I’ve been working with my current therapist for two and a half years, and I love working with him. He laughs at my jokes (crucial for me), but he also pushes back when I’m deflecting with humor. I told him on day one that he would have to be firm with me because I am very self-aware, and it’ll look like I’m doing the work on the surface because I know all the right words to say, but I avoid actually feeling and embodying my emotions.
It’s taken me a while to find a therapist that I felt truly comfortable with. Sometimes the vibes just aren’t right. There’s a hint of judgment, or a lack of understanding, and this is an area where trust is crucial, so the smallest hurdle can become insurmountable.
If you’ve ever been in therapy, you know how difficult it can be to find the right fit. You need a therapist who understands what you’re going through and who knows you well enough to keep you accountable when you’re on the precipice of self-understanding.
The same applies to hiring any expert who’s going to spend time getting to know you and contributing to your overall work-life balance. Especially a career coach!
The wrong (for you) approach can set you back and make you feel like you’ve wasted your time and hard-earned money working with a coach who didn’t really get you and your goals. To help you vet your career coach, we’ve put together a list of questions to ask when you’re thinking about working with a new pro.
Who is your ideal client?
This question is great to ask upfront, because it’s in your best interest to hire a coach who understands your perspective. If the coach’s ideal client is C-suite executive women, and you’re a recent grad with a Bachelor’s degree in marketing, that’s not a good fit.
A bad fit doesn’t mean anything about you or the coach; it’s just that you’re not ideal for each other.
Ask about their work with people from your community. Have they worked with queer or trans clients? Neurodivergent clients? Black clients? Clients with OCD or anxiety? And if so, what techniques have they used with those clients that helped accommodate the clients’ needs?
Where would we start?
The first step to asking for help is understanding what help you actually need. And it’s a big part of your career coach’s job to understand what you need, even if you aren’t a hundred percent clear on your next steps.
Ask your coach something like this, then check in with yourself to make sure their response lands for you. Some examples:
what would our first session look like?
how would your approach differ between [two coaching options]?
based on our conversation so far, what do you think my top priority should be for this job search?
Do you have experience with [your biggest career fear]?
This one requires you to dig deep before coming to the discovery call, so you know the biggest hangups you have about job searching or your next career step.
Worried about making a pivot from one industry to another? Ask them if they have experience with either or both. Worried about balancing pay, benefits, and personal fulfillment? Ask how they’ve handled that issue in the past.
Don’t ever forget that you’re interviewing an expert to make sure they are the expert for you. If they aren’t, that’s okay!
Practice on us!
Book a vibe check with Caitlin or Liora today and practice asking these questions. You might be surprised how good the vibes are—but even if they aren’t right, that’s allowed. No hard feelings!

