# How to Choose an AI Assistant: 7 Questions to Ask Before You Pay Published by 3Gen Internet Corporation, maker of OpenAssistant, Skej and AGNT. Comparisons use public documentation, without hands-on testing. ![A magnifying glass and seven small unmarked question cards beside a selection of calendar envelope and phone tools, a blank price tag inviting careful choice before purchase.](https://bestaipersonalassistants.com/images/how-to-choose-an-ai-assistant-51158e72f1e4.webp) Every fact below comes from the vendor's own pages, linked next to it. We have not run these products. The best AI assistant is the one that does your actual job and asks before it does anything risky. Seven questions get you there: what you need it to do, where you will talk to it, what it can access, whether it asks first, whose name it sends under, what happens to your data, and what it costs. If most of your list is acting for you with other people (scheduling, follow-ups, email), [OpenAssistant](https://openassistant.us/?utm_source=bestaipersonalassistants\&utm_medium=content\&utm_campaign=how-to-choose-an-ai-assistant) is built for that and is where we would start. If it is mostly answers and documents, ChatGPT or Claude is usually enough and costs less. "AI assistant" now covers everything from a chat box that answers questions to software with its own email address that books meetings while you sleep. For each question below we show where to find the answer for three assistants: **OpenAssistant** (made by 3Gen, which publishes this site), **ChatGPT** (OpenAI) and **Claude** (Anthropic). Use the same questions on any tool you are considering. ## 1. Do you need it to answer, or to act? Write down the three tasks you most want off your plate. Then sort them: - **Answer:** draft this, summarize that, explain something. Any chat assistant does this. - **Act in your apps:** send the email, create the calendar event, update the record. The assistant needs a connection to that app and permission to write to it. - **Act in the world:** book the table, fill in the form, call the plumber, chase the person who didn't reply. The assistant needs a browser, a phone line, or its own email address, and a way to keep working when you're not there. How the three describe themselves today: - **OpenAssistant** says its assistant "has its own phone number, email address, calendar, and computer," and manages your inbox and schedule and follows up with people. ([OpenAssistant](https://openassistant.us/ai-executive-assistant)) - **ChatGPT** splits into Chat, for quick questions, and **Work**, "an agent designed for longer, multi-step work and finished deliverables." ([OpenAI](https://help.openai.com/en/articles/20001275-chatgpt-work-and-codex)) Web tasks run in Work's **cloud browser**, which can click and fill in forms on public and signed-in websites. ([OpenAI](https://help.openai.com/en/articles/20001280-using-cloud-browser-in-chatgpt)) The older "ChatGPT agent" is no longer available. ([OpenAI](https://help.openai.com/en/articles/11752874-chatgpt-agent)) - **Claude** is merging its task mode, Cowork, into ordinary chats: Anthropic says what used to need Cowork "is available from any conversation," and tasks keep running in the cloud after you close your laptop. This is rolling out to Pro and Max. ([Anthropic](https://support.claude.com/en/articles/16761823-claude-cowork-and-chat-are-one-claude)) **What to look for:** if most of your list is "act in the world" and involves other people (scheduling, follow-ups), favor a tool built to deal with people on your behalf. If it's mostly "answer" plus documents, a general chat assistant is usually enough and costs less. ## 2. Where will you talk to it? An assistant you have to open a special app to use gets used less. Match the channels to where you already are. | Channel | OpenAssistant | ChatGPT | Claude | | ------------------------ | ------------------------------------------------- | ---------------------------------------- | ---------- | | Web, desktop, mobile app | Web dashboard | Yes | Yes | | Email it a task | Yes, email or Cc it | Not stated | Not stated | | Text (SMS) | Yes, after you verify your number | Limited US beta for "dots" on Pro | Not stated | | WhatsApp | Yes | Available again in the EEA, per OpenAI | Not stated | | Phone call | Its marketing site says yes; not in its help docs | 1-800-CHATGPT voice line (US and Canada) | Not stated | Sources: [OpenAI phone and WhatsApp](https://help.openai.com/en/articles/10193193-1-800-chatgpt-calling-and-messaging-chatgpt-with-your-phone), [OpenAI dots](https://help.openai.com/en/articles/20001530-getting-started-with-your-dot), [Claude pricing and