Do you know there's a problem with your assistant or associate but you keep putting off doing anything about it?
This is how you know you're avoiding:
👉 you don't make time for meetings with them, or
👉 you feel resentful and angry towards them but tell yourself, “There's nothing I can do,” or
👉 you hope they'll magically get better over time
You may think that the problem is with the employee.
The actual problem is that you're ignoring your needs.
You're not creating the boundaries you need to make your practice run more smoothly.
The longer you put off addressing the issues with your employee, the more the problems snowball.
Then you'll be left with a larger problem within your practice on top of the work you're already doing.
This episode of Be a Better Lawyer Podcast will give you:
✅ a step-by-step framework to create new boundaries with employees even if you've never created them before
✅ an understanding of how our past histories can prevent us from communicating our needs clearly
✅ tips to create job descriptions that attract better-fit employees
✅ how NOT to think about boundaries
✅ and more
Whether you have an assistant or an associate, listen in to get help thinking through any problems you're having with them and create a communication plan to create better boundaries moving forward.
- My favorite book on boundaries is Boundary Boss by Teri Cole. You can get it here.
- BBL #188: The Co-Dependent Lawyer (For High-Achieving Lawyers)
- BBL #151: 8 Billing Mistakes Costing You Big Time
- Book a Strategy Session with me
- Follow me on Instagram
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Thanks for listening, and I'll talk to you next week.
Boundaries with Employees
Let's talk boundaries. Specifically. Let's talk boundaries with employees. I have several clients that have employees and they have found that managing their employees is a challenge. They think it's a challenge because their assistant doesn't know what they're doing or they're not doing things right or their employee is just bad. But what has really happened is that they have abdicated responsibility for the practice they want to create for themselves.
I know, I know I'm not telling you in this episode not to find a new employee, but what I do want to create here is a framework for you to think clearly about your next move. I don't want you making a move out of reaction and resentment and anger. I want you to be able to make a calm evaluation of what is happening in your practice. Be able to make corrections to what you see happening in your hiring practices and your communication skills. And one of the biggest issues that I see is a lack of boundaries with employees.
Our Personal History Can Make it Difficult to Create Boundaries with Employees
The first thing that I wanna do here is give you a understanding of why you may be having difficult boundaries. So we're gonna start with that, and then I'm gonna give you a framework for how you can think through what is happening in your practice with your employee, so you can begin problem solving and then make some decisions from that place.
A lot of times we think that we're bad employers or that we are bad at communication. No, I want you to, to know that this is not your fault. A lot of times I hear, but I'm just afraid of conflict. I don't wanna have conversations with them, and that is understandable. And I'm gonna tell you why. All of our communication patterns are formed at a very young age.
So I wanna give you an example of me and how my communication patterns were formed. And this might give you a better understanding of how your communication patterns may have been formed. So my experience with boundaries is that I had zero boundaries as a child. So what I wanted very rarely mattered. And when it did, it was like, what candy bar do you want? Or would you like another soda? And oftentimes I would say yes to things, oftentimes all the time.
<Laugh>, I would say yes to things even though I didn't want to because I was very fearful of my dad. My dad, if you've listened to other podcasts, was very authoritarian. It doesn't mean he didn't love me, it didn't, he didn't beat me or anything like that. You know, I got some occasional spankings, but he was a very angry person and he brought that anger into our relationship. And so I wasn't allowed to ask for what I wanted. And as long as he was pleased, right?
As long as he was getting what he wanted and I wasn't misbehaving, then everything was copacetic. He wasn't yelling. There wasn't anything like that. My body and my brain was picking up on cues on how to survive. So your brain did the same thing as you were a child, depending on who raised you, you picked up these communication cues, the these you found out if it was safe to ask for what you want or not by how you were raised.
Childhood Cues that Can Make it Difficult to Communicate Your Wants and Needs
So here's how some of my habits were formed by the cues I was picking up. So one, if I worked really hard, I received praise. Two, if I listen to the person in authority, my dad in this case, and do what they say, I stayed safe. Three, if I lie about my needs and say things like, oh, that's okay, or it's fine, then everything is safe. So I was training myself.
