Understanding Your Audience

The Gen Z Perspective

Understanding how Gen Z thinks about feedback and AI is essential for effective communication. This generation brings unique attitudes shaped by growing up with technology—but that doesn't mean they automatically embrace AI.

How Gen Z Wants Feedback

Gen Z values direct, honest feedback delivered with authenticity. They prefer regular check-ins over annual reviews, and appreciate context about why feedback matters. They want to understand the "why" behind decisions and expect two-way dialogue rather than top-down criticism.

How Gen Z Views AI Use

Contrary to assumptions, Gen Z is actually skeptical and anxious about AI. They've grown up seeing AI's limitations and are wary of "AI slop"—generic, low-effort AI-generated content. They accept AI for routine tasks but strongly value human authenticity in meaningful interactions.

Key Attitudes and Best Practices +

Understanding Gen Z's Mindset

Skeptical but Open: Gen Z doesn't automatically trust technology. Trust must be earned through consistent, authentic interactions.

AI for Low-Stakes Tasks: They're comfortable with AI handling administrative work, scheduling, and routine communications—but not replacing human judgment on important matters.

Authenticity is Non-Negotiable: They can spot inauthenticity quickly. Any communication—AI-assisted or not—needs to feel genuine and caring.

Best Practices

Do This	Avoid This
Be transparent about AI use	Pretending AI content is fully human-written
Keep human effort visible in outreach	Sending obvious mass AI-generated messages
Model AI as augmenting skills	Positioning AI as a replacement for learning
Continue teaching foundational skills	Assuming AI makes human skills obsolete

Key Takeaway

When working with Gen Z, position AI as a tool that enhances your ability to connect authentically—not as a shortcut that replaces genuine human engagement.

The Superpowers

What AI Does Exceptionally Well

Despite valid concerns about AI, it has genuine superpowers that can help bridge communication gaps—including with Gen Z. The key is knowing what AI excels at and using it strategically.

Tone and Empathy

AI excels at adapting communication style to different audiences. It can help you strike the right balance between professional and approachable, formal and friendly.

Judgment

AI can provide perspective on decisions and tradeoffs by considering multiple angles simultaneously. It surfaces considerations you might miss.

Reorganizing

AI is excellent at restructuring information for clarity and impact. It can take disorganized thoughts and transform them into coherent narratives.

Understanding Nuance

Modern AI handles nuance, context, and ambiguity remarkably well. It can read between the lines and navigate complex situations.

Practical Examples of Each Strength +

Tone and Empathy Example

Your input: "Rewrite this feedback for a Gen Z team member who's struggling with deadlines. Make it direct but supportive."

Judgment Example

Your input: "I need to choose between promoting an internal candidate or hiring externally. What are the tradeoffs I should consider?"

Reorganizing Example

Your input: "Here are my notes from three meetings about the project. Organize these into a clear status update for leadership."

Understanding Nuance Example

Your input: "The client said 'we'll think about it' after our proposal. Help me interpret this response and suggest next steps."

The Fix

Context is Everything

Context is the difference between thoughtful and lazy AI use. When you get a generic, sloppy AI response—what went wrong? Usually, you expected AI to read your mind. It can't. But give it proper context, and everything changes.

The Big Shift: Modern AI can now handle very large amounts of information (called "tokens"). This means you can give it extensive context—entire documents, multiple files, detailed background—and it will use all of it to give you better responses.

The Mind-Reading Problem

When AI gives you bad output, ask yourself: "Did I expect AI to know things I never told it?" Generic prompts produce generic results. Specific context produces specific, useful results.

From Oracle to Collaborator

Stop thinking of AI as a magic oracle that should just "know" what you need. Instead, treat it as an informed collaborator. The more you share about your situation, goals, and constraints, the better it can help.

See the Difference: With vs. Without Context +

No Context

"Write an email about the project update."

Result: Generic, vague email that doesn't match your voice, audience, or situation.

With Context

"Write a project update email."

+ Audience: Executive team
+ Project: 3 weeks behind
+ Reason: Vendor delays
+ Good news: Testing +40%
+ Tone: Confident, honest
+ Length: 3-4 paragraphs

Context Checklist

Who is the audience?
What are you trying to accomplish?
Why does this matter?
What constraints exist (length, tone, format)?
What background would a smart colleague need to help you?

