AI Toolkit | Hey Aspiring Leaders

AI Prompt Toolkit for Aspiring Leaders

Smart prompts. Stronger thinking. Sharper leadership.

These prompts were crafted for real work... real growth. I want to help leaders think more clearly, communicate more confidently, and grow with intention.

Whether you're experimenting with AI for the first time or looking for ways to lead more effectively, these prompts are designed to support real leadership moments—from writing stronger emails to designing your own growth plan.

You’ll find two categories:

✓Quick Prompts: immediate, copy-and-paste value

✓Coaching Prompts: guided interactions that help you think and plan like a leader

Each prompt includes a follow-up challenge to reinforce your learning. This is more than productivity—it’s a practice.

Quick Prompts for Confidence

Perfect for first-time AI users or moments when you just need a lift, a nudge, or a quick win. These prompts help you communicate with clarity and confidence—right now.

✨ Humanize My Writing

Prompt:
"I have a piece of writing that sounds too polished or "AI-generated." I want to adjust the tone to sound more natural and human while keeping the core message intact.

Please rewrite this with the following adjustments:

• Vary sentence length: Mix short, punchy sentences with longer, more complex ones. Avoid the monotonous rhythm that screams AI.

• Add conversational elements: Include phrases like "Here's what I've learned," "Look," "And honestly?" or "But here's what I'm learning" — the kind of connective tissue real people use.

• Remove corporate speak: Replace phrases like "leverage synergies" or "drive outcomes" with plain language. If a phrase sounds like it belongs in a press release, kill it.

• Inject personality: Add a touch of opinion, mild sarcasm, or vulnerability where appropriate. Real people have perspectives, not just information.

• Use contractions: "I'm" not "I am." "You're" not "You are." Unless you're being formal on purpose.

• Break some rules: Start sentences with "And" or "But." Use fragments where they create emphasis. Real writing isn't always grammatically perfect.

• Show some texture: Include a specific example, a metaphor, or a moment of self-reflection. Abstract concepts need grounding.

[Paste your text here]

The goal: Make this sound like a smart human wrote it, not an algorithm trying to sound like a smart human.

Follow-up Challenge:

Take something you recently wrote with AI assistance—an email, a post, a presentation deck—and run it through this prompt. Then compare the before and after.

Ask yourself: Which version sounds more like you? Which one would you actually say out loud in a conversation?

If the "after" feels more authentic, you've just learned something valuable about your voice. If the "before" already felt right, then congratulations—you're already using AI as a tool, not a replacement.

Either way, you win. Because self-awareness about how you sound is half the battle.

✨ Rewrite My Email with Confidence

Prompt:
"You are a communications coach. Review this email and remove softening language like ‘I think’ or ‘just.’ Make it sound more confident while staying respectful. If possible, preserve a warm, collaborative tone."

Follow-up Challenge:
Send both the original and AI-edited version to a peer or mentor. Ask: Which one sounds more like a leader? Or read both out loud. Which one makes you sit up straighter?

✨ Summarize My Meeting Notes

Prompt:
"You are my assistant. Summarize this meeting in three key takeaways and two action items, using clear and professional tone."

Follow-up Challenge:
Paste your AI-generated summary into your next follow-up email. Track what happens: faster replies? Fewer clarifying questions?

✨ Clarify My Pitch

Prompt:
"You are a messaging strategist. Help me turn this idea into a 3-minute pitch. Keep it simple, clear, and persuasive."

Follow-up Challenge:
Record yourself delivering the pitch. Watch it back and ask: Would I say yes if I heard this?

Coaching-Style Prompts

These prompts guide you through a thoughtful dialogue—one question at a time—and help you build something real: a plan, a strategy, or a courageous next step. They’re designed to stretch your thinking—and your confidence.

✨ Design a Career Growth Plan

Prompt:
"You are a leadership development coach. Guide me through creating a career growth plan I can bring to my leader. Ask one question at a time. Then turn my responses into a plan that includes my long-term goal, skill gaps, milestones, and how we’ll track progress together. I want it to show initiative, not just aspiration."

Follow-up Challenge:
Use the finished plan in a meeting with your leader. Frame it as: “Here’s what I want to grow into—and how I think we can get there together.”

✨ Set Clear, Measurable Goals

Prompt:
"You are a growth strategist. Ask me questions to help define 3–5 SMART goals that reflect both my development and the priorities of my team. Then format the final goals clearly for tracking."

Follow-up Challenge:
Add a calendar reminder for quarterly self-checks. Update your manager on your progress before they ask.

✨ Weigh a High-Stakes Decision

Prompt:
"You are an executive coach. Help me assess a major decision. Ask one question at a time. At the end, summarize the pros and cons, the key priorities, and what emotions I may need to acknowledge along the way."

Follow-up Challenge:
Return to your answers 30 days after making the decision. Reflect on what surprised you—and what affirmed your instincts.

✨ Identify and Own a Value-Add Project

Prompt:
"You are a strategic mentor. Ask me questions to identify an unmet need on my team. Help me choose one and create a plan to take ownership—even if no one asked me to."

Follow-up Challenge:
Bring your idea to a team meeting and say: “I’ve noticed this gap, and I’d like to take the lead on solving it.” Watch what happens.

✨ Prepare for a Difficult Conversation

Prompt:
"You are a leadership coach. Help me prepare for a tough performance conversation. Ask questions to clarify my intent, tone, and what the other person may need to hear. Then write a short script I can use."

Follow-up Challenge:
After the conversation, journal: What worked? What will I handle differently next time? Confidence grows through practice, not perfection.

Let’s Keep the Conversation Going

Have you tried one of these prompts? Did something surprising happen? I’d love to hear how this toolkit is showing up in your work or your growth journey.

Drop a message, share your experience, or even suggest a new prompt idea. We're building this together.

© 2021 Folded Page Publications. All content published under Hey Aspiring Leaders! is the original work of Folded Page Publications, owned and operated by Beth Estrada. This content may not be reproduced, redistributed, or used in datasets for AI training or content generation without written permission. All rights reserved.