Begin with the task and existing systems
A team that works heavily in Microsoft 365 may value assistance close to its documents, email, and meetings. Another team may prioritize a general-purpose drafting, research, or analysis interface with approved connections to several systems. Test representative work before deciding that one product replaces the other.
Microsoft's current documentation uses Microsoft Copilot and Microsoft Copilot Chat for work offerings previously described with Microsoft 365 names. Some screens and materials may still use the older labels. Confirm the exact offering, license, and environment before comparing features. [S16]
Compare data handling at the plan level
OpenAI says business products and API inputs and outputs are not used for model training by default. Do not automatically apply that statement to a personal ChatGPT account or conclude that it means no processing, storage, or retention. Review the applicable contract, settings, connected apps, and recovery controls. [S15]
Microsoft describes enterprise data protection for eligible work Copilot experiences. Its guidance also distinguishes the handling of web search queries and the terms that may apply to agents or other services. "Inside Microsoft" should not become a shortcut for skipping the scope review. [S16]
Access can matter more than the answer quality
Ask what the assistant can read and what it can do. Test document permissions, shared links, connected apps, and sensitive repositories. An assistant can make existing oversharing easier to discover even if it does not create the original permission problem.
Check who can enable connectors, whether actions require approval, and how the organization removes access when an employee leaves. A strong writing demonstration does not answer any of those questions. Keep administrator controls, auditability, retention, and support needs in the comparison.
Run a side-by-side pilot
Use a small approved test set: an internal procedure, a routine analysis, and a drafting task with known facts. Measure useful completion time, correction effort, unsupported statements, and user adoption. Do not upload sensitive material merely to make the demonstration realistic.
Compare total cost rather than just subscription price. Include licenses, implementation, permission cleanup, training, review, and ongoing maintenance. Pricing and product features change, so obtain current terms during procurement rather than relying on an old comparison table.
Blue Tree Technology® can help frame the evaluation around business needs and security requirements. Choosing both tools for different approved tasks may be reasonable; choosing neither for a particular workflow may be reasonable too. The decision should follow evidence from your work, not a universal claim that one assistant is best.
Verification sources
S15 OpenAI: How data is used to improve model performance
S16 Microsoft: Enterprise data protection in Copilot and Copilot Chat