Almost Timely News: 🗞️ How To Land A Job Using AI (2025-08-31)

Plus what NEVER to do with AI and interviews

Christopher S. Penn

Aug 31, 2025

Almost Timely News: 🗞️ How To Land A Job Using AI (2025-08-31) :: View in Browser

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

Last week, we covered the first part of the job search process, enabling you to hunt jobs faster, apply to them in a more focused way, and hopefully get your foot in the door.

This week, let’s tackle the obvious question: okay, I got my foot in the door, now what? How do I navigate the process of interviewing?

Fortunately and completely unsurprisingly, generative AI can be a big help here - but it can also go disastrously wrong if you execute poorly. Let’s give you some tools and tactics to do it well.

Disclaimer: you'll see me doing this process live in the video and talking through it. I'm not looking for work. I am available for hire as a consultant through my company, Trust Insights, but I am not available as a candidate for employment.

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

Last week we looked at the process of job applications but we neglected one very important part: the infrastructure around the job search. I said that job search is the worst B2B sales job ever, and that’s true in more ways than one. Because it’s B2B sales, you need to have B2B sales infrastructure in place.

Like what? Like a CRM. Now, you don’t need a full CRM by any means; a spreadsheet will do just fine for the most part. But you want to track the major components tracked in any CRM. That means:

People: who are the people, if you know, you applied to?
Companies: what companies did you apply to?
Opportunities: what jobs did you apply to?

You could put this all on one sheet, with different columns, but the key is to keep track of what you’ve done so that you can follow up. It’s been said, quite accurately, that 90% of sales is good followup.

Here’s the process I recommend: using the voice memos on your app, recite a basic script at the end of each job search session (whether that’s an hour of focused work or an entire day):

Today is {the date}. I applied for {job title} with {person if known} at {company}

Recite the things you applied for over and over again, then take the transcript from your voice memos app (or any other equivalent transcription service) and load it into the generative AI tool of your choice. Feed it the transcript along with this prompt:

Transcribe the attached transcript into a tab-separated table with 4 columns. Column 1 is the date. Column 2 is the company. Column 3 is the job title. Column 4 is the person, and may or may not be included. Ensure your output is a tab separated table. If you are unclear about any given piece of data, ask me questions to clarify.

Why this specific prompt? Almost every piece of spreadsheet software copies and pastes in tab-separated values, so by having your AI tool transcribe in that format, it makes it fast and easy to copy and paste. Yes, if you are more data and tech savvy, you can export CSVs and do joins and all that fancy stuff, but that’s honestly just a distraction from the job applications process. The goal is to free up as much time as possible for more job applications.

Besides a CRM, be sure you have all the materials from last week's issue - your CV, your durable skills inventory, your personality analysis, job descriptions and job links that you applied for, etc. - you want to have all the pieces ready to go. If you don't have that information organized, take a few moments to do that now.

Part 2: Followups

If you did a good job keeping track of all the data, then generating follow-ups should be relatively straightforward. Using the job descriptions from last week, you’ll re-use your GPT/Gem/Project that has your CV and durable skills inventory, the job description, and whatever other data you used to tune and tailor your CV.

Use this straightforward prompt:

I’ve already applied for this job so my CV and cover letter are all set. Using the background knowledge you have and the data I provided, I need help crafting a followup email to the company/hiring manager. Read through the job description I’ve attached and infer what the highest likely priority is of the hiring manager or company, the thing that they’re probably looking for most in the candidate. Be sure to consider both hard skills and soft skills (durable skills). Think through how my CV and durable skills inventory can address that critical need. Then write a single paragraph followup email I can send to the company using the Reframe step of Dixon and Adamson’s Challenger Sales Methodology. Here are your three cardinal rules to follow for this task, in order of priority: 1, always be truthful and factually accurate. Never misrepresent facts. 2, write in the active voice, using my durable skills inventory and personality traits to guide you. 3, be as persuasive as you can be while adhering to other constraints.

Like any good sales, we’re tailoring our followup outreach, calling specifically on the Reframe step of the Challenger Sales Methodology, which takes a common problem and helps reframe it so that we are the obvious solution.