I was being trained not to ask for what I needed.
Four, if I close down my emotions, especially crying, I remain safe because if I cry or get emotional, if I show any emotion, then my dad will be angry. These were patterns that were formed at a very young age, and I had to unravel them. Most of us don't get that kind of awareness, so we don't have the opportunities to unravel them.
And it doesn't mean I never have any fears. What it means is I recognize them and I don't allow them to guide my decision making or my problem solving people pleasing and boundaries go hand in hand. So I am going to link to an episode I did on co-dependency. And this is for high achievers, right? Like the co co-dependent lawyer. That episode I did is for high achieving lawyers.
These are things that I have noted, noticed through the years of my coaching practice, and I wanted to bring some awareness around these patterns so you can bring this into your practice, because boundaries are important in every area, whether it's with clients, employees, personal relationships, sometimes those are combined. I have several clients who have brought in their spouse into their practice. So these are really important things to know about yourself so that you can begin problem solving.
And because you've learned these habits at a very young age, it's important to know that this is not your fault. That the problems that you're having communicating or really setting these boundaries isn't your fault. It's about what you've learned in the past, and now you have the opportunity to unravel them. And I work extensively with this with my clients, and so that they're not basically reacting to what they're seeing in the world. Basically their assistant, right?
Their assistant doesn't behave the way they think they should, then they react and they find themselves entering patterns that they have established from years ago. So let's talk about the problems that can come up when you don't have boundaries with employees.
A Boundary Hypothetical
Let's say you've hired a new assistant and you've had them for a while, maybe several months, but you're noticing that some things aren't quite up to snuff.
They're not performing the way that you would like them to, but you're not setting up a meeting. You are not setting up regular weekly meetings. You're not having really calm conversations with them, and you're starting to feel some resentment, maybe some anger, and those are feelings.
We are taught to snuff out when we are a child and not say anything, not ask for what we need, not make any demands, not make any requests. What I hear clients come to me with are these feelings of resentment and anger and frustration because their employee isn't behaving the way they want them to, but they're not thinking through what might need to happen now and in the future.
So instead, what they do is they avoid conversations with their employee. Maybe they make snarky comments, maybe they gossip with other people about their employee, but they're not actually doing anything about the employee.
They're doing a lot of complaining about it. Though sometimes they might make an ultimatum that uses having a meeting or a conversation almost like punishment, or they hope in the back of their mind that they quit if it gets hard enough. Or maybe you just get so angry one day and so frustrated that you just fire them. All of these actions are reactionary. They're not coming from a place of calm and curiosity.
And I wanna teach you in this episode, the framework to help you get there so that you don't take these kinds of actions and maybe blow up your practice, blow up a relationship that doesn't need to be blown up or not find solutions to maybe what is going on at a deeper level in your practice that you just don't have awareness around. And these actions all stem from believing that they should be working more, that they should be on time, that they should know better, that they should know how to do X assignment by now.
Maybe you're asking yourself what's wrong with them. Just know that your thoughts are creating the anger, the frustration, and the resentment and those feelings are then leading you to behave with the snarky comments or the passive aggressive behaviors. You might think that lawyers are supposed to be great with conflict, but now that you know the past history that can influence how we behave, you might now have a better understanding of why you're behaving the way you're behaving. You're suppressing your emotions, you're not asking for what you want. Things that are instilled in us at a very young age. And one of the things that I hear from my clients is that, well, I'm just bad with conflict. And they talk about this in the, in the sense of that's why I don't do litigation. That's why I don't do conversations with employees. That's why I hate litigation, and I'm doing it just for the money.
