Chickens, it’s your lucky day because I’m joined on the podcast by my first-ever full-time employee, Elana McKernan, and we’re pulling back the curtain on my coaching business. If you’ve ever wondered what it’s like not only to work for me but to work in any company or organization where coaching tools are integral to the way the business runs, you’re going to find this episode incredibly valuable.

Elana McKernan is the Director of The Clutch and my acting COO. After her own journey of encountering coaching for the first time, becoming a coach herself, and supervising in my business, she’s got the full picture view of the impact of incorporating thought work into the workplace, so we’re answering all the questions you might have. 

Listen in this week as Elana lets us into her experience of getting acclimated to the coaching world, and some of the obstacles she faced at the very beginning of working together. She’s sharing her thoughts on the power of the model for both managers and employees, and I’m offering my own insights on this as a business owner. 

We are hiring! If you want to check out the job descriptions and all the info, click here. You can also text your email address to +1-347-997-1784 and use codeword HIRING to get sent everything you need to know. 

Joining The Clutch is even easier now! All you have to do is text 347-934-8861 and we will text you right back with a link to all the information you need to learn and join. It comes with a five-week self-coaching course that will walk you through exactly how to apply this life-changing work to anything you experience. Hope to see you there!

What You’ll Learn From This Episode:

  • Elana’s experience of getting acclimated to coaching.
  • The process Elana went through from first encountering coaching to starting to embrace it.
  • Why being open about her thoughts and feelings in a workplace environment felt dangerous to Elana. 
  • What you have to model as a boss or a manager if you want to use coaching in your workplace. 
  • How we use the model to manage staff in the company. 
  • The key to unleashing your employees’ best and most creative thinking. 
  • How the model invites everyone in the workplace to take ownership and see their power in any situation. 
  • Elana’s thoughts on the most expected and surprising thing about working for me. 

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 is your chance to see inside the black box of my coaching business and working for me and what it is like to both work for me personally, but also just to work in a business where coaching is so integral to the way that business is done and employees are guided and mentored and managed and feedback is given.

I think it’s going to be really valuable no matter who you are, certainly if you are an entrepreneur or a manager, it’s going to be really helpful to hear how we use coaching in the business.

But even if you work for yourself or you work for someone else, thinking about how to use coaching tools in the context of how you relate to your work and to your performance and how you kind of coach yourself when something goes wrong, all of that is really good stuff in this episode.

So this also seems like an appropriate time to tell you about how we’re hiring right now. So if you listen to this episode and you think, “Yeah man, that sounds like someplace I want to work,” because we all talk to ourselves with “yeah man” at the beginning of our thoughts, then you are going to want to look into whether you are a good fit for one of the two positions that we are currently trying to fill.

We are looking for an incredible, organized, strategic, unflappable COO to be my righthand person and keep the lights on and the trains running and whatever those metaphors would be. To handle all the logistics and execution and coordination and managing employees while I focus on that big picture and that big vision.

So if you are someone who thinks that sounds like fun and a good fit for your skillset, you should check out that posting. We’re also hiring for a marketing director.

So if you are someone who loves the podcast, loves this work, if you evangelize to your friends about it unpaid and you are great at communicating and marketing and selling things that you care about, including this work, and have experience in digital and online marketing, especially for a coaching business or some other kind of direct online service business, then you should check out our post for marketing director.

You can see both of our job descriptions, and they include the benefits, the salary. We’re very transparent about all of that. You can check them all out at unfuckyourbrain.com/hiring. Or you can text your email address to +1-347-997-1784 and the codeword is hiring.

So you’ll get a text asking for the codeword and it is hiring, and we will send you the info. So all the info is at those links or at that phone number. You can check it out. And remember that studies show that men will apply to jobs when they meet anywhere from 40% to 60% of the criteria, and most women will not apply to jobs unless they meet 90% to 100% of the criteria.

