This week, I’m going to be answering questions I’ve gotten on social media lately. These questions were mostly from other coaches, but whether you’re a life coach yourself or not, I guarantee you’ll find some gems here that you’ll be able to apply to your life. 

The questions I received run the gamut from coaching in general, the practice of coaching, and questions to ask in coaching sessions, to more business-related questions about entrepreneurship and my best advice for those of you in the first few years of your practice. 

Join me on this episode as I answer your coaching questions! You’ll learn what my go-to favorite question to ask is during a coaching session, what is most helpful when you find yourself coaching someone on the same thing repeatedly, when it might be time to switch from one-on-one coaching to group, and so much more. 

If you’re a coach or thinking about becoming a coach and listening to this podcast has made you realize that you don’t want to be coaching inside that white box, you have got to sign up for the free training I am doing with teachings from my Advanced Certification in Feminist Coaching. At the end of the training, I’ll give share some details on when enrollment will open. To grab your spot in the training, text your email to +1347 997 1784 and use the codeword ‘feminist coaching’ when you’re prompted. Or you can go to unfuckyourbrain.com/feministcoaching.

What You’ll Learn From This Episode:

  • My favorite question to ask in a coaching session.
  • What happens when you surprise your brain by considering different perspectives. 
  • Why you might be getting caught up in self-coaching without taking any action.
  • How I decided my coaching niche.
  • When it’s time to switch from one-on-one coaching to group coaching. 
  • The best advice I can give those of you in the first few years of business.

Listen to the Full Episode:

Featured on the Show:

Full Episode Transcript:

Welcome to Unf*ck Your Brain, the only podcast that teaches you how to use psychology, feminism, and coaching, to rewire your brain and get what you want in life. And now here’s your host, Harvard Law School grad, feminist rockstar, and master coach, Kara Loewentheil.

Hello my chickens. Today we are doing a kind of a Q&A. I’m going to be answering some questions that I have gotten on social media lately. Some of them are about coaching in general, the kind of practice of coaching, questions in coaching. Some of them are about coaching businesses, some of them are about kind of entrepreneurship in general. So, there’s really something for everyone, just kind of an overall Q&A but particularly with questions from coaches is kind of the majority, but by no means the totality.

Okay. The first question that I got is what is the question that you love to ask during a coaching session with someone? So, there’s obviously a million questions that I love to ask, depending. Sometimes I just like to look at you with a raised eyebrow. It’s been called a coaching smirk before. But if I had to pick one question for the rest of my life, if I was going to be limited to one coaching question, I think it would be why. The question why gets you 90% of where you need to go in a coaching session.

It really is such a deep all-purpose question because it just always gets you to the next layer. Somebody can come in and say, “Well, I want to talk about my boss.” And then you say, “Why?” And then they say, “Well, because my boss is just, I think that they’re disrespectful.” And then you just say, “Why?” And then they tell you what the circumstances are. And then they say, “And that’s a problem.” And then you say, “Why?” So, I feel like really why is the all purpose workhorse of coaching sessions.

So, I do love that question, everybody asks that question. That is my favorite. And then there’s so many that are kind of similar or different versions. But the other thing that I sometimes love to ask, this is what I find the most helpful to ask when you have tried 13 different routes to get to where you’re going. You’ve asked a bunch of different questions or you’ve coached someone on something frequently.

You’ve coached them two, three, four, five times about it, still coming back, or they know that their thoughts are irrational about it but they really don’t want to let them go, whatever. You’re sort of like, this isn’t the first time you’re coaching them on it, or they’re really stuck, whatever it is. I like to just ask, “What do you think you are gaining or benefitting? How is this story or this behavior or whatever it is, how is it helping you? What are you getting out of it?”

Because so often if we have been coached a lot on something, or we have a lot of judgment about a behavior, we only see the negative of it and that’s really blocking us from understanding what it’s doing. Why are we holding onto it? We’re holding onto it because it is doing something for us. It’s answering some need, it’s making sense of something for us. It’s providing some kind of psychological safety for us. It is keeping our ego feeling intact and coherent, or something. It all depends on what the issue is.

