101 Coaching Questions Employees Wish You Would Ask

As Bill Gates famously stated, “Everyone needs a coach. It doesn’t matter whether you’re a basketball player, a tennis player, a gymnast, or a bridge player.” Likewise, every employee needs a coach, and that coach is you, their direct supervisor.

When being coached, employees want two things from their leaders: to ask great questions and listen to understand their point of view. To help you do so, we’ve compiled 101 coaching questions your employees want you to ask to help them uncover answers, develop skills, and grow in their careers.

Types of Coaching Questions

1. Kick-off and relationship-building 
2. Career aspirations
3. Goals
4. Problem-solving
5. Skill development
6. Resilience, encouragement, and motivation
7. Action planning and accountability

Kick-Off and Relationship-Building Coaching Questions

To kick off your coaching conversation, you want to build rapport and set the tone that this is a collaborative process. To do that, use the following coaching questions to start the discussion.

• How are you showing up today?
• What’s on your mind?
• What do you want to accomplish from this coaching conversation?
• What is your focus right now?
• What would make this a worthwhile conversation today?
• What would be the most helpful to cover today?
• How can I best help you?
• Based on your priorities and accountabilities, what would you like to focus on today to help you move forward?
  
  
  

Coaching Questions About Career Aspirations

Your employees want you to take an interest in their success, and one way to do so is to have career conversations. As the primary goal of coaching is for your employees to learn, grow, and develop as professionals, you’ll want to make an effort to understand what they want out of their careers, which you can do by asking the following coaching questions.

• What motivates you?
• What makes you feel fulfilled at work?
• What matters the most to you at work?
• What are your strengths?
• Are your strengths being used?
• Who do you admire at work? Why?
• What do you need to do to move closer to your career goals?
• What would be an inspiring future role for you to work towards?
• If you attained this role, how would your life look like a year from now?
• Are you pleased with your career’s trajectory? If not, what would you change?
• What is the best possible career outcome that could happen?
• How does attaining a certain role fit into your values in life?
• How do you measure success in life?
• What do you like most/least about your role?
• If you had a magic wand and could change anything about your work life, what would that be? 
• Have you ever wanted to expand or change your role?
• What project have you enjoyed being a part of?
• How do you feel you can best contribute to helping the company achieve its objectives?
• What would others most likely come to you for help or advice on?
• What new responsibilities would you like to take on?

Coaching Questions About Goals

Helping employees identify and define their goals is foundational to coaching and employee success. Ask the following questions to create development goals that are realistic and grounded with timelines and a plan.

• What do you want to achieve?
• Why do you want to achieve this goal?
• What does success look like?
• How will you know you’ve achieved it?
• What progress have you made toward your goal?
• What’s helping/what’s holding you back?
• How will you start?
• What resources are you missing? How would it help if you had it?
• Do you know anyone who has achieved a similar goal? How did they do it?
• Who have you asked for help or advice? What did they say?
• What are your milestones? How will you measure progress?
• What’s your timeline for achievement?
• Why do you want this?

Coaching Questions That Encourage Problem-Solving

Often, employees want your coaching to help them wrestle with a problem. Your role as the coach is to help them focus and formulate a decision to move ahead confidently. You can do this by asking probing questions that encourage an individual to evaluate the situation and uncover solutions they may not have seen without your help.

• What would you do first?
• Have you encountered something similar previously? What did you do?
• What options/alternatives do you have?
• What would happen if you did nothing?
• What’s the cost of doing nothing?
• What could happen? What are the consequences?
• Who may benefit or be harmed by this?
• Who is most directly affected?
• What is the best and worst-case scenario?
• What is the actual problem you’re trying to solve?
• What information are you missing to make a decision?
• When did this become a problem? Why now?
• Why did this happen?
• How can you test assumptions/alternatives?
• How could you prevent this from happening again?
• How could you broaden your perspective/thinking?
• How have you handled a similar situation?
• What if you secretly have the answer?
• What have you tried?
• What would you do if you were asked to do something you didn’t know how to do?

Coaching Questions That Support Skill Development

When direct leaders engage in coaching with their employees, they are, in a structured way, passing on their knowledge and strengths to their people. Every leader possesses skills and knowledge that have helped get them to where they are, and sharing them is how to grow those around them. Use these 15 skill development questions with your employees to identify what could be strengthened so that you can create a development plan that informs any ongoing coaching conversations.

• What do you want to learn, develop, or enhance to help you in your role?
• What do you want to learn or develop to help you in a future role?
• What do you find challenging today?
• How would developing this skill help you and the team?
• What’s holding you back from learning this skill?
• What skills would you need to expand or change your role?
• Have you taken any steps to learn [skill]?
• What skill, if you learned, would make your job easier?
• What do you think is an area you need to develop professionally?
• What new skill do you hope to have six months from now? Why?
• What new skills do you feel you need in preparation for a promotion?
• What skills would make it easier for you to achieve your goals?
• Are there any learning/mentoring opportunities you’d like to pursue?
• What experiences do you feel you need to prepare you for your next role?
• What opportunities do you have to learn and practice this skill?

Resilience and Motivation Coaching Questions

Setbacks, mistakes, and disappointments are bound to happen occasionally at work, and coaching is a vehicle to help employees bounce back and provide encouragement and motivation. Use these questions to uncover what happened and give perspective to the adversity they’re experiencing.

• How will you overcome setbacks and challenges?
• What do you feel you’re missing to help you move forward?
• How will you stay motivated throughout the process?
• How will you respond to this situation?
• What is in your control?
• What’s holding you back? How can we change that?
• What is the worst that could happen?
• What’s another way you could look at this situation?
• What can you learn from this situation?
• What might be another interpretation of that situation?
• What would you do if you knew that you couldn’t fail?
• If you could change the situation, knowing what you know now, what would you do differently?
• How can you grow from this situation?

Action Planning and Accountability Questions

All the coaching in the world won’t have the optimal outcome without a plan and someone holding the individual accountable for implementing it. These last 12 questions are ones that you will frequently use to co-create action plans and follow up on progress.

• What are your steps?
• How will you get started?
• What are your milestones?
• What’s the timeline?
• What tactics will you use?
• What will you do to prepare for each step?
• How will you stay on track against your timelines and milestones?
• How can we turn that into an actionable step/tactic?
• When will you have this done?
• Are there any obstacles that we need to remove?
• How can I support you?
• How will you hold yourself accountable?