AI role-plays for leaders
Learning to Conduct Coaching Conversations
Does your team need development, but your advice falls flat? Learn to conduct coaching conversations that create real breakthroughs through AI role-playing. Realistic AI characters respond like actual employees—practice risk-free and become the coach who truly makes a difference.
Try an AI role-play – now, without registration!
Have a Coaching Conversation with AI employee
AI employee
Coaching Conversation: Practice scenario
The Challenges in
Coaching Conversationsn
In the Leadership context, conducting Coaching Conversations confidently is one of the most demanding tasks. You should know these typical pitfalls to successfully master Coaching Conversations.




MasterCoaching Conversationswith Careertrainer.ai
From scenario selection to detailed feedback – Careertrainer makes Coaching Conversation training in the Leadership context simple, effective, and measurable.

Select Scenario
Choose the appropriate scenario from various Coaching Conversations or create your own individual training scenario.
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Conduct Conversation with AI
Conduct a realistic Coaching Conversation with our AI. Train different situations and conversation flows in a safe environment.

Receive Feedback
Receive detailed, constructive feedback on your Coaching Conversation and concrete improvement suggestions for practice.
The 5 Phases for successful Coaching Conversations
Follow this proven 5-phase structure for professional and successful Coaching Conversations.
1Trustful Introduction
Begin the conversation with an open, positive attitude. Create a pleasant atmosphere where the employee feels comfortable speaking honestly.
5-10 minutes
Trustful Introduction
Begin the conversation with an open, positive attitude. Create a pleasant atmosphere where the employee feels comfortable speaking honestly.
About this Phase
Begin the conversation with an open, positive attitude. Create a pleasant atmosphere where the employee feels comfortable speaking honestly.
Practical Tips
- Warmly greet the employee and ask how they are doing.
2Reflection & Current Analysis
Analyze past performances and challenges together with the employee. Focus on specific examples and encourage honest reflection.
15-20 minutes
Reflection & Current Analysis
Analyze past performances and challenges together with the employee. Focus on specific examples and encourage honest reflection.
About this Phase
Analyze past performances and challenges together with the employee. Focus on specific examples and encourage honest reflection.
Practical Tips
- Ask targeted questions about recent projects and their outcomes.
3Developing Goals & Visions
Assist the employee in formulating clear and achievable goals. Collaborate to create a vision for their professional future and discuss their ambitions.
15-20 minutes
Developing Goals & Visions
Assist the employee in formulating clear and achievable goals. Collaborate to create a vision for their professional future and discuss their ambitions.
About this Phase
Assist the employee in formulating clear and achievable goals. Collaborate to create a vision for their professional future and discuss their ambitions.
Practical Tips
- Ask the employee where they see themselves in one year.
4Action Planning & Resources
Collaborate with the employee to develop concrete measures for achieving the set goals. Identify the necessary resources and support they may require.
15-20 minutes
Action Planning & Resources
Collaborate with the employee to develop concrete measures for achieving the set goals. Identify the necessary resources and support they may require.
About this Phase
Collaborate with the employee to develop concrete measures for achieving the set goals. Identify the necessary resources and support they may require.
Practical Tips
- Inquire about the essential resources the employee needs.
5Commitment & Next Steps
Summarize the discussed goals and actions, and ask the employee for their commitment. Clarify the next steps and schedule follow-up appointments.
10-15 minutes
Commitment & Next Steps
Summarize the discussed goals and actions, and ask the employee for their commitment. Clarify the next steps and schedule follow-up appointments.
About this Phase
Summarize the discussed goals and actions, and ask the employee for their commitment. Clarify the next steps and schedule follow-up appointments.
Practical Tips
- Summarize the key points of the conversation.
Train Coaching Conversations with AI characters
Every employee is different – and reacts differently to feedback. Our AI characters are based on the Myers-Briggs model and simulate realistic conversation dynamics: from the insecure junior employee to the critical senior developer.
Lade Charaktere...
Prepared for everything
Practice with introverted, extroverted, defensive, or emotional characters – just like your real employees.→ No surprises in real conversations
Real reactions
The AI becomes emotional, blocks, or opens up – depending on how you conduct the conversation.→ Learn to respond to different reactions
Safe practice space
Test different approaches without consequences. Find out what works – before it matters.→ Making mistakes is allowed
More Leadership Training with Careertrainer.ai
Train different conversation types and challenges in the Leadership context with our AI role-plays.
Mediation Conversations
When team members block each other and positions harden, it's crucial to learn how to facilitate mediation conversations that transform adversaries back into colleagues. Engage in AI role-play scenarios where intelligent AI characters simulate emotional escalations and hidden power dynamics, allowing you to practice the mediator role without igniting real conflicts.