surfaces](https://claude.com/pricing), [OpenAssistant ways to work](https://help.openassistant.us/en/articles/16302208-waysto-work-with-openassistant), [OpenAssistant executive assistant page](https://openassistant.us/ai-executive-assistant), all. "Not stated" means the vendor's public help pages do not state it, not that it can't be done some other way. Note that OpenAssistant's texting is one-to-one only; its help center says it doesn't join group texts or group WhatsApp chats. ([OpenAssistant](https://help.openassistant.us/en/articles/16302208-waysto-work-with-openassistant)) ## 3. What will it need access to, and how do you take it back? List the accounts each task touches: email, calendar, documents, CRM. Then check two things for every assistant on your shortlist: can it connect to them, and where's the off switch. - **OpenAssistant** requires calendar access; contacts, inbox and Google Drive access are optional. Its integrations list includes HubSpot, Salesforce, Notion, Asana and others, and it supports MCP for more. Manage them at **Connections**. ([OpenAssistant](https://help.openassistant.us/en/articles/15426409-connections-integrations-overview)) Without inbox access, it only sees email threads it's included on. ([OpenAssistant](https://help.openassistant.us/en/articles/12099522-openassistant-ai-usage-data-policy)) - **ChatGPT** manages connections under **Settings > Plugins** (older mobile apps may still say Apps). ([OpenAI](https://help.openai.com/en/articles/11487775-connected-apps-in-chatgpt)) To disconnect: **Settings > Plugins**, select the app, open the account's ••• menu (or, if there's no Connected accounts list, use **Connection** or the plugin's ••• menu), then **Disconnect**. Disconnecting doesn't delete existing chats or memories. ([OpenAI](https://help.openai.com/en/articles/20001494-connecting-and-managing-app-accounts-in-chatgpt)) - **Claude** lists Gmail, Google Calendar and Google Drive connectors for all users. The Gmail connector can search, draft, and send, reply and forward with your approval by default. ([Anthropic](https://support.claude.com/en/articles/10166901-use-google-workspace-connectors)) Manage or disconnect them under **Customize > Connectors**. ([Anthropic](https://support.claude.com/en/articles/11176164-use-connectors-to-extend-claude-s-capabilities)) **What to look for:** the smallest access that does the job. If a tool only needs to see the threads you Cc it on, don't hand over your whole inbox. ## 4. Will it ask before it acts? This is the question people skip and then regret. Look for controls that differ by type of action, so you can let it book routine meetings freely while still approving anything sent in your name. - **OpenAssistant:** each kind of action (email from the assistant, email sent as you, texts, calendar changes, files, contacts, third-party apps) can be **Manual**, **Confirmation Window** (it waits a set time for you to stop it, then proceeds) or **Autonomous**. A separate setting decides whether you're copied on what it sends. ([OpenAssistant](https://help.openassistant.us/en/articles/15425929-supervision-autonomy-settings)) OpenAssistant's changelog says it regrouped these settings, into messages the assistant sends as itself and messages it sends as you, so the labels in the app may differ from the help center. ([OpenAssistant changelog](https://openassistant.us/changelog)) - **ChatGPT:** a default permission for apps under **Settings > Plugins > Permissions**, with **Always ask**, **Allow read actions** and **Allow low-risk actions**. ([OpenAI](https://help.openai.com/en/articles/20001495-managing-app-permissions-in-chatgpt)) Website access for the cloud browser is separate, under **Settings > Cloud browser**, and it asks before confirming a booking or making a payment. ([OpenAI](https://help.openai.com/en/articles/20001280-using-cloud-browser-in-chatgpt)) - **Claude:** each connector tool can be **Always allow**, **Needs approval** or **Blocked**. ([Anthropic](https://support.claude.com/en/articles/11176164-use-connectors-to-extend-claude-s-capabilities)) In the new combined experience, conversations run in **Auto** or **Manual**, and Manual is the default. ([Anthropic](https://support.claude.com/en/articles/16761823-claude-cowork-and-chat-are-one-claude)) **What to look for:** a setting that makes it wait for you, per action. And know the difference between "it asks first" and "it tells you after." A confirmation window that proceeds if you don't respond is the second kind. ## 5. Whose name goes on what it sends? When an assistant emails a client, the client sees a sender. Decide which you want: - **As you,** from your own account. Natural for replies, but