So if you meet less than 90% of the criteria, you should still apply. If you meet at least, I don’t know, let’s say 60% to 70%. Make a case for yourself. Tell me why I should hire you. Tell me why you would rock this job and what you would bring to the business. You’ll never find out unless you try.

And to answer the one question that we always get asked, these are both full-time, remote positions, occasional travel required, and they are open to folks who are legally able to work full-time in the United States, regardless of where their physical bodies might be.

Okay, let’s get into this conversation with my very own, the one and only Elana McKernan. Let’s take it away.

Kara: Alright my chickens, my chickadees, my friends, my potential friends. I know that some of you have maybe wondered, what the fuck is it like to work for Kara? Or to be a coach, or to work for a coach, or what would my job be like if everybody used the model?

So we’re going to answer all these questions today. I am here with my very own – what should we call your title? Person who keeps the business running or I would die, Elana Mckernon, who’s otherwise known as the Director of The Clutch and currently also my acting COO.

And we are going to talk about what it’s like to work for a coach. Elana is in the position of – the enviable position of being a coach herself, using coaching on herself at work, using coaching with the people she supervises in my business, using coaching on herself with the feedback she gets from me, working for me. She’s got the 360 view of the whole thing.

Elana: All of the coaching.

Kara: All of the coaching, all of the things. I thought we would talk about it because I think the more that I grow my team and manage my business, the more I’m like, how the fuck does anybody manage anyone without using the model?

I just am so baffled by how anyone tries to do anything, managing other people without thinking about their thoughts. It’s mind-blowing to me. So that’s what we’re going to talk about. Do you want to tell the people anything else about who you are first?

Elana: I coach artists. I’m an artist myself. My background is in theatre and I am delighting in converting Kara into hiring a bunch of theatre people in the future. My secret mission.

Kara: The secret to finding an Elana is hire an off Broadway theatre producer to be your assistant, and then just watch her rise.

Elana: That’s right. Turns out we know how to be nimble and scrappy and problem solve. I think you covered it. I guess I started out with Unfuck Your Brain three years ago now. 2018.

Kara: It’s 2021, time has sort of lost all meaning. I want to say it was 2018 I heard. Three years.

Elana: And in that time I would say I’ve gone from – we’ll talk about this more, but I definitely had an initial point where I was like, what the fuck? Is this coaching with work? What’s going on here? I need to look at my thoughts in this meeting, to I now share your thoughts Kara of like, how does anyone work without this?

Kara: When Elana came to work with me, she was not a podcast listener all sold on coaching. She had no idea what was happening here and I think in that kind of like, it could be a cult but I’m open-minded kind of mindset. I don’t really understand what’s happening here but seems interesting.

Elana: Theatre is kind of cult-y too sometimes.

Kara: There you go, you’re used to it. You’re like, sure, insert group of people with their own language. So let’s just start there. Why don’t you tell the people what was your experience of coming to work? And when Elana joined me, she was my only employee for – I’d had a part-time VA that I let go to create this full-time position.

She was my only employee for about six months. Then we hired Kristy. But what was your experience of coming in and being like, what is happening? And then how did you get so sold, maybe a year later you were like, so I’m going to go get certified as a coach, and I was like, okay. What was that?

I think that was actually kind of a surprise to me. I had no idea that you were thinking about that. So I’m curious to hear, what was your conversion process to the coaching? How did you get acclimated into the cult?

This is not really a cult. She did not convert. But how did you come to sort of be – what was your experience of encountering it and then how did you end up being so excited about it that you wanted to do it yourself?

Elana: I would say that when I came onboard, of course, this job, it was in a new industry. I hadn’t really used any of these tools before. It was kind of like learning a new language. And it was also a point in your business, as you say, where a lot was happening.

You were growing very quickly, and we were doing a lot of new things. And so of course it brought up all of my shit. All of my I’m not doing enough, I’m not moving quickly enough, I don’t understand. And so I think my first step of both I think coming to see how powerful these tools are and also coming to integrate these tools into my role was actually seeing the impact that the model and coaching tools had on my experience of anxiety, of time scarcity, and the job itself.

