How to Ask Great Questions

As a coaching leader, the skill of questioning will be one of your most powerful tools. When you listen deeply you are naturally led to ask questions that help people clarify their goals and discover their direction.

Of the 5 key coaching skills, questioning may be the most difficult to master. I’ve met very few people who are gifted with the ability to ask great questions. What I have found while training many leaders is that the skill of questioning must be developed over a period of time through intention and practice.

question things1To help you continue your development as a coaching leader I have listed 5 ways you can develop your ability to ask great discovery questions.

1. Ask questions that encourage discovery. The role of questioning is to help a person gain clarity of the situation, think deeper, expand perspective, and help you as the coach better understand the situation. The number one rule for asking questions that lead to these outcomes is to ask open-ended questions. In other words, don’t ask questions that can be answered with one or two words. Your objective is not only to increase your understanding but also to help the person to begin discovering his/her direction.

2. Be curious about their world. Put yourself into a mindset of listening and learning. Seek to learn about the person you are coaching and understand exactly what the person is experiencing. In this mindset you will find it easy to ask good questions. When you catch yourself thinking “what is a good question to ask next”, remind yourself to listen and learn.

3. Be conversational. It’s important to help the person you coach relax and not feel like they are being interrogated. Use positive body language, smile, and make appropriate eye contact. Allow a two-way dialogue to occur.

4. Create some default questions for each step of the Goal Model. This is a great way to build a repertoire of questions you can easily remember. I have provided a list of coaching questions here for each of the 4 GOAL steps. Take some time to read each section of questions and highlight or mark 2-3 questions, in each area, that you can see yourself using while coaching. Read through your list of preferred questions before having your next coaching conversation. It will not take long before these questions (or variations of the questions) become natural and easy to use.

5. Practice, Practice, Practice. Challenge yourself to practice asking questions as much as possible. You can do this at home, with friends, on the job, and anywhere you are conversing with others. Determine that you will use the conversation to practice asking questions to better connect with the person and understand their situation or perspective.


Step 1: Goals
What outcome do you want?
What do you want to focus on?
What is your goal?
What do you want to achieve?
What problem are you trying to solve?
What is your top priority?
What one thing do you want to change?

Step 2:  Options
What options are available to achieve your goal(s)?
What are the possible ways to reach your goal(s)?
What have you done before in similar situations?
What have you not tried?
What is missing?

Step 3: Action Planning
What are the most viable options?
What needs to be the first step?
What is your step-by-step plan?
What resources will your need?
When do you plan to accomplish each step?
What roadblocks might you encounter?

Step 4: Lead the Action
What will you have accomplished by this time next week?
How will you stick to your commitment?
How would you like for me to hold you accountable?
When would you like for me to follow-up with you?
What can I do to support your efforts?
How do you plan to measure your change?