QUESTIONS YOU SHOULD ASK WHEN CONSIDERING WORKING WITH A COACH OR A COACHING PROGRAM

So, you are considering working with a coach…Congratulations! As a coach I am honored that you see the value that coaching inherently has and the impact it makes in people’s lives and businesses. As a person who has benefited beyond works by working with coaches and coaching programs throughout my life – I am also excited for you to share in the incredible experience of working with a coach, whether it’s on a one-to-one basis or within a group coaching program.  

 Coaching is a wonderful support and finding the right coach for you and your goals + needs is important. Here are a few questions I recommend you ask or take into account when considering working with a coach or enrolling in a coaching program. These include questions about the coach/coaching program as well as questions to ask yourself as you are also part of the equation. 

For You: 

Question #1) Am I willing/ready to challenge some of my beliefs and to step beyond my comfort zone? It’s important to remember a good coach isn’t going to “DO” the things for you that you need to do for yourself. It’s a coach’s responsibility to empower you, not enable you. Asking (and being honest) with yourself about whether or not you are really ready to make changes is important. It’s not enough to just “want” things to be different, you have to also “do” things differently. 

Question #2) What level of commitment can I truly make and am I willing to prioritize myself right now?  Personal growth is work. It often requires you to set boundaries, dedicate time to and prioritize yourself. It requires a commitment to yourself, your goals, your dreams, your hopes/desires and your vision. It requires an openness to try, to work, to fail and to redirect. It requires a consistent commitment. While the process of coaching and growing isn’t always linear, it does require you to show up for yourself consistently and it’s important that you are committed not to flake on yourself, even if things get a little tough through the process. You have to be committed to the process. Making sure that you are on team YOU is a necessary thing to ask of yourself. 

Question #3) Am I willing to invest in myself? Similar to the question above, it’s important to consider whether or not you are willing to invest in yourself (which might also be outside of your comfort zone). 

Question #4) What am I hoping to get out of coaching? This is a great question to ask yourself. What is it that you are hoping to get out of coaching? Another way to ask this, is what is it that you are wanting to grow or change? Remember, you only get out of coaching what you are willing to put in, which is why question #2 /#3 are also important to ask yourself. 

Question #5) What things do I want/need in a coach? Finding the right coach for you can feel a little like dating… it’s important to have an idea of things you are looking for and things that are “deal breakers” for you, but at the same time, it is incredibly important to being open as the right coach for you might not always come in the exact package you imagined. It’s nice to have a few things you might be looking for in a coach, but don’t forget to remain open. 

For the Coach/Coaching Program: 

Question #1) Are you the coach I’ll be working with? One of the very first 1:1 coaching programs I ever took part in, I found a coach who I felt connected to right away based on her social media, website and the program description. Everything she said was exactly what I was looking for and hoping to work on. I set up a consult call – and felt like we’d be a good fit working together. I signed up for the coaching program AND THEN found out I’d actually be working with one of her “team members” instead of her. Someone I’d never talked to, heard of and didn’t even know if this team member and I’d be a good fit. (Spoiler Alert, we weren’t). 

I don’t have a problem with coaches having teams and would say that for the most part in that situation, team members are generally incredible and in line with the philosophy of the coach/coaching program they work with. What I do take issue with is not disclosing that you’d be working with someone other than who you are talking with on a consult call. 

I encourage everyone to ask this question either on a consult call or an email. If the answer is “no” that doesn’t necessarily need to make it a deal breaker, but you may also want to consider asking if you can have a 15-minute call with the actual person you’ll be working with just to make sure it’s a good fit. 

Question #2) How do we work together? Whether you are doing 1:1 coaching or a group program, this question might look a little different. Group programs might be a combination of recorded videos, worksheets and live calls or everything could be live coaching. It could take place on a social media platform, via email or a member portal. Individual coaching can also take place on a variety of platforms and in a variety of ways so it’s important to know how you’ll be working together. 

Question #3) What is the time commitment? This is another important question to ask as well as can have a few off-shoot things to get clarity on as well:  

Is there a minimum commitment for coaching? (For 1:1 Coaching) 

How long does the group program run?

Will I have access to the course once it’s completed? 

If so, how long will I be able to access it? 

What if something comes up and I end up behind the course schedule?

What if I need to reschedule a 1:1 Session? 

What is your cancellation policy if I have to cancel a scheduled coaching session? 

Question #4) Do you have a specific coaching philosophy or approach to coaching? Do you incorporate __________________? Asking about a particular coaching philosophy can help you learn more about the coach you are considering working with as well as might bring up some additional questions you might not know you wanted to ask. Also asking if they incorporate things that you might be interested in is another wonderful question to ask. For instance: Do they incorporate law of attraction or spirituality into their coaching style (or whatever you might be interested in/looking for). 

Question #5) What is the cost of coaching / the coaching program? Is there a set date the price might increase? I always encourage people to ask this question last – after you have gotten information about working together and a feel for the coach and the course. Why? Because instinctually most people have “stuff” around money and around spending money – especially on themselves and their growth. 

Asking about the cost last empowers you to make an informed decision- for you- about whether or not the course and the coach is a fit for you, whether or not this is your next step in your growth. A decision that isn’t necessarily driven by or clouded the anxiety that money often causes. If this is the right course and/or the right coach for you and for your growth, then you know…and if the money doesn’t work out in this moment, you’ll have a clear vision of what you might want to work toward. Also, see next question.  

In terms of rate/price increases – it is common for coaches and program rates to increase at times- find out if the price you were quoted is a “special” at all, if there is a time limit and in general how the coach you are talking with approaches this issue. 

Question #6) Is there a payment plan or payment options? Many coaches do offer payment plan options, split tender, etc. and can talk with you about what might work for you.

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Cassie Gaub

Cassie Gaub

Cassie Gaub is the trusted business and mindset coach for empowering service-based providers, particularly those working as "helpers" in some capacity. With expertise in pricing, outreach, heart-centered sales, and overall business strategies, Cassie ensures helpers thrive both professionally and personally. You can learn more about working with Cassie at cassiegaub.com or by following on Instagram @ cassiegaubcoach.

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