Kara: Did I teach you the model?

Elana: I mean, I think I was like, oh, they’re talking about this model thing, there might have been some self-study. I think it was like, assumed.

Kara: Maybe I gave you the intro course.

Elana: Yeah, Unfuck Your Brain was the small group program at the time and so I think I probably learned from that. But to be honest, I don’t really remember very well.

Kara: I definitely remember after a month or two being like, okay wait, I think we need to use the model here. I think that we should go over the model, make sure she understands how to do it. I was like, oh yeah, okay, we need to actually use this.

And my experience with you was that you were super defensive at the beginning and you have relaxed so much. Maybe super is a strong word, but I would not say that your first – from my perspective, your first experience of coaching was not like, this is fun and I love it.

Elana: It’s still not that all the time. Is that for anybody?

Kara: I mean, no, we all get defensive I guess when we’re really in it. But I don’t know, sometimes I feel very like, cool, we’re just looking at these thoughts together. Sometimes I’m like, get the fuck away from my brain. So I think it depends on what’s going on.

But one of the things I see in you is that I think I saw your receptivity to coaching really open up over time. And I’m curious, what kind of process do you feel like you went through from first encountering it to really embracing it?

Elana: I think actually now that I’m thinking about it, I probably did learn through the Unfuck Your Brain intro course, but it was in a very utilitarian manner because I was also writing some of your content. And it became very clear that I needed to have a better understanding of this in order to represent your ideas.

And by writing your content, I mean like, drafting social media posts and stuff like that. And so I do think – it was a very unusual experience. I had never encountered this in the workplace, to be invited to take a look at not just my thoughts but also the feelings they created and how I showed up when I had those thoughts and take radical responsibility for my experience.

And so I’m sure I was fairly defensive in the beginning. It felt kind of dangerous to me to open up in that way in the workplace environment. I think I actually got a coach, a one-to-one coach.

Kara: Yeah, I think we hired you a one-to-one coach.

Elana: Yeah. And I think that helped me see the impact of this work. And explore coaching in an open way that didn’t feel charged at all to me, I didn’t have thoughts of this is dangerous around that.

Kara: Can we pause? Your thought about why it was dangerous was like, I’m going to tell my boss the truth about what I’m thinking and feeling about the work. Is that what seemed dangerous?

Elana: I think so. I think I had this thought at the time like, “This is going to be used against me.” I also, as someone with perfectionist tendencies, always have this underlying thought that I’m not good enough or I’m not doing enough.

So I think for me being open and honest in a workplace environment meant you would see the ways in which I’m not good enough and I would get fired or judged.

Kara: That’s so important. I remember when I had this brief lived theory, it was brief lived, that my business was going to be – this was back when I coached lawyers, going to law firms to do workshops and stuff, which just – let’s just pause and say a blessing for that not having turned out to be my life.

Elana: For everyone, for the world.

Kara: My business path. Yeah, and just so funny that I was like, this is how I’ll make that $100,000 back in the day. But I had this experience where I was like, oh, one reason this doesn’t work that well is that no one here is willing to tell the truth about how they think and feel in front of their colleagues.

There was, especially in law firms, all perfectionists, all high anxiety, there’s this feeling of competition, often with the associate class. And even though I was being invited – I did a couple that was like, at the law firm. That was the worst. People’s bosses were in the room and everything.

But even when I would get invited to – I would do talks for a firm’s women’s association retreat, which would be off site and at somebody’s house, and it was supposedly more laidback, there was still the same problem. Nobody would talk about what was going on because there’s so much stigma around admitting that we don’t know what to do, or that we made a mistake.

It’s just so counterproductive. As an employee, your boss fucking knows if you made a mistake. So this sort of knee-jerk thing of I don’t want to tell you my thoughts because then you’ll know why, it’s better if your boss doesn’t know why you made the mistake and doesn’t understand how it can be ameliorated in the future.

