What is AI coaching?
A Guide for Talent Development Leaders
TL;DR
AI coaching is software that gives people specific guidance for real work situations, like delivering critical feedback or preparing for a first 1:1 with a new direct report. Effective coaching accounts for how both people work, drawing on market-leading assessments to personalize the guidance. Coaching can reach employees through Slack, Teams, Workday, LLMs, or email. AI coaches should help people work through challenges together, with the ability to measure if behavior is changing.
See how AI coaching platforms help people connect
What is “AI coaching”?
AI coaching is like having a professional coach available at any moment. It’s a powerful tool that knows your people, their team, and the dynamics that enable success. It’s always there to guide and challenge you in real-time.
The best AI coaches understand your personality, work context, calendar, and team dynamics. They can account for how both people in a situation might work and know when they are working together. That context ensures the coaching helps people understand each other and choose a useful next step, no matter what they’re working on.
An AI coach for teams is an always-available, context-aware tool that accelerates performance by helping people work together inside their workflow.
What should AI coaches know about a team?
AI coaching needs four layers of data:
01
How the person asking for coaching communicates, what motivates them, and how they prefer to receive feedback, based on their assessment results.
02
How coworkers communicate, what motivates them, their feedback preferences, along with where any two people may work well together or run into friction.
03
What is happening inside the organization or other changes that could affect the conversation.
04
The growth areas the person is already working on, conversations they have practiced, and coaching they have already received.
When and where should AI coaching be available?
AI coaching should be available before moments that shape a working relationship, such as a 1:1, a performance review, or a first week on a new team. Employees can access coaching through tools they already use, including Slack, Microsoft Teams, Workday, email, and supported AI assistants. Cloverleaf can bring assessment and relationship insights into assistants such as Claude, Microsoft Copilot, ChatGPT Enterprise, and Gemini.
Coaching can be timed to what is about to happen: a 1:1 on tomorrow’s calendar, a new person joining a team, a manager change after a reorg. When someone joins, leaves or moves teams, the coaching for everyone affected can sync at the same time. Coaching proactively shows up at the correct time for the right moments in the flow of work.
Why do validated assessments matter to how accurate AI coaching can be?
AI coaching needs a clear understanding of how people communicate, think, and work together. Five types of assessments provide useful context for tailoring guidance to each person and situation.
Cloverleaf brings these perspectives together to ground coaching in assessment results. With context about both people, guidance can suggest specific ways to explain an idea, give feedback, or work through a disagreement.
Emotional Intelligence
Insights Discovery
BlueEQ
Productivity & Energy
Strength-Based
Cultural & Motivational
How do you compare AI coaching platforms?
Ask vendors to show how their coaching understands employees, accounts for working relationships, and reaches people when they need support. Your evaluation should also cover how each platform protects employee data and measures progress.
Cloverleaf’s AI Coaching RFP Template helps you turn those questions into a consistent way to compare providers. The download includes:
- Ready-to-use questions covering coaching capabilities, assessments, integrations, security, implementation, and pricing.
- Customizable priorities so you can identify the requirements that matter most to your organization.
- An evaluation scorecard and guide to help your team review responses and compare vendors.
- Use the questions to prepare for demos or customize the full template for a formal request for proposal.
How do you embed AI coaching into your organization?
Start with a program employees already participate in, such as onboarding, mentoring, or leadership development. Choose a specific moment where coaching can help and build the instructions into the preparation or meeting agenda.
Give employees a clear first step:
During onboarding: Explore how a new teammate communicates before your first 1:1.
Before a mentoring session: Use coaching to identify a development goal and prepare questions.
In manager training: Practice an upcoming feedback conversation.
During team meetings: Invite people to share a coaching insight and discuss how to apply that insight together.
Explain how employee information will be used, make coaching easy to access, and ask which suggestions people tried and what happened afterward. Use that feedback to improve the experience before expanding to more teams.
See how MacLean-Fogg built AI coaching into mentoring, onboarding, and recurring meetings, including what the team learned along the way.
