1. Set up and follow up are key. Allow time to explore and listen where you are not rushed. Following the conversation, make a note of the things that stand out, and when / how you will follow up. Then actually follow up.

2. Deliberately schedule your coaching sessions so that you’ll be able to get into that place of listening, and if you anticipate being frantic in the hour leading up to your session take a few minutes out to pause, take a few deep breaths, and get yourself physically centered. Pull up your notes from previous conversations to reconnect to the conversation as it stands now.

3. Begin by planning out what you’ll ask and get yourself into the right mindset before the conversation begins. There are many questions to choose from…select 3-5 that will allow you to connect best with your employee. Close your laptop and put away your phone. Focus only on your employee and on the conversation.

4. The questions are not a prelude to telling your employee what to do…they ARE the conversation, not the lead up.

5. Asking the right questions means the difference between a one-way interrogation and a dynamic conversation. Good questions allow space for self-examination. The right question can stop us in our tracks as we finally see our own actions from a different perspective or envision a new solution to an nagging problem.

6. After you ask a question, pause and listen…really listen to what others are saying. Then, ask another related probing question to dig deeper. That shows you are listening, interested and engaged.

7. Suspend your need to rush the conversation along, stop yourself from answering the question for them, and approach every conversation with a sense of wonder…I wonder what really inspires this person…I wonder what they want to get out of this opportunity…I wonder what skill they really want to develop. Be genuinely curious! People can tell if you’re just asking a question because it’s what you’re “supposed” to do.

8. Ask open-ended questions that start with “what,” “how,” “who,” “where,” and “when.” Stay away from “why” – it can feel confrontational and judgmental. If you really are interested in the why behind an action, instead ask, “What was your intention with that?”

9. Once you understand your new employee’s point of view on a given situation, be careful not to let the session turn into venting or blaming others. Instead of asking questions that might reinforce the emotional charge, ask questions that open up possibilities that may have not been considered. Ask questions to move forward or initiate action.

10. The bottom-line is, engaging employees in solving their own problems values their intelligence, cultivates their own independence, and enhances their independent problem solving capabilities. Doing this requires an investment of your time, and a willingness to experiment with your approach as a manager. But the investment is worth it. You can reduce dependency, boost morale, increase employee capabilities and develop better solutions leading to better results.


We are confident that if you just START the conversation with a GREAT QUESTION, you will begin to connect, and the conversation will happen naturally. The questions are in no particular order, and they are divided into categories that every manager can use. So dive in, experiment and explore…let the conversation begin. Click here to jump into the questions!