But I think that what you’re saying is so important. If you want to use coaching as a manager, as a boss, you do have to be creating a situation where – you have to create a climate that allows for that openness, where it’s not used against you.

I’ve never been like, “Elana, that thing you said in the coaching session, how stupid was that?” However somebody would use something against you. You have to model that. How did you learn to trust it was safe to tell me what your thoughts and feelings were?

Elana: Well, just one thing before I jump to that. I want to acknowledge that you have created a unique environment. There are places in which it is, being vulnerable, or at least telling the truth in that way is not met in the same way as it is here.

And to that, I’ll also say that I think it was a process of building trust. I think incrementally, I learned – for one thing, you were also kind of open. The more you opened up about your process and owning mistakes you had made in the business, or thoughts you had that didn’t create the results you were looking for, I then was able to think like, okay, it’s safe to have that level of conversation.

And I also think there were probably a couple of big fuckups that I was like, oh God, let me own this and see what happens. And that was met with curiosity by you and exploration by you and it wasn’t immediately – you didn’t shut it down or use it against me. So I think seeing that, I was able then to take greater risks in our relationship as I perceived them and share more. And now you know I’m like, yes, I did this wrong.

Kara: Fun times, guys, excitement, I made a mistake, let’s talk about it. Yes, so many things there. So one, absolutely, your point, and this is part of what I was trying to say also is as a manager – if you are the boss or the manager listening to this, you have to make that safe space, which means you have to be managing your own mind in order to not take things out on your employees, or not be reactive, or not whatever.

It all will show up. You have to create that space. And I think the second point of transparency is one of the ways – we just had a staff retreat and I was coaching a team member who still has the belief that she shouldn’t make any mistakes.

And we literally – I told them about a bunch of mistakes I made, and then we went around and more senior employees who have been there longer were like, “I deleted the whole backend of Ontraport. I sent out an email telling people to do this dumb thing.”

Whatever it was, we all went around and were like, here’s the mistakes I made. Being transparent about that is what will build trust, so people can see that you walk your talk. So you cannot be not managing your mind and then trying to use the model to encourage your employees to manage their minds.

And I will say, even within the coaching industry, even among very successful coaches, there is a real range of how much people are managing their minds about their employees. And it’s not always related.

You can make a lot of money not managing your mind about your employees. But if your workplace culture is something that matters to you, and I think for me and I teach this in the advanced certification also, what does it mean to run a feminist business?

It’s not just like, having maternity leave or covering a portion of your healthcare plan or whatever. It’s also what is the company culture, what kind of human experience is modeled? I was just filling out this form for, Elana knows, I was a little late to the call because I was filling this out and it was for an employee who left the company because her position became full-time and they didn’t want a full-time position.

But I still had to fill it out, and it’s asking, what are the incidences that led to this? And it’s so interesting because I was like, well, even if I had fired someone for cause, it would never be an incident. I now think about thought processes.

It would be like, if somebody’s not the right fit for my company, it’s because I don’t seem to be the right kind of coach for them in some way. I’m not able to coach them through whatever kind of performance or culture issues are coming up.

But it was such an interesting example of like, oh yeah, I’ve never really fired someone for this one mistake you made, then you get fired. And I see this with people, with bosses and managers, where I’ll coach a colleague or a friend who will be like, “Well, I’ve told them three times,” and I’m like, okay, but did you coach them?

Because if we don’t know what thought is creating that action, how well does it work when you yell at yourself to stop taking an action when you haven’t looked at the model and you don’t understand what thought is leading to it?

So I’d love to hear from you also how you use the model when you are managing the other people in the company. What it’s like to work at a place where the way we give feedback is basically okay, well, what was the thought that caused this kind of action that went wrong? What are we missing here?

Elana: I think what’s been so critical, both for how you manage me and how I try to manage the staff as well is there’s some de-conditioning that has to go on around making it clear that we’re more interested in understanding the thought process than we are in being perfect. Perfection is not necessarily…

Kara: It’s definitely not the goal. There’s an expected error rate. I expect a certain amount of things to get fucked up every week.

