Teachers Make the Leap

The Good, The Bad, and The Boundaries: Real Talk About Client Relationships Part 1

• Kristin Macintyre

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Ever had that pit-in-your-stomach feeling when opening an email from a client? In this candid episode, Kristin and Hillary pull back the curtain on their most challenging client experiences and the powerful business lessons they learned along the way.

They share:

  • A detailed story of receiving harsh feedback and how to handle it professionally
  • Why ignoring red flags can lead to difficult client situations
  • The importance of trusting your gut when something feels off
  • How setting clear boundaries transformed their businesses
  • Why letting go of challenging clients often leads to better opportunities

Plus, discover why getting negative feedback doesn't mean you're bad at what you do - and how to use these experiences to grow stronger as a business owner.

Stay tuned for Part 2 where Kristin and Hillary dive into their BEST client experiences!

Want to ask Kristin and Hillary a question? Click here to submit your question to the podcast. We'll answer it on an upcoming episode of Teachers Make the Leap!

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Welcome to Teachers Make the Leap, a show that empowers educators to build online businesses they love and revolutionize the way work shows up in their lives. I'm your host, Kristen. And I'm your host, Hillary. We're two former teachers who have successfully made the leap from classroom to entrepreneurship. If you dream of finally leaving teaching to be able to make your own schedule and increase your earning potential, join us each week as we explore real ways to get there through online business.

Hillary:

Welcome to this episode of Teachers Make the Leap. Now, in this conversation, Kristen and I are excited to get really candid about, so many experiences that we've had in our businesses, working with particular clients. We really want to kind of pull back the curtain for people to see that, you know, when you're working with clients, there's a wide range of experiences that you might have with clients. And so we'd love to just share a couple of stories today about. Some of the worst experiences that we've had with clients and kind of what we've learned from those and how we've taken those lessons and move forward with them. And then we also want to share some of the best experiences that we've had with clients as well, because I would say far in a way, we've had more. Great experiences with clients than bad experiences. And so we just want to talk about kind of what it looks like and what it can feel like to have these really, really great client interactions and projects and experiences, and, and all the good things that come along with that.

Kristin:

I'd love to echo that truly truly when I think of my best client experiences I have so many that pop into mind and when I think of my worst client experiences I truly have one client. I'm sure there were others. I just, they don't come to mind. I have one client that comes to mind as this just experience that was kind of a nightmare and was like my worst client experience. Maybe we should share kind of our worst client experiences first and then end on a high note by talking about our best client experiences and what those are like.

Hillary:

Yeah. And why don't we start with yours? Because yours just, it really just, I even remember like you didn't even tell me, but you know, before we hit the record button, you didn't even tell me what client you were going to talk about. And I already knew what client you were going to talk about. I remember the day it was like snowing outside and you and I were supposed to meet later that afternoon. And we did.

Kristin:

