44 coaching questions to help your team succeed in 2019


We often promote great workers into people management positions, without knowing if they want that responsibility or if they’re prepared for the job. 

Let’s consider the effect of this. 

The main task of a manager is to ensure that their employees succeed. If their employees succeed, they succeed.

Often employees don’t understand what their goals are, what they’re hoping to achieve, or what their intrinsic motivators are. These become barriers to their success and discourage them achieving their full potential at work. 

So how do you - as a manager -  make sure your employees succeed?  

It’s most important to understand how each employee is unique and how to motivate a diverse team. Diversity of thought and experience can increase innovation, so although it is easier to motivate people like ourselves, it is crucial that your team’s personalities differ from your own. Understand how each individual likes to work, and create the work environment they can excel in, so you can help them and your whole team succeed. 

Here are some useful coaching questions that can help you understand how you can create the conditions for your team to succeed. 

Team Health Coaching Questions

These questions give you a pulse on how your team are feeling. I’d suggest asking these questions to guide into the more context-driven action questions.

  1. Do you enjoy your work?

  2. Do you feel motivated to go above and beyond in your role?

  3. Do you feel clear on how your career will progress over the next two years?

  4. Do you feel you are learning from your team mates?

  5. Are you able to discuss any issues or problems with your team?

  6. Do you feel like your ideas and contributions are respected?

These are simple but revealing questions if answered honestly and can be a good indicator or if role design shift is needed. You will discover if your employee needs more defined goals and a transparent career path, or if their work environment needs adjusting.

Without transparency in the workplace it is difficult to determine what is actually needed for your team to feel happy and productive in the workplace. Employees stop sharing ideas and helping each other if they feel that their contribution is not appreciated. 

Work environment Coaching Questions

Structuring team dynamics to match an individual's intrinsic motivation is crucial to getting the most out of your employees.

  1. Do you prefer working independently?

    Do you prefer to work with your team and bounce ideas off each other?

  2. Do you like to work on problems alone?

  3. Do you like to work on problems by discussing them with your team?

  4. Do you like to take on responsibilities?

  5. Do you need structure and scheduling?

If your employees like to work independently, they need a quiet secluded space to work in. By understanding whether an employee requires autonomy and support to discover how to reach the goal by themselves, or whether they need to bounce ideas off the team and prefer to have team goals, will allow you to structure the ideal work environment.  

Job Design Coaching Questions

Poor job design can be a core component of losing talent. Design the job to leverage your employees’ strengths and motivators. This will make your team far more productive.

  1. Are you motivated by learning and teaching?

  2. Are you motivated to become an expert and apply your knowledge?

  3. Are you a principled person with strong beliefs?

  4. Do you like to take responsibility for others?

  5. Do you like to mentor or teach others?

If they are intellectually motivated then you want to make sure they are constantly learning, trying new things, bringing in new information to help the team develop, as opposed to applying what they know in a more operational role.

If they want responsibility you can give them the opportunity to lead an intern so you can see how they handle that responsibility or test them in a mentoring role and see how effective they are at encouraging others 

Self-development Coaching Questions

Take time to understand how confident your employees are, and structure their development on the foundation of boosting their soft skills so they can succeed.

  1. Are you comfortable speaking at meetings?

  2. Do you feel comfortable trying new things?

  3. Do you feel comfortable taking responsibility?

  4. Do you feel you have the knowledge to do your job?

  5. Do you feel you have the support to do your job?

  6. Do you offer to help to others on your team?

  7. Are you confident in sharing your experience and expertise?

  8. What is the one thing you feel you are missing right now?

These are sensitive topics, but if you are able to support your employee’s growth and development they will be far more likely to give back to their organisation, and rise to challenges they face at work.


Skill development Coaching Questions

Employees can lack skills that can help them succeeding in their role or with gaining a promotion. Here’s what you can ask to help them develop those hard skills:

  1. What do you feel are your strengths?

  2. Do you feel we are leveraging those strengths in your role?

  3. Where do you think they can be more useful

  4. Where do you currently feel you are challenged?

  5. Are you taking steps to develop those skills?

  6. Is your role giving you the opportunity to grow those skills?

  7. Have you explored courses that can help improve those skills?

  8. What is the one thing you wish you could change right now?

Understand that developing new skills probably matters most to your direct report. Without taking on these new skills, they’ll become bored and will be more likely to leave. 

Mentorship Coaching Questions

Having a mentor and mentoring others is a crucial part to learning and taking responsibility of career and career progression.

  1. Do you have a mentor within the company?

  2. Do you have a mentor outside of the company?

  3. Are you receiving career guidance?

  4. Do you have a life mentor?

  5. Are you leveraging experts in the areas you want to grow?

  6. Do you feel confident in your skills at mentoring others?

  7. Are you providing mentorship to your colleagues?

Help them to find a mentor that can help them develop in the skills they seek and guide them in an objective manner. By encouraging them to mentor new employees they can develop confidence and skills for the future.  

Action Coaching Questions

Creating action and forward momentum at the end of any coaching is key. Here are some questions for you to consider when creating action from the coaching session:

  1. Did you focus on one segment, one topic for the coaching session?

  2. Did you identify one goal by the end of the coaching session that can be improved?

  3. What is the easiest step to begin with?

  4. Have you identified a plan and check in points?

Don’t try to boil the ocean, create one core element to focus on in each session and conduct regular coaching sessions. The goal can be personal or professional, a hard or soft skill, as long as there is something identified then there is forward motion as quick wins encourage confidence. 

Next steps

If your direct reports cannot easily answer these questions, we’d recommend using a psychometric test to help you understand their personalities, their intrinsic motivators and identify opportunities for development. Use this guide to build a work environment that works for your employee; design a role that fits with what motivates them; and help your employees succeed.  

By Raj Hayer, Co-founder and Managing Director at Weavee

Blog postsAlan Wanders