Could you set up a custom GPT or a gem separately from this one that was made mostly for tuning resumes and cover letters that we did last week? Yes, absolutely. And if you're gonna be doing a lot of follow ups, it's probably a good idea to do that. I did that for convenience for this week's newsletter.

After you do a session of follow-ups, create a new column in your spreadsheet called Followup 1, and put the date in. Then create a second column next to that called Next Followup and add a simple formula that adds 7 days to the Followup 1 date, indicating your next date to followup.

The set up the process for columns to have a total of 3 follow-ups; modify the prompt as well for follow-ups 2 and 3 accordingly.

Part 3: The Interview

Interviews take a variety of forms, from phone screens to multi-person sit downs, depending on the job, the company, the seniority, and frankly how risk averse a company is. It’s not uncommon for even mid level roles to have multiple rounds of interviews now because companies are so risk averse to making a bad hire (and yet somehow still manage to do that quite often).

Interview prep is often the hardest part of the process because many people don’t do it well. And the reason people don't do it well is because they don't do it often. It's not a skill that you do a lot. It's a skill that hopefully you use relatively infrequently.

Preparing for an interview is part sales pitch, part therapy. Your role is to be just as much an active listener as it is to explain to a company why they should hire you; the rule in sales forever has been that you have 2 ears and 1 mouth and should use them in that proportion.

Our job is twofold. First, we need to anticipate all the kinds of questions we could be asked and have answers prepared for them. Second, we need to actually practice the interview process itself, ideally with the kind of person that we might be interviewing with.

So here’s how we’ll do this. Assuming we have a genuine interview opportunity, we want to knock their socks off. This process that we're going to walk through is extensive. It'll take time - that's why we don't do it until we get to the interview stage. There's no reason to do this much work for an application alone without stronger intent or interest fro the company.

We need some background information about the company. We have the job description already, so now we need to add in data that will backfill the context around the interview. Remember that companies don’t make hires unless they have a critical need. Hiring is time consuming, resource intensive, and very expensive - so if a company is hiring, they really, really need the help for a reason. We need to understand that reason.

In the AI tool of your choice that has Deep Research capabilities, get the job description data from part 1 handy and provide that along with this prompt:

We need to understand the greater context of why a company is hiring for the attached position. What are the macro reasons this company needs to hire for this position now? Use the job description to extrapolate what their priorities are and how it fits into the bigger picture at the company. What unstated needs will this job role also be expected to contribute to? What are the company’s goals, and how does the job description support those goals? What did the hiring manager likely omit or forget about in the job description that would support those goals? What challenges or troubles in the marketplace or industry is the company facing? Use the company’s website plus credible publications such as trade publications, industry news, company research sites like D&B or Crunchbase, research papers, as well as hiring portals like Glassdoor, to understand what’s really happening at the company. Restrict your sources to anything published in the last year, so after 2024-09-01.

What we’re doing is building an understanding of the company itself, and how the job fits into the company’s big picture - because knowing what’s going on will let us anticipate questions better as well as ask better questions.

Wait for the Deep Research report to complete, then download the contents.

Once you’ve got the report ready, head back into your regular AI tool and give it a prompt like this. Be sure to include your CV, your durable skills inventory, the job description, and the research report.

I’m about to interview for the attached job description. I’ve provided my CV and durable skills inventory, plus background information on the hiring company. Let’s generate the 10 most likely interview questions I’ll be asked in the interview, based on the job description, the background information, and my CV. Here are your three cardinal rules in order of importance: first, rely most heavily on the job description itself and my CV. Second, when the primary documents don’t provide enough information or context, refer to the background information. Third, never fabricate information; if you need more information to complete the task, ask me for it.

Let it generate the top 10 interview questions. Save those to a document with a clear heading like MOST PROBABLE INTERVIEW QUESTIONS.

When you're doing documents in any word processor that you're later gonna use in AI, make sure that you're using the built in structural things like headings and subheadings and stuff, because that will help AI parse it later. AI will get a copy of the structure of the document and will understand where sections begin and end. So don't like modify fonts and things, just use the built in headings. You will save yourself so much time later on down the road.