But I find that can be a kind of unexpected question that really makes a person think about something from a really different perspective. And sometimes with coaching, what you’re actually asking, matters less than if you are just able to get the person to look at something from a different perspective. So, it’s not always even the case that what happens is I say, “What are you getting from this? How is it helping you?” And the person comes up with a one line answer that unlocks the whole thing. That’s not necessarily what happens.

But the mental flexibility, and shift, and creativity that is required for them to unhook from the way they’ve been thinking about it and look at it from the completely opposite direction of how is this helping me, how is it serving me, why am I attached to this? They’ve been so identified with, I don’t like this thought, I don’t like this pattern, I want to get rid of it. And sort of, it just surprises their brain basically. When you surprise your brain you come up with a lot more insight and you start to see and notice different things because you’re not just looking for the same thing over and over again.

So that is one of my favorites. And then another kind of general kind of coaching question. Somebody said, “How do you balance managing your thoughts and actually taking action?” Balance makes it sound like there’s an intentional 50/50 going on or something. There is not, my friends. We’re not, nobody is living a Martha Stewart life other than Martha Stewart probably and probably not even her. So, I think the question is really, how do I know when to manage my mind and when to take action?

And I think the answer is always just you look at your results. If you’re taking a bunch of action and you’re not getting the results you want, then something’s going on in your thoughts and it’s impacting how you feel, which is impacting how you show up in the actions that you take. And that’s why you’re not getting the results you want. So, if your thought is, I suck at selling coaching, you might be taking a lot of action going out there to make offers and do podcasts, and talk to people and blah, blah, blah.

But if your thought is that you suck the whole time, it doesn’t usually produce the result you want because the way you’re doing it is driven by that negative thought and feeling. So, if you’re taking a bunch of action and you’re not getting what you want, that’s when you want to look at your thoughts, for sure. On the other hand, I think part of what this question is kind of gesturing at is that it is possible to get too caught up in self-coaching and not take any action.

But I think that the reason that that happens is that people think, well, because my thoughts will show up in my results, I need to be in the perfect place to take action. And that is a very perfectionist thought process that is also not helpful because thought work, and action, and learning, and changing results are all iterative processes which means you have to iterate. You have to do it over and over again, learn something each time. You can’t just coach yourself to a perfect state of calm and positive emotion and then take action.

Because honestly, the minute you start taking action some new shit’s going to come up that you didn’t expect. You’re going to have to coach yourself again. So, there isn’t really a point to waiting to that. You want to coach yourself enough to take the action, take the action, evaluate, see what happened, did you take the action you wanted or not? Did you get the result you wanted or not? Coach yourself as needed, do it again. And you’ve got to keep iterating forward, do it, evaluate, coach yourself, do it, evaluate, coach yourself, do it, evaluate, coach yourself.

Whatever the thing is, whether you’re trying to get yourself to the gym three times a week or you’re trying to make a million dollars in a coaching business. It really doesn’t matter, it’s the same thing. So, I wouldn’t call it a balance because that makes it sound like there is a correct ratio. I just think of it as more of a dialectic. You are continuously doing both things and they are building on and feeding off of each other and you are continually evaluating what’s happening and adjusting based on that.

Okay, I’ve got some coaching business questions. So one was, how did you know your niche and then how did you know it was time to switch from one-on-one coaching to a group? And the answer to this is, and this is going to be useful to those of you who aren’t coaches too because of how I’m going to answer this. There’s no such thing as knowing your niche. Your niche is not a thing that exists, that you stumble upon and know it. That’s like saying, how do you know if someone is your soulmate?

It’s not a thing that exists that you stumble on and have to recognize or not, it’s just a decision you make. I just decided that my niche was lawyers. And this isn’t an issue of semantics, it’s really important how we think about it and phrase these things. How did you know your niche sort of implies that there’s some mystical or receptive thing happening, that I am discovering it, or I have to recognize it. Or I have some knowledge that’s come from within me about something that already exists or is already true.

As opposed to I had no niche because I didn’t have a business and then I decided what my niche was. Some people say niche, some people say niche, I go back and forth. So, I decided it was lawyers and I took my coach, Brooke Castillo’s advice. And I mean I have many coaches, Brooke was the person who trained me in coach certification at the time and is still one of my mentors.

