Difficult Conversations Coaching Program for Middle Managers
4-month coaching program equipping middle managers with emotional intelligence and structured frameworks for effective difficult workplace conversations.

Program Goal
Develop middle managers' ability to conduct difficult conversations
Program Duration
4 Months
Target Audience
Employees
Key Points
- ✓ Master the OCEAN conversation framework (Open, Engage, Create, Next Steps) for structured, effective dialogue in challenging situations.
- ✓ Develop emotional intelligence to recognize triggers, manage responses, and create psychological safety for constructive feedback exchanges.
- ✓ Apply skills through real-world practice with 70-20-10 learning model: 70% experiential, 20% coaching, 10% formal training for sustainable results.
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Program Management Guide: Middle Manager Difficult Conversations Coaching Program
1. Program Introduction & Benefits
This program is a structured, 4-month coaching initiative designed to equip middle managers with the practical skills and emotional intelligence framework necessary to conduct difficult workplace conversations effectively. It is built on the proven 70-20-10 Learning Model, emphasizing experiential, on-the-job application (70%), supported by personalized coaching (20%) and formal training (10%). The core methodology integrates the OCEAN model for conversation structure and emotional intelligence-based coaching to transform conflicts into collaborative problem-solving opportunities.
Strategic Benefits for Employees (Direct Reports of Participating Managers):
- Enhanced Psychological Safety: Employees will experience more constructive, empathetic, and clear communication from their managers, fostering a safer environment for dialogue and feedback.
- Improved Conflict Resolution: Issues will be addressed more promptly and effectively, leading to clearer expectations, reduced workplace tension, and more mutually agreeable solutions.
- Increased Engagement & Clarity: Through managers' improved active listening and feedback delivery, employees will feel heard, understood, and have a clearer path for performance and development.
- Professional Development Modeling: Employees will benefit from observing and experiencing advanced communication techniques, which they can adopt in their own professional interactions.
2. Program Expansion Strategy
Evaluation: This is a Coaching Program. While the core program is robust, integrating a supplemental Peer Mentorship layer among the participating managers would significantly enhance outcomes and sustainability.
Value Addition & Implementation: A structured peer mentorship component, launched after Month 2, creates a continuous support network. It reinforces learning through shared experience, provides a safe space for managers to discuss challenges without formal evaluation, and fosters a culture of collaborative leadership. This directly supports the 20% "learning from others" component and the final milestone on sustainability.
- Implementation Note: Pair managers from non-competing departments. Provide a simple framework for monthly peer check-ins focused on sharing real-world application stories, problem-solving specific scenarios, and holding each other accountable to their development plans. This can be facilitated through the Internal Social Network or Coaching Software.
3. Implementation Roadmap
Launch Phase (Pre-Month 1)
- ✓ Secure executive sponsorship and communicate program strategic value.
- ✓ Finalize participant selection criteria and nominate cohort of middle managers.
- ✓ Onboard and align external/internal coaches on program methodology, milestones, and KPIs.
- ✓ Distribute pre-program 360-degree feedback and communication health assessments to participants and their teams.
- ✓ Schedule kick-off workshop and all major coaching session blocks for the 4-month period.
- ✓ Set up all tracking dashboards in the selected Program Software (see Section 4).
Tracking & Operations (Months 1-4)
- Weekly: Coaches log session notes and participant progress in Coaching Software. Program manager monitors engagement metrics.
- Bi-Weekly: Deliver micro-learning content (videos, articles) via the LMS aligned with the current Actionable Content Pillar.
- Monthly: Conduct cohort check-in workshops for skill practice (e.g., role-play labs). Review tracking dashboard with sponsors.
- Milestone Gates: At the end of each milestone month, collect required outputs (e.g., reflection journals, completed role-play certifications, documented conversation plans) and update participant progress.
Success Measurement
- KPIs & Feedback Mechanisms:
- Quantitative:
- Pre/Post 360-Degree Feedback: Measure change in communication competency scores.
- Team Engagement Survey Scores: Track improvements in psychological safety and "manager communication" items.
- Program Completion & Application Rate: >90% completion of all modules and coaching sessions; each manager documents at least 3 real-world difficult conversations during the program.
