What to Look for in a Lawyer Career Coach 

So you’ve decided to seek the help of a lawyer career coach to help you redirect your work path? That’s a good first step.

You obviously want a change in your current work life but you may have some misgivings in terms of where you’re headed. It’s not an easy situation, and a good lawyer career coach should be able to help you navigate this transition.

But as someone who went through the same predicament, I learned that there are certain vital things that must be present in a lawyer career coaching experience that will enable you to successfully make that change. Otherwise, you might find yourself more confused than when you were trying to figure things out on your own.

A good career coach should be able to lead you in the right direction, not drag you to a formulaic path that’s not going to work out for you in the end. When thinking about what you should expect from a good career coach as a lawyer, here are my 4 top requisites: 


Wanting to take that leap to another job or career is not exactly a straightforward path for many. Oftentimes, your thoughts and plans can get quite scattered, leaving you with more questions than answers. The point where you are now and the point where you want to be could look like a hot mess of meandering thinking and doing and redirecting if there is no sense of structure to it.

A good lawyer career coach should be able to provide you with a framework, not a regimented method, of what you need to work on now and work on next in a well-defined way. This will allow you to see where you are currently in the process and the rate of progress you’re making. 

Identifying the progress in your transition path can help you organize plans towards implementation in a clear and strategic way. Remember, a lack of structure can not only waste your time and energy, but also lead to missed opportunities.


A good career coach for lawyers must implement accountability. Otherwise, there would be no way to check your progress and motivate you to responsibly move along. 

Being a lawyer, you probably have some answers to the what, why, and how of your career shift, but for various reasons, like busyness in your schedule and your mental space, you may find yourself unable to turn your ideas and plans into action on your own.

An effective career coach must be able to do a check-in with you and ask about development and whether you are making any headway. He or she must be able to make you see how your actions (or inactions) can speed up or slow down your transition. 

For you to succeed with your objective, this collaborative nature is necessary for career coaching to move you in the right direction. Think of it as getting a good push, not in a parental or bossy kind of way but in an agreeable and cooperative manner to get you to where you should be.


When it comes to defining and moving to a new job or career path, it is best to heed another head that can help you see, realize, and do things. Yes, you have your perspective, but it is often helpful to have an outsider’s perspective from someone else who can see things beyond your usual visual range and assumptions. Someone objective who sees you, your history, your strengths and weaknesses, and can say, “Oh, hey, I’ve noticed this,” or “Have you considered this idea?”

This diversity of wisdom and inputs is the reason why you have a board of directors instead of just one person making the decisions. A career coach specializes in the very thing you need help with, and his or her vast experience with different clients allows for coaching that is based on real-world situations and not just on ideals and naïve dreams. I have interviewed many lawyers making a shift in their jobs in my past podcasts and many of them have shared how they have benefited a lot from a coach’s perspective in terms of realizations and direction. 

Working with a lawyer career coach is like bringing in another experienced mind and voice who can give you that necessary perspective. And if you’re in a program like The Collaborative, you will also have the perspectives of other people who are in similar places as you, or maybe farther along on that journey that could help you gain more insights and inspiration.

Guidance (not enforcement)

A good career coach for lawyers does not make career decisions for you, he or she guides you to make the right decision for yourself. Because, at the end of the day, nobody knows you better than you do. 

A lawyer career coach is not one who claims to know the answer and moves you in that direction. Career coaching for lawyers, or for any profession, is all about providing an assessment, looking at all possibilities and scenarios, crafting a suitable plan or course of action, and helping you make progress and get there. It is about managing the whole process in a collaborative way that empowers you to figure things out and make the right decisions for your career.

Because the reality is, no matter how well a career coach knows you, they can never know all of the many facets of who you are, what you want, and what you might want in the future. You want a coach who will help you see a clearer picture of who you are, your experiences, values and priorities, and what makes you tick, so you can gain some clarity about what is the right next step for you.

I know firsthand stories where people went to someone for career coaching or counseling and were practically pushed in a particular direction. They found themselves more confused and frustrated and have said things like “I don’t actually know what it is that I want” or “I ended up in this new thing, but it’s not really working.”

Your transition doesn’t have to be stressful

Getting help from a lawyer career coach should help get the weight off your shoulder and not add your stress. 

Allow me to provide you with insights for your journey through my past podcasts where I help former lawyers like me and lawyers like you find their path to a fulfilling career that adds to their life, not depletes it. 

I urge you, too, to join my program The Collaborative where we can help each other reshape the life we want and deserve — to thrive, breathe, and truly live.

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Hi, and welcome to the Former Lawyer podcast. I am your host, Sarah Cottrell. And on this show, I interview former lawyers to hear their inspiring stories about how they left law behind to find careers and lives that they love. Let's get right to the show. Hello everyone. This week on the podcast, I want to talk to you a little bit about what you can expect if you work with a career coach as a lawyer. So people often ask me for referrals to one-on-one work for people who I recommend who do one-on-one work or have questions about the work we're doing inside of The Collaborative. And I wanted to talk a little bit about what you should be looking for and what you can expect when you work with a career coach as a lawyer. And in particular, I think these are the things that you need to look for that are going to be helpful for you.

