18 Of The Best Questions To Kick Off New Coaching Engagements

The beginning of a coaching engagement with a new client can be an exciting time, as coach and coachee explore that person’s potential and possibilities together. The first question a coach asks a client is not simply a conversation starter, but rather a foundational tool to uncover insights and align expectations going forward.

Here, 18 Forbes Coaches Council members share the first question they like to ask a client at the start of a coaching engagement. Read on to learn why they believe these opening queries help to lay the groundwork for more focused and impactful coaching relationships.

1. ‘What do you think the problem is you’re trying to solve?’

I ask new clients what they think the problem is that they’re trying to solve, and I follow that up with, “Do you know how you do what you do?” Many “problems” are outcomes, not problems—a result of how you do what you do. If you want different outcomes, you first need to understand the way you operate. Study the system you have created. Implementing solutions first will result in improvement by accidental occurrence only. – Nigel Thurlow, The Flow Consortium

2. ‘What would the title of your TED Talk be?’

Because my service as a coach and consultant involves developing story angles and thought leadership, I ask, “If you had a microphone and a Ted Talk audience, what would be the title of your talk?” Often, my clients have a tangled knot of ideas about what they want to talk about, but can’t streamline them into a clear thread. This question enables their most salient talking point to surface. – Helen Croydon, Thought Leadership PR

3. ‘What is your current situation?’

The first question I ask is, “What is your current situation?” I ask this to identify what their current position is in their career. This gives me an understanding of their starting point as part of their career road map. – Shezad Shafiq, Transform Learning Academy Limited

4. ‘Are you willing to put 100% effort into this?’

I ask, “Are you willing to put 100% effort into this program with me?” If the client gives me 50%, this will be a major challenge. That is why a strong commitment on both ends is crucial to generate successful results. – Wasim Hajjiri, Wasim The Dream LLC

5. ‘How can I help you?’

When I start a new engagement, I like to start with a very general question such as, “How can I help you?” From there, and based on that answer, we can discuss gaps or competencies. I prefer to start very broad and then home in on the outcomes the client seeks. – Peter Accettura, Accettura Consulting LLC

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6. ‘How do you feel about this coaching engagement?’

I ask, “How do you feel about this coaching engagement?” It invites the client to express any doubt or resistance they may have. I always let them know it isn’t personal; we can work from wherever they are. I have succeeded in engaging even the most resistant (”too busy for this”) clients by opening with this frank exchange. – Emily Grandinetta, MCC, Grandinetta Group, LLC

7. ‘What are you most hoping to accomplish in this work?’

I ask, “What are you most hoping to accomplish in our time working together?” A client’s answer to this question allows me to hear, in their own words, what success looks like for them, and it uncovers their challenges and opportunity areas so that we can get focused on where to put our energy. It also helps the client to reflect on what outcome is most important to them and already start envisioning what this can look like. – Tiffany Uman, Tiffany Uman Career Strategy Coach Services Inc.

8. ‘What kind of approach and accountability do you need?’

When starting a coaching engagement, I love to ask a brand-new client what they need from me in terms of my approach and accountability. What coaching style will work best? And would they like accountability? Without a sense of safety and trust, they will not perform at their best. And focusing on goals and outcomes too soon without establishing trust and safety can be counterproductive. – Abe Brown, Certified Flourishing Coaching

9. ‘What is your context?’

Whether it’s a leader being coached as an individual or a team being coached, what culture, systems, functions, metrics and history surround them? Understanding context allows me to understand the reality of the client and their situation, seeing the world through their eyes. By doing this, I can understand the correct approach, what success could look like, and so on. – Julian Lighton, Moo Pie Advisors Inc

10. ‘What success story do you imagine sharing?’

Try asking, “Imagine we’re at the end of our coaching journey and you’re telling a friend about the incredible success you’ve had—what would you be sharing?” This future-backward approach inspires clients to envision their desired outcomes vividly, creating a powerful and motivational framework for the coaching process. – Don Pippin, area|Talent

11. ‘What are you celebrating right now?’

Most leaders focus on what’s not working, and when I ask this question, it creates a pattern interrupt in their brain by having them focus on what’s working versus what feels broken. Later, when I address the challenge they’re facing, they see it through a different lens and, often, the challenge seems smaller and the solution clearer. – Lisa Marie Platske, Upside Thinking, Inc.

12. ‘Why are you really here?’

While a simple, “Why are you here?” is an effective way to start a coaching engagement, it may need to be followed by, “Why are you really here?” I’ve found that encouraging clients to be honest with me—and themselves—about what brought them to coaching opens a treasure trove of clues to uncovering their hopes, dreams and pain points, as well as how open they are to doing the hard work of transformation. – Joanne Heyman, Heyman Partners

13. ‘What’s the biggest career risk you’re avoiding right now?’

When meeting a new client, I ask, “What’s the biggest risk you’re avoiding in your career right now?” This provocative question cuts through the surface and directly probes potential growth and discomfort areas. It challenges my clients to confront what they might be shying away from, encouraging a level of honesty and vulnerability essential for effective coaching. – Patricia Burlaud, P. Burlaud Consulting, LLC

14. ‘How will you recognize that you’ve reached your goals?’

At the start of our coaching engagement, I inquire about their desired outcomes and success measurement: “What would you like to achieve by the end of our time together? And how will you recognize that you’ve reached those goals?” This sets a clear direction and establishes criteria for measuring progress, ensuring our efforts are aligned with their objectives. – Martha Jeifetz, MJ – Executive Coaching & Advising

15. ‘Why are you looking for some help right now?’

I start with why. The answer will give me a sense of how much thinking they have done already or where they are at mentally in terms of wanting to move forward. Of course, I would quickly move to the end game to get a sense of what a successful outcome would be for them. – Ricky Muddimer, Thinking Focus

16. ‘What would make this a successful experience for you?’

“If we were to fast-forward to a year from now, and you were looking back on our coaching journey, what would need to happen for you to consider it a successful experience?” The question invites the client to think beyond immediate goals and consider the broader, long-term impact of coaching. It also helps in aligning expectations and measuring progress throughout the coaching journey. – Dani Watson, The Clique

17. ‘Have you been coached before?’

My first question as a coach is, “Have you been coached before?” If so, perfect—what works best for you? What was your best experience? If not, I’d ask what the client understands coaching to be. Start the conversation from there. The coach will get the opportunity to explain what coaching is and isn’t! The client gets the opportunity to talk about what to expect and how the process works. – Cellene Hoogenkamp, KokuaHub Inc Coaching

18. ‘What are three things you want me to know about you?’

My opening question is, “What are three things you would like me to know about you?” This question serves as a powerful icebreaker, fostering rapport and trust from the outset. By inviting the client to share insights about themselves, they know the focus is on them, their wants and their needs. This sets the stage for the coaching work by exploring purpose, motivation and confidence in achieving goals. – Thomas Lim, Centre for Systems Leadership (SIM Academy)