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đźš©The 21-Step AI Tool Evaluation Plan for Project Managers

Author

Justin Bateh
February 25, 2025

In partnership with

Hey, it’s Justin.

Today, we’re diving into a 21-Step AI Tool Evaluation Plan that can be used by managers looking to adopt AI into their team processes.

In this issue:

🔹 21-Step AI Tool Evaluation Plan
🔹 Where Leaders Can Feel Assured with AI
🔹 The Next Great Leap in AI
🔹 Free Live Webinar coming up

And more…

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DEEP DIVE

The 21-Step AI Tool Evaluation Plan for Project Managers

Most AI tool evaluations fail.

Why?

Because they focus on the wrong things—vendor hype, bloated feature lists, and vague promises.

You need a real framework—one that cuts through the noise and forces AI tools to prove their worth.

Here’s how to evaluate AI tools like a ruthless strategist, not a tech enthusiast.

1. Start With the "Job to Be Done"

❌ Don’t ask, "What can this tool do?"
âś… Ask, "What job do I need done that AI can handle better than a human?"

Action: Write down the exact pain points your team faces. If you can’t define a clear use case, don’t waste your time with AI.

2. Ignore Features, Focus on Outcomes

❌ Don’t get distracted by AI-generated buzzwords.
âś… Only pay attention to measurable improvements (e.g., 50% faster reporting, 3x fewer errors).

Action: Demand specific before-and-after case studies from vendors. If they can’t provide proof, walk away.

3. Reverse Engineer Your Current Bottlenecks

❌ Don’t assume AI will magically fix inefficiencies.
âś… Identify the biggest friction points in your workflow and only look for AI tools that target them.

Action: Ask, “What’s the most expensive, time-consuming, or error-prone process in my team?” If AI doesn’t solve that, skip it.

4. Force the AI to Compete With Your Current System

❌ Don’t assume new tech = better tech.
âś… Run a side-by-side A/B test with your current process.

Action: Use a pilot project to measure real performance gains. No improvement = no adoption.

5. Ask: Will This Save Me at Least 5 Hours a Week?

❌ If AI only makes things 10% easier, it’s not worth the headache.
âś… Focus on AI tools that create game-changing efficiency gains.

Action: If an AI tool doesn’t save you 5+ hours per week, cut it.

6. Check If It Works With Dirty, Messy, Unstructured Data

❌ Most AI tools work great on "perfect" data. But real-world data is messy.
✅ If AI can’t handle incomplete, inaccurate, or unstructured data, it’s useless.

Action: Feed the AI raw, chaotic data and see if it still delivers accurate insights.

7. Make It Survive a Stress Test

❌ Don’t judge AI on a controlled demo.
âś… Force it to handle high-volume, real-time, unpredictable scenarios.

Action: Throw worst-case scenarios at it (e.g., rapid-fire requests, conflicting data inputs). Watch if it crashes or adapts.

8. Force It to Prove It’s Smarter Than a Human

❌ AI should do more than just automate manual tasks.
✅ It needs to think—predict trends, analyze risks, and suggest improvements.

Action: Give it a complex problem with multiple solutions and see if it recommends a better approach than your team.

9. Cut the Learning Curve in Half

❌ If it takes months to train your team on the AI, it’s a failure.
âś… AI should be usable with minimal training.

Action: Challenge a non-technical team member to start using it in under 60 minutes. If they struggle, move on.

10. Test It With Zero Context

❌ AI that needs excessive hand-holding isn’t real AI.
âś… It should figure things out with minimal input and still deliver useful insights.

Action: Give it an ambiguous task with no detailed instructions. See if it produces meaningful results.

11. Demand 10x ROI, Not Just “Improvements”

❌ A 5% boost in efficiency is not enough.
✅ If AI doesn’t return at least 10x what you invest, it’s a waste.

Action: Do the math—if you spend $1,000/month, it should generate at least $10,000 in efficiency or revenue.

12. Ignore Industry Hype, Focus on Niche Use Cases

❌ The best AI tools aren’t the ones trending on LinkedIn.
âś… They are the ones solving specific, high-value problems.

Action: Find AI that excels in your exact industry, not just “AI for businesses.”

13. Assess If It Can Eliminate Entire Roles (In a Good Way)

❌ If AI only supplements your team, it’s an expensive assistant.
âś… The best AI replaces redundant manual processes completely.

Action: Ask, “Which 3 jobs could this AI eliminate or automate entirely?”

14. See If It Adapts to Your Company’s Unique Way of Working

❌ AI that forces your team to change their workflow is a headache.
âś… The best AI adjusts to your existing structure.

Action: If AI demands an entire new process or system, rethink the investment.

15. Run a “Worst Case Scenario” Test

❌ AI that works only in ideal conditions is useless.
âś… It needs to function under high pressure, missing data, and extreme conditions.

Action: Throw in flawed inputs, missing values, and conflicting instructions. If it still delivers results, keep it.

16. Watch How It Handles Edge Cases

❌ Most AI fails when things get complicated or ambiguous.
âś… The best AI tools think outside rigid rules.

Action: Feed it an unconventional problem no AI was trained for and check its logic.

17. Ignore the Demo, Ask for Real User Testimonials

❌ Vendor demos always look flawless.
âś… Look for unscripted, unfiltered user experiences.

Action: Demand direct access to real users who have used it for 6+ months.

18. Check If It Passes the “Hands-Off” Test

❌ AI should not require constant babysitting.
âś… The best AI works without daily intervention.

Action: Set it up, leave it alone for a week, and see if it still performs.

19. Verify If It Can “Think Ahead” and Not Just React

❌ AI that only responds to inputs isn’t real intelligence.
âś… It should predict and prevent problems before they occur.

Action: Ask, “Can this AI foresee risks and suggest fixes before I even notice them?”

20. Put It in a High-Stakes Environment

❌ AI that only works in low-risk tasks is a toy.
âś… It should be able to handle real decision-making in critical areas.

Action: Assign AI to a high-risk decision and see how well it performs.

21. Ask: Will This Still Be Relevant in 3 Years?

❌ Many AI tools won’t survive long-term.
âś… Choose AI that will keep evolving and improving.

Action: Check the company’s roadmap, funding, and innovation cycle.

Final Thought:

Most AI tools are overhyped and underperforming.

The best ones?

They save you time, make better decisions than humans, and create 10x ROI.

Use this framework and force AI to prove its worth—or don’t waste your money.

THAT’S A WRAP

Last Thing: Join me on March 21st for my free live webinar

The best project management jobs don’t go to the best applicants. They go to those who get seen first. Most people are stuck using outdated tactics—this session reveals modern, high-impact strategies to accelerate your career. I'll also cover my upcoming Project Management Certificate Program, and you'll get the recording + a cheat sheet to use right away - just for attending.

Until next time,
Justi