In the same chat, follow up with this prompt:

Next, let’s build 10 less likely interview questions that would naturally cascade from the answers I’m likely to give to the first set of questions. What less likely, more challenging questions am I likely to be asked in the interview? Where would the hiring manager or interviewer challenge me on my CV or durable skills? Generate 10 challenging interview questions. Here are your three cardinal rules you must follow for this task, in order of importance: first, rely on the documents I uploaded. You may need to draw from the background information more. Second, take a neutral or even slightly confrontational tone in the questions, as the purpose is to challenge me, not placate or praise me. Third, never fabricate information; if you need more information to complete the task, ask me for it.

Let it generate the more challenging interview questions. Save those to the same document with a clear heading like MORE CHALLENGING INTERVIEW QUESTIONS.

What we're effectively doing here is having the AI discount the questions it already asked. We want to eliminate those from consideration so we can get to a more unique set of questions.

Next, in the same chat, follow up with this third and final prompt:

Let’s build 10 of the most challenging questions that would naturally cascade from the answers I’m likely to give to the first two sets of questions. What are the most challenging questions I am likely to be asked in the interview? Where would a hiring manager really press me on how good a fit I am for this position or why I might not be right for this role? What doubts would they have that they’d express as questions? Generate 10 of the most challenging interview questions. Here are your three cardinal rules you must follow for this task, in order of importance: first, rely on the documents I uploaded. You will definitely need to draw from the background information more to devise the most challenging questions. Second, take a confrontational, adversarial tone in the questions, as the purpose is to deeply challenge me, not placate or praise me. Third, never fabricate information; if you need more information to complete the task, ask me for it.

Let it generate the final set of questions. Save those to the same document with a clear heading like MOST CHALLENGING INTERVIEW QUESTIONS.

Once you’ve got all the questions, it’s time to study. Sit down with the beverage of your choice and the questions, and the voice memos app, and record your VERBAL answers to the questions. It’s very important that you do this by voice and not writing or typing, because you want to simulate the actual act of answering the questions as you would in an interview.

Record your answers to the questions. I would suggest doing them in blocks - record the obvious questions and answers first, then the medium difficulty, then the hard questions. As you do this, read each question aloud first and then answer it. This will be important in the next part.

Part 4: Interview Tune Up

The next step should be absolutely no surprise. Going back to your AI of choice, start a new chat. In the new chat, upload your CV, durable skills inventory, the job description, company background information, and the transcript of the questions and answers for the obvious questions (save the medium and hard questions for later). Ask the AI the following:

I’m practicing interviewing for the attached job. I’ve included information about the company, the job, my CV, my background, and the interview questions and answers I’ve given. You’ll take on the role of a professional recruiter to evaluate my interview questions. Evaluate me on four criteria for each question and my answer: first, what did I answer well? Second, what did I answer poorly, where I need to improve my answers? Third, what did I miss or omit from my answers? Fourth, what was unnecessary in my answer? Present your results as a markdown list by question with your evaluations as bullet points underneath each question. Here are your three cardinal rules you must follow for this task, in order of importance: first, be objective and critical. Placating or pleasing me harms my ability to interview well, and you must avoid harming me. Evaluate in a neutral point of view and an objective, critical, thoughtful tone. Second, be thorough in your answers, so that I have concrete details I can use to improve. Third, never fabricate information; if you need more information to complete the task, ask me for it.

Read and review the answers! Take notes. Understand what it thinks you missed.

Provide the second transcript along with the same prompt (the AI model will understand) and repeat the process, and then again for the third transcript. You want to do this in stages so that the model doesn’t get overloaded trying to process 30 questions and answers.

Once that’s done, then prompt with this:

Based on the entire conversation, and all the questions and answers I’ve given, evaluate my overall interviewing skills. What consistent things do I get right? What consistent things do I get wrong? What consistent things do I miss? What consistent things are unnecessary? Evaluate me as a candidate overall, independent of any one particular question, so I can improve my interviewing skills. After you provide your evaluation, give me the top 3 things I need to work on to improve. Here are your three cardinal rules you must follow for this task, in order of importance: first, be objective and critical. Placating or pleasing me harms my ability to interview well, and you must avoid harming me. Evaluate in a neutral point of view and an objective, critical, thoughtful tone. Second, be thorough in your answers, so that I have concrete details I can use to improve. Third, never fabricate information; if you need more information to complete the task, ask me for it.

