The AI People Pleaser Problem: Why Your Team Needs Better Training


Hi Reader,

I've been having conversations with business owners and leaders across various industries lately, and they're all seeing the same troubling pattern: AI is making their quality and productivity problems worse, not better.

Employees are taking AI's first response without providing proper context. They're accepting solutions without understanding the underlying logic. Teams are skipping the critical thinking steps that ensure quality deliverables—the very skills that separate good work from mediocre work.

These aren't lazy employees—they're falling into AI's hidden trap.

AI: The Ultimate People Pleaser

Here's what most leaders don't realize: AI is designed to validate whatever you give it. As one participant in a recent webinar put it perfectly, AI is like "an eager college intern—it wants to be liked, it wants to please, and it says yes to everything."

Unlike a seasoned colleague who might push back on your assumptions, AI lacks the ability to challenge your thinking or question whether you're solving the right problem. This creates a dangerous blind spot where teams mistake AI's agreement for validation.

Recent research backs this up—there's a strong negative correlation between AI tool usage and critical thinking skills. The more people rely on AI, the less they engage their own analytical abilities.

The Foundation Test Every Leader Needs

Before investing in AI training, ask yourself these three direct questions about your team:

1. Do your employees challenge assumptions and think critically? When someone brings you a problem, do they also bring potential solutions and reasoning? Or do they wait to be told what to do?

2. Can your team provide context and connect the dots? When asking for help, do they explain background, objectives, and constraints? Do they understand how their work fits the bigger picture?

3. Do they know how to iterate and refine their thinking? Do they treat first drafts as starting points, or do they stop at the first reasonable answer?

If you answered "no" to most of these, you've identified exactly what needs to change before AI can be effective. The same skills that make employees valuable independent thinkers are what make AI interactions productive.

The Path Forward

The solution isn't more AI training—it's building the foundational skills that make AI interactions meaningful:

Encourage questioning: Make it safe to challenge assumptions and ask "what if we're wrong?"

Demand context: Require background, objectives, and success criteria before anyone can use AI tools

Reward iteration: Celebrate employees who come back with better questions, not just quick answers

The Bottom Line

AI amplifies whatever communication and problem-solving patterns already exist in your organization. If your team struggles with critical thinking and providing context, AI won't fix these issues—it will reinforce them.

The most successful AI implementations happen in organizations that already have strong foundational skills. These teams can immediately leverage AI's capabilities because they know how to provide context, ask good questions, and evaluate outputs critically.

Ready to assess your team's AI readiness? Check out the full article here to learn what gaps exist in your current foundation and how to strengthen the critical thinking skills your team needs before AI integration.


What concerns you the most about integrating AI into your business or team? If you'd like to explore how coaching can help you through this process, click below to book a complimentary Discovery Call, and let’s create a roadmap for effective and sustainable AI integration.


As always, please feel free to reply directly to this email with any questions, suggestions, or topics that you'd like to see covered in subsequent issues.

See you next month!

Cheers,

Anais

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"The real problem is not whether machines think but whether men do." - B.F. Skinner

Anais Babajanian

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