Coaching is evolving. Traditional box-ticking is giving way to a more meaningful approach—one where generative AI works alongside leaders to create stronger teams and lasting impact. This “Somewhat Contrarian” Prompting Guide for Executives help you apply AI in everyday coaching, moving beyond routine reviews to conversations that actually matter.

We focus on what works: real examples, actionable steps, and key questions for driving development, not just performance metrics. If your goal is to support people, uncover growth opportunities, and maintain a genuine human touch—even as you integrate advanced tools—this article is for you.

Handling Tight Corners: Getting help from generative AI in reprimands and difficult conversations
Managing a operational means balancing targets, morale, and policy. When repeated lateness or underperformance emerges, addressing it isn’t easy—leaders may hesitate or rush tough conversations, despite knowing these moments matter most for team growth and culture.
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Also refer to our guide on the value of AI for reprimands & difficult conversations.

1. Executive Summary: Beyond the Checklist

Progressive operations are ever evolving beyond metrics-driven environments into spaces where human potential flourishes. Generative AI offers unprecedented opportunities to transform coaching from transactional reviews into catalysts for genuine growth and innovation.

This guide provides practical applications of AI that go beyond conventional coaching approaches. We'll explore how AI can reveal blind spots in leadership, facilitate uncomfortable but necessary conversations, and create psychological safety that traditional methods often miss.

For leaders ready to pioneer the integration of technology with human-centred. This goes beyond operational efficiency to improve interactions, develop talent, and create a lasting impact in your organisation. coaching, we offer concrete strategies that leverage AI's unique capabilities while preserving the irreplaceable human connection.