Episode 039 - The Difficult Episode

In this episode of the Content Amplification Podcast, Shaun Whynacht and co‑host (Speaker A) discuss practical strategies for dealing with difficult clients in a service‑based agency. They cover how to set clear boundaries by explaining pricing formulas and project timelines, establishing firm due dates, and getting verbal and written commitments from clients. They stress the importance of collecting 100 % of required content before starting work and using organized asset repositories (Google Drive folders) to avoid fragmented email exchanges. The hosts outline a payment milestone system—initial deposit, staged invoices tied to project phases, and a final payment upon launch—to protect cash flow and motivate timely client delivery. They share how automation tools like Trello, Google Keep, and custom reminders keep projects on track, and how regular check‑ins can prevent last‑minute rushes. Drawing on retail experience, they describe a customer‑service mindset: acknowledge clients, make them feel heard, but maintain firm boundaries (e.g., coupon expiration). They also discuss the nuance of “favorite” clients who may push limits, recommending disciplined over‑delivery only when it adds strategic value. Throughout, the conversation is conversational, anecdotal, and offers actionable advice for agency owners to streamline workflows, enforce contracts, and maintain healthy client relationships.
Chapters
I think a part of that as well, to kind of setting those boundaries, is, you know, simply explaining to the client how you calculate, you know, your pricing and, you know, how long a project would be because it's completely dependent on the amount of time that you've allotted for it.
We are back with another episode of the Content Amplification Podcast, take 2. I'm going to admit this, we were trying out a new feature when we weren't in the same location using Riverside, and being new to that platform, I thought I was recording both sides of the conversation. Come to find out, I just recorded mine. Yes, yes, you did. So now we're, so we're going to give this another go. With it. So we wanted to talk about dealing with difficult clients. Now we've already been through this, so this shouldn't be too hard. Now I think there's, there's different parts of difficulties that we're going to talk about. There's, you know, clients who just are asking too much, right? They're, you know, they're, they're feeling, um, I don't know if it's entitled or pushy or whatever it is, so they're just kind of pushing the boundaries. And how do you deal with that? And then there's also the difficult clients that are fantastic, but they just make doing your job difficult because they're not getting you what you need. And we're, you know, we've had experience in both those cases.
Yeah, definitely. And, you know, especially on the social side of things where, you know, the way we work is I rely on the clients to get us the actual content, and then we schedule and design and that, that side of things. So we've I definitely have a lot of experience with the having to push and push and push to get what it is you need to be able to do your job well.
For sure. And you know, you try to set and plan, especially if you got, you know, multiple clients you're handling at the same time. You know, especially when we're building out Keep automations and things like that. You know, we go through different milestones where, you know, you meet with the client, you figure out what you're going to build in that sprint, you build it, and then you need to, you know, either send it to them to look over and get back to you. And then you don't hear from them and you're just chasing them and chasing them and chasing them and it just pushes out the project so far and it's not that enjoyable. Also, you've planned that time to work on it and now it's free. You didn't have that space to fill before and basically you could have had paying work in that spot, right? So it's a bit of a challenge.
Yeah, exactly, and as we discussed in our first time recording this conversation.
Which nobody heard.
Except your voice.
That's right.
Yeah. The strategy that I've kind of taken on is setting those really hard due dates. And when you're having that meeting with them, you know, face-to-face or virtual, making sure that they agree to that due date. And that's what I've been calling them. I do my little, you know, air quotes due date, 'cause it's kind of funny. It reminds me of being a teacher, but you know, just making sure that they're on the same page with you about when they can get it done and also explaining why it's necessary to have a due date, right? Not only, you know, does it make it easier on them because they have the content out of the way and then they can forget about it, but then I also have the, you know, enough sufficient amount of time to be able to, you know, do my work the best that I can. So really it's a win-win for everyone if they're on time.