But when I say my coach on this podcast I could be talking about 12 different people that I work with or have worked with on different aspects of my life. But in this case I’m talking about Brooke who really taught, stick with your niche for a year. And I did that and I’m really glad that I did. I learned a lot and it made me commit to it and really work at it rather than changing my niche when it didn’t work immediately. So, I decided that based on the fact that I had been a lawyer. I mean for lots of reasons, some that I stand by, some that are not how I would decide it now, but who cares?

That’s where I was then. And my thought process then was based on both my professional expertise, my professional network but also what I thought sounded kind of plausible and made sense. So, it was a variety of reasons. And then after about 18 months I had already made my first 100,000 in a year, coaching lawyers and I just started to see that I was being feeling drawn to add stuff. This is a good thing because I feel like this is a good example for how to know if you’re just trying to run away from a niche because you have niche drama or whether you really want to do something else.

I wasn’t like, “I want to stop coaching lawyers, I don’t like them. They’re not buying. They’re not cooperating”, whatever. I had no negative thoughts about the people who are in my niche. I just kept wanting to add to it so I was like, “I want to also do this body image retreat. And then I want to also coach on dating.” So, it wasn’t a rejection of my current niche, it was but I want to help people with all these other things too. And so, in that point I started the process of saying, “Okay, well, is there a way that all these things fit together?” And that was how I sort of created Unf*ck Your Brain.

And I did that work with a business coach, I did a day long intensive with Rachel Rodgers in 2000 and, I guess, 17, 18. Anyway I did a one day retreat where we talked about everything I’d been doing, my core niche, all the other stuff I’d been doing. And talked through kind of what brought those things together, how to pull together my expertise, what to call it, all of that. And that was how I figured it out but the point is you don’t just know your niche, you decide it, it’s an action. The decision is an action.

And then somebody said, “How do you know it’s time to switch to group?” I really just am by the book with this. It’s time to switch to group when you have a waitlist for one-on-one coaching and you are now booking people to start several months out. That’s when you switch to group. Listen, I’m not a sort of mainstream business coach. I mean I offer some business coaching to people who have gone through my Advanced Certification. We really focus on deprogramming kind of the patriarchal thought patterns that are keeping you from making money.

But I’m not somebody who has a whole patented system for start from scratch and go to a million dollars with these steps of these kinds of programs and whatever. That’s not my expertise. But I will say that when people ask me, this is what I say, which is in my experience and in many people’s experience it is harder to sell a group than it is to sell one-on-one coaching. You need more people coming through your consult process to fill a group. So don’t start a group until you have a waitlist for one-to-one and you are signing people up.

So, when I started my first group I was at that point doing consultation calls and taking people’s deposits and signing them up to start working with me one-to-one two to three months ahead of time. My consults were booked out two months or so.

Okay, biggest piece of advice for folks in the first few years? So, I think this applies to any business probably but I feel like it’s more intense for coaches for some reason. Your business is not supposed to just work magically overnight. I think that this is a disservice in a way that – I don’t know – there’s so many complicated factors with this. But one of the things I see so much in my students is that because people become coaches without really often much business experience. Nobody’s gone to get an MBA, most people haven’t studied business in college.

People are drawn to helping people and they’re drawn to coaching and they want to be entrepreneurs. And then they don’t really have an understanding of what entrepreneurship is like. Being an entrepreneur is inherently a rollercoaster experience. And you have to learn the whole thing while you’re doing it. Just the first few years, especially just can be really tough. And that’s not a reason not to do it. Lots of shit is really hard. Going to Harvard Law School was hard. I’m glad I did it.

Clerking was hard. I’m glad I did it. Being a reproductive rights litigator was hard. I’m glad I did it. Doing the work on my body image to love my body was hard. Some days it’s still hard. I’m glad I do it. Something being hard is not a reason to not do it. But so much of the suffering I see from coaches especially but lots of kind of first early entrepreneurs who don’t have any background in business and haven’t studied it in any way and don’t really know what’s going to happen. Is that they think that it’s supposed to be this smooth ride where everything goes easily.

