Chapter 4 of 32 · Start
Talking to Winston
Winston AI is a conversation with your butler. Ask about your business or your life the way you'd ask a capable person. He can read files you attach, and the prompt library gives you dozens of ready-made questions and answer styles so you never face a blank box. Every chat is saved so you can pick it up again.
How it works
What you can do here
- Ask anything in plain words and follow up as long as you like
- Attach up to 5 files per message (PDF, image, Word document or text, up to 10 MB each)
- Start from ready-made playbooks such as First 10 customers or Am I charging enough?
- Choose an answer style: shorter, more detailed, as a teacher, as a consultant and many more
- Keep, reopen and delete past chats
1. Your first chat
- 1
Open Winston AI
Pick it from the Start group in the menu. Winston greets you with "Good day. What shall we attend to?"
- 2
Check the mode
At the top right of the chat, Chat should be selected. The next chapter covers the other modes.
- 3
Type your question
Write it the way you'd say it, for example "How should I price a monthly lawn care plan?" Press Send or Enter.
- 4
Follow up
Winston remembers the whole conversation. Reply with "make it shorter", "explain step 2" or "turn that into an email".
The more context you give, the better the answer. "We're a three-person roofing company in Tampa" beats "we're a business".
2. Attaching files
- 1
Press the attach button
It's beside the message box.
- 2
Choose your files
You can add up to 5 files to one message, each up to 10 MB: PDFs, images, Word documents and text files.
- 3
Remove a file
Press the cross on any file you added by mistake.
- 4
Ask about them
For example "Summarise this contract and list anything I should worry about".
3. Using the prompt library
The prompt library has two kinds of shortcut: ready-made prompts for common jobs, and answer styles that change how Winston replies.
- 1
Open the library
Press the ready-made prompts button beside the message box.
- 2
Pick a ready-made prompt
These are grouped as Customers, Market, Money and Paperwork, for example First 10 customers, Competitor teardown, Monthly money check-up, Contract read-through, Client proposal and Hiring kit. Picking one fills in the message for you.
- 3
Fill in the blanks
Replace anything in [square brackets] with your own details, then send.
- 4
Pick an answer style
Under Answer styles, choose how Winston should answer: Writing (professional, simplify, summarise, an email), Roles (expert, teacher, consultant, devil's advocate), Content (Instagram, YouTube, a content calendar), Sales, Planning, Thinking, Learning and Formats.
4. Managing your chats
- 1
Find old chats
Your chats are listed on the left, newest first. On a phone, press Show chats.
- 2
Reopen one
Click it and carry on where you left off.
- 3
Start fresh
Press New chat.
- 4
Delete one
Press the delete button beside a chat you no longer need.
Try it yourself
Doing is the fastest way to learn. Open the tab and try these:
- Open the prompt library and run the Monthly money check-up.
- Attach a PDF and ask Winston to summarise it in five bullets.
- Ask a question, then use an answer style to have it explained like a teacher.
Common questions
Is Winston always right?
No. Winston can make mistakes, and says so under the message box. Check anything important, especially numbers, legal and tax points.
Does Winston know about my business?
Yes. Winston reads your business's details and memory, so you don't have to explain the basics every time.