Salary Negotiations
Conquer salary negotiations without the stress. Learn to conduct salary discussions that are fair yet economically viable through AI role-playing scenarios. Various AI characters simulate different negotiation styles—from the reserved to the assertive employee.
Employee Development Conversations
Conduct career conversations without empty promises? Learn to lead employee development discussions that inspire rather than frustrate through AI role-playing scenarios. Practice with intelligent AI characters in various development scenarios and accurately identify potentials.
Frequently Asked Questions
When is the right time for a coaching conversation?
A coaching conversation is beneficial when you want to actively support the development of an employee—regardless of immediate issues. Ideal situations include: an employee facing new challenges (such as project management or new responsibilities), showing potential but having an uncertain self-assessment, or stagnating in their development despite good performance. It can also be preventive in response to changes within the team or after successfully completed projects for reflection. Important: Coaching only works when there is a willingness to develop—if acute performance issues are present, a feedback conversation is the better first step.
How can I optimally prepare for a coaching conversation?
Effective preparation includes: gathering prior observations (employee strengths and areas for development), clearly communicating the framework ("I want to support you in your development – this is not a performance appraisal"), preparing open questions instead of having ready-made solutions, and allocating sufficient time (60-90 minutes without interruptions). Mentally attune yourself to the coach role: you are not the problem solver, but the development facilitator. The 5-phase structure helps you approach the conversation in a structured manner, from building trust to assessing the current situation and planning actions – without becoming directive.
What should I do if the employee is blocking or remains closed during the coaching conversation?
Resistance is normal and often indicates that you are touching on important issues. Instead of giving up or switching to a directive approach, acknowledge the resistance neutrally: "I sense some resistance right now. What makes it difficult for you to talk about this?" or "I notice that you seem hesitant – is there something that is blocking you?" Often, underlying fears (such as judgment, vulnerability, or lack of trust) are at play. Give the employee time, offer perspective shifts ("If a colleague were in your situation – what would you advise them?"), and reassure them once again that this is about development, not evaluation. Sometimes it takes several attempts – patience is key.
Why should we systematically train coaching conversations within the company?
Coaching conversations are the lever for sustainable employee development – yet very few leaders truly master them. A common issue is that, out of uncertainty, they resort to directive leadership ("Do it this way") instead of asking coaching questions ("What options do you see?"). The consequences are: employees do not develop a sense of ownership, innovation is stifled, and talents leave the company due to a lack of development prospects. Systematic coaching training with Careertrainer.ai empowers leaders to transition from directive instructors to developmental guides. The result: 2.5 times higher engagement, reduced micromanagement, and stronger internal talent development instead of costly new hires.
How do we implement training for 50+ executives with varying levels of experience?
Careertrainer.ai enables personalized scaling without coordination effort: Each executive trains at their own pace and level. Implementation is achieved in three steps: 1) Book a demo and set up the admin dashboard (1 day), 2) Onboard executives via an invitation link with individual access, 3) Training starts immediately – from beginners with "How do I ask open questions?" to advanced users with "Overcoming emotional blocks." The 16+ AI characters simulate various personality types (from the reserved analyst to the self-critical perfectionist), allowing each executive to practice relevant scenarios. Available 24/7, with 15-minute sessions possible between meetings. The HR dashboard shows who is training on which scenarios and identifies skill gaps for targeted re-training.
How do we measure the success of coaching conversation training within the company?
The HR dashboard provides concrete KPIs: 1) Completion Rate (How many leaders are actively training in coaching conversations? Target: >70%), 2) Average Score per Scenario (Indicates whether leaders are applying coaching rather than directive techniques – evaluated based on criteria such as "Open questions asked," "Self-reflection encouraged"), 3) Skill Gap Analysis (What challenges are predominant? E.g., "Finding the balance between leadership and coaching" or "Handling emotional topics"), 4) Usage Trends over 8 weeks (Shows learning consistency – continuous training outperforms one-time seminars). Additionally: a comparison between baseline skills (generic conversation management) and scenario performance (specific coaching competence). Unlike external seminars, which only provide participation certificates, you gain data-driven insights for strategic talent development.