11 Jul
Career Coaching for Lawyers: Working 1:1 with Sarah Cottrell [TFLP327]
Knowing you want to make a change in your legal career doesn’t necessarily mean you know what you want to do instead. Maybe you’ve already tried a different legal job and weren’t any happier, or maybe you’re wondering whether a different practice area would be enough. Career coaching for lawyers can help when you know you can’t keep doing what you’re doing, but every time you consider another possibility, you find a reason it wouldn’t work.
Sarah calls this “lawyering yourself,” and it’s something she sees all the time with lawyers who are trying to figure out what comes next. It’s easy to rule out a potential career before you’ve actually learned much about it, especially when you’re already unsure what might be a good fit. That’s why a big part of Sarah’s process involves exploring different possibilities, gathering information, and figuring out what actually makes sense for you before narrowing down your options.
In this episode of The Former Lawyer Podcast, Sarah Cottrell walks through what it’s like to work with her one-on-one, from the initial consultation to the exercises, assessments, and informational interviews that help lawyers figure out what they actually want to do. She explains how the Former Lawyer Framework provides structure while allowing flexibility for what’s happening in your life, including situations where you need to get out of a toxic job before you’ve figured out your longer-term plans.
0:57 – The initial consultation and figuring out whether you’re a good fit
1:49 – Career coaching for lawyers who have no idea what they want to do next
4:37 – What the one-on-one coaching package includes
5:16 – The Former Lawyer Framework and flexibility around your schedule
6:37 – Starting with reflection exercises, assessments, and possible career options
7:15 – Why lawyers talk themselves out of career options too soon
9:21 – Learning to trust yourself instead of relying on someone else to make career decisions
11:01 – Finding a bridge job while figuring out your longer-term plans
12:18 – What happens during coaching calls and between sessions
15:38 – Why Sarah starts with a six-call coaching package
18:32 – Upfront pricing, no hard sales tactics, and deciding whether to work together
Mentioned In Career Coaching for Lawyers Who Don’t Know What to Do Next
First Steps to Leaving the Law
Sarah Cottrell: Hi, and welcome to The Former Lawyer Podcast. I’m your host, Sarah Cottrell. I practiced law for ten years, and now I help unhappy lawyers ditch their soul-sucking jobs. On this show, I share advice and strategies for aspiring former lawyers, and interviews with former lawyers who’ve left the law behind, to find careers and lives that they love.
Let's talk about what it's like to work with me one-on-one. So, as you know one-on-one work, right now, is where I am focusing most of my time. And people who are thinking about working with me one-on-one often have questions about like, what is it like? Or even people who listen to podcast, who maybe aren't necessarily thinking about working with me but, you know, hear me talk about it a lot. So, I thought I would sort of, lay out the process for you, as it would unfold, if you are someone who is working with me.
So the first step is that, if you're interested in working with me one-on-one, you schedule a one-on-one consult with me. It's 30 minutes, and honestly, they're basically two main goals for me in that consult. One is to make sure that you understand all of the details. And the second is, for you to get to know me, and for me to get to know you so that I can figure out whether we're a good fit. Or whether I should consider referring you to someone else. Because, the thing is, like, I can do lots of different types of career coaching, and I have worked with people, for example, who are just moving from like one lawyer job to another lawyer job. Or people who have narrowed it down to like, one or two options that they know that they want to pursue, and are just like, trying to decide between them, or like, actually get to the point where they're moving into one of those other options.
But for me, the thing that I like the most, and the thing that I have the most experience with, and the thing that I think is different than what a lot of career coaches do is that, I focus on working with people who have no idea what it is that they want to do. Most of the people I work with, come to me and say “Sarah, I don't like what I'm doing, but I don't know what it is that I want to do. I don't even know whether I want to leave law. I don't like this, I've maybe done some other law jobs, didn't like them. Maybe I, it's the only law job I've had, so I don't know. Like, should I change to a different practice area? And if I'm not going to change practice areas, then like, should I go to some other career entirely? and if so what?” Just no clue.