That will give you the best experience and also, for those of you who haven't worked with a career coach, hopefully this will give you an idea of what it actually is like to work with one. So there are four things that you should get from any good career coach, from working with any good career coach. The first one is structure. So a lot of us when we go into this space of wanting to figure out another career, another job, it feels a bit scattered, I guess the word would be, and we don't necessarily know what thing to work on first, what thing to work on next, where to go. So one of the things that you should look for in a lawyer career coach is someone who has a well defined structure in terms of a path for you to follow.

And I don't mean it needs to be a regimented path and everyone needs to be sent to the same type of job. Actually, that would be very bad. I mean, some framework that you can work through so that you have some idea of where you are in the process to give you more structure than what you might have on your own, which again, can feel a little bit more scattered. So when you're working with a career coach, one of the things that they should be doing is giving you some framework that will help you assess where you are and where you need to go and how you're moving through the process. Another thing that working with a career coach provides for you is accountability. This is a big one, right? Because I think a lot of lawyers pretty much have some idea of what they probably should be doing if they're interested in doing something else, but there's a difference between knowing it and actually doing it, right?

So there's having the information and the knowledge, and then there's actually implementing. And one of the biggest benefits in my view of working with a career coach whether it's one-on-one or in a program like The Collaborative is that you have some built in accountability where you can say to someone, "I am planning to do X by Y date," and then that person is checking in with you and saying, "Hey, how did X go?" And if it didn't happen, then you can talk about why it didn't happen and troubleshoot. And this is not like if you're working with a good and gifted career coach, it should not be a parental, well, you haven't done this thing, tsk, tsk. It should be more of collaboration, right? So a situation where someone is taking an interest, knows what you need and is just following up and giving you those benchmarks to know, hey, I'm going to have this check-in, and this is what we're going to talk about.

And sometimes that's enough, right? Because again, in many cases, it's not that you don't have some knowledge about what you potentially should be doing, it's that you need some structure and accountability in order to make it happen. The reality is that many lawyers think that they should be able to figure out everything about a career transition on their own. And that's just not in my experience necessarily very realistic for a very busy, understandably so, focused professional. I think lawyers get it in their heads, "Oh, well I have all the knowledge and theory somewhere, I have to pull it together, but I, in theory could figure this out on my own and so, I should." And again, it is not at all that you cannot do it on your own.

But what I find often is that there are people who are telling themselves, "Well, I should be able to do this on my own, so I'm going to beat myself up about the fact that I'm not doing it on my own, but I'm also not making the progress that I want to make and I'm also not looking for help with getting this whole career transition done because I feel like I should just be able to do it on my own, except it's not happening on my own." Do you see how this cycle plays out? And I speak from experience here. So structure and accountability are the first two things that are a part of any good experience working with a lawyer career coach. And the third one is perspective, right? You have your perspective, but sometimes it is helpful to just have a outside perspective, someone looking at you, who you are, your history, all of that, who can say, "Oh, hey, I've noticed this.

Or, "Oh, hey, I've noticed that," or, "have you considered this question?" It's the whole idea of why do you have a board of directors and not just one person. It's to get that diverse input into the process. And in particular, again, to go with the board of directors example, in some cases you pick directors who have expertise in particular areas that will be helpful for the company. And so, working with a lawyer career coach is like bringing in another experienced mind and voice who can give you that perspective. And of course, if you're in a program like The Collaborative, you also have the perspectives of other people in the program who are in similar places to you, or maybe farther along on that journey and that can also be really helpful.

And the fourth thing, and this is truly the most important thing that I think you really need to look for and that is present in any good experience with a career coach as a lawyer is someone who is not just going to "give you the answers". It can be very easy, and I completely understand this because I remember feeling this way when I was practicing law, to just want someone to tell you what you should do. It feels really murky, it feels like there are a million options and no options at the same time and you're just like, "Please just give me an answer. I just want to be done with this and doing something else." I completely understand that feeling. But I think any career coach that is going to tell you that they have the answer for you is not someone who I would recommend you work with.

Because it has been my experience over and over and over and many of my observations and also in talking with other people who I now know through this work with former lawyer who worked with lawyers on career coaching, it is vastly more successful, people have a much more successful transition and by that, I mean, choose something that works better for them when they're the ones who are empowered to figure out what works for them. Because the reality is no matter how well a career coach knows you, they can never know all of the many facets of who you are and what you want and what you might want in the future. And so, you really want to be looking for someone who is going to help you get behind your own assumptions about yourself, and to really look at yourself and your experiences and your values and priorities, what you like and what you dislike and your personality so that you can figure out what is the right next step for you.

And again, I truly cannot emphasize this enough, I know firsthand of stories where people went to someone for career coaching or counseling, and basically they were pushed in a particular direction. And then they end up needing to go to someone else and saying, "I don't actually know what it is that I want," or, "I ended up in this new thing, but it's not really working." And the reason for that is that they were basically given a "answer" that is not the right answer them. So those four things are the things that you should be looking for when you're looking for a career coach as a lawyer. And those are also things that in any good career coach relationship or career coaching program you should experience.

I hope that it's helpful for you to have a sense of what it's like to work with a career coach and also what you should be looking for if you are looking for a career coach. I'd love to hear from you if you have worked with a career coach as a lawyer, what was good about your experience? What was bad about your experience? Shoot me an email at [email protected] and I will 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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