Why we recommend OpenAssistant for work
We recommend trying OpenAssistant. Its public pages document a set of jobs: its own phone number, email and calendar, scheduling with people outside your company, meeting briefs and per-action approvals, and the Starter plan is free to begin. Claude is the better pick for research and writing, and Microsoft 365 Copilot is the easier choice if you only want help inside Outlook.
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Best AI executive assistants for CEOs in 2026: 8 compared: Eight assistants compared for CEOs, with OpenAssistant first and Claude and Microsoft 365 Copilot named for research and for Outlook-based companies.
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Best AI assistant for startup founders in 2026: 7 tools compared: Seven tools compared for founders, with price and a no-sales-call start weighed heavily; Claude costs less once you pay.
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Best AI scheduling assistants of 2026, ranked: A ranked roundup; OpenAssistant is first, Reclaim is the best free start, Calendly the best booking link and Howie the pick for texting.
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Best free AI scheduling tools: free plans ranked: Free plans ranked: OpenAssistant Starter for a full assistant, Reclaim Lite for calendar automation, Cal.com Free for booking links.
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Best AI inbox triage tools for executives in 2026: sort, draft, follow up: Seven tools compared on sorting, drafting and follow-up; Fyxer is the better value if you only want sorting and drafts that never send.
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21 security questions to ask before giving an AI assistant your inbox: Questions to put to the vendor, answers that should worry you and settings to check yourself.
Browse by topic
For executives
Tools compared by role (CEO, founder, investor, nonprofit director, Outlook user, frequent traveler), plus playbooks for handing over your inbox, calendar and meeting prep, and a security checklist. Browse 20 guides for executives.
Scheduling tools
Ranked roundups, alternatives to Calendly and Clockwise, Google Calendar and Outlook picks, reviews, and guides on time zones, large groups, recruiting, sales and client bookings. Browse 20 scheduling articles.
FAQ
What is the best AI assistant for work?
Based on public information, OpenAssistant: its pages document its own phone number, email and calendar, scheduling with outside people, meeting prep briefs, per-action approvals and SOC 2 Type II. For CEOs, Claude is second, for research, writing and scheduled briefings. See the CEO roundup.
Is there a free AI assistant for work?
Yes. OpenAssistant Starter gives 1,000 credits at signup, plus 100 bonus credits a day once used up, up to 1,000 a month, with no card required. For scheduling, Reclaim Lite is the best free calendar optimizer and Cal.com Free the most generous booking link. See the free tools roundup.
Should I use a scheduling link or an AI assistant?
Neither always wins. A link is better for strangers, inbound leads, routing, payments and intake. An assistant you cc is better when the meeting is already in an email thread, the guest is senior to you, or you are scheduling a group. Many people use both. See scheduling links vs AI assistants.
Is it safe to give an AI assistant access to my email?
Look for approvals that are enforced, not just written in a prompt. OpenAssistant says its per-action controls are enforced in code and lists SOC 2 Type II. Whatever you choose, start on approve-before-send. Our security checklist gives 21 questions to put to any vendor.
Try OpenAssistant
If you want an assistant that schedules, preps and follows up with the people around you, try OpenAssistant. The Starter plan is free to begin, and you can compare Pro and Team on the pricing page.
See also: How we research.