That is hilarious. I don't even remember those details. That's so funny. Um, but I do remember the client experience very well. So just to give like kind of the key takeaway, and then I'll get into the nitty gritty. Now, I want to share some more details and talk about this a little bit more just to normalize this. You're going to work with clients that you probably won't have great experiences with, and you're going to work with people who you can not stop talking about because you love them so much. And they might even become like friends of yours, right? So, the client experience can, you know, fall along a spectrum. this client in particular was a coach for women in the, uh, like job market, she was somebody who taught women how to be more empowered when they were asking for raises or negotiating salaries, or how to, you know, help them really see their worth so that they could really advance in their careers. On its face, like an amazing business to work with, this client in particular had some credentials under her belt. Um, she had some notoriety. she was an up and coming business owner. She had some clients she worked with that had great success. So I was really excited to get on a call with her. Now, when we got on the call and, uh, we were talking about potentially working together, there were a few red flags in that initial discovery call. Um, just to go over them super quickly. The client started to talk pretty badly about other service providers she had worked with before. So, super red flag. we've done a, uh, an episode on, the Teachers Make Believe podcast about client red flags. Go back and listen to that one if you haven't. We talk about this in more detail. But speaking poorly about other service providers was a bit of a red flag for me on the discovery call. Now, when we ended our discovery call, I actually told this potential client that we probably weren't the best fit to work together because she needed a bit more work and kind of like deep messaging help in the business that I wasn't providing. So I basically told her, This was probably not the best package for you. And she came back to me and said, no, no, no. I want to move forward anyway. So I gave her kind of a fair warning that the way we were going to work together is probably not going to meet her needs. And my mistake was that I let her kind of, you know, book me for the project anyway. Probably in hindsight should have just said no, and that should have been my decision. Anyway, you live and you learn. So, I did the project and delivered it to this client and, You know, you always get a little nervous when you deliver a client project because as much as you want to be very objective about your work, uh, you always say to yourself like, oh, I hope, I hope this resonates with them. I hope I hit all the points I needed to, you know, I hope they were really proud of the work and they're, they want to showcase it in their business. And I had sent off this project to this client and she got back to me, I think almost. immediately with very, very harsh feedback about how I, that I missed the mark on a lot of it. Now, I think there's some shared responsibility here. I think she actually had some great points in hindsight, and also I think she took, you know, took the buck a little too far with what she was expecting from me with the project I told her. Probably wasn't going to suit her that well in the 1st place, but when I got her feedback, and it was an overwhelming amount of very negative feedback, and there was a huge email. Uh, there was a, I think, over 100 comments in the document that I left her and they were not nice. They were not kind, which I think was the piece that was hardest for me because. That criticism delivered in a softer, kinder, you know, more, more inquisitive way. Would have been fine. take constructive criticism all the time. Right? but the, the way it was delivered was really harsh. And I do remember getting that feedback and I remember the blood just kind of draining from my face and my stomach dropping because I, I started to feel all these things. I felt embarrassed that I delivered something that she didn't think would work in her business. I felt kind of ashamed that I, you know, thought I was writing something that was really going to hit the mark and it was just totally off base. I felt defensive because I had put, I mean, this is the part I left out. I had put tons of hours into this project. This was not something small that I did in a few hours. This was something I labored over and I agonized over and I switched things out and I revised. So I had put a ton of work into this that I felt was not appreciated at all. And I the first thing I did was I cried. Because I was, I was upset and I reached out to a few folks in my network, Hillary, you were one of them. Our friend Olivia was another one. And a third was a business coach I had at the time. And I was just in full panic mode. About how do I deal with this? Am I going to have to rewrite this entire project that I had already spent tons of time on? how do I find that line between what edits to implement and what to reject? so that this project is still fair to me and also fair to my client. So many questions, so many things to navigate. To be fair, also, this was a time in my business where I was very overworked. So it was almost like the straw that broke the camel's back where, and I just had a lot of projects I was doing kind of back to back. and this one in particular, just getting that negative feedback, it just kind of broke me a little bit. I know you remember that, that day too, Hillary.

Hillary:

I do remember it. And I actually remember so many details that I don't know if even you remember, but you had told me that morning you were like, I actually saw all this feedback come through at like midnight the previous night and I went through it and it just like I was up all night agonizing over it. I remember thinking to myself too though, and I just think this is really important to bring up, when you were telling me that this had happened, I was like, Wow, it truly doesn't matter how great of a copywriter you are, everyone is gonna have an experience like this, because Kristen, you truly are one of the best copywriters I have ever encountered in my entire life. And I know that's probably uncomfortable for you to hear, but, uh, it truly is. And so honestly, for me at that point, it was like, Oh, that actually lessens for me the impact of some of the harsh criticism that I've received on my copy projects. Like it's clearly not like a lot of times it's really nothing to do with you or the copy you've written or the skills you have, right? It's truly that. I was not a good fit for this client. This client was not a good fit for me and you had told her that. And so I think that even makes it harder too. so what did you do moving forward? I actually don't remember how you moved forward. I do know that you didn't end up completely rewriting the project. You did kind of stick to your boundaries there.

