Buying Software With AI Assistance

A Comprehensive Guide

Reviewed AI Research Tools

To get you started, we tried some current popular AI research tools. We tested them with the prompts we are providing here for enterprise software shopping with a few composite company use cases. Everything in AI is changing rapidly. We expect your experience will vary from ours, depending on what tools you use, the prompt changes you make, when you make your calls, and your specific use case. By sharing our experiences, we hope to illustrate the variances you might see across AI tools, encourage you to experiment, but also always ensure humans are in control. For our tests, we successfully ran the prompts using free versions of these platforms (except Microsoft 365 Copilot Researcher, where we used our corporate domain license).

Logo-Claude Ai

Claude Sonnet 4.0

Pros

  • Best clarifying questions before executing the task
  • Provides a high-level summary and then extended response in well-structured format
  • Provides a scoring matrix and results, along with its reasoning

Cons

  • In the free version, you can run out of daily credits if you iterate on the prompt results without moving to another AI chat

Fine-Tune

None

Logo-ChatGPT

ChatGPT

Pros

  • Clarifying questions before completing task

Cons

  • Not particularly “deep” research. Sources consist mostly of vendor websites or vendor-written articles on content sites
  • Does not consider the longevity of data and provides information on solutions no longer sold or available

Fine-Tune

Deep research mode

Logo-Microsoft 365 Copilot

Microsoft 365 Copilot

Pros

  • Deep analysis of the solution options, including considerations not specified in the prompt
  • Provides a high-level summary and then extended response in well-structured format

Cons

  • Clarifying questions can try to limit scope to a list you want to consider
  • Can ignore the specific requirements or constraints provided in the prompt.
  • Will not provide ranking or recommendation comments unless prompted to do so

Fine-Tune

Use Researcher agent if available

Logo-Google Gemini

Google Gemini

Pros

  • Will provide a research plan for Gemini to undertake and prompt user for modifications
  • Very educative: best at showing its work, and in results, providing user with a summary of the topic itself

Cons

  • Did not ask any clarifying questions before executing the task
  • Has tendency to provide incomplete thoughts/sentences
  • Will not provide ranking or recommendation comments unless prompted to do so

Fine-Tune

Deep Research option