Most of my clients practice coaching to develop their employees. Yet the development conversation is only one of four types of coaching conversations. Coaching conversations can be focused on development, problem solving, performance feedback and career planning. It’s important to understand coaching is an artful process between you, the leader, and your employee. And the goal of your conversation will determine how you will deliver your coaching conversation.

The Problem-Solving Conversation

This coaching format is used when an employee has hit a roadblock and has asked you to help them solve a problem. They need help thinking through the issue and possible solutions. Instead of providing them with a solution, empower them to create their own solution through questions such as the following:

  • What will success look like in the end?
  • What is getting in your way to this end result?
  • What options are available to you that you haven’t tried?
  • What changes can make the biggest impact on your success?
  • Which direction are you committing to?

When an employee creates their own solution, they truly own it and are committed to solving the problem. And for you, you have helped them improve their problem-solving skills. In the end, they will be approaching you less to help them solve their problems.

The Performance Conversation

The Performance Conversation is used when an employee needs to improve a skill or change a behavior to improve their job performance. The conversation will start with recognizing what is going well. By starting with what is going well and providing specific instances of behaviors that are helping the employee’s success, you create a baseline of what they can build on to improve performance.

Listen to what they have to say and encourage them to share their opinions and perspective. What support can you provide them? And get clear on what needs to happen next and in what time frame. Make sure the next steps are mutually agreed on and there is a specific timeline. As coach it’s your job to hold them accountable to their actionable goals.

The Career Conversation

When helping an employee craft their long-term career goals and plan for achieving them, you’ll want to follow the Career Conversation process.

If you haven’t started the process, your initial conversation will be understanding the employee’s desire to take on added scope and responsibilities.  Get curious and learn about your employees’ values, gifts, interests and skills. Your goal is to understand the whole person not just the person’s performance. Create a list of questions to help the employee self-reflect on where they want to be in the future. A few questions to start you off are:

  • Tell me about the significant points in your life
  • How would you describe success in your current role?
  • What would be the perfect role for you in 2 years?
  • What will you be doing at the pinnacle of your career?

There may be points at which they don’t have an immediate answer, or they may feel uncomfortable with the questions. After all, many employees have never had a real career conversation. Get comfortable with silence and give them the time to reflect. What you learn in this conversation will be important in the Development Conversation. You will want to align the employee’s career aspirations with some of their development goals.

The Development Conversation

This conversation should take place after the Career Conversation and is when the manager and employee discuss employee development goals, progress being made, and how development is impacting job success. It’s also time to update the employee’s development plan.

Often this type of conversation is used with a high performing employee and is about preparing them for the next level of skill or responsibility to prepare them for greater responsibilities. Yet it is used with all employees being developed.

Before launching into the conversation, it’s important the employee has the start of a development plan to use as a guide for the development conversation. In Chapter 10 of Replaceable, An Obsession with Succession I describe the development conversation in detail. You and your employee also need to agree on the skills and behavior gaps to be developed. During the conversation, the development plan can be finalized or adjusted from your previous career conversation.

And it goes without saying that appropriate praise and recognition for accomplishments be delivered.


It’s important to remember that you keep each of these coaching conversations separated. I often find leaders combining the development and career conversations into one conversation which dilutes the conversation and can cause confusion in the objective of the conversation.

Ultimately coaching successfully executed coaching conversations require clear objectives, great questions leading to insightful answers, and action by the coached. Take time to prepare before having your coaching conversation to ensure short- and long-term success.