Absolutely. And it's coming down to just getting your client to acknowledge when they're going to deliver it, or even when they are going to review something, or even if they even understand what you're asking them to to do. You know, a lot of times if you've got a client who's, who's new to the marketing space, we're gonna talk about marketing, this can, can relate to, I think, anything, um, that you need to look at making sure your, your instructions are clear, right? So, you know, just getting them to say back what they're going to do, what they're going to deliver, when they're going to do it, and just verbalizing that is a way of them to commit it.
Absolutely. And, you know, in addition to verbalizing that, also having it in a document, right? Like, just today I had a client who had asked me multiple times for the same piece of information. And because I wrote that down and highlighted exactly where, you know, when the content was due, all that, that, uh, that stuff, I was able to say, just refer to the document, which is the document that we both had that mutual verbal agreement as well as the kind of have it written down and summarized so they can just refer back to it. And, you know, not to say that the blame is off you, but in a way, you know, they understand that it's— the frustration isn't, you know, placed on me, I guess.
For sure. Now let's talk about those clients who are pushing the boundaries. You know, it's very important in any kind of service-based business to outline what the project is and what the deliverables are. Now in our business, what we tend to try to do with a new client is start off with a project so we know there's a definitive start and end date. To that, and then what is going to be encompassing those, those elements of that project. And a lot of times where we've ever fallen short, and I've fallen short in the years past, is not clearly defining that endpoint, right? So it's, it's kind of like, you know, if you've ever been running and you start to trip and you think, I can save myself, and you keep trying to run faster, but you never, and you end up stumbling. That's what it feels like when you're at that point, you don't know how to just stop that.
Yeah, definitely. Um, yeah, and you know, a client that we had recently, uh, especially with the website, website design, if you want to speak on that.
Yeah, for sure. Yeah, for sure. And a lot of times, um, and this was a fault on ours, um, on my end more so, uh, is that, you know, we did a project, we scoped on a project that should have been a very clean, clear project. You know, here's everything we need, get it to us, we'll build the site, you look it over, you know, any corrections we fix, right? So, um, it fell short and started stumbling with getting fragments of information given to us. And in the past, I'd done that before, and I started to implement a fact that we won't start working on the site until we have 100% of the content. And I think that's a good point to make. You know, the same thing is, you know, if you're going to start to frame a house, if you're a contractor, or build a garage, you know, you're not going to start to go if the lumber that you need to get to that point is not there, right?
Yeah.
So you want to make sure you have everything to go forward. So that was the first part, it just pieces dripped in. It makes it very, you know, messy because you've got multiple emails that are coming in. So, you know, what we've implemented on the social side has been You know, let's create a Google Drive folder and have the client put all the assets they're creating in there. So it's siloed, it's very organized, we know where to go to get it versus, hey, just email us stuff and then you've got multiple emails and, you know, that kind of thing.
Yeah, absolutely. And I think a part of that as well to kind of setting those boundaries is, you know, simply explaining to the client how you calculate, you know, your pricing and you know, how long a project would be because it's completely dependent on the amount of time that you've allotted for it. And so if you start to go over, you know, there's a reason for that because, you know, you've been doing this for years and if one project doesn't go a certain way, it's definitely not, you know, on the service provider's fault because they've done it hundreds of times with other clients successfully, right? So I think just explaining that, you know, there's a process to this and, you know, when I say I need something, it's for both of our benefits. And when I say I need it at a certain time, again, for both of our benefits so we can both get what we want.
Yeah. And even asking them like, when is a realistic timeframe for you to get this to me? Right? Because maybe they're super busy. Right? And they say, I can't get it to you till next week. Right? So that's, that's a good way to have that part in there.
Yeah. Because, you know, then you're able to work around it as well and, you know, plan your schedule instead of having that, you know, 2 weeks of frustration. And we all know that frustration doesn't make us very productive.
