If your company already gives you access to Gemini through Google Workspace, or Claude through a team subscription, the hardest part is often just getting started. Craig Bryson, founder of Admin AI Insights and a 20 year executive assistant, ran a live comparison of both tools in a recent Pally Talk training session, using a fictional executive’s chaotic Monday inbox. Here is what assistants need to know before choosing, and how to set either one up properly.
Connecting Claude to your Gmail
Unlike Gemini, which sits natively inside Google Workspace, Claude needs to be connected to your inbox manually if you want it working with real emails. Craig walked through the steps: click the plus sign in Claude, go to Connectors, then Manage Connectors, find Gmail, and select Connect. You will be asked to sign into your Gmail account and answer a few setup questions.
A few settings are worth paying close attention to here. You will be asked whether to allow your chats to be reviewed to help improve Claude’s models. Craig’s advice, and ours, is to decline this if you are working with any sensitive or confidential information, which as an EA you almost certainly are. You do not need to opt into marketing emails either. If you are a virtual assistant setting this up yourself, this is a five minute job. If you work in a company, your IT team may have already done this in the background for you.
Gemini and Claude produce different results from the same prompt
Using an identical BRIEF style prompt (background, role, instructions, expectations, format) asking each tool to summarise, prioritise, and flag genuine urgency across a messy inbox, Craig ran the same request through both tools side by side.
Gemini, being built directly into Gmail, returned a clean priority table quickly, with one line summaries for each email and clear urgent, important, and routine groupings. It correctly caught a travel booking expiring the same day at 5pm and flagged it as genuinely urgent rather than just noisy.
Claude, once properly connected via the Gmail connector, went noticeably deeper. It also produced a table sorted by urgent and important, but added more surrounding context and reasoning for each item. Craig’s own preference, after using both extensively, leans toward Claude for this reason, though he is clear that both are genuinely useful and the right choice often comes down to what your company already has access to.
One important technical note: because Claude does not sit inside Gmail the way Gemini does, your prompt needs to explicitly tell it to search your connected account. Simply pasting the same prompt Gemini understands will not work in Claude unless you add an instruction such as “search my connected Gmail account” first.
A trick for finding specific emails in a crowded inbox
If your executive’s inbox has hundreds or thousands of emails, asking AI to summarise everything is not always precise enough when you need two specific messages. Craig’s tip is to include the exact subject lines in your prompt, for example asking it to find and read the emails titled “Can you sort my trip please” and “Fare hold expires at 5pm today,” and use only those as source material. This narrows the search dramatically and produces a far more accurate, focused answer than a broad request across a full inbox.
How to stop either tool from hallucinating
A natural concern raised during the session was accuracy. Craig’s answer was simple: build the instruction directly into your prompt. Tell the AI not to invent information, to work only from what has been provided, and to flag anything unclear or unconfirmed rather than guessing. Adding this single instruction noticeably improves reliability in both tools.
What it costs to go further
Free plans in both Gemini and Claude cover a large amount of everyday assistant work, including inbox summaries and drafting replies. Where cost comes in is more advanced use, such as Claude’s coding tools for building or editing a website, which Craig uses on the Pro plan at around 20 pounds a month. If you only need help with emails, calendars, and drafting, the free tier is often enough to start.
Frequently asked questions
Can Claude automatically create folders or labels in my inbox? Not automatically. Claude and Gemini can both suggest a labelling structure and colour coding for you, but you will need to create the labels manually in Gmail yourself.
Is it safe to connect my executive’s inbox to Claude or Gemini? Both allow you to control data and training settings. Turn off chat review and model training options if you are handling confidential information, and check your company’s IT policy before connecting a work inbox.
Should I learn both tools at once? Craig’s advice to assistants feeling overwhelmed is to pick one AI tool and one prompt, get confident with that, and build from there rather than trying to learn everything at once.
Craig Bryson delivers this kind of practical, tool by tool training through Admin AI Insights as part of Pally Talk’s community sessions. Get in touch with Pally Talk to find out about upcoming training dates.