What is Conversational Coaching?

Sometimes you don't need a specific output — you need advice. Conversational Coaching in Coach Pilot provides an open-ended chat experience with an AI that understands your company's sales methodology, your assigned playbooks, and your live deal data.

How It Works

Start a coaching session from the Workspace by selecting the Coaching option. Unlike skill-based objectives that produce a specific deliverable, coaching sessions are free-form conversations where you can explore any sales-related topic in depth.

The AI draws on multiple sources of context to provide relevant, personalised guidance:

• Your company's methodology — Whether you're using MEDDIC, MEDDPICC, BANT, SPICED, Challenger, or any other framework, the AI coaches within that context

• Your assigned playbooks — Company-specific sales guidance and best practices inform every recommendation

• Your deal data — When you reference a deal, the AI pulls in the full CRM record for context-aware coaching

What You Can Discuss

Conversational Coaching is flexible and adapts to whatever you need help with:

• Deal strategy — Talk through your approach to a specific opportunity and get AI-powered recommendations

• Objection handling practice — Rehearse responses to common and uncommon objections before a real conversation

• Negotiation approaches — Explore different negotiation tactics and strategies for upcoming discussions

• Difficult prospects — Work through challenges with tough prospects or complex buying committees

• Methodology application — Get guidance on applying your sales methodology to specific situations

• Skill development — Ask for feedback on your approach and learn new techniques

Tagging CRM Records

During any coaching conversation, you can tag a CRM deal or contact to bring that record's data into the conversation context. This allows the AI to provide specific, data-informed coaching rather than generic advice. Simply reference a deal or contact mid-conversation, and the AI will pull in the relevant CRM data including deal stage, value, key contacts, recent activity, and more.

Privacy

Coaching conversations are private to you by default. You can choose to share a session if you want feedback from a colleague or manager, but no one else can see your coaching conversations unless you explicitly share them.