowledge work job - even a junior one - this might be a useful lens to use.

And I wouldn’t do this for every role you’re applying to - do this in advance of a phone screen or interview, or to build an enduring portfolio on your personal website (you have one, yes?) that that you can show off to prospective employers in that industry or space, regardless of the individual company.

Once you’ve got the motivations and strategy lens assessed, it’s time to dig into the role itself, and how AI applies to it.

Part 2: Job to AI

The next step is to figure out what in the job is exposed to AI - and how you might be a part of it. After all, a job that has high exposure to AI means that potentially you might get hired, only to get laid off a short time later (especially if the company has a leader who doesn’t know squat about AI and thinks ChatGPT can run everything).

At Trust Insights, we built a plugin and skill for this called Job to AI which is available in the Merch Store, based on our TRIPS Framework by Trust Insights. At its core, every task has 5 attributes that help us understand whether a task is suitable for AI or not; the Job to AI software automates this scoring process. So whether you use the free framework or the paid plugin, our goal is the same - to understand what tasks in a job are suitable for AI, and whether the task is automatable (meaning AI will consume it) or augmentable (meaning AI can help but a human fundamentally has to do it or review it).

If you’re applying for a job at a company, go and do a quick search for who that company’s peer competitors are and maybe an aspirational competitor, and then see if they’re hiring for a similar job. Gather up the job descriptions for that role across a few different companies, then run them through the Job to AI process. What you’ll end up with is a report of which tasks in that role are best suited for AI.

That right there is the meat and potatoes of Margie’s question. If you want to demonstrate your contributions in a role that show off your AI skills, these are the tasks that will be the “easy wins” or whatever overused business cliche you want to drop.

The obvious question is, do you know how to perform that task with AI? If the answer is no, then, as Katie said in last w