And your business just starts out self-supporting from the ground up. That’s just not realistic. Most people who start a business either are working a day job to pay their expenses while they get their business up and running or are using capital of their own, if they have money, or they’re borrowing from other people, whether that’s a bank, or family and friends, or getting business partners, or getting investment from people they know, whatever it is. That’s normal. It’s a normal thing. To build a business requires time, and money, and effort.

But for some reason people get into it and they somehow think that it’s not going to require those things. Or that it is all going to happen overnight. So, my biggest advice for people in their first few years is just keep going, just keep going.

My student, Cory, just posted something about how three years ago she was at a retreat with me in New Orleans. And she had made, her goal was to make 100,000 in a year. Actually, she came to two retreats with me. The first retreat her goal had been to make 100, and she made 12,000 or 14,000. And I coached her quite a lot. And then the next year I think was the year she made a 100 for the first time. But anyway, so she was just reminiscing about how at this point in the year, maybe three years ago or something, she had made 35,000.

And that this year now she had made 200,000 in the first six months of this year. And I remember watching her go through what it was like in the beginning, the year that she made 14 when she wanted to make a 100. And then the year where she got partway through the year and she was still only at 35 and she had wanted to be at a 100 or be at 50, whatever it was. Just watching her go through this process, I obviously don’t have all the math exactly. I don’t remember all the math exactly.

But I remember coaching her about the 14,000 which she told me at the time was 12,000 because our brains ignore money when we have thoughts like this. But I remember coaching her about the 12, then I remember when she made her first 100K. And now she’s made 200 and we’re only two-thirds of the way through the year. She stuck with it. And the scheme of time, it has not been that long. She’s been doing this for three or four years. But we get so fixated on the first year or the first two years.

And everybody’s path is different. Sometimes it takes five years or 10 years, whatever it takes. So, my biggest advice is stick with it but be all in for it. Don’t become an entrepreneur if what you want is a really chill, non-challenging, risk free experience. That’s not on the menu. That’s not what we’re doing here. So, you’ve got to be up for it. You’ve got to be in for it. You’ve got to be ready to do that work.

So, if you have been listening to this podcast for a while you would not be surprised to hear that I call myself a feminist coach and that kind of coaching that I teach and train coaches in is feminist coaching. But feminist coaching can mean a lot of different things. And what you may not know is that I actually have a signature framework that builds on the concept of feminist coaching and teaches a principle for actually each letter in feminist coaching.

To give you the kind of 101 of it, feminist coaching, the way that I teach and train it is facilitative and empowering, mutual, intersectional, non-hierarchical, inclusive, safe and transparent. Those are the characteristics that I believe coaching has to have to be truly feminist coaching. And because I think this is so important I am going to be teaching it for the first time outside of my Advanced Certification in Feminist Coaching on a totally free training that you can sign up for.

So, if you are a coach this is a no brainer, it is a must know, need to know framework. It will help you understand how to create more transformation with your clients, how to create a coaching experience that’s actually in line with your values, instead of replicating different kinds of hierarchy and oppression in your coaching experience and as a coach in your coaching session. If we’re not aware of the kind of active principles we need to have we will unconsciously revert to patterns and programming that we haven’t really looked at or considered.

So, this is a totally free training and I’m going to teach you what each of these words means in the context of coaching which is different from the dictionary definition sometimes. And how to bring these values and principles to your coaching to make it more feminist, to make sure that your coaching is facilitative, and empowering, mutual, intersectional, non-hierarchical, inclusive, safe and transparent.

So, we are going to be doing that on this free training. You can get all the information, find out when it is, sign up to attend live or you’ll get the replay if you can’t attend live, just text your email address to +1347 997 1784, again that’s +1347 997 1784, and the codeword when you get the text prompting you for the codeword is feminist coaching, two words, feminist coaching or go to unfuckyourbrain.com/feministcoaching, where it’s all one word, unfuckyourbrain.com/feministcoaching, all one word.

And if you have been waiting for the Advanced Certification in Feminist Coaching to open again, we only open once a year for application, at the end of this training I will be giving details on when and how that is happening. So, if you want to be the first to know and get in first since we do rolling applications and rolling admissions, this is the place to find out first. I’ll see you there.

Enjoy the Show?