Kristin:

I did. Yes. This is how whole thing got resolved, which in hindsight, I took some amazing advice from my business coach and you and Olivia as well, and I did not respond to her immediately. And I think that was important because sometimes my inclination is to just get back to somebody immediately. I like being efficient. I like responding. I like being responsive and my inclination can just be like to fix it and to say something. But I took a beat and I, I think I gave it 24 hours or somewhere in that ballpark. I collected myself. I wrote an email back to her. I had, I think my business coach look at it. And I drew some boundaries with her and it was so much easier to respond to this client from a space of kind of more reason and logic rather than that sheer emotion that I felt immediately. I did, I did set some boundaries. I remember telling, I remember being very fair with her and saying, I hear everything you're saying and these are the spaces in the project that I will go back in and rework and re-look at and revisit. And these are the things that are quite outside the scope of the project we're working on. So I delivered, you know, some refreshed pieces of the copy to her. and really kindly just let her know that the project was complete. Ironically, she reached out to me to do more work with her, and I, so, which was an interesting experience, because I was like, Oh, this, this, this client, we are not a good fit. We are not a good fit at all. and in her eyes, she's, she wanted to do another project. So I was just a little, I was just like confused about, our relationship and our rapport. but yeah, she wanted to do another project with me and I, I kindly. declined that project because I knew it was going to be another repeat of what we had just done. So it actually ended up okay. I collected myself. I responded, set some boundaries, and we both, you know, moved on. which is how it should have been.

Hillary:

Yeah, absolutely. Well, I also just want to ask you another follow up question, how long do you think it took you to kind of like get over that experience? Because as a business owner, I mean, that's like a really vulnerable thing to be, to have your work attacked like that. I really do think like that's what it feels like is your work is being attacked and your self worth even. So how long do you feel like it took you to like get over that and move on and build that confidence back up?

Kristin:

That is such a good question. You know, I don't know if I have a finger on the pulse of like, how long it took me to get over it. Clearly, it's still something that I remember very well. So it's, it's left its mark for sure. But I think what was Good in like the recovery process was that I, I had a lot of work at the time. Which on one hand is like, Oh no, all of this insecurities flared up. And on the other hand, I just had all of these other amazing clients who were giving me really positive feedback. So it was, it was a negative experience kind of in a host of other really positive experiences. And I think that helped lessen the blow for me. Um, but I could see it playing out a different way where I, you know, didn't have other projects to work on or wasn't, you know, getting, other types of feedback from my clients where I really probably would have taken what she had had said to heart a bit more.

Hillary:

right, right, right, right. I'm really, really glad that you shared this story and that you were willing to share this story because I think it's so important for people to realize that just because you get negative feedback from one person, It doesn't mean that you can't do this and it doesn't mean that you failed and it doesn't mean that you're bad at this. Right?

Kristin:

I actually have like so much to say here and I don't want to get into the weeds too much, but it really is for me, what that client experience taught me was not that I was a bad writer. Like, it didn't teach me that at all. What it taught me was that, A, I should listen to my gut because I knew that we weren't a great fit to begin with, B, that I needed to set more firm boundaries as a business owner, because what happened was I let her book the project anyway. And that should have been a boundary that I really kept. And C, I learned that communicating expectations. is really, really important because I think the client had mismatched expectations for what I was going to deliver to her. And, those are the lessons. So, so it's not at all about, you know, can I write copy or am I good at what I do? Actually, the lessons are, how do I interact with my clients and be, become a better business owner? and so, It's so, so important to reiterate. Truly. When I think back on my four and a half years of writing copy for clients, this is the one client experience that stands out to me as like, Oh, that, that went wrong somewhere, so it's definitely the exception and not the rule.

