Selecting enterprise software for your team is a challenging exercise. Making the right decision solves problems, reduces company risk, and has your team sending celebration memes over Slack. Making the wrong decision not only doesn’t solve problems, it can create new problems, increase the risk of the company achieving its goals, stress people out, and negatively impact your career.
Artificial intelligence (AI) is increasingly integrated into both workplace and daily life tasks. In the workplace, employees rely on AI to accomplish substantial objectives—such as researching topics, assisting with content creation, and contributing to strategic planning. AI is also a valuable tool for shopping for software solutions within a business. The process outlined below—including suggested prompts—can help any organization identify the best enterprise software choice for its needs, whether seeking PLM, QMS, MES, ERP, CRM, or other solutions.
a. Choose the right AI.
Not all AIs are equal, and many are designed for specific use cases, from finding the perfect restaurant for an offsite to developing revolutionary eco-friendly waterproof coatings. There are many types of AI (and it can get esoteric to try to agree on the number and divisions). Even within a category of AI, different AI offerings use different large language models (LLMs) with varying constraints and reach. You may use Midjourney or Canva if you need cosmic squirrel art or new LinkedIn banner images. Grammarly’s powerful AI features are great for getting your first novel out of your brain and to the finish line. StyleAI might help you with that special outfit for your cousin’s wedding.
For enterprise software shopping, you need a research-oriented AI that can perform web searches for the most up-to-date information possible.
Use an AI with a “research” mode turned on to make sure it is double-checking its work and providing sources for all facts that you can double-check and explore. It may take a while to generate output, but the quality will dramatically improve. Remember that cloud-based enterprise software like Arena continuously releases new features and updates. Using an AI with stale data may give you inaccurate information and should not be trusted. We’ve provided some AI recommendations in the table below based on our testing to get you started. You can also use AI to help you find new AI research tools.
b. Explore your AI’s settings.
Start by asking your AI if it has special settings or access to private data. Some AIs, like Microsoft 365 Copilot and Claude, may have access to special settings that are designed for your specific use case. Your AI may also have access to your company’s internal documents and communications, which can help it tailor its findings to your specific needs.
a. Requirements are, well, still required.
Before you can construct a good prompt, you need to identify business needs and capture your requirements. What your team needs is not identical to what other teams need. AI will provide generic non-actionable results if you don’t provide the context of your business needs and requirements. If you aren’t entirely sure if your requirement list is complete or accurate, consider also using AI to help review it. You can refer to our How to Buy Software Guide on the process of building a team and doing this work if you aren’t sure where to start.
b. Good input = better output.
Prompt engineering is a skill, and every AI has its own personalities and peculiarities. Getting one AI to generate useful information may require a very different prompt from another. Some may work best with a detailed, lengthy prompt while others generate more useful answers from shorter, general questions. Others are sycophantic and work best when you tell them to act as devil’s advocate. However, you don’t have to have a degree in machine learning or AI to construct a good prompt. You do need an understanding of what a good prompt is, an iterative experience, and the willingness in the community to share good prompts. And, we are a sharing people at Arena by PTC, so use these starter prompts and go from there.
c. Try multiple AI!
In our experiments, the results can vary dramatically. Go wild and try several. If this is your first time using AI for a structured research project, running the prompt through multiple will help you see the differences between tools and give you better overall content to use in your search.
a. AI is fallible and AI hallucinates.
Hallucinations are when our sensory perception does not correspond to the external stimuli. AI hallucinations occur when the algorithmic system gives information that seems plausible but is false, inaccurate, or misleading. (Dive deeper into this topic with researchers here.) This is particularly true when asking questions about enterprise software, for which publicly available documentation is often unavailable. You can mitigate this issue by turning on “Research mode,” but even this is not a guarantee. Software selection is important to your company and, therefore, to you and your team. AI hallucinations can cause real damage to yourself, your colleagues, and your business when used unchecked. If something sounds too good to be true, make sure to verify by reviewing the AI’s sources. See step 4 for more recommendations on how to mitigate this risk.
b. Iterate with the AI to improve the results.
Ask follow-up questions to dig deeper into a topic or have the AI consider the issue from a different perspective. You can have conversations with the AI to improve the results (until you run out of credits if using a free or limited version of the tool). You may also find that the AI’s clarifying questions or results give you improvements to the initial prompt that you want to re-run or run in another tool.