Elana: Yes. The point is not to be perfect and to create a perception that you are perfect. We’re much more interesting in collaborating with you, getting curious about your thoughts. What led to this?

And I think the biggest difference I’ve seen in using the model in how I manage is I find that people tend to jump frequently to identifying the wrong problem when something goes wrong. There will be a sense of this decision that I made, the concrete circumstance as you would put it, the facts of this decision were wrong.

And so they fixate on that and beat themselves up for not having made the right decision when it’s more about how were you thinking that led to that result? We recently had a situation where this came up where we did an event and there was something we didn’t think through.

Kara: The problem was that people were taking their thoughts to be circumstances. It was like, people would be like, I had this thought that led to this result, which turned out to not be the result we wanted. But my thought was a circumstance, so how can I think differently about that circumstance?

So it’s almost like you’re like, we tried to sell these shoes at the shoe store and no one bought them. And without coaching, you’re like, well, I guess no one wants shoes. That’s the circumstance.

But with coaching, you’re able to dig so much deeper I think and problem solve within an organization, which is like, well, is it true that nobody wants shoes? How did we sell the shoes? How did we publicize the shoes? Was the shoe store even open that day? What was going on?

Elana: Did we think the shoes were valuable when we were trying to sell them?

Kara: Did we assume that people wanted the shoes? I think what that leads to is coaching and thinking about minds really helps you coach people to ask more powerful questions. I find one of the most challenging places to coach or train an employee is when someone doesn’t think to ask something.

It’s one thing to be like, these are my premises, these are the actions and results. And be like, okay, I see where we went wrong, that premise is not useful or is factually incorrect. Or I think one of the things we both see come up again and again is that we need to use coaching with employees to deal with anxiety that leads to rushing that leads to mistakes being made.

But I’ve also found that it’s sort of helpful when you are trying to teach someone how to think in a way they aren’t thinking, that I think coaching – if you don’t have coaching, you’re not thinking about their mind. You just get stuck at, well, why wouldn’t someone think of this?

It comes to me naturally, I think of this, why wouldn’t someone else think of this? And I think coaching helps you see, okay, well, what are the thoughts that lead me to think of the thing? What are the thoughts that lead me to troubleshoot in this way or to brainstorm in this way? What are my beliefs about myself?

I think so often what comes up in coaching employees, your employees, like anyone else is like, what are their thoughts about themselves and the job? I just had this hilarious to me interaction on Facebook where – so many interactions on Facebook are hilarious to me.

Where I had posted, I just did a staff retreat, here’s how we did it, I tried to share whatever I’m figuring out with my followers. And this woman who is sort of an acquaintance I know who’s not in the coaching world commented, and in the staff retreat, a lot of what we did was coach people on their self-conception about the business, which is everything.

If all my employees have the thought, which they all do because they are humans and they happen to right now all be women and several of them are woman of color and people have other marginalized identities, some people have just been subject to all the socialization.

When people in the business have thoughts like, “My job isn’t that important, or I don’t know what I’m doing,” or whatever else, of course that’s going to show up in their performance. People are not going to be operating at their highest creativity when that’s their thought process.

But so I had this experience where I posted about it and some acquaintance I know who must have a business doing this commented and was like, “I find staff retreats really aren’t worth it but I would love to do a consult to help you learn how you can give your employees better rewards,” whatever, something like that.

I’m like, listen, we send flowers, we do Christmas gifts. I’m totally not against giving gifts also and recognition obviously. But the idea that the best way to motivate employees would have nothing to do with looking at their thoughts and would just be like, you should give more Starbucks gift cards, that is not how humans work. That’s not really how you unleash the best and most creative thinking.

Elana: 100%. And it’s also – inviting and exploration of this is also how we create an environment where it’s expected that you’ll also be lobbying for your own career growth. And that you will also be thinking about potential projects you can take on and to develop certain skills professionally that you want to develop.