And like, those are the people who I love working with. Because the process that I have refined over these years, of running Former Lawyer, is designed to help people who are in that position of, you know, they want to make a change but don't know what that change is. And of course, like, it's a whole process right? So like, the things that are later in the process, for example, revising resume, interview prep, making a job search plan, all that kind of stuff, are things that can be done if someone's further along in the process when they come to me. But for me, I really love working with people who just feel like I don't even know where to start, I just, it can't be this.
Okay, so you come to the consult, we talk, I make sure all your questions are answered, I refer you out to someone else, or give you some suggestions of people you might talk to if I don't think that I would be the best fit for you. ‘Cause here's the thing. This is the main reason why, you can't just like, go to my website and sign up for a one-on-one package with me I don't want your money if we are not a good fit.
I am very aware that there are lots of lawyers out there who are unhappy in their jobs, and are like, desperate to get out. And it is really important to me that I feel like us working together is in your best interest. If it, if I don't think that, I will give you recommendations for other people to talk to or consider working with. Because that just, for me, for like, my own integrity as like, a business owner. But also just like, a person and a human and a former lawyer, that's really important to me.
So, let's assume we talk. And that we are good fit, which is generally, are most people who I end up having consults with. Because a lot of people listen to the podcast before they come to a consult. And so, they have a pretty good idea of, sort of like, who I am and what I'm about, and blah blah blah. Right now the way that my one-on-ones work, it’s structure is that you enroll in a package, it has six one hour one-on-one calls, that you can use within 6 months. You also get email support from me, in between calls and you also get a couple of paid assessments that I recommend, or like the report cost like, whatever, like 40 or 50 or $60 included, as part of the package.
And the structure of those calls, is, so, there's, there's structure but it's also flexible. So here's the thing. I have an idea of the things that are the most helpful. I have this framework, it's called the Former Lawyer Framework. And, going through the steps in the framework, help you to get clarity about what it is that you want to do. And ultimately, figure out what you want to target. And then of course, position yourself to actually land those jobs. So, there's an overall structure to like, the kinds of exercises, and assessments, and other things that I recommend, recommend about the process, informational interviews, and when those should happen. And, all these sorts of things.
But here in the real world, there are a lot of things that come up, right? So, the 6 one hour calls, we can meet once a month for 6 months. A lot of people are going to meet with me more frequently than that, especially in the beginning when they're doing assessments, and we're debriefing their results. A lot of people are going to meet with me every other week. And the reason that I allow for that flexibility is that, one, lawyer life, right? Like, we all know that we need some sort of deadline to get things done, and know that it needs to get done, which is why the calls are good for 6 months. But, if there's too much rigidity, as a lawyer you're going to be in a position where like, stuff comes up and we can't change it, and I don't want that for people.
So we start working together, generally speaking I have you do some reflection exercises and then assessments, so I've talked about them before on the podcast. Personality tests, strengths assessment, several values assessments, likes and dislikes exercises. Basically put together a personal brand statement, essentially a matrix of like, all of the things that you know to be true about you. And also, at the same time, putting together a brainstorming list of all of the possible things that might be a good fit, based on all of the things that are coming up. Or things that you've thought about in the past, or things that you're interested in, or..? Pretty much anything, right?
One of the things that I think is really important, in the process is not to, close your option set too soon. Like, premature closing of the option set is a huge problem for lawyers. And I've described this before as, lawyering yourself. Which is a reference to How I Met Your Mother, one of my problematic fave shows. Where you like have an idea and then immediately talk yourself out of it, or tell yourself why it wouldn't work. And I'm not saying that when I work with people I'm like “Here, follow this idea that isn't going to work.” That's not what I'm saying.
But what I am saying is, like, if there are things that call to you, and are, you're interested in, it is so much more valuable to you to actually pursue those things, and get information about them, and talk them through with a career coach, for example like me. Like, about the answers you’re getting, how it fits with your overall profile. If it, still feels like a fit, if it doesn't, why that is, if there are other things about that particular type of job that you could look for in other types of jobs, or like other industries. There's so much to be gained from not prematurely closing your option set. And lawyers do it themselves all the time.
