I've Talked to Hundreds of Companies About AI & Jobs: Here's The Jobs Guide No One is Writing (+ Prompts)

I had a conversation three weeks ago that I can’t shake.

A product manager with eight years of experience—someone who’d shipped products at scale, navigated reorgs, built teams—looked at me and said: “I know I need to demonstrate I’m using AI effectively. I just don’t know what that actually looks like in practice. Do I need to become an AI expert? Do I rebuild my resume around it? What do I actually DO?”

She wasn’t alone. Over the past six months, I’ve had nearly identical conversations with junior engineers trying to move beyond execution work, with mid-career specialists wondering if their domain expertise still matters, with senior leaders worried the grace period on AI adoption is shorter than they think.

Here’s what makes this urgent: the gap between what companies say publicly and what they’re actually doing is massive. Publicly, they’re talking about “AI transformation” and “upskilling everyone.” In closed-door strategy sessions, they’re asking different questions: “Who can we replace? Who’s demonstrating they can do more with AI? Who’s stuck in production mode?”

The people I talk to know this. They’ve read the positioning think pieces. They understand the stakes. They can read between the lines.

But when I ask “what are you actually doing differently?” I get the same answer every time: “I’m using ChatGPT more” or “I’m trying to stay current on tools” or “I’m not really sure.” That gap—between knowing positioning matters and knowing what to actually do about it—is why this guide exists.

You can understand that problem-solving beats production work. You can recognize that domain expertise needs AI amplification. You can know that strategic judgment is your differentiator. But knowing what matters and demonstrating it are two different things.

This guide gives you both.

First, the strategic framework—the honest assessment of where juniors, mid-career professionals, and seniors actually sit in this transition, based on what companies tell me privately.

Then, the tactical playbook—specific exercises, prompts, and positioning frameworks you can use this week to demonstrate value at your career level.

Here’s what you’ll get:

• Reframing exercises that shift you from production to problem-solving mode—stop looking like a task executor and start demonstrating you understand business problems. Includes the specific questions to ask before starting work, the language to use when presenting results, and how to document this shift for performance reviews. Juniors use this to reposition, seniors use it to show execution capability.

• Domain expertise mapping—prove your accumulated knowledge matters in an AI world by showing what you know that can’t be learned from ChatGPT. Includes exercises to separate your learnable skills from your deep expertise, plus specific actions that make your domain knowledge visible to managers and interviewers. Essential for mid-career, but helps everyone understand where differentiation actually lives.

• Strategic judgment demonstrations—make years of experience visible by showing what AI analysis misses and why your pattern recognition matters. Includes worked examples of catching what models overlook, language for positioning experience in interviews, and practical adoption plans that don’t require you to become an AI expert overnight. Critical for seniors, but juniors benefit from learning how to demonstrate judgment early.

• Positioning language that doesn’t require expertise you don’t have—talk about your AI work in performance reviews, interviews, and internal conversations without sounding like you’re either clueless or overselling capabilities. Includes specific phrases that demonstrate strategic value and scripts for common questions like “how are you using AI?”

• Before/after frameworks that prove AI makes you more valuable—document productivity gains with actual numbers, show how you verify AI outputs, and demonstrate that your workflows are reusable by others. Turns “I use ChatGPT” into concrete proof of multiplied impact.

• Working prompts you can use with AI—6 structured prompts that apply these frameworks to your actual job, generating positioning language for your specific situation and creating action plans you can execute this week.

What you won’t find is generic advice about “staying current” or “being adaptable.” You’ll get frameworks that reflect what’s actually happening in strategy meetings, not what’s being said in press releases. The strategic analysis explains why your position matters. The tactical guide shows you how to act on it.

I created both together so you’d have a map of the territory and clarity on the path you want to take.

Q: Nate, why do this as one guide with Juniors, Mid-Level, and Seniors?

A: It’s useful to read tactics from all three levels regardless of where you sit. Juniors benefit from demonstrating strategic judgment that looks senior. Seniors need to show they can execute with AI tools like juniors do. Mid-career professionals pull from both directions depending on the situation. The boundaries aren’t rigid categories you slot into—they’re a toolkit you draw from based on what you need to prove in any given conversation, review, or interview. Understanding all three levels means you can deploy the right positioning for the context, not just your job title.

And with that, let’s dive in!