I want you to know that that conflict that you're feeling, the frustration, the nervousness, the anxiety, all stems from how you are thinking about the situations. That's all things that I can coach you on. But I want you to know that if you're a litigator or you're a avoid litigation because you wanna avoid conflict, which is what our brain says is gonna happen if we have a conversation with an employee, I'd be really curious to know if anything that I said about how you grew up and who parented you in their parenting style, if that resonates with you, because you might think that it's opposing counsel or being in court that is stressing you out. But what's really happening is your brain is making interpretations based on an old pattern, based on old habits and the way that it learned how to think. The great news here is, is that we have what's called neuroplasticity in our brain, which means we can form new connections.
We can start to unravel these, which is also what we're gonna be doing in this episode today. So know that you can not only work on your communication style with your employees, you can also work on your communication style in court and how you show up in court. I do this with my clients all the time. It is a hundred percent within your power. All right?
The Framework for Creating Boundaries with Employees
So let's talk about the framework of really thinking through what's happening in a calm and methodical way so that you can make the choices that you want to make.
Again, it doesn't mean that you don't ultimately make the decision to release this person and hire somebody new, hopefully, with some new things implemented, which I'm gonna talk about here in terms of job description and hiring.
But it does mean that you're thinking calmly and methodically through this.
Step One: Personal Awarenesss
The very first step of this framework is to get awareness of how you feel and accept those feelings.
So if you're feeling resentment, anger, frustration, no, it's okay. One thing I want you to recognize though, that it's not a them problem. It's a you problem <laugh>. And I don't mean that in a judgmental way. I mean that in a, let's take a hundred percent responsibility for the environment that you're creating within your firm and the environment that you want to create within yourself. If you're feeling frustration and anxiety and you hate those feelings, you are the one creating them. And so you get to be the one who helps yourself. And it doesn't mean that your assistant doesn't have issues, okay? It doesn't mean that there's not things that that you don't want to change.
But what will make it easier to go through this process that I'm gonna work you through is just to recognize, okay, I have a hundred percent authority over my life and the firm that I'm creating, and I'm gonna take the steps necessary to make it happen.
Step Two: Get Curious and Ask Questions
So once you have that, then you can begin to get curious, okay?
So what I want you to do is to just write down everything your brain is saying that your assistant should be doing.
It's gonna be like a job description. Well, they should be checking the mail. They should be doing the email, they should be doing the calendaring. They should be doing certain tasks. What are those tasks? Write everything down in your brain that your brain says they should be doing. After you've done a brain dump, that should probably take 15, 20 minutes, right? You've done a brain dump.
Then you're gonna ask yourself, what is she doing well or he, what are they doing well?
What is happening right now that they're actually doing well? Right? Are they talking to clients in a respectful way? You like that? Maybe you like the calendaring.
There has to be something. Just write it down.
Then write down what she's not doing well or at all.
So it could be filing deadlines, spelling errors, how she talks to clients, putting hearings on calendar. Maybe she's not doing that. Maybe she's not billing her hours. Just know in your brain, what is she not doing? You wanna write that down, okay?
Take a step back.
Now that you've written all of that down, I want you to be really honest with yourself and ask you in that first part, when you wrote down everything that you said that your assistant should be doing, does your assistant know that?
Or is it just a wishlist? Are you expecting her or him to read your mind?
Because we want to be really clear about what the expectations are so that you are setting them in front of your assistant and going through them line by line.
We wanna know what your expectations are and they need to be on the same page. Oftentimes, we think they should just know a hundred percent, not the case. <Laugh>, they can't read your mind. And if you start and stop on things. So for instance, if you say, you know what? It's really important that you get this calendaring done and then you interrupt her one day and she's doing the calendaring, and you say, no, I have a more important task for you. You need to do this thing.
Assistants might get confused. They don't know what the priority is. So if you are really clear on the priority, then you can be really clear when you communicate with your assistant about the priority. All right? I want you to ask this next in this process. So there's four questions I want you to ask yourself here. One is, write down everything your brain is telling you that she should be doing.
Two is write down everything that they are doing well. Three is write down everything they are not doing well or at all.
