Leadership Development

Pocket Coach: How AI Is Making Feedback and Coaching More Accessible

Discover how AI tools help new managers give better feedback—faster, safer, and with more confidence—through private, on-demand practice.

Pocket Coach: How AI Is Making Feedback and Coaching More Accessible

Giving feedback is one of the hardest things new managers have to learn. It takes confidence, tact, and timing. And it’s not just about what to say—it’s how to say it.

Traditionally, developing that skill takes time, practice, and often a coach. But now, AI is making that development more immediate and accessible—without waiting weeks between 1:1s or relying solely on memory and emotion.

What AI Coaching Tools Can Do

Emerging tools like Cultivate, BetterUp, and ChatGPT-powered roleplay bots are helping managers:

  • Practice difficult conversations in private, low-risk environments

  • Receive feedback on tone, clarity, and empathy

  • Explore multiple ways to frame the same message

  • Reflect on their own patterns and communication style

Some tools even let users simulate coaching scenarios or rehearse key talking points before a real conversation. It’s not about replacing human wisdom—it’s about offering it on demand.

Real-World Use Case

Imagine a first-time manager about to give critical feedback to a team member who’s consistently missing deadlines. Instead of going in cold—or rehearsing in their head—they use an AI tool to simulate the conversation. The AI offers three versions of the message, flags language that could come off as too passive or too harsh, and suggests a structure that starts with shared goals.

When the real conversation happens, it’s smoother, more constructive, and more confident. The manager feels ready—and the team member feels respected.

What This Means for L&D Professionals

As someone responsible for developing leaders, you don’t have to wait for coaching sessions to create growth moments. You can:

  • Integrate AI roleplay tools into training modules

  • Encourage managers to use AI to prep before giving or receiving feedback

  • Pair AI coaching with peer feedback to increase reflection and learning

And because AI tools don’t get tired or busy, they’re always available—for the moments that matter most.

Ethical Use and Clear Boundaries

Of course, AI coaching is only useful if it’s trustworthy. Make sure tools:

  • Keep all interactions private and confidential

  • Avoid collecting or storing sensitive employee information

  • Emphasize human judgment over automated scoring or advice

Used ethically, AI coaching can feel like a supportive mentor in your pocket—not a robotic manager looking over your shoulder.

Final Thought

Confidence doesn’t come from knowing what to say. It comes from preparing to say it well—practicing. AI is making that preparation easier, faster, and more accessible—for every leader, not just the lucky few with a coach on speed dial.

Coming next: how AI can help managers connect insights across their teams with personalized, real-time people analytics.

About the author:

Jared is the founder of Leadership Progress Cycle and a co-founder of Niche Academy. He is a teacher, a learner, and an entrepreneur. People are his passion and he believes great leaders help others realize their full potential.

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