Claude, ChatGPT, Gemini or Copilot: how to choose an AI assistant for your team

Clients ask us this every week, and the honest answer is that for most everyday work — drafting, summarising, analysis, planning — the leading assistants are close enough that a benchmark table will not settle it. What settles it is fit: where your files live, what your data rules require, and which specialised jobs matter to you. Here is how we run the decision with teams, and the trial that ends the debate in two weeks.

Start with where the work already lives

An assistant that can read the document you are working on, search your shared drive and draft inside your email client saves more time than one that is marginally better at reasoning but lives in a separate tab. That is why Microsoft Copilot is the default in Microsoft 365 organisations and Gemini in Google Workspace shops: not because they win on every task, but because they are already where the work is. Claude and ChatGPT both connect to those ecosystems too, through integrations and connectors, so the question is how much of your day happens inside documents versus in a separate conversation.

Data handling is a filter, not a feature

Whatever you pick, buy the business or enterprise tier. You need three things: contractual terms that exclude your prompts and files from model training, an admin console with single sign-on so you can remove leavers in one place, and a data residency or retention setting you can point a client to. Consumer accounts on a company card fail all three. If your organisation handles health, financial or public-sector data, add the questions from our security and compliance page to the vendor review.

Where the assistants differ in practice

Differences show up in specialised jobs rather than everyday ones. Long documents and careful writing, coding and software agents, image and video generation, and voice interaction are the areas where teams notice a gap. Test the ones you care about rather than reading about all of them.

The two-week trial that ends the argument

Pick five real tasks your team does weekly: a client email, a meeting summary, a spreadsheet clean-up, a proposal section, a piece of analysis. Give three or four people the same tasks in two assistants, one week each. Score each output from one to five on “would I send this with light edits,” and note the time saved. At the end, ask one question: which tool did people keep opening without being told to? That answer is usually unanimous and it is usually right.

The best assistant for your team is the one that is still open on the second Monday.

When to use more than one

A second assistant is justified when it does a job the first cannot: a developer team on Claude Code or Cursor while the rest of the company uses Copilot, or a marketing team using a dedicated image model. It is not justified because two people prefer different chat interfaces. Standardise on one, document the exceptions, and revisit each quarter. If you want the trial designed and run for you, that is part of our AI consulting work.