Kara: 100%. I think that is also big. Whenever I’m coaching my employees about their belief in themselves and the job, I’m like, listen, if you’re going to want a promotion, you got to come sell me. I’m not going to – obviously I do give merit-based – we do cost of living, it increases every year, and I give merit-based raises where I see it’s appropriate.

But I want my employees to be thinking about it. I am not going to spoon-feed advancement to people. I think it’s important to mentor and coach and support people, but when you’re trying to get hired, it’s your job to sell the employer on hiring you. It’s my job to sell you on why you should work for me.

And if you want to move up, like at the staff retreat we had the team set impossible goals for themselves in their roles, and two of the part-time people wanted to become full-time. And I was like, great, now your job is to go figure out what is the value you can add to the business that is going to make that a no-brainer for me.

Setting the goals has been like, okay, I set the goal and then I just manifest every day, I hope Kara decides to make this position full-time and she comes up with another 20 hours of work a week I could do. You come pitch me. I’m sure customer service could be full-time. You figure out how and come tell me.

And of course, people need support, people need coaching, we provide all of that. But I think it’s impossible to argue effectively for your own advancement when your thought is my job doesn’t matter, which most people’s thought was, which also I just wanted to be like, see how we all have this thought? Why would I pay all of you if none of your jobs mattered? If I could do this all on my own, then I would, and I would save all that money I pay you.

Elana: You’re not just in the habit of throwing money away.

Kara: It’s not like a charity. I’m like, well, I don’t need any of these people but let’s set up a charity system here where we hire people just to pay them.

Elana: I see fundamentally the power of the model is that it invites you to take ownership and see your power in any situation. And so layering that over the workplace environment, adding a coaching element into workplace is essentially giving staff the tools with which they can take ownership of their roles, of their careers, of their relationship to the business, of their relationship to the world.

And that ownership is something that I think by default, employees don’t necessarily have that level of ownership. But it’s something that I think you and the coaching tools have really invited everyone on staff to embrace. And that I think makes for a really unique and unlimited potential for growth environment.

Kara: And I think also, I don’t know what the term for this is but I guess it’s sort of culture of employee interaction. I feel like we have very low drama on the employee interaction with each other front, even though we’ve grown so much recently.

And I think that’s because people are using coaching and taking responsibility for themselves. That doesn’t mean that they would never approach a supervisor with, “Hey, I have this issue.” I think everybody in the company knows where our values are.

And if an employee, a coworker was acting outside those values in some way, they would totally approach a supervisor about it as they should. But there’s just none of this petty drama of, “I thought what so-and-so said in the meeting was like they were trying to take credit for me.”

There’s just not that bullshit because I think everyone knows that if they take that to their manager, the first thing they’re going to hear is, “Let’s see your model. What was the circumstance and what was your thought about it?” Everybody’s coaching themselves.

And I would also say we provide coaching. Now we have coaches in-house, so everybody gets a weekly half hour coaching session. Before that, we had a coaching stipend. The business would pay for you to get an outside coach. I think all coaches should be putting their money where their mouth is and giving their employees access to coaching.

If you’re just starting out and you have a part-time VA, maybe that’s you. That’s fine. Maybe you find someone who needs a free client even. It doesn’t have to be – not everybody’s going to have multiple coaches full-time like I do.

But we’ve had that from the very beginning, and I think that has been huge. It has been so important. And to give your employees a chance to get coached, often by someone who isn’t you because you are their boss, and I think you can learn to coach them effectively as we’ve been talking about, but obviously it may be easier for them to talk to someone else.

I think the benefit to your business of teaching people to manage their minds and getting them coaching that half hour a week is just really immeasurable.

Elana: Yeah, I think the coaching that I received and then eventually learned to provide myself, though of course I also get coached still, I think that’s integral to how I’ve developed in the company. I certainly would not be here…

Kara: I wish I had the video of the first month maybe. And how much coaching you need as a boss. Elana was my first full-time employee and I worked with an executive coach. I had to get so much coaching because of my thought.

