Want to generate repeat business? How you start working with clients is a huge part of that. When you’re starting to work with a new client, it’s important that you have some pre-session questions to ask, or at the very least, some questions that you make sure you cover with every client, in every session.

These are five questions that I find important to ask either on a pre-session questions document or during a first session. In fact, question #1 is something that I ask during every session.

1.) What would you like to focus on, during our session?

You’d be surprised by how often coaches don’t ask this. This is a question that best serves the client while also being a question that best serves you–ask people what they want, and give it to them, and you’ll see your retention rates improve.

Note–this question is asking what someone would like to FOCUS on. If someone then responds by saying, “Well, I’ve been having some issues with such-and such, and…” followed by launching into a Story, take a moment to clarify– “So what would you like to focus on over the next hour, regarding such-and-such?”

2.) What’s the best thing to say to you if you are feeling triggered and in a place of resistance?

This is one of my favorite questions to examine, mostly because my courageous clients offer up their responses, so willingly. I love that they are willing to help me help them, by “outing” themselves and their places of resistance.

3.) What’s the current state of your finances?

It might seem invasive to ask this, but–this is an important question that I wish more coaches were asking. Aside from it being a clue as to where your client is at, emotionally (how someone treats money is often indicative of how someone treats their life–are they rigid with it? unaccountable with it?), it’s imperative that we ask: Can our clients actually afford coaching?

4.) Are you currently, or have you recently, seen a therapist? Are you, or have you been, under treatment for any psychiatric or mental disorders?

I know–these are loaded questions, questions that in the coaching world are often hotly debated. After all, who defines so-called “mental health”? Any of us looking at the DSM would see shadows and shades of ourselves in those profiles.

At the same time, you need to make sure that your clients are getting the best possible support that they can get. For some people, the best support they can get is someone who is in-person, who can see how they’re doing visibly and who is local who can be of help to them if they had an emergency. I would encourage any coach to know what boundaries they will put in place about who they will and will not work with, and prepare how you’ll address such situations if they arise.

5.) Finally, ask a question that relates to the specific type of work that you do. For instance, I ask questions about what people fear. I ask this because fear is *specifically* where I focus my attention.

It’s important for me to ask these questions, because while I would support any of my clients in their artistic endeavors, I’m not (specifically) a creativity coach. I don’t specialize in helping people to put their artistic visions out in the world. Thus, I want to make sure that on my pre-session questions I’m asking the sorts of questions that I would actually ask about in a session.

  • If you’re a creativity coach, are you asking *specifically* about someone’s creative process? Are you getting a complete profile of what kind of artistic work they do?
  • If you’re a health coach, are you asking *specifically* about someone’s health–and not just their nutrient intake, but your specific approach to health?
  • If you’re a business coach, as you asking the hard questions about someone’s finances and business dealings? Are you looking for the pockets that are commonly ignored in setting up a business?

This week’s exercise to benefit you and your business:

  • Check out your current pre-session questions, or your “first session” questions. What kinds of questions are you asking? Are they the same old questions that your coaching school suggests everyone ask? or–Are they a reflection of you, and the types of things that you want to focus on with your clients?
  • Are you safeguarding yourself and your practice, as well as your clients, by asking the questions about finances and work with therapists that ensure your clients are getting true support? We don’t want our clients to come to coaching when they really need therapy, nor do we want them to go into financial distress to pay for coaching.
  • What might you add to your pre-session questions, to make them more powerful?
  • Here’s how you’ll know that you’re on track with what you ask: People will turn in the questions saying, “Just answering these questions opened up a lot.” The process of examining the questions, in and of itself, will be illuminating and powerful.


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