The Method

Three Steps to Thoughtful AI

Here's a systematic approach to working with AI that consistently produces better results. Master these three steps and you'll avoid the "AI slop" that Gen Z (and everyone else) can spot instantly.

01

Context

Provide background, constraints, audience, and goals. This is the foundation—without it, AI is just guessing. Include relevant documents, prior conversations, or data that will help AI understand your situation.

02

Prompt

When you need structure, use a thoughtful prompt. Better yet: ask AI to write the prompt for you! Describe what you're trying to accomplish, and let AI help you formulate the best way to ask.

03

Output

Expand beyond email! Think bigger: scripts, infographics, action plans, structured analyses, and even autonomous AI agents that can execute multi-step workflows.

Step 1 Deep Dive: Context Best Practices +

Context is the most important step and where most people underinvest. Here's what to include:

Upload Documents: Rather than summarizing, upload the actual files. Modern AI can read PDFs, spreadsheets, and documents directly.

State Your Goal: "I want to..." is more useful than "Write me a..."—it helps AI understand what success looks like.

Share Constraints: Time limits, format requirements, political sensitivities, things to avoid—all of this shapes better output.

Describe Your Audience: Their knowledge level, what they care about, their likely objections or questions.

Step 2 Deep Dive: The Prompt Generator Trick +

Instead of struggling to write the perfect prompt, ask AI to help you write it:

Meta-prompt: "I want to create a presentation about our Q3 results for the board. Help me write a detailed prompt that will get me the best possible outline and talking points. Ask me any clarifying questions first."

AI will ask you targeted questions about audience, key metrics, narrative angle, length, and more. Then it will generate a comprehensive prompt you can use—often better than what you'd write yourself.

Pro Tip

Save good prompts that work well for you. Build a personal library of prompts for recurring tasks—feedback conversations, status updates, meeting summaries, etc.

Step 3 Deep Dive: Output Types Beyond Email +

Most people only ask AI to write emails. But AI can create many types of output:

Output Type	Use Case
Scripts	Difficult conversations, presentations, video content
Infographics	Visual summaries, process diagrams, comparison charts
Action Plans	Project breakdowns, implementation roadmaps, checklists
Analysis Frameworks	Decision matrices, pros/cons, stakeholder maps
AI Agents	Autonomous workflows that execute multi-step processes

Tools

AI Platforms and Tools

Different AI platforms have different strengths. Here's a guide to the major options, how to use each one, and when to choose which.

Google NotebookLM

Context-first AI — No web search

▼

What it is: NotebookLM is Google's AI research assistant that only uses sources you provide. It doesn't search the web—forcing you to practice context-first AI use.

Why It's Great for Learning

Because NotebookLM can't access external information, you must upload your context. This builds good habits and ensures responses are grounded in your actual materials.

Key Features

Upload PDFs, Google Docs, websites, YouTube videos
Chat interface for Q&A about your sources
Audio overview feature (creates podcast-style summaries)
Automatically cites which source each answer comes from

Getting Started

Go to notebooklm.google.com
Create a new notebook
Upload sources (click "+" to add PDFs, docs, links)
Start asking questions in the chat

NotebookLM Tutorial Audio Overview

ChatGPT

OpenAI — Most popular AI assistant

▼

What it is: OpenAI's flagship AI assistant. Versatile, widely used, and constantly improving. Available in free and paid versions.

Key Features

GPTs: Custom AI personalities with pre-set instructions
File uploads: Analyze documents, images, and data
Web browsing: Search the internet for current info
Image generation: Create images with DALL-E
Code interpreter: Execute Python for data analysis

Getting Started

Go to chat.openai.com
Create a free account
Start chatting—use the paperclip to upload files
Explore GPT Store for specialized tools

Beginner Guide Custom GPTs

Claude

Anthropic — Thoughtful AI assistant

▼

What it is: Anthropic's AI assistant, known for nuanced responses, strong writing ability, and handling long documents. Excellent at analysis and complex reasoning.

Key Features

Projects: Organize work with persistent context
Large context window: Analyze very long docs (200K+ tokens)
Artifacts: Interactive documents, code, visualizations
Strong writing: Nuanced, professional content

Getting Started

Go to claude.ai
Create an account
Start a new chat or create a Project
Add files by clicking the attachment icon

Claude 101 Projects

Google Gemini

Google — Integrated with Workspace

▼

What it is: Google's AI assistant, deeply integrated with Gmail, Docs, Sheets, and other Google services.