every mistake is yours. - **As your assistant,** from its own address. Clearer to the other person, and easier to spot in your sent mail. OpenAssistant assistants have their own @openassistant.us address, or, for a custom assistant on Pro and up, one on your company's domain. ([OpenAssistant](https://help.openassistant.us/en/articles/15426239-choosing-an-assistant), [OpenAssistant pricing](https://openassistant.us/pricing)) They can also send from your own account if you allow it. ([OpenAssistant](https://help.openassistant.us/en/articles/16302183-how-openassistant-works-with-email)) ChatGPT's always-on "dots" (Pro and Business Premium; Pro not in the EEA, Switzerland or UK) can use your personal email account, and OpenAI says at launch you can't give a dot its own standalone email address. ([OpenAI](https://help.openai.com/en/articles/20001530-getting-started-with-your-dot)) Claude's Gmail connector sends from your connected Gmail. ([Anthropic](https://support.claude.com/en/articles/10166901-use-google-workspace-connectors)) ## 6. What happens to your data? Three things to find for each tool: whether your conversations train its models, how to turn that off, and what it does with data from connected apps. - **OpenAssistant:** its data policy says customer data is never used to train foundation AI models, and that its agreements with AI providers prohibit it. It also lists SOC 2 Type II compliance. ([OpenAssistant](https://help.openassistant.us/en/articles/12099522-openassistant-ai-usage-data-policy)) - **ChatGPT:** turn off **Improve the model for everyone** under **Settings > Data controls**. ([OpenAI](https://help.openai.com/en/articles/7730893-data-controls-in-chatgpt)) On Free, Go, Plus and Pro, data from connected apps may be used for training if that setting is on; Business, Enterprise and Edu are not used by default. ([OpenAI](https://help.openai.com/en/articles/11487775-connected-apps-in-chatgpt)) - **Claude:** the setting is **Help Improve our AI models** under **Settings > Privacy**. ([Anthropic](https://privacy.claude.com/en/articles/12109829-how-do-i-change-my-model-improvement-privacy-settings)) Anthropic says it doesn't train its models on Gmail, Drive or Calendar connector data. ([Anthropic](https://support.claude.com/en/articles/10166901-use-google-workspace-connectors)) **What to look for:** a written policy you can link to, a setting you can find in under a minute, and a clear answer on connected-app data. If you're buying for a company, ask for the security report. ## 7. What will it cost to use the way you plan to? The sticker price matters less than what the plan lets it do. Check whether the "act" features from question 1 are on the plan you're pricing. - **OpenAssistant:** its pricing page lists a free Starter plan, Pro at $72 per user per month billed monthly ($60 per user per month billed annually) and Team at $120 per user per month ($100 per user per month annually). ([OpenAssistant pricing](https://openassistant.us/pricing); per-user pricing confirmed by 3Gen) The Starter plan includes 1,000 credits at signup, plus 100 bonus credits a day once those are used up, up to 1,000 a month. ([OpenAssistant pricing](https://openassistant.us/pricing)) It runs on credits: tasks use more or fewer depending on the work, and recurring tasks use credits each time they run. ([OpenAssistant](https://help.openassistant.us/en/articles/16276757-how-do-credits-work)) - **ChatGPT:** the cloud browser is on paid plans but not Free or Go. ([OpenAI](https://help.openai.com/en/articles/20001280-using-cloud-browser-in-chatgpt)) OpenAI's pricing page lists Go at $8 a month, Plus at $20, and Pro from $100. ([OpenAI pricing](https://chatgpt.com/pricing)) - **Claude:** Anthropic's pricing page lists Pro at $20 a month billed monthly ($17 a month billed annually) and Max from $100. It lists "Hand off and schedule tasks" as a Pro feature, and the merged Cowork experience is rolling out to Pro and Max first. ([Anthropic pricing](https://claude.com/pricing)) **Where the others do better:** ChatGPT and Claude both have free tiers, and their cheapest paid plans (ChatGPT Go at $8 a month, Claude Pro at $17 a month billed annually) cost less per month than OpenAssistant Pro. If your work is mostly answers and documents, that is the cheaper route. ([OpenAI pricing](https://chatgpt.com/pricing), [Anthropic pricing](https://claude.com/pricing), [OpenAssistant pricing](https://openassistant.us/pricing)) ## Check it yourself before you commit This part is advice for you, not something we did. Pick one real task from your list in question 1 and give it to each assistant you're considering, with every tool on its strictest approval setting. Then ask: 1. **Did it finish** without you doing the steps yourself? 