Ian O’Byrne
Overstory Writing

Seven Critical Decisions to Make When Trying New AI Tools

How to evaluate new AI tools before you trust or buy them.

Posted
Aug 29, 2025
Last revised
May 1, 2026
Author
Ian O’Byrne
Read
4 min
Topics
ai · generative-ai · writing

The world of AI tools is expanding at breakneck speed. Every week seems to bring new applications promising to revolutionize how we work, teach, and create. But with this abundance comes a challenge: how do we thoughtfully evaluate which tools deserve our time, trust, and potentially our money?

During my weeklong workshop at CSPD (Computer Science Professional Development) Week this past summer, I developed a practical framework for making these decisions. Rather than jumping into every shiny new AI tool that crosses my feed, I now ask myself seven key questions that help me make more intentional choices.

1. Purpose: What Am I Actually Using This Tool For?

Before diving into any new AI tool, I start with the most fundamental question: what specific problem am I trying to solve?

Are you looking for:

  • Brainstorming support to generate ideas or overcome creative blocks?
  • Feedback mechanisms to review and improve your work?
  • Tutoring assistance to explain complex concepts or provide personalized learning?
  • Content creation help with writing, images, or multimedia?
  • Data analysis to make sense of information or identify patterns?

Being crystal clear about your purpose prevents the common trap of adopting tools simply because they’re impressive, rather than because they’re useful for your specific needs.

2. Data Handling: Where Does My Information Go?

This might be the most critical question in our current AI landscape. Every tool handles data differently, and the implications can be significant:

Key questions to investigate:

  • Is your data stored on their servers permanently or temporarily?
  • Do they use your inputs to train their models?
  • Can you delete your data, and is the deletion actually complete?
  • Are there geographic restrictions on where data is processed?
  • What happens to your data if the company changes ownership or shuts down?

For educators, especially, student privacy laws like FERPA add another layer of complexity. Always check whether a tool complies with relevant privacy regulations before introducing it into your workflow.

3. Trust & Transparency: Who’s Behind the Curtain?

The AI tool landscape includes everything from established tech giants to two-person startups. Understanding who created a tool and their track record matters enormously.

Research the creators:

  • What’s the company’s history and reputation?
  • Are the founders and key team members identifiable and credible?
  • How transparent are they about their technology and limitations?
  • Do they have clear terms of service and privacy policies?
  • How do they respond to problems or controversies?

A tool built by a reputable organization with clear accountability is generally a safer bet than one from an anonymous or secretive source.

4. Cost: Beyond the Dollar Signs

Cost analysis for AI tools requires thinking beyond just subscription fees. Consider the full spectrum of what you’re investing:

Financial costs:

  • Free tiers vs. paid subscriptions
  • Per-use charges vs. unlimited plans
  • Hidden costs that emerge with heavier usage

Time investments:

  • Learning curve and setup time
  • Time spent managing and maintaining the tool
  • Potential time lost if the tool doesn’t work as expected

Resource considerations:

  • Compute power and internet bandwidth requirements
  • Energy consumption (especially relevant for local AI tools)
  • Opportunity cost of time spent on this tool vs. alternatives

5. Control & Updates: Who’s in the Driver’s Seat?

AI tools evolve rapidly, but not always in directions that serve your needs. Understanding your level of control is crucial:

Version control questions:

  • Can you choose which version to use, or are updates automatic?
  • Do updates sometimes break existing workflows?
  • Can you export your data and work if you need to switch tools?
  • How much customization and configuration control do you have?

Tools that force automatic updates without user control can suddenly change their behavior, potentially disrupting established workflows at inconvenient times.

6. Support & Community: When Things Go Wrong

Even the best AI tools will occasionally confuse you, break down, or behave unexpectedly. Having good support structures makes all the difference:

Evaluate the support ecosystem:

  • Is there comprehensive, up-to-date documentation?
  • How responsive is customer support?
  • Is there an active user community or forum?
  • Are there tutorials, examples, and best practices readily available?
  • Do they provide clear guidance on limitations and appropriate use cases?

Tools with strong communities often provide the most valuable real-world insights about effective usage and common pitfalls.

7. Ethical Alignment: Does This Match My Values?

Finally, consider whether the tool aligns with your personal and professional values:

Key ethical considerations:

  • Equity and accessibility: Does the tool work well for diverse users and use cases?
  • Bias awareness: Are the creators transparent about potential biases in their AI models?
  • Privacy respect: Do their data practices align with your privacy values?
  • Environmental impact: Are they considering and minimizing their environmental footprint?
  • Labor practices: How does the tool’s development impact workers and creators?

For educators, additional considerations might include whether the tool promotes genuine learning versus shortcuts that undermine educational goals.

Putting It All Together

This framework isn’t about finding perfect tools. They don’t exist. Instead, it’s about making informed decisions that align with your specific needs, values, and constraints.

I recommend creating a simple spreadsheet or document where you can quickly evaluate new tools against these seven criteria. Over time, you’ll develop intuition for which factors matter most in your particular context.

The AI landscape will continue evolving rapidly, but thoughtful evaluation practices will serve you well regardless of what new tools emerge. By asking these questions consistently, we can move beyond the hype cycle and make choices that truly serve our goals and values.


What frameworks do you use for evaluating new AI tools? I ‘d love to hear about your experiences and additional considerations in the comments.