Take the evaluation and read through it. Understand it, and then put the top 3 items into action.

How? This is where things get fun. For all the major paid accounts like ChatGPT, Gemini, and Claude, the mobile apps offer voice mode. Voice mode allows you to speak to the AI in real time, asking and answering questions, having conversations. Lots of people use these but forget one key thing about them: they operate in the context of the chat.

Why is that a big deal? Because instead of just turning it on and giving it a naive prompt like “help me interview fo this job”, you can start the conversation in text and THEN turn on voice mode. Which means we can provide all our background information to simulate the interview as closely as we can. This is a big deal, and something almost everyone gets wrong with voice mode.

In the mobile or desktop app of your AI service (depending on what’s supported), you’ll want to have all your background information ready. Mobile apps tend to work best with cloud documents or single files, so it’s probably a good idea to copy paste your CV, durable skills inventory, the job description, the 30 interview questions (NOT your transcripts or answers), and the company background information into one document, like a OneDrive doc or a Google Doc. That way, there’s less administrative work to get set up.

Paste this at the TOP of the document with a big heading called SYSTEM INSTRUCTIONS:

You’ll be roleplaying the hiring manager for the job description in this document at the company in the document. My CV and background information is also provided, as well as the company’s background information. I’ve also provided a selection of up to 30 interview questions. You’ll be helping me practice interviewing for the position. Using the interview questions I’ve provided as a guide, start with an obvious question and then dig deeper, simulating a hiring manager who wants to find the right fit for the job and is looking for a reason to weed me out. Use the challenging and most challenging questions as a guide, but feel free to ask related questions. The interview should last for a total of 8 questions. At the end of the interview, draft an assessment of what I answered well, what I answered poorly, what I answered incompletely or avoided, and what I answered unnecessarily or where I lost focus. Here are your three cardinal rules you must follow for this task, in order of importance: first, be objective and critical, even adversarial where it’s contextually appropriate. Placating or pleasing me harms my ability to interview well, and you must avoid harming me. Second, be thorough in your answers, so that I have concrete details I can use to improve. Third, never fabricate information; if you need more information to complete the task, ask me for it.

Be sure to save it as a PDF that you can get onto your mobile device.

Then start a new chat in the mobile app, attach the document to it, and give it the simple prompt:

Follow the system instructions in the attached document strictly.

What should happen is that it will read the document, understand the context, and begin the mock interview process.

Interviewing well is a matter of practice, and generative AI allows you to practice as much as you want. You can modify the instructions to be as confrontational as you want, or give it a specific persona, especially if there’s a certain kind of person you know you don’t interview well with. You can even give it specific biases, something like “Bob has a latent bias against Koreans, and I am Korean. This should color the tone and style of his questions, helping me to interview successfully even if someone has a latent bias against me.”

Save the chats from these mock interviews! They’ll be useful at some point, partly as a reference to help you improve your interview skills, and partly to see how closely the actual interview adheres to your prep.

Part 5: The Clincher

We now arrive at the final part of our process, and the part that drives me up a wall when I’m interviewing people. This is the dreaded question, “what questions do you have for me?”

The worst possible answer to this interview question is “I don’t have any.” Hands down, that’s a deal killer UNLESS you’ve been asking questions all along - and even then, you should have a closer question that shows you did your homework.

