
Questions to Ask when Working with a Coach

I’ve been in the field of psychology for over 15 years and in the business of therapy and coaching for over 7. I’ve watched it evolve from something people talked about in hushed tones to a massive multimillion-dollar self-help and self-development industry, complete with slick personal brands, sponsorships, and Instagram personalities. All of the marketing and huzzah can drown out the truth of the matter: people need this work, and they need people who do it well and with integrity.
Because of all the noise, it can be difficult to know which coach is right for you. Maybe you connect with someone’s online presence or love their brand but don’t gel one on one. Some of (ok, many of) the most effective healers I’ve met don’t even have big online followings. Figuring out who makes sense for you isn’t easy, and that can get discouraging in the process of trying to find a professional to support you.
A recent New York Times article asked, “Does therapy really work?” To see such a major publication cover this while we are simultaneously living through a mental health crisis is “big.” It’s never been more critical to think about who we are as humans – and if we’re “humaning” well. Regardless, coaching is an incredibly effective add-on or alternative to therapy. Many people are seeking ways to get out of the programming placed on them by society and their families. Most people don’t even know where that programming ends or is beneficial and where they begin. But that’s a conversation for another blog post…
In the meantime, I’ve put together some questions to ask yourself when you want to work with a coach or if you’re working with one to discern a path forward. These are a combination of questions that are both practical and even verge on the esoteric – because this sh*t is personal and “deep.” This work also isn’t for the faint of heart. Many people say they want to make the changes and then get highly triggered when they find a no-BS coach who asks them to do it. In the end, only you can shepard YOU, but the right coach can help you get unstuck and grow exponentially.
Here are some questions to ask yourself when working with a coach:
1. Can I afford this?
We all hear those stories online from people who say they “took the leap” and invested their savings into a coach who changed it all. Sounds great, right? Thing is, you dont hear about the people who walk away “with nothing.” And, typically, those winning stories are by people who are also trying to sell you THEIR service; so, one has to wonder if that isn’t a scripted line (insert multi level marketing schemes).. What I am trying to say here is – don’t spend money you don’t have, don’t spend money you will regret spending, and only spend money if you believe it will yield a return on your investment. Ask yourself if you’ll regret the decision immensely if you don’t get your desired results. Some people walk away and are left more caught up with the loss of money than any benefit they received. You do not want to be that person. So, think carefully. Yes, invest in yourself and invest in good coaches, but make sure it’s a decision you are ready to invest in.
2. Do I feel this person possesses the knowledge and skills to get me where I am trying to go?
Do your homework on the person and check out their background. While education doesn’t always mean someone is a good coach, it’s important to ensure they’re credible and have studied the modalities they work with. One note here: education and training also vary by coach and modality. If you want a business coach, check and see if they have a track record of working with successful business owners and executives or if they themselves have a background in corporate or business development. Maybe they even have an MBA! If you’re studying something indigenous or shamanic, find an indigenous person. If you want a coach with a mindfulness background, see where they did their training and how many years they’ve practiced it. Many coaches will complete a training and immediately start teaching something before having embodied it. Don’t be afraid to ask, on intro calls, how long the coach has worked with whatever skill or modality they’re selling you.
3. Do I feel like this person will challenge me?
This is a big one. Will they coddle you and tell you what you want to hear or help you finally take those big leaps – the ones you’re craving and thus hiring a coach for? I’m known for a no-BS approach, and my coaches and I aren’t afraid to push your buttons. It’s also why we see results. Seek out coaches who you know will challenge you to break free of your comfort zone – that is where your success lies.
4. Does this person have a voice that I want to add to the voices in my head?
People we work in close proximity with and/or people we surround ourselves with often tend to have a large impact on us, and little blurbs you hear from a person will stick in your head. When working with a coach, this is going to happen, more often than not. Therefore, ask yourself, do I want to develop myself based on this person’s voice? Am I solid with this person’s voice helping me sort through things in the back of my mind? It’s an interesting question to think about, as this person’s voice will be in your consciousness for a long time.
5. Do I feel this person genuinely has my best interests at heart?
Or do I feel I am another client and paycheck? I think this question speaks for itself. Trust your gut here.