A huge part of my job when I'm working with you is, making sure that you don't do that. To the extent it's within my power. Because obviously, you have agency. And, ultimately, like, what works for you and your decisions, are the things that are going to govern, right? I think it's really important when we're working together, that you know, that I'm here to support you, I'm here to help you brainstorm, I'm here to help you connect with people in various industries or types of roles, if you're looking for people for informational interviews. I'm here to provide structure, I'm here to provide a process. I'm here to let you know, that when you feel like you're flailing, that's actually okay. That's normal, that's very normal. That's expected, and it doesn't mean you're doing everything wrong. And it doesn't mean you're failing. And it doesn't mean you're meant to be a lawyer forever.
Those are my jobs. But ultimately, it is, I think it's really important when you work with a career coach, that they recognize that like, you are the one with the ultimate agency. And, that you can provide suggestions or ask questions, as a coach, but if you are trying to tell someone what to do? Especially when you're talking to a lawyer. Especially when you're talking to someone who became a lawyer because they thought it was the right thing, and it turns out that it's not quote unquote the right thing, and you're trying to figure something else out. You need to know that you can trust yourself.
And part of what this process, that I work with people on, going from like the assessments to informational interviews, iterating, refining, figuring out exactly what the specific things are that are going to work for you, and then ultimately like, doing a job search and resume revisions and interview. Like, all of that is sort of, built on the structure of me helping you, fill in the knowledge gaps that you might have, and trust yourself, and actually be able to access your own intuition, and wisdom about these opportunities, and not outsource it to someone else.
So, that's how the process goes. And I've talked about the framework before. Like, sort of separately, in a separate episode. But basically, when we're working one-on-one, we're going through that framework, and then also other stuff comes up. So for example a lot of people I work with are also looking for bridge jobs. Which means they're trying to figure out what they, ultimately, want to do, but also they're in a situation that's super toxic, or really bad for them, and they need to get out ASAP. And so they’re basically, trying to move to like, a law or law adjacent job, while we’re also trying to do this work to figure out what they ultimately want to do.
So sometimes we're running parallel tracks. In other words, I'm like, we're doing that like, high-level, background, overall, meta work about who you are, and what it is that you want to be doing. And we're all so talking about, the specific jobs that you're applying for as bridge jobs, and potentially like, doing some resume revisions, and other things related to that as well. Or sometimes I'm working with someone, and something completely random comes up, like, some job opportunity that they've never thought about before, and it isn't legal, but it's something that they're really interested in. And we're still like, somewhere in the process, but they're wanting to pursue it. And so, one of the reasons that I like the way that the package is structured is that, you have those six calls. But the content of the call is basically determined as we meet on each call, as opposed to me saying to you “You have a six calls, and these are the things we have to talk about in each call. Like this call is blah, blah, blah. And call number two is blah, blah, blah.”
In between each call, you will know what to work on. And that provides the structure, but the call itself can be very flexible. So you enroll, I send you an email, I say “I'm super excited to work with you.” Which is true, because literally every time I have a consult with someone and I think they're a good fit, and they won't want to work with me, I'm like “Hurray!” I send you the email with some stuff to do before our first call, you do those things, you come to the call, and I will ask you on every call, some variation of “What would be the most helpful thing for you to get out of this call today?”
Now that doesn't mean I'm like “I don't know what you should do, or I don't know what direction you should go.” In terms of like, the work that you're doing outside of calls. It just means that like, there are a lot of different things that we could do with that work. And depending on where you are, and what's going on, and also if you have something like a bridge job situation also going. The things that we should talk about, about on the call, should be responsive to whatever is the most useful to you.
So often in the the process that, something like, debriefing you're various assessments, or like, talking about some of your insights from some of the exercises that I recommend. Or talking about some of the overall themes that are showing up multiple times, like, in the various exercises and in the assessment reports. And thinking about what that means in terms of like, what you bring to a job, and how that connects to your transferable skills. Which also, you have tons of transferable skills. I know I say it all the time, but just in case you're listening here, like “I don't have transferable skills.” That's not true.
Okay. You come to the first call, we we talk about, whatever is the most helpful thing for us to talk about, on that call. At the end of the call, we'll talk about what you're going to work on between that call and our next call. So you're never going to leave a call, and be like “I have no idea what I'm doing. I don't know what I'm supposed to do next, I don't know what's like, expected of me.” You always will know, the plan is for me to do XYZ, whatever things that you and I have discussed. And when I've done XYZ then like, I'll schedule my next call. Or in some cases it'll be like, I'm going to schedule a call for 3 weeks from now, and I will do XYZ before that call.