I think a lot of people go through this where you hire people and your immediate thought is just like, “Why can’t they already know everything I think and do everything the way I want them to?” And you learn – as a boss, coaching has been so important for me because it has allowed me to get to the place where my operating thought about my business is I’m responsible for whatever happens.

So when something goes wrong, yes, there might be a model problem in the employee, but there’s also like, okay, how was I not clear about this? How did I not supervise correctly, how did I not empower somebody else to supervise correctly?

Usually for me it’s like, how did I not explain what I actually wanted or how did I not say it clearly? You can only learn by doing. We just don’t know how much stuff is assumed to us about how we do things. And you only learn it by something going wrong and then getting to be like, okay, now I see, this is where we need coaching.

But I think it’s so important because employees and employers both think that the ideal situation or some achievable situations is where nothing goes wrong. But that’s just not reality. And that’s like being in your own life and being like, okay the perfect experience is one in which I’m never challenged.

You can do that if you never leave your house and you numb out 23 hours a day. But otherwise, that’s going to happen. And if your business is growing, you’re doing new things, and you’re hiring people, and you’re trying to empower them to do their jobs and not micromanage them, shit’s going to go wrong. The question is just do you learn from that or not.

Elana: Yeah. And if you’re encouraging your employees to develop into new roles and take risks and challenge some of the beliefs that they have that they can’t do certain things. That process is going to be a little messy, as it should be.

Kara: And as an employer or a manager, you also have to be coaching yourself on your own people-pleasing tendencies, and your own – I think one of the hardest parts of being a boss, especially if you’re an entrepreneur, you’ve built a team, people have been with you for a long time is when the business starts to outgrow people and when there isn’t a space for them anymore, or they can’t move up the way they want, it’s not the right fit, that’s really hard work you have to do.

That is something that without the model, because it’s not actually a kindness to keep someone in a job that they’ve outgrown, or in a position where they can’t grow the way they want in the company. It’s like, outstripped them, or the company has gotten too complex or whatever.

But if you don’t do your own work on that, it’s so easy to just want to take everyone – my teacher Brooke Castillo used to say this to us all the time. You just want to take everyone with you. The people you started with, you just want to carry them with you, you want to take them all the way.

And I think that is another place that if you believe you cause other people’s feelings, you will keep people in jobs for a very long time that aren’t the right fit for them, you will hold off on – you won’t hire the right way, you won’t fire the right way.

I see that come up for me as well. And it’s also such a place that self-coaching or getting coached makes a huge difference. Okay, I have one or two last questions but anything else you want to say about this before we…

Elana: No, I think we can dive in.

Kara: This is like the lighting round.

Elana: I feel like you’re going to ask me like, what is my favorite food?

Kara: No, I know what your favorite snack is. It’s Takis. We went over this.

Elana: Now the world knows.

Kara: Now the world knows, Elana likes some kind of snack that is like Gatorade sold by color, which I always think is a concerning sign about a food. There’s no flavors, it’s just like the blue ones. Okay, here’s the two questions. These just came to me, I thought they might be fun for people listening. First, what’s the most expected thing about working for me? The thing everyone would think is true and is true.

Elana: I think that you show up directly and as a coach in the workplace. You show up as yourself. You’re not going to – if you work for Kara, you’re not going to get a version of Kara that’s like, the corporate Kara. You get…

Kara: The corporate Kara definitely does not exist.

Elana: Does not exist, no.

Kara: That’s true. For better or worse, I am myself everywhere. On the plus side, I don’t have to remember to be anybody else and it’d be really hard to blackmail me. What are you going to tell people that I don’t talk about on the podcast? What do you think is the most surprising thing about working for me?

Elana: I guess because you’re – I don’t know that I have this belief necessarily but because you were a lawyer and I tend to think of lawyers as wanting to have control over things, you actually prefer to not have to look at things. You’re not a micromanager.

Kara: Trying to have as little to do in my business as possible.