And you have. Boy have you. Start a new chat. Take your CV, latent skills, job description, company background, and the transcripts from your practice interviews, and give your favorite AI this prompt:

Hiring managers and interviewers often ask the question ‘What questions do you have for me’ at the end of the interview. This question is partly informational and partly a test to see if the candidate has been paying attention or done their homework on the company. Based on all the background information I’ve provided, the job description, and my answers to probable questions, let’s devise a list of 10 questions for me to ask the hiring manager. We must avoid questions that have been answered in the job description or in the company background, and instead infer second order questions from the data. What questions would help me demonstrate that I have the skills and aptitude to not only satisfy the role, but help the hiring managers and the company make progress towards their overall goals? What information is not present in the information I’ve provided that would be useful for making those inferences? What questions will help me understand how my hard skills and soft/durable skills fit into the needs of the company and the role, or critically might highlight that this job isn’t for me? What questions would tease out the actual motivations of the hiring manager or their latent worries and problems? Here are your three cardinal rules you must follow for this task, in order of importance: first, rely most heavily on the job description itself and my CV. Second, when the primary documents don’t provide enough information or context, refer to the background information. Third, never fabricate information; if you need more information to complete the task, ask me for it.

What should be produced is a comprehensive list of non-obvious questions, questions that indicate you’ve given some thought to everything discussed, that you’ve anticipated and planned, that you’ve done your homework. Due diligence in the interview process hints at due diligence in the role itself.

Have this list of questions present during the interview, and save at least half of it for the end.

Part 7: Wrapping Up

The key thing to remember when interviewing is that you’re selling a solution to a problem the hiring manager has. Unconsciously or consciously, the hiring manager is asking themselves three fundamental questions:

Is this person going to make me look good or bad?
Is this person going to take things off my list or add to them?
Is this person someone I want to spend any amount of time around?

These are human questions, selfish questions that we all have as hiring managers, even if we don’t vocalize them or honestly admit them. When we hire, we hire someone to make our problems go away, not cause more of them. A bad hire is worse than no hire, even though it might not feel like it in the short term.

Job hunting is B2B sales, and what we’ve done in this issue of the newsletter is take proven B2B sales processes and apply them specifically to the interview process, which is the sales pitch.

I’ll end on a final note of what to absolutely, positively never do in a job interview, because this happened to me recently. We’ve used a lot of generative AI in this process to prep for interviews and do our very best. What you must never, ever do is use AI during the interview itself. There are tools out there that can run during a Zoom or phone call, recording, transcribing, and providing suggested answers using generative AI.

These are terrible for a couple of reasons. First, these tools tend to help you misrepresent yourself, letting you answer questions that you don’t have the answers to in real life. A clever interviewer can tell in relatively short order whether you’re using one of these tools because AI, in the realtime context, doesn’t do well at filtering down to what you actually know.

You might pass the phone screen or initial interview like that, but then in either an in-person interview or the actual job, you’ll get busted - and that is ruinous to your reputation.

Second, if you do use these tools and end up misrepresenting yourself, when it comes time to do the actual job, you’re pretty much screwed. Unlike regular sales, where the salesperson doesn’t have to provide service to the account, you are both the salesperson and the product, and if the product doesn’t live up to its billing, everyone is worse off. That’s why you see so many clauses in my prompts about being factual and honest. AI makes it easy to lie, but no lie is sustainable in the long run.

When I was interviewing a candidate on behalf of a client, one of their answers immediately sparked suspicion that they were using a real-time AI tool. Their answer was correct but uncommon, a feature I had built into the question to mislead AI. A human wouldn’t have picked up on it. So I asked a followup question:

“What’s your favorite kind of sandwich?”

Their answer? “I’d probably go with something classic like a turkey with avocado on sourdough. It combines the best texture and flavor - savory, creamy, with a little crunch.”

Guess who that sounds like?

Yup. They literally read the response given by an OpenAI model in their interviewing copilot. Unsurprisingly, I recommended to the client that they never, ever hire this candidate, and to inform the recruiter that sent the candidate along that the candidate was highly problematic and likely misrepresenting themselves to all the companies the recruiter had sent them to.

Don’t do that.

Use AI to challenge you, not to sit in for you. Because if AI can answer all the questions on the interview, why would anyone need to hire you in the first place?

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ICYMI: In Case You Missed It

This week, an absolutely killer episode of the Trust Insights livestream as we wrote a book using generative AI. Watch it for step by step explanations of how we turned existing content into a 65,000 word business book.

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Events I'll Be At

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Marketing Profs Working Webinar Series, September 2025
SMPS, Denver, October 2025
Marketing AI Conference, Cleveland, October 2025
MarketingProfs B2B Forum, Boston, November 2025

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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

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