And four is get curious about the list. Why is she missing deadlines? Why is he not asking you questions? How did you talk to them when they missed a deadline? What is happening? What's the environment that you are creating? Are you creating an environment where they can ask questions about these things that they're missing that they are not doing so well at? Or are they afraid of you?
A lot of lawyers are unaware that people find them intimidating. That assistance oftentimes will not ask you questions because when they come into your office, you huff at them or you roll your eyes or you make a big dramatic sigh or something like that, and they pick up on it because you're frustrated. They get scared.
And if they grew up in an envi in an environment like the one I described, where there's an authoritarian parent, they're gonna have some of the same things come up for them. They're gonna shut down. They're gonna think it's not okay to ask for what they need. They're gonna think that it's not a safe environment. So if you notice any of those behaviors, know that it's up to you to start recognizing what's creating that. What thoughts am I having and what feelings am I having that are creating those reactions that I'm having when they step into my office and interrupt me? That's something I work with my clients on. Because those awarenesses are going to shift how you practice and it's gonna shift your relationship with the people in your office. I also want you to ask yourself other questions. When you're getting curious about what you've just learned, why am I seeing these problems?
Why am I seeing spelling errors? Did I address it in the job description? Is she in a hurry? Does she manage your calendar well? Is that why she's in a hurry? Did I create a training for her to address that calendar management? Was that in the job description? Maybe she has other problems happening, like maybe she's not in a hurry because of her calendar. Maybe it's because she doesn't spell.
How did I address that in the, the job description? And one of the things that I talked to clients who are now going through exactly what I'm going through in this episode with a employee who maybe has very common errors, is to start going through this process of questioning. You want to just understand like what could be the problem before you even talk to your assistant. It could be that in your job description, you didn't put in a task that required them to demonstrate the skill of spelling.
You took them because of one reason, because they seemed really nice, but they didn't actually have the skills that you required them to do to have. So one of the things that I've done with clients is that when they're creating a job description, is that in the job description at the bottom? Cuz this will show you if they have attention to detail, you say something like, write a one page cover letter, at least 1000 words, 1500 words, whatever it is you want describing why you're a great fit for this position. And when they write that cover letter, they are going to immediately weed you out. You'll be immediate, you'll immediately be able to weed them out. You'll be able to see, oh, they can't spell or they can't follow directions. They didn't see it in the job description. So they don't have attention to detail if that is an essential aspect of the job that you want them to fill.
This is why it's incredibly important to know exactly what your expectations are of an assistant.
We're gonna talk a little bit more about this in a second. After you've created the awareness of how you're feeling and what you're thinking, and after you have gotten curious and you've started asking those four questions, right? Understanding what you think she should be doing, knowing what she's doing well, knowing what they're not doing or at all doing, and getting really curious about why is this happening? What is the problem here? And looking especially at you and how this is being created by you, right? Not saying again that she's not doing things or not doing things she needs to be doing, but we wanna understand how we played a part in hiring him. Because if we are not paying attention to that, we're gonna make the same mistakes over and over again.
Step Three: Create a Hypothesis
You've asked yourself tons of questions. You've thought about it, you've probably ruminated about this on in the past. I don't want you to use your ruminations and your brain complaining as the data. I want you to follow this framework so you can get the data and then take that data into the hypothesis. We don't want this to be emotionally charged. We want this to be methodical, thoughtful. So when you create this hypothesis, you're gonna be asking yourself, why is this happening with him? Okay, A) I'm making assumptions about what they should or should not know or what their abilities are. Maybe B), I didn't address it in the job description. I totally slipped my mind. So they may not even know what their expectations are. They may not even know the skill. C) I didn't actually specifically train them on it.
So that makes sense that they wouldn't understand how to manage their time or manage my calendar. Or D) it could be all of the above. Maybe it's something else, but really create a hypothesis about it, right?
There's no right or wrong here. We just wanna start getting some sort of understanding around this so that we can make the changes that we need to make.
So once you have these hypotheses, check in with yourself. How are you feeling? Are you feeling angry or resentful? Are you feeling calm and interested?
