For a CEO, AI earns its place in four jobs: the morning briefing, meeting prep, decision memos and reading long documents. The tool matters less than the plan. Use a business plan that does not train on your data by default, and check the settings yourself before you paste in anything sensitive.
Prices and policies below are from each vendor's own pages, as of October 2026, in US dollars.
The four uses that matter
1. Briefings. Ask AI to summarize what changed since yesterday: the long email threads, the notes from your team, the documents you were sent. Gemini in Gmail can summarize threads and find details in old emails (Gemini in Gmail help). Copilot in Outlook can summarize a thread and link each point back to the message it came from (Microsoft support).
2. Meeting prep. Before a meeting, ask for the last three emails with that person, the open questions and what you promised. After it, a note taker gives you the action items. See Fathom vs Otter for the main options.
3. Decision memos. Write your thinking in rough notes. Ask AI to turn it into a one-page memo with the options, the cost of each and the risks. Then ask it to argue against your preferred option. This is where AI saves the most thinking time, because a weak argument shows up on paper.
4. Reading long documents. Contracts, reports, due diligence packs. Ask for a summary, then ask specific questions and request the page or section for each answer. Claude's pricing page lists context windows of up to 1 million tokens, depending on the model (Claude pricing). Always check the clauses that matter in the original.
Everything else, from slide drafts to social posts, is useful but not where a CEO's hours go.
Which tool fits
- Your company runs on Google Workspace. Gemini is included in Gmail from Business Starter at $7 per user a month on a yearly plan. Docs and Meet need Business Standard at $14 (Workspace pricing).
- Your company runs on Microsoft 365. Copilot Business is $21 per user a month paid yearly, or $25.20 monthly, as an add-on. Microsoft offered $18 for the first year on yearly purchases between July 1 and December 31, 2026 (Microsoft pricing).
- You work across many apps. ChatGPT Business and Claude Team both cost $20 per user a month billed yearly, or $25 monthly. Both start at 2 users (OpenAI billing help, Claude pricing).
If you are the only user, a personal plan at about $20 a month works too. Then the data settings are your job.
Privacy: what each vendor says
This is the part to read twice. Business plans and personal plans handle your data differently.
OpenAI. By default, OpenAI does not use content from ChatGPT Business, Enterprise or Edu workspaces to train its models. On personal plans, turn off Improve the model for everyone under Settings, then Data controls (OpenAI data controls).
Anthropic. The Claude pricing page lists model training as opt-out on Free, Pro and Max, and none by default on Team and Enterprise. On personal plans, the setting is Help Improve our AI models under Settings, then Privacy (Anthropic privacy center).
Google. The Workspace privacy hub says your prompts and content are not used to train generative AI models outside your domain without permission. They are also not shared with other customers.
Microsoft. Microsoft's enterprise data protection page says prompts, responses and data accessed through Microsoft Graph are not used to train foundation models.
These are the vendors' own statements. Your contract and your admin settings decide the rest. Check with your lawyer before you put client or employee data into any tool, because rules differ by country.
Settings to check on day one
- Confirm which plan you are on. Business, Team or Enterprise, or a personal plan.
- On a personal plan, turn off model training in the privacy settings.
- Turn off memory, or review what it stores, if you discuss people or deals.
- Check which apps are connected, such as email, calendar and drive, and remove the ones you do not use.
- Set connected apps to ask before they send, delete or share anything.
- Write down what may never go in: passwords, bank details, health data, anything under an NDA.
If you have a team, put these rules in writing. The AI policy template is a starting point.
A briefing prompt to start with
You are helping me prepare for my day. I run [company], which [what it does]. My priorities this quarter are [1], [2], [3].
From the emails and documents I give you, list:
- Anything that needs a decision from me today, with the deadline.
- Anything that changed on [priority 1, 2, 3].
- People waiting on a reply from me for more than two days.
Keep it under 200 words. Quote the sender and date for each item. If something is unclear, say so instead of guessing.
Give the assistant a standing brief about your company so you do not repeat it each time. Here is how to write one, and why chat tools forget without it. For the weekly routine around these uses, see how to use Claude for your business.