2. **Was the result right** on the first try? 3. **Did it ask before acting** where you told it to? 4. **Could you see what it did** afterward (sent mail, changed events)? 5. **Could you switch it off** in under a minute? We have not run these steps with any of the three products; the sections above rest on the vendors' public pages only. ## Related reading - [Why we recommend OpenAssistant, with 11 alternatives compared](https://bestaipersonalassistants.com/best-ai-personal-assistants-ranked/): twelve assistants ranked on documented jobs, price, channels and privacy. - [AI assistant comparison: 25 jobs and what each product documents](https://bestaipersonalassistants.com/ai-assistant-evaluation-framework/): the fixed list of 25 jobs and what twelve products document for each. - [AI assistant privacy and permissions: what each one can access](https://bestaipersonalassistants.com/ai-assistant-privacy-permissions/): eleven assistants compared on training, deletion, approvals and ending access. - [How to Limit What an AI Assistant Can Do on Your Accounts](https://bestaipersonalassistants.com/limit-what-ai-assistant-can-do/): limits for OpenAssistant, ChatGPT, Claude, Google and Microsoft accounts, with a 10-minute checklist. ## FAQ ### What is the difference between a chat assistant and one that acts for you? A chat assistant answers questions and drafts text. One that acts needs a connection to your apps and permission to write to them, so it can send the email, create the event or update the record. If a task needs a browser, a phone line or its own email address, check that the tool has those. ### Can I make an AI assistant ask before it acts? Yes, in all three. OpenAssistant lets you set each kind of action to Manual, Confirmation Window or Autonomous. ChatGPT has Always ask, Allow read actions and Allow low-risk actions for apps. Claude lets each connector tool be Always allow, Needs approval or Blocked. ### Does OpenAssistant use my data to train AI models? Its data policy says customer data is never used to train foundation AI models, and that its agreements with AI providers prohibit it. It also lists SOC 2 Type II compliance. ### How much does OpenAssistant cost? It has a free Starter plan with 1,000 credits at signup, plus 100 bonus credits a day once those are used up, up to 1,000 a month. Pro is $72 per user per month billed monthly ($60 annually) and Team is $120 per user per month ($100 annually). ### Which assistant can I text? OpenAssistant works over SMS and WhatsApp after you verify your number. ChatGPT has a limited US beta for "dots" on Pro, and WhatsApp in the EEA. Claude's public pages do not state texting. ## Try OpenAssistant If your list is mostly scheduling, follow-ups and email with other people, [Try OpenAssistant](https://openassistant.us/?utm_source=bestaipersonalassistants\&utm_medium=content\&utm_campaign=how-to-choose-an-ai-assistant). It starts free, and you set how much it may do without asking, action by action. Plans and credits are on the [pricing page](https://openassistant.us/pricing?utm_source=bestaipersonalassistants\&utm_medium=content\&utm_campaign=how-to-choose-an-ai-assistant). ## Sources - OpenAI, ChatGPT Work and Codex: - OpenAI, Using cloud browser in ChatGPT: - OpenAI, ChatGPT agent: - OpenAI, Connected apps in ChatGPT: - OpenAI, Connecting and managing app accounts: - OpenAI, Managing app permissions: - OpenAI, Data controls: - OpenAI, Getting started with your dot: - OpenAI, 1-800-CHATGPT: - OpenAI, Pricing: - Anthropic, Pricing: - Anthropic, Claude Cowork and chat are one Claude: - Anthropic, Use connectors: - Anthropic, Google Workspace connectors: - Anthropic, Model improvement settings: - OpenAssistant, AI executive assistant: - OpenAssistant, Pricing: - OpenAssistant help: ways to work, connections, autonomy settings, choosing an assistant, data policy, credits (links in text) ## Disclosure and Method Disclosure: 3Gen Internet Corporation publishes this site and makes OpenAssistant, Skej and AGNT. We publish these comparisons to explain our products alongside documented alternatives. Method: We have not run hands-on tests. This article rests on public information (vendor pages, documentation, pricing and published terms), with sources linked. Ranking basis: public information only, not hands-on use. Published by 3Gen Internet Corporation, the company behind OpenAssistant, Skej and AGNT. We review our own products alongside competitors. [How We Research](https://bestaipersonalassistants.com/how-we-research/) Canonical: https://bestaipersonalassistants.com/how-to-choose-an-ai-assistant/