PROMPT This AI Challenge

"What AI Still Misses in Leadership Coaching" featuring Dr. Shelli Hendricks

Every episode of the PROMPT This podcast includes an AI Challenge for the audience.  Follow the instructions below to complete this episode's challenge.

Most leaders are using AI to move faster. Fewer are using it to become better humans.

This challenge is about setting a boundary. AI as a thinking partner, not a voice replacement. AI that sharpens judgment without sanding down empathy. It is short, personal, and intentionally uncomfortable in the right way.

This challenge is inspired by a leadership reflection exercise focused on preserving human judgment and authenticity while working with AI.

The Premise

AI can help leaders become more human only if it is used deliberately.

Left unchecked, AI tends to optimize for clarity, polish, and confidence. Leadership often requires vulnerability, hesitation, and emotional nuance. This challenge exposes exactly where AI helps and where it should step aside.

The Challenge

Time required: 10 to 15 minutes

Step 1: Choose a real leadership moment

Pick something from the last one to two weeks where you know you could have shown up better.

Examples across roles and industries:

• A manufacturing leader who rushed a corrective conversation on the floor

• A services executive who avoided giving hard feedback to a high performer

• A product leader who made a fast call without listening to dissent

• A sales leader who optimized for speed over care in a deal review

Choose something that still has emotional residue.

Step 2: Write the human-first version

Write 5 to 7 sentences with no AI involved.

Cover:

• What happened

• How you showed up

• What you wish you had done differently

• What you learned

Do not polish. Do not reframe. This version is for honesty, not performance.

Step 3: Let AI strengthen, not replace

Paste your reflection into AI and ask it to:

"improve the thinking without replacing the human"

Step 4: Compare side by side

Read both versions carefully and answer:

• What did AI clarify or sharpen?

• What emotional nuance did it miss?

• What part of your voice felt diluted or lost?

This comparison is the point of the exercise.

Step 5: Set your AI boundary

Finish this sentence and write it down:

“Going forward, I’ll use AI to help me with ________, but I’ll keep the human part of ________ for myself.”

This becomes a repeatable leadership rule, not a one-time insight.

AI Prompts

Use these prompts directly or adapt them. Each is designed to keep AI in a supporting role.

• Strengthen this reflection while preserving my voice, vulnerability, and emotional nuance. Do not make it generic or overly polished.

• What parts of this reflection are analytical versus emotional? Call them out separately.

• Where does this reflection show good judgment but weak empathy?

• Rewrite this reflection focusing only on clarity, not tone.

• What questions should I ask myself that AI cannot answer here?
  
  

Final Thought

AI is excellent at structure, clarity, and pattern recognition. Leadership still requires discernment, courage, and emotional presence.

The leaders who win will not be the ones who delegate thinking to AI, but the ones who use AI to see more clearly where thinking must stop and humanity must lead.