Elana: I mean…

Kara: That’s not true. That’s been a big change also. I think over the time we’ve worked together is as the business has grown, I’m not a micromanager. I think it’s important to know your strengths and weaknesses.

Strengths, not a micromanager. Weaknesses, sometimes a little too hands off. It’s a hard balance, as you’ll discover when you grow your business, when you eventually leave me, because I’m not allowed to kidnap you. This is a thing that happens where if you’re trying to really grow something, you have to be thinking about this big picture vision, so your head is always like, where are we in three years?

I’m running the five-million-dollar version of this business, but I’m thinking all the time about what’s the 10-million-dollar version of this business and how do we get there. And I have to live as that person. And the 10-million-dollar version of the business owner doesn’t pay attention to the same things the five-million-dollar version does, or the one-million-dollar version did.

So I think I am concerningly to people sometimes hands off. But I also think I definitely believe – it’s so interesting to also look at where you have different thought patterns. For a long time I had a very fixed mindset about my romantic life of kind of like, there was a solution to figure out and you had to know what was going on in my business.

I have been much more like, I don’t know, we’re going to try and see what happens. And I think if you want to empower your employees to grow, you kind of have to be like, I learned this actually from my colleague Corinne Crabtree who is always three steps ahead of me.

And when I was first hiring, she was kind of like, alright, just remember, you got to let them fuck up. You just got to be like, okay, you guys are in charge of planning the event. Obviously you have to give people some structure. Don’t let people lose before they’re trained.

But ultimately, that’s how people learn is to take responsibility for something. What goes great, awesome, what gets fucked up, they’re like, well, okay, got to do that differently next time.

I think for any of you listening who are entrepreneurs or business owners or even just a manager in a corporate situation, what is your thought process around letting go of the reins? What is your belief about making mistakes and how comfortable are you with your own mistakes, with your employees’ mistakes?

I think it’s a balance that everybody has to figure out for themselves. But yes, I can see the surprise that I’m like, please, I don’t want to look at that, just do whatever you want.

Elana: I actually do not want to look at that.

Kara: I do not want to see that again. I just was saying to my partner last night if I’d known there was so much fucking math involved in starting – I was like, why do I have to look at all this math? Isn’t this somebody else’s job? It is not, unfortunately.

Elana: That’s something that actually resonates with me very deeply because also this year I’ve gone from managing one person to now managing 10.

Kara: We like to just balls to the wall around here.

Elana: I think I’ve learned that actually from you Kara, I think having been with you as your first full-time employee three years ago, I have felt a shift in your willingness to just let me try things and fail and then explore what happened. And have that just be a naturalized part of the process.

Because I found myself also having to embrace that as well and it’s invited me to confront my own relationship with failure in order to empower the people that I’m managing to discover for themselves.

Kara: I love that. Alright, any parting words of wisdom?

Elana: No, I think – I don’t know if you know this about me Kara, but you talk about the one problem, the thing that’s always the problem in a person’s life and how you might be addicted to having that be the problem. And prior to meeting you, that was my career.

I was always like, I had a dual career as an artist and something else, and I was always wanting to do something more meaningful and had this vision of a career that would fulfill me in every way. And not only has working with you allowed me to step back from that and figure out how to create meaning for myself, but it has also allowed me to find this new passion for coaching and to explore in this amazingly supportive environment.

And so I am just so grateful. I now am not relating to my career as this problem anymore. And in fact, I feel that I’ve grown so much and I’m so excited and optimistic, both about the work that I’m doing with you and in the world. Very grateful for that.

Kara: That’s so beautiful. And this is a good pitch, because listen, Elana’s going to leave eventually and I have to hire a new COO. So we will be hiring in 2022 and if you are a COO type, keep an eye out for that because Elana needs some help here.

Elana: Yeah, come take some work.

Kara: She can’t handle me all on her own. It’s too much for any person to deal with. Thanks for coming on and sharing your thoughts.

Elana: Thank you.

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