Key Features

Gems: Custom AI personas with specific expertise
Google integration: Access Gmail, Drive, Workspace
Image understanding: Strong multimodal capabilities
Extensions: Connect to YouTube, Maps, Flights

Getting Started

Go to gemini.google.com
Sign in with your Google account
Enable extensions for your Google services
Create Gems for specialized tasks

Complete Guide Creating Gems

Microsoft Copilot

Microsoft — Built into Office 365

▼

What it is: Microsoft's AI assistant, integrated into Windows, Edge, and Microsoft 365 apps.

Key Features

Office integration: AI in Word, Excel, PowerPoint
Email drafting: Compose and summarize in Outlook
Meeting summaries: Recap Teams meetings
Enterprise-grade: Security and compliance

Getting Started

Access at copilot.microsoft.com
Or look for the Copilot icon in Office apps
Use in Edge browser via sidebar
Requires M365 license for full integration

Overview In Office

Quick Comparison: Which Platform to Choose? +

If you need...	Use...
Grounded research from specific sources only	NotebookLM
General assistance with web access	ChatGPT or Gemini
Long document analysis or nuanced writing	Claude
Integration with Google Workspace	Gemini
Integration with Microsoft 365	Copilot
Custom AI personas for specific tasks	ChatGPT (GPTs), Gemini (Gems), or Claude (Projects)

Applications

Real-World Use Cases

Adding context lets you use AI to consider perspectives and frameworks you might not think of on your own. Here are practical examples combining different tools and approaches.

01

Bridging Generational Gaps with Gen Z

Chatbot + Upload

Upload context about Gen Z attitudes and communication preferences, then ask AI to help you craft communications that will resonate.

Example prompt: "Based on the Gen Z research I've uploaded, help me rewrite this feedback email to a junior team member. I want to be direct but also show that I genuinely care about their development. They value authenticity—help me avoid sounding corporate or condescending."

02

Personal Career Audit: Three Lenses Framework

AI Agent

Use Dylan Davis's "Three Lenses" framework to get multi-perspective career advice. Give AI context about your situation and ask it to analyze from three different viewpoints:

Executive Coach

What's the goal?
What's the reality?
What's the gap?

Economist

What's the tradeoff?
What are you giving up?
What's the ROI?

Provocateur

What assumption is wrong?
What breaks trust?
What's contrarian?

03

Getting Things Done (GTD) Workflow

Gem + NotebookLM

Use the GTD methodology with AI to organize projects and next actions.

GTD Quick Reference

Capture: Get everything out of your head
Clarify: Decide what each item means
Organize: Put items where they belong
Reflect: Review regularly
Engage: Do the work with confidence

04

Combining Multiple Frameworks

Claude Project

The real power comes from combining frameworks. Use Claude Projects to create a persistent workspace with multiple frameworks loaded as context.

Combined prompt: "I need to have a development conversation with my Gen Z direct report. Using the Gen Z communication insights, the executive coach lens from the Three Lenses framework, and GTD principles for defining next actions—help me structure this conversation and prepare talking points."

More Framework Combinations to Try +

Scenario	Frameworks to Combine
Strategic planning session	SWOT Analysis + Three Lenses + Scenario Planning
Team retrospective	Start/Stop/Continue + Psychological Safety
Product prioritization	RICE Framework + Jobs-to-be-Done + User research
Difficult conversation prep	NVC + Gen Z preferences + Radical Candor
Personal productivity audit	GTD + Eisenhower Matrix + Energy Management

Safety

Essential Guardrails

Thoughtful AI use requires knowing when and how to apply appropriate guardrails. Here's what to keep in mind as you integrate AI into your work.

Always Review Before Sending

AI output is a draft, not a finished product. Read everything AI produces before sharing it. Make sure it sounds like you.

Verify Facts and Claims

AI can hallucinate—confidently stating things that aren't true. Double-check any specific facts, statistics, or claims.

Be Transparent When Appropriate

With Gen Z especially, don't pretend AI-assisted work is 100% human-created. Authenticity matters.

Keep Building Human Skills

AI should augment your abilities, not replace foundational skills. Continue developing your writing and critical thinking.

Quick Checklist Before Sending AI-Assisted Work

Have I read the entire output?
Does it sound like me (or appropriate for the context)?
Are all facts and claims accurate?
Would I be comfortable if the recipient knew AI helped?
Have I added my own insights or personalization?