Become A Stronger Leader With Compassionate Coaching And These 25 Questions

Developing compassionate leadership skills requires proficient coaching skills. Coaching can be practiced with any stakeholder you want to have a more authentic relationship with while supporting them to be their best. Stakeholders can include clients, vendors, peers, bosses, or employees.

Here is the definition of coaching provided by the International Coaching Federation:

Partnering with stakeholders in a thought-provoking and creative process that inspires them to maximize their personal and professional potential.

At Compassionate Leaders Circle, we teach compassionate coaching skills and take this practice a step further:

Partnering with stakeholders in a compassionate, present, and in-depth process enabling them to slow down, assess progress, and trust their inner wisdom for transformation.

How is coaching different than just meeting with a stakeholder?

Coaching conversations shift the focus from the leader to the stakeholder. And change the leader from doing most of the talking to doing most of the listening. Here is the Compassionate Leaders Circle Recipe for creating an excellent coaching conversation:

Structure and Skillful Questions: 30%

Silence: 60%

Support and Suggestions: 10%

Why is courage critical in creating effective coaching conversations?

Courage is a core attribute of compassionate leadership defined by advocating strongly for yourself, your values, and your stakeholders. To lead an effective coaching conversation, you must balance courage and compassion.

Twenty-five Coaching Questions

Asking the right questions and taking the time to really listen to the answers can transform just a discussion into a remarkable conversation. Here are twenty-five sample coaching questions for your reference, broken into five categories:

One – Professional:

1. What is going well with your business/job/role?

2. What could be better?

3. From 1 to 10, how would you rate your current stress levels regarding your professional life?

4. If high – What is the source of the stress, and are you doing anything to address this? If low – What’s your secret?

5. Is there anything I can do to support you in creating less stress and more happiness at work?

Two – Personal:

1. Have you discovered any new and fun hobbies or movies/TV shows during this time?

2. Are your close friends and family members healthy? If not, what can I do to support you through this time?

3. From 1 to 10, how would you rate your current stress levels regarding your personal life?

4. If high – What is the source of the stress, and are you doing anything to address this? If low – What’s your secret?

5. Is there anything I can do to support you in creating less stress and more happiness at home?

Three – Annually:

1. What did you learn about yourself in 2023?

2. How can you take those lessons to make 2024 better?

3. What is one specific thing you want to create or, build or develop yourself professionally this year?

4. What is one specific thing you want to create or build or do to develop yourself personally this year?

Four – Monthly:

1. Tell me about the best thing that happened (personal/professional) last month.

2. What did you learn from that situation?

3. Tell me about the most challenging thing that happened (personal/professional) last month.

4. What did you learn from that situation?

5. Would you do anything differently if you had to do it over?

6. What are your top three priorities for next month?

Five – Weekly:

1. From 1 to 10, how would you rate your productivity for last week?

2. If high –What’s your secret? If low – What can you do this week to improve it?

3. Is there anything I can do to support you in creating more productivity?

4. What are your top three (personal/professional) priorities for this week?

5. How can you have more fun at work this week?

Action Plan – Answer these four questions to create a plan for becoming a stronger leader through compassionate coaching:

1. How can you bring more compassion to coaching others?

2. How can you bring more courage to coaching others?

3. Which stakeholder may benefit from your coaching this week?

4. What are three skillful questions you can ask that stakeholder to help you have a productive conversation? (Refer to the previous list and develop your own.)

Learn more about compassionate leadership and compassionate coaching here.