Software vendors do not publish everything about their companies, product roadmaps, functionality, and customer commitments. As AI-powered search and research tools have gained dominance and are fast replacing traditional web searches, all companies are now working to rapidly catch up to the new AEO (answer engine optimization) that is replacing traditional SEO (search engine optimization). What does this mean? All of us—including your own company—are busy re-evaluating the content breadth, depth, and structure on our public sites and other locations.
a. Don’t abdicate to AI.
Humans need to be in the loop at every step—from identifying business needs and requirements to running well-executed AI research to giving vendors the chance to respond to what you have learned so far in your research—answering your questions, providing customer references, and all the other critical information you need to make a great decision. Additionally, you may have a very detailed requirements list with weightings and other roll-up considerations. Generic AI research tools often lack access to the proprietary or nonpublic data needed to fully understand your requirements. As a result, they may misinterpret what you’ve uploaded or fail to assess whether a specific vendor can meet your needs. Just like working with a colleague, asking the AI to rephrase your requirements in its own words can help surface misunderstandings and clarify intent.
b. Help vendors help you.
Vendors can better respond to your search when you are transparent about your business needs and requirements. And, if you have used AI tools for research, let the vendors know and ask them to respond to the results and prove out solutions.
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).
Claude Sonnet 4.0
None
ChatGPT
Deep research mode
Microsoft 365 Copilot
Use Researcher agent if available
Google Gemini
Deep Research option
Step 1: Fill in the Industry/Domain and Organization Context sections with your specific details.
Step 2: Provide as much detail as possible in the Specific Needs & Examples section.
Step 3: Submit this information and be prepared to answer follow-up clarifying questions if the AI asks.
Step 4: Review the structured analysis for each recommended solution.
Step 5: Ask the AI to refine results based on your review. You may notice sections where you have failed to provide guidance on requirements, business needs, or constraints. You may want the AI to summarize the research. You can continue to refine the results (you may run out of daily credits, though).
Copy these prompts to a document and then complete the sections for your needs. Always save your prompts. Then copy and paste the prompt into the AI tool of your choice. Note: Some AI tools don’t support copy and paste of text (Gemini, currently). You can upload the saved prompt document instead.
You are an expert enterprise software consultant helping a team select the optimal software solution for their organization. Your role is to guide them through a comprehensive evaluation process. You should provide pros and cons. You should ask clarifying questions as needed. You should provide clear next steps and a decision framework. Provide potential challenges and risk mitigation strategies. Include sources.
Objective, analytical, and professional.
You should cover the following in the comparison:
[Edit this list if you have specifics or consider splitting the list into high priority and lower priority]
Here are the details on needs.
[Provide the type of software you are looking for. E.g., CRM, ERP, PLM, HR management, project management, marketing automation, etc.]
With this prompt, there is an option to upload to the AI documents provided by a vendor (e.g., corporate financial reports, customer story deck, detailed third-party reviews). The prompt directs the AI to consider these if provided. If not, the AI is directed to utilize public domain data it can access.
Note: This prompt can be run against a vendor and then re-run against a second. Some AI tools will automatically compare the two vendors in the second response if done in the same session. Alternatively, you could expand the prompt to analyze multiple vendors and provide a comparison.
You are a business decision-maker, evaluating potential enterprise software vendors. Include sources.
Objective, analytical, and professional.
Conduct a comprehensive review of the provided information about [Vendor Name], focusing on financials, business performance, and customer base to assess viability as a long-term partner.
[Describe your industry, e.g., large manufacturing company, midsize financial services firm] is evaluating [Vendor Name] for [Describe the software need, e.g., a new ERP system, a cloud-based CRM solution].
Key priorities are:
Search for publicly available data and analyze the following information. Include the data I have provided in the upload, if any.
Provide a structured report that includes:
Now that you have some starter prompts, you can start vendor evaluation. Obviously, finding your next software solution won’t end here. Our How to Buy Software Guide provides you with a step-by-step process from building full requirements, gaining executive sponsorship, and building team consensus to important considerations in evaluating vendors when you are engaged with them directly. And you will most likely find other uses for AI as you go through the full process.