- Software Analytics: Engagement with LMS content and peer interaction metrics.
- Qualitative:
- Mid-Point (Month 2) & Final (Month 4) Reflection Surveys: Participant self-assessment on confidence and capability.
- Coach Summaries: Qualitative analysis of skill progression across the cohort.
- Documented Case Studies: Collect 2-3 anonymized examples of successful conversation turnarounds.
- Exit Interviews: 30-minute interviews with a sample of participants to capture nuanced feedback and stories.
- Quantitative:
4. Approved Tools List
- Coaching Software: Primary Tool. This is non-negotiable for managing the 20% coaching component. It will be used for scheduling one-on-one sessions, storing coach notes, tracking action plan progress, and aggregating qualitative data for measurement.
- LMS (Learning Management System): Primary Tool. Essential for delivering the 10% formal training component asynchronously. It will host micro-learning videos on the OCEAN model, emotional intelligence modules, role-play simulation guides, and housing the Resource Library.
- Internal Social Network: Supporting Tool. To foster community and the supplemental peer mentorship layer. A dedicated group will allow managers to share resources, ask questions, and support each other between formal sessions, enhancing collaborative learning.
- Personality Test: Supporting Tool. To be used in Milestone 1 (Foundation Assessment) to increase self-awareness. A tool like a DiSC or similar assessment can help managers understand their own communication styles and potential triggers, feeding into Pillar 1 on Emotional Intelligence.
Justification: Mentorship Software is not required as the primary relationship is coach-coachee. ERG and Onboarding Platforms are not relevant to the program's core goal. The selected tools directly enable the 70-20-10 model: LMS (10%), Coaching Software (20%), and Internal Social Network supports the social learning aspect of the 70%.
5. Resource & Content Library
Training Content for Coaches
- Guide: "Facilitating the OCEAN Model in Role-Play Scenarios"
- Video Series: "Identifying and Coaching Emotional Triggers in Managers"
- Article/Guide: "Structured Feedback Techniques for Coaching Conversations"
- Template: "Coaching Session Debrief Template" (focused on real-world application)
- Guide: "Measuring Behavioral Change: From Role-Play to Live Application"
Training Content for Coachees (Managers)
- Micro-Learning Video 1: "The Anatomy of a Difficult Conversation: From Fear to Framework"
- Interactive Module: "Self-Assessment: Your Communication Style & Triggers"
- Video & Worksheet: "The Preparation Phase: Gathering Facts vs. Stories"
- Step-by-Step Guide: "Executing the OCEAN Model: Phases 1-3 (Open, Engage, Create)"
- Simulation: "Virtual Role-Play: De-escalating an Emotional Response"
- Toolkit: "Scripting Templates for Common Difficult Conversations"
- Guide & Template: "Creating a Shared Action Plan (OCEAN Phase 4: Next Steps)"
- Reflection Journal Template: "Post-Conversation Analysis: What Worked, What Didn't"
- Video: "Building Long-Term Trust: Following Up After a Tough Talk"
Frequently Asked Questions
This is a structured 4-month program following the 70-20-10 learning model: 70% experiential on-the-job application, 20% personalized coaching sessions, and 10% formal training through micro-learning content.
The program integrates the OCEAN model for conversation structure (Open, Engage, Create, Next Steps) combined with emotional intelligence-based coaching to transform conflicts into collaborative problem-solving opportunities.
Employees experience enhanced psychological safety, improved conflict resolution, increased engagement through better listening, and professional development modeling of advanced communication techniques.
Essential tools include Coaching Software for one-on-one sessions, an LMS for micro-learning content, an Internal Social Network for peer support, and optional personality assessments for self-awareness.
Success is measured through pre/post 360-degree feedback, team engagement surveys, program completion rates, documented real-world conversations, coach summaries, and qualitative case studies.
A supplemental peer mentorship layer is launched after Month 2, pairing managers from non-competing departments for monthly check-ins to share experiences and reinforce learning through collaborative support.
Managers receive micro-learning videos, interactive modules, role-play simulations, scripting templates, reflection journals, and step-by-step guides on the OCEAN model and emotional intelligence application.
Thank you!
Thank you for reaching out. Being part of your programs is very valuable to us. We'll reach out to you soon.
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