Lesson 5 of 23 · Start
Winston AI
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.
What this tab is for
- 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
- Dictate a message instead of typing it
- Talk hands-free: speak, and hear Winston answer
- Have every reply read aloud, or stop him mid-sentence
- Council: get one verdict from several AI advisers, with where they agree and differ
- Research: a sourced report on any topic, in a few minutes
- Python: write, explain or fix code, attach data files, and run examples
Option 1 of 10
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".
Option 2 of 10
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".
Option 3 of 10
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.
Option 4 of 10
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.
Option 5 of 10
Dictating a message
- 1
Press the microphone
The button's tip reads Speak your message instead of typing it. Your browser may ask permission to use the microphone the first time; allow it. Dictation works in Chrome, Edge and Safari.
- 2
Speak naturally
Your words appear in the message box as you talk.
- 3
Check and send
Fix anything misheard, then press Send.
Option 6 of 10
Talking hands-free
- 1
Press hands-free
The button's tip reads Hands-free: talk to Winston and hear him answer.
- 2
Talk
Speak your question. When you stop, Winston sends it.
- 3
Listen
Winston replies in writing and reads the answer aloud.
- 4
Carry on
Speak again to continue the conversation. Press the button again to stop.
Hands-free works best in a quiet room with a decent microphone or headset.
Option 7 of 10
Hearing replies read aloud
- 1
Turn on read aloud
Press the speaker button, labelled Read replies aloud.
- 2
Stop at any time
Press it again to stop speaking, or to stop reading replies aloud.
Option 8 of 10
Council: for big decisions
- 1
Choose Council
Press Council in the mode switch. The box asks: What decision shall the council weigh?
- 2
Describe the decision
Give the options and what matters to you, for example "Should I hire a salesperson or spend $4,000 a month on ads?"
- 3
Wait while they confer
Winston shows who he's consulting. Each adviser answers on its own, using web search where facts matter.
- 4
Read the verdict
Winston opens with his recommendation, then Where they agree and Where they differ, naming which view he sides with and why. Each adviser's full answer follows below.
Council uses every AI engine connected under Integrations. With only one connected, Winston answers on his own.
Option 9 of 10
Research: for facts you can trust
- 1
Choose Research
The box asks: What shall I research?
- 2
Ask a clear question
For example "What do HVAC companies in Ohio charge for a maintenance plan?"
- 3
Let it run
Winston plans the research, searches several angles at once and writes a report. It takes a few minutes.
- 4
Check the sources
The report lists its sources so you can open and check them.
Option 10 of 10
Python: for code and data
- 1
Choose Python
The box asks you to describe the Python you need, or paste code to fix.
- 2
Attach data if needed
Attach a spreadsheet exported as CSV, or a code file.
- 3
Run the example
Winston's Python examples can be run right in your browser to see the result.
Your exercise
Before you finish, open the tab and try:
- 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.
- Dictate a question about your week.
- Have a two-question hands-free conversation with Winston.
- Ask the Council a real decision you're weighing this month.
- Run a Research question about your competitors' prices.
Worked through every option above? Finish the lesson to tick it off.
Want more detail? Read Talking to Winston, Speaking with Winston and Council, Research and Python in the manual.