Hillary:

Right. Right. Well, let me share a little bit about my worst client experience because mine is a little bit different, but it also, it does all come back to boundaries, which I think is so interesting. Um, and my worst client experience is actually, it's all kind of around one boundary, but I, I have three clients that come to mind to kind of cross to this boundary. And, and I'm going to share after I give a few specifics about these three clients, how that has impacted my business. Today. So the first one that comes to mind was, this CPA, this tax advisor, who was really pivoting from working as a CPA with, uh, individual clients to sharing his knowledge and expertise with other financial advisors, which is, actually something that's pretty common, nowadays, but at the time he was, he was kind of one of the only people in the space doing this. And I did a test project with him and they had come to me and I had met with multiple people on the team. Like, it felt like very kind of like formal. The expectations were very high. I did a test project with them and they loved it. And they were like, Oh my gosh, you were the first person to ever like fully understand what it is we do. Right. And so they had paid me 250 for this one blog post that they absolutely loved. So then, They spend some time putting together like a marketing plan or whatever. It might be literally all they were going to hire me to do was to write blogs for them on a consistent basis. And so all I needed from them was a list of topics and. I could get started, And I went back and forth with them for literally months, trying to get this list of topics. I was sharing my ideas. They were sharing their ideas. They kept changing things. They kept wanting to get on the phone to talk about things. And I just let this go on for way too long. And so finally, after probably three months of only getting paid for this one project, 250 and having been on multiple calls with multiple people in their team to just literally talk about a list of topics that I could get started writing on. I finally sent an email and just said, you know, unfortunately my calendar is booked up. I'm no longer going to have time to work on these projects since we haven't been able to iron out the details and things like that. And my main point of contact. Email me back probably within 10 minutes or so with the most guilt, trippy, condescending, manipulative email I have ever received in my entire life. Uh, and, and I used to work with college students, I mean, you know, as a teacher and so like I've had my fair share of like kind of nasty emails from college students. And I just remember taking that to heart so much and just. Feeling like really questioning, like, am I doing something wrong? Am I a bad business owner? Should I not have done this? Have I totally inconvenienced them? Like now they're going to have to find another copywriter. Like I just felt so bad about it. and I, and I really hated that feeling, you know, it definitely. did not make me want to backtrack and continue working with them, even though I felt like I kind of had to in a way. Fortunately, like you, Kristen, I reached out to a couple of people and I was just like, what do I do? Do I apologize and say, okay, sorry, I'll make time on my calendar or you know, whatever it might be. Luckily, the people I talked to, We're like, no, absolutely not. And so that was kind of my first experience. My other two experiences with clients who crossed boundaries were also clients that I just let stuff go on for a little bit too long. Right. And the way that they were speaking to me and giving me feedback was very condescending. It was very personal, right? It was just not, constructive in any way. And they were just asking me for way too many provisions and edits on pieces that, you know, were totally outside of the scope of the project. And so what happened with these 2 clients? I actually remember. I was working with both of these clients prior to going on my 1st maternity leave and I was just really reluctant to let them go because they were. You know, they were each paying me like 2, 000 a month. They felt like a really significant part of the income that I was bringing in at the time. And I was afraid I wasn't going to be able to replace them with better clients and things like that. of course this crazy thing happens in your business that when you do let go of a bad fit client, oftentimes. A better fit client comes in the door pretty soon after. It's kind of this weird phenomenon that I've seen play out a couple different times in my business. and so what I really learned from that was to trust my intuition. And if I have a client now, where if I see their email, you know, their name pop up in my inbox, and I get a sense of dread because that's what was happening with these. three particular clients, I immediately kind of know, okay, it's time to start thinking about letting this client go. that has been a really great kind of intuition that I've been able to lean into because I just don't want to feel that way anymore. That's something that I felt as a teacher all the time. I'd see an email pop into my inbox from that one student, right? That was always challenging me or whatever it might be. And I always had that sense of dread about opening this Email like, Oh, what is it going to be this time? And I, I do love as a business owner, having the choice to not have that in my life anymore. And so, uh, I'm so, so happy to say that today of all the clients that I work with, I work with about between 10 and 12 clients now on an ongoing basis. Not a single one of them causes me to feel any dread when I get an email from them. And I just love, I love having a business like that. It is So freeing in that way,

Kristin:

That is so important again, the lesson is listen to your intuition and it's, like, pay attention to that sinking stomach feeling, like pay attention to that. love that so much. So with these clients in particular, where they kind of crossed the boundaries and they ended up just being relationships that you were like dreading interacting with.

