In our recent post ‘Stop Fighting with AI’, we explored how better prompts get better answers – adding context, being specific, and demanding structure. But there’s another way AI can help that goes beyond getting tasks done: it can help you actually understand things you find confusing.

 

You’re in a meeting or training session. Everyone else seems to get it. You’re completely lost but too embarrassed to raise your hand and say, “Can you explain the last 20 minutes again?” So you stay quiet. Hope it’ll make sense later. It doesn’t.

 

Here’s where AI becomes genuinely valuable: it never judges, never gets frustrated, and never makes you feel stupid. You can ask the same question ten different ways until something clicks – and nobody ever needs to know.

 

The Ladder Method: Build Understanding Step by Step

When a concept isn’t landing, ask AI to explain it at progressively higher levels. This helps you pinpoint exactly where your understanding breaks down.

Try this approach:

✅ “Explain compound interest like I’m 12, then 16, then as someone starting their first job. Build complexity each time, starting with the absolute basics.”

You’ll find the exact level where you get lost – then work from there.

 

This technique works brilliantly for financial concepts, technical processes, software features, or any workplace jargon that’s gone over your head.

 

 

The “What Should I Ask?” Technique

Sometimes you’re so lost you don’t even know what questions to ask. This is more common than people admit – especially when starting a new role, learning new software, or returning to study after years away.

Try this prompt:

✅ “I’m trying to understand [topic] but I’m completely lost. What are the 5 most important questions I should be able to answer about this? Then help me work through them one by one.”

For example: “I’m trying to understand our company’s new CRM system but I’m completely lost. What are the 5 most important questions I should be able to answer about using it effectively?”

 

AI gives you a roadmap out of confusion – and working through each question builds genuine understanding rather than surface-level familiarity.

 

The Patient Tutor Approach

You can actually set up AI to be the kind of teacher you wish you’d had – one who explains things multiple ways without sighing or checking their watch.

Try this setup prompt:

✅ “You’re my personal tutor for [topic]. I’m struggling and feeling behind. I need you to explain things multiple ways until I understand, check I’ve grasped each point before moving on, never make me feel stupid for not knowing something, and use examples from everyday situations. Let’s start with [specific confusing concept].”

 

This works because it sets a supportive tone from the outset. AI will literally ask “Does that make sense?” and wait for your response. You can say “No, still confused” as many times as you need.

 

The Foundation Check

Often we’re confused because we’re missing something fundamental – not because the new concept is too hard. AI can help diagnose what’s actually missing.

Try this:

✅ “Test my understanding of [topic] by asking me 5 questions, starting very basic and getting harder. After each of my answers, tell me what gaps you notice in my knowledge.”

 

What you discover might surprise you:

• “You understand the concept, but you’re missing some key terminology…”
• “You know the process but not why each step matters…”
• “You might need to review [specific prerequisite] first…”

Now you know exactly what to fix, rather than repeatedly failing to grasp something because the foundations aren’t there.

 

Real Examples by Situation

➡️ New software or systems: “I don’t understand how to use pivot tables in Excel. Start by checking if I understand basic sorting and filtering. If I don’t, teach me those first. Then build up to pivot tables step by step.”

 

➡️  Financial concepts: “Everyone in my team seems to understand profit margins except me. Use examples from running a small café to explain gross margin versus net margin. Keep trying different analogies until one clicks.”

 

➡️  Professional qualifications: “I’m studying for my AAT qualification and cash flow statements confuse me. Explain the difference between profit and cash flow using a real business example, then show me how this appears in the statements.”

 

➡️  Workplace processes: “I’ve been pretending to understand our project management methodology for weeks. Teach me agile basics from the beginning without any judgment, assuming I know nothing.”

 

The No-Shame Prompt Collection

Copy these for when you’re stuck:

1. “I should understand [topic] by now but I don’t. Teach me from the beginning without any judgment.”
2. “Explain [concept] using only everyday words – no jargon or technical terms.”
3. “I’ve been nodding along in meetings about [topic] but I’m lost. Help me actually learn it.”
4. “Try 5 completely different ways to explain [concept] until one makes sense to me.”

 

Why This Matters

Everyone gets confused. The people who progress aren’t the ones who never struggle – they’re the ones who find ways to fill the gaps. AI gives you a private, patient space to do exactly that.

The shame of not understanding something dissolves when there’s no one to be embarrassed in front of. You stop pretending and start actually learning.