If you feel angry and resentful, ask yourself why. And sometimes I get this, this thought that comes up, I should have addressed this sooner. Have you ever thought that that thought is the kiss of death? When you're trying to think calmly and clearly because you start beating yourself up, you start telling yourself, I'm a bad employer.
I don't know what I'm doing. I should have figured this out sooner. All of these things, when your brain, if your brain does that, press pause. Okay? You didn't know. You didn't have these skills. You didn't listen to this podcast before. It didn't exist to you before you listened to it. You weren't aware of what was influencing your behaviors. Chances are you didn't know how to formulate a job description. You were just doing the best that you could. So just remind yourself if this is coming up for you, you did the best that you could. Because we can't solve problems when we're blaming ourselves. We just feel really bad about ourselves. And then we take it out on the people around us, including our assistants. So clean this up before you do these next steps, okay?
Step Four: Be Honest About Your Needs
Remember if you related to what I shared at the beginning of this podcast, you may not be used to asking for what you need. It wasn't safe for you to ask for what you need. What are your needs? List them down, let it be okay to write them all down. What are your non-negotiables for this position? Is it an absolute requirement that she knows how to spell <laugh>?
Is it an absolute requirement that she knows how to talk on the phone? It might not be. Depends on what your needs are. Did you hire her primarily to handle your calendar and talk to clients, which she's great at, but she's not so great at spelling, which you don't really need her for and that's not a deal breaker. Know what it is that you need. Did you hire him primarily to do your billing and to do some billable work for you?
But he's not doing it properly and he's not billing the hours you expected And the only thing he does well is talk to clients that you didn't hire him to talk to clients you needed other things. Be honest with yourself so you can be honest with your assistant and then prepare for what might be next. You might want to release them. We don't know yet, right? There's another step here. We wanna, we wanna understand more, but we want to be really honest with ourselves about what we need and what our non-negotiables are.
Because your brain might just be complaining about things like she's misspelling names on documents when really you didn't hire them to put names on documents. You hired them to primarily be somebody who is engaging with clients and taking payment. And that's not something that is essential. So be clear with yourself.
When you're clear with yourself, you can be more clear with your assistant.
Step Five: Make an Agenda for Yourself and Make Time to Meet with Them
Alright, step five, make an agenda for yourself. You don't need to make one for your assistant, you just make it for yourself with everything you want to talk to them about everything that is a non-negotiable. And you wanna get curious about, cuz what you're gonna do next is you're gonna set up an appointment with them. You may not have regular meetings with them. I notice that when we tend to avoid conflict, we don't wanna set up a meeting, we avoid those meetings. I highly encourage you to have weekly meetings with your assistant. It doesn't have to be a long one, but it does have to be there so you can understand what your assistant is doing and not doing. And allow an open and safe space for them to ask you questions and make sure you're both on the same page about what is expected this week.
When they understand what is expected of them this week, then you are both on the same page. And then if they're not fulfilling their end of the bargain, you can readdress it and say, look, this is a non-negotiable. This is what I need. If you can't fulfill that, then that's something that we're gonna have to address and we're gonna either change your job description and reduce your pay or we're going to fire you, right? You don't have to say it like that, but those are things to be thinking about as you're getting curious about what's happening within your practice versus avoiding what's going on in your practice. So in this meeting where you've created an agenda for yourself, the things that you wanna ask your assistant about and get clear on and make sure they're clear, clear on, and make sure that they have the training that they need.
This is your opportunity to be very open and honest.
And I will offer to you being vulnerable and being really clear with them about like, Hey, look, I know we have not been, I have not been the greatest at setting up weekly meetings. I want that to change, okay? Because what I am seeing in my practice is that I need to have a bigger role in communicating with you and my other employees about what my expectations are and make sure that you have the training that you need. And this is our opportunity to get to a fresh start. So I would offer to you, you can do that. I think so many of us are afraid to admit when that we've been wrong or that we did something wrong or that we, you know, didn't have it all together.