Hillary:

Yep.

Kristin:

they were all necessary to kind of get you to a place where you are now, which is basically like, I don't really take on clients like that anymore, or if I noticed that, thing happening, we were thinking about letting the client go or severing the relationship. It's like,

Hillary:

well, you know, it's so interesting too Is I think that maternity leave kind of forced me to let go of these clients and and I'm literally just making this connection right Now as I'm talking Because I didn't want my team to have to deal with the kind of negative things that I was dealing with when communicating with these clients and literally the connection that I'm making right now is I'm not If I cared about my team that much and I didn't want them to have these negative interactions, why didn't I care about myself that much at the time? You know, if I hadn't gone on maternity leave, would I have had the courage to let these clients go? I hope so, but I don't know. And so I think that's also a really valuable lesson to learn is if I wouldn't be comfortable referring this client to a friend of mine, you know, or I wouldn't be comfortable letting a member of my team totally take over communication with them. Why am I torturing myself with working with this kind of person, right? and then to speak to your question, I actually got a LinkedIn DM maybe a month or two ago from someone who is looking for a large amount of copywriting help, you know, 3 years ago, I would have been so excited. Like, oh, this person needs so much work. I can help them. I can learn these different new types of projects. This is going to be so great. But his, you His initial LinkedIn message was this is what I expect from a copywriter, all these things. Here's some examples. I'm looking for a copywriter who can do as good or exceed the expectations of what I'm looking for. You know, things like that. It was very an off putting message. Now, I still share my calendar with him. I shouldn't have done that, but I still shared my calendar with him. And his next message was your hours are very limited. Can you meet at these hours? You know, that kind of thing. And I'm, again, I got that sense of dread similar to the email I got from the first client that I shared of like, Oh, am I a bad business owner? I'm not available at all hours of the night. I'm not available at convenient times for this guy. I have no idea where this guy lived. Right. I'm sure he was in a different time zone or something like that. and I just, Immediately, I was like, No, I don't feel that I don't like to feel this way in my business. I'm cutting this off right now and not continuing the conversation. I did take screenshots of it and I asked a few of a few other finance copywriters if they would like to be referred to him. They all said no. Thank you. And so I too was just like, Sorry, good luck in your search, you know, that, that kind of thing. So I am glad that I've had those experiences and, you know, eventually did listen to that gut feeling and terminated relationships because now I feel like when I get, Inquiries, you know, from potential clients, I can recognize those things. And I'm a lot more comfortable. Just, I just don't even want to get on a call with this person because I'm already feeling the dread in the pit of my stomach and I'm not going to feel that way in my business anymore.

Kristin:

BS gets less and less and less

Hillary:

it does. And, and it's so interesting too, as the tolerance for the BS gets less and less and less, the revenue is not getting less and less and less, the revenue is still really going up, right? There's tons of great clients who are still out there.

Kristin:

I just want to say it is so fun kind of looking back on these experiences, even though we're talking about kind of, you know, negative client experiences. There's so many good, like, learning things in here, right? Like, good, juicy nuggets about. Like, Oh, that's when I learned how to respect my business boundaries. And that's how I learned to listen to the dread when I, you know, I'm talking to somebody on LinkedIn or a potential client. I want to say, I think we should wrap up here. Why don't we talk about our best client experiences in a next episode. So we'll do a part two And I know we've got lots of great things to share around our very best clients. Best client experiences as well. So thank you so much to everybody who's tuned in to this episode. And we'll catch you on the next episode of Teachers Make Believe.

Thanks for joining us on this episode of Teachers Make the Leap. We can't wait to help you make the leap from teacher to thriving business owner. If you liked what you heard today, subscribe to the show on your favorite listening app and leave a review on Apple Podcasts. We'll see you back here next week.