AI Isn't Google
Your guide for today's session.
- Meet Alex & Jamie7 min
- Pick your tool2 min
- Exercise 1 — Tell it your why12 min
- Exercise 2 — Push back with context12 min
- Exercise 3 — The real conversation20 min
- Take it with you5 min
Meet Alex and Jamie.
Two new leaders on your team. You've managed both of them. Maybe you've been both of them.
5 years retail experience. Runs with a brief immediately. Fills the gaps with how things were done at their last company — not with your why.
Brand new. Only knows what you tell them. Give them everything — the situation, the people, the constraints, the intent — and they deliver something that actually works.
Your AI is both at once. It arrives with Alex's confidence — it's read everything, seen every format. But underneath, it's Jamie. It knows nothing about your specific context, your team, or your why. If you don't give it that, it defaults to how everyone else does it.
The Alex coaching conversation
Monday morning. You sit down with Alex.
Alex filled the gap with their own experience. Confident. Competent. Wrong for your context. That is exactly what AI does when you give it a vague brief.
The Jamie coaching conversation
Same Monday morning. Same task. But this time you sit down with Jamie.
That is what happens when you brief your AI properly. You are not just giving it a task. You are onboarding it the way you would onboard Jamie — context, intent, constraints, and the why behind what you are trying to do.
Pick your tool.
All free. All work in Hong Kong. Tap yours and keep it open alongside this page.
Using something else? Stick with it.
Tell it your why.
Gives a confident, structured answer based on generic best practice. Looks good. Built for someone else's store.
Has no idea about your culture, your guests, or the intent behind what you do. Without the why — it defaults to everyone else.
The Alex brief
"Plan a community event for my store next month."
The Jamie brief
"I'm a Key Leader at a retail store in Hong Kong. I need to plan a community event next month. For us, these events aren't about selling product — they're about genuine connection with our local guests. Guests are young professionals aged 25–35. Budget HK$3,000, space 800sqft, team briefed within two weeks. Help me plan something that feels real, not corporate."
The Jamie brief included the why — "not about selling, about genuine connection." That one line changes everything AI produces because now it understands the intent, not just the task.
Without the why, Alex takes over. Confident, generic, and built for someone else.
Your turn
Think of something real — a staff meeting, a product rollout, a team conversation. Brief your AI with the what AND the why behind it.
Paste it into your app. See what comes back.
Compare it to what you'd have got with one line. That difference is the brief.
Push back with context.
The first answer looks polished and credible. That confidence is the trap. It's built from general experience — not your context.
Don't just say "that's wrong." Say why it doesn't fit. Jamie can't improve without understanding the gap.
You wouldn't say to Jamie: this isn't good enough, do it again. You'd say: this section — the tone is too corporate. Our team doesn't respond to that. Rewrite it with that in mind. That's the coaching that gets results.
"This is too formal — our team culture is casual and direct. Rewrite it in that tone."
"This event format assumes we have tables. We don't — it needs to work standing, more like a social gathering."
"This reads like any brand. We want it rooted specifically in our neighbourhood. Adjust with that in mind."
Specific context gets specific results. Coach it like you'd coach Jamie.
Your turn
Take your Exercise 1 result. Find one thing that doesn't fit your context. Push back — and tell it why.
First answer is a starting point — not a finished product. The conversation is the skill.
The real conversation.
Think about something you have genuinely been sitting on. A project, a conversation you need to have with someone on your team, a decision you keep pushing to next week.
Think about it the way you would think about coaching it. Who is involved? What is the dynamic? What outcome do you need — not what looks good on paper, but what actually works for this person, in this store, with this team?
When the answer comes back — does this reflect how we actually do things here? Or how everyone does things?
Generic result means shallow brief. Look at your prompt first — what's the why that's missing?
Step 1 — What's the situation?
Step 2 — Write your Jamie brief
Include the what, the why, who's involved, your constraints, and what good looks like for your specific situation.
Paste into your app. Come back when you have a response.
Step 3 — Coach it further
Does it reflect how you actually do things — or how everyone does things? If something's off, coach it. Tell it what's wrong and why. Stay in the conversation.
Take it with you.
You are all managers. You have always been managers. You know how to onboard someone properly. You know how to give a brief that sets someone up to succeed. You know how to push back on a first draft and coach someone toward something better.
You just haven't pointed those skills at this yet.
Once you're comfortable — ask it: what if I approached this differently? What am I not thinking about? What are the risks? That's where it stops being a tool and starts being a thinking partner.
The principles — tap to check off
- ✓Tell it the what AND the why — brief it like Jamie
- ✓Confident output doesn't mean correct — check it against your context
- ✓Push back like a manager — specific, contextual, grounded in your why
- ✓Generic result means shallow brief — look at your prompt first
- ✓You already have this skill — you just haven't pointed it here yet
Facilitated by
Hong Kong