So, so, every call you're coming to, you know what to bring to the call. There's flexibility within each call, to talk about whatever it is that is the most helpful to you. Although, obviously, they’re structure, because of the work that you're doing, that's part of the overall Former Lawyer Framework. And then every time you leave a call, you know exactly what you're going to be doing between that, and the next call. And sometimes people will ask like “Can I add on calls? What if I want more calls?” Yes, generally speaking, you can. When you enroll, you can also enroll instead of just having six calls, you can have 12. So that, for example, if you want to meet every other week for 6 months, and know that that's going to be the schedule, that's something that we can do. Obviously, of, adding on calls, is subject to like my own availability. But apart from that once we've worked together one-on-one, there's more flexibility in terms of like, scheduling a one-off call, or like a smaller package of calls, like a four pack or whatever.
But the reason that I only offer the 6 call package on the front end, is that, I have never encountered someone in all of these years, now like 7 years of Former Lawyer, who could figure all of this out, or like get at quote unquote get an answer, in like one call or two calls. Like, 6 calls is the amount of calls, and the amount of time and support, that I feel like is necessary for someone to have a good outcome. And it's important to me that when you're working with me, you know that you're going to have a good outcome.
I do not want people to be put in a position where, they are investing money with me and then they are not being set up for success. My goal as your career coach is to set you up for success, and to support you in all the ways that are going to be most helpful, and most meaningful for you, and ultimately get you into whatever job or career is the right one for you at the time. And also, to help you build your skills so that, you, going forward if you end up in a job where you're like “Well this was a good fit at the time, but now they're these other things, and I need to figure out something else.” That you feel equipped to be able to do that. Because you've built the skills through our work together, to be able to do that. That to me is, one of the most important things. Because again, I think that a big part of coaching is making sure that you know that you are the one with the power, that you know that you are the one at the agency, and that you are the expert on you. I am the expert on some other things, like the process that works best for lawyers when they're trying to figure out what it is that they want to do, that isn't practicing law. But you are the expert on you.
And that's why, when we work together and put those two things together, there can be so much clarity. Because I have a lot of knowledge about the process, and what you need to do in order to get to a place where you can identify things that work for you, and target them, and get them. And you, know about you. And going through this process with me, means you're going to know even more about you. And ultimately, be able to position yourself better for whatever it is that you end up deciding that you want to do.
So, if you've been wondering what it's like to work with me one-on-one, this is a not so brief summary. If you have any questions, please send me an email. I might even do other episodes, if there are specific questions that people have, that come up a lot. Or I'm just happy to answer you, you can always email [email protected] and again, if you want to work with me, just go to the website. There's a work with me tab, you can see all the info, and you can scroll down and schedule a consult. Oh, and all the information about pricing is on the page too. I do not, okay. Side rant. I do not believe in not telling you, what you have to pay me in order to work with me, until you talk to me. I believe that you should be able to know on the front end, before you commit to a call with me, what is going to be involved.
There are some sales tactics that would say, to not tell you. And that is not an approach that I agree with. So, whatever the current pricing is, for the package, is going to be right there on the page. So there's not going to be any secrets, it's not going to be hidden, and when you get on the consult, like, I am not going to try to convince you to work with me. I'm going to make sure you understand what it is like to work with me. And I'm going to answer your questions, but I do not do any sort of hard sales tactics. I do not expect you to decide on the call, whether or not you want to work with me. Like, it is purely so that you can get the information you need, and so that I can get the information I need, so that we can both make the best decision about whether or not to work together. And I believe that that happens when you have as much information about what it's like, and what it costs, and everything else, as humanly possible. So. That's it from me. Thanks so much for listening, and I'll talk to you next week.
Thanks so much for listening, I absolutely love getting to share this podcast with you . If you haven’t yet, I invite you to download my free guide “First Steps to Leaving the Law” at formerlawyer.com/first until next time, have a great week.
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