I think it's a refreshing change of pace when we can be honest and open with people and say, look, this is where I have been with this and I, I really wasn't prioritizing the calendar the way that I needed to these meetings the way that I needed to.
And this is something that we're gonna do now, and we're gonna do it every week at such and such time unless there is an absolute emergency. But I want you to know that I want your input and I wanna know what your expectations are too.
So this is a two-way conversation, and when you're honest about that, it leaves it, it leaves it open for them to communicate with you what they need. Those are the things that we didn't get maybe when we were kids that now we need to open up and say, okay, if I'm offering them vulnerability now they feel safe to be vulnerable with us. So be honest, open, allow yourself to feel things that come up without reacting to them. So maybe while you're in this conversation, you might feel some of that anger and resentment come up, and then you just pause and you just say, okay, is, is that really helpful right now?
Is that how I wanna go with this? Do I wanna react to that? Or do I wanna stick to my game plan because my game plan's really good? Got it on that podcast, it's really, really good. So let me just know that I can be safe here and I can communicate with them. Now, listen, be open to feedback, but also be honest about your needs. It's so easy for us to ignore our needs. To ignore those non-negotiables that you've already outlined for yourself because we don't wanna hurt their feelings, right?
We don't want them to feel bad, but it's your responsibility to look out for your practice.
It's your responsibility to look out for how it's being managed, the environment that you're creating for the culture that you're creating.
And part of that requires communication. And so if you are communicating about your needs and they're saying, that's not something that I am able to do or, or want to do, then at that point you can make your decision about, okay, well I'm going to release you.
Or you can tell them, I'm going to give this some thought. Thank you for being honest with me. And then take a step back and make a decision. Allowing yourself to have needs, allowing yourself to have those needs fulfilled by someone you are paying because you are paying them to do a job. You may find that you need to redefine the relationship because you weren't clear in the beginning about the job description that you had in mind for them. You never expressed those needs. And so now you might be in a position where they're not filling the needs that you put in the job description, but that's because they're not the right person for the job and that's not their fault. It's just something that you are learning about how to hire and hiring as a learning process, right? You're gonna be hiring people, you're gonna be letting people go, they're gonna be leaving, and that's normal based upon the needs and wants of both parties.
I hope that this has given you a place where you can really think through what's happening in your practice and how you're communicating with employees and where you're creating boundaries in your life.
How NOT to Think About Boundaries
Because those boundaries aren't there as like a defense mechanism with which oftentimes, I think we tend to believe that boundaries are there to protect us from the world, when really all it is, is us expressing what we want and allowing ourselves to express what we want and letting it be okay if somebody else can't fulfill those needs. And us walking away. I'm just saying, okay, well you can't fulfill those needs. I'm gonna walk away. And those are non-negotiables for me.
So you don't have to go into this from a very defensive place. You can go into this conversation just being open and knowing like, this is what I want. And if you can't meet that, that's okay.
It's okay. It just means that we're not meant to be working together. All right? If you want help with us, this is something I work with my clients on all the time, is establishing boundaries and not just boundaries with employees, but boundaries with their loved ones, right, boundaries with their clients. And I've done other episodes on that.
In the future, I'll do one on boundaries with clients, but I've talked a lot about boundaries. I'm gonna link to a couple episodes about money because I see this show up a lot with lawyers who aren't charging their clients or discounting their, their charges to clients because they have a lack of boundaries with them. So those episodes will also help you. You can go to dinacataldo.com/ 262 for those.
If you want to take this work further, book a call with me. You can book at https://dinacataldo.com/strategysession.
These are not skills that most of us were taught growing up. Most of us were taught to just keep our head down. Don't make any waves. Just work really hard, especially if you had an authoritarian parent. You simply weren't taught these communication skills. So it's up to us to relearn these types of skills and help us communicate our needs so that we can have them met. All right, my friend. I hope you have a wonderful day. I will talk to you soon. Bye.