So that's right. And, you know, another kind of advice that I can give you from, uh, you know, running an agency or even a business when it's project-based is that, you know, you quote the project and, you know, you start the project with, you know, up to like a 50% deposit, um, that's on there. And the benefit of that is to cover your costs in that initial phase. So you vote line that, you know, from— we'll use website again as an example— from the moment we start to the moment we show you first draft, right? That's covering that 50%. When we deliver the first draft, maybe you want to say, okay, we're going to then invoice you for, you know, the next 40% of that, right? So now you've got 90% of the budget paid, and then the last 10% is paid when it goes live, right? So that's kind of the milestone that's there. The other thing too is setting it on a time frame. So you say we're going to deliver this project start to finish in 6 weeks. Right? We start at 50% at 5 weeks, the other 40, and the 6, you know, the last 10% is at week 6, right? If we delay the project for some reason, like we just go over that, we won't charge you at those milestones. We will, you know, scale them out. But if you're delaying the project, we're still going to hit those, those time frames, right? Sounds a little harsh, but it's motivation on the other end. And get them to agree to that, you know, even in the beginning. Don't Don't sign them on to your project and then say, "Oh, by the way, this is how we're going to do that." It's kind of a bait and switch. It's not a great way to start.
Having everything out on the table before you agree to anything is definitely the route to take. And something I wanted to talk about too is just the kind of human nature of compassion side of things, right? So, you know, we have clients that are difficult that we don't have a particular liking for, And that's, you know, kind of separate from a different— from a—
and if you're one of those listening to this podcast, it's not you. It's not you.
No, but then you have the clients that you're particularly fond of. And so, but they both can be difficult clients, you know, like a client that you are really fond of might push more and more and you might be more likely to kind of go past those boundaries that you've set and do more for them and end up losing money on a project. So what do you kind of recommend for those situations?
I think, you know, you got a business to run, right? So the idea of losing money, I think it's better to try to stick to that constraint as much as possible. And if you feel like it's going really well, maybe you want to overdeliver to them. Right? So not only do they essentially get more value, but they've got more of a wow factor. So now they're going to talk about it, they're going to tell people, they're going to send those referrals and that type of thing, you know, versus just, you know, letting them push boundaries because they're a nice person and that kind of thing. That's what, that's what I would say is try to keep it there because, you know, humans are all like from habit. So if you start to have a run of really good clients, and that's where I felt into this, this trap was had a really good run of clients that weren't pushing boundaries. They were really nice and that kind of stuff. So I let things slide, right? And I just got in that habit. So when somebody came on board, my guards were down and I just let it slide and they just started taking advantage of that and keep going that way. So you just got to keep that system in place and sticking to it. People are going to miss deadlines. That's okay, right? You know, it's just how you handle it. So, you know, if you were supposed to get these social images for posting today because that's the day you're scheduling it didn't come. Just gently reach out, just say, you know, I was looking for those, just wondering if you had a chance to do that. And they understand, they might be like, oh yeah, I forgot, you know, I got them here, I just didn't upload them, or whatever that case is with it.
Yeah, definitely. And I mean, there's also, you know, the opportunity for you to be helpful and, you know, check in every now and again to make sure that your client is on the right track. And, you know, with Keep too, you can even make that an automation. So you don't even have to have to think about reminding them, you know, just sending a kind of update halfway through that work period saying, you know, how's it going? Is there anything I can do to help? You know, just that type of thing is, it really helps them to stay on track because, you know, we've all been in that situation where we have, you know, say 2 weeks to get something done. And, you know, that first day we're like, oh my God, it's so far away. I don't have to worry about it. Oh my God, it's so far away. I don't have to worry about it. And then all of a sudden it's the night before and you're like, Oh crap.
Yeah, so doing your major project the night before it's due, right?
Oh yeah, I'm a master at that coming out of school.
For sure. You know, and you know, there are tools out there that help you do that and keep your project laid out. I mean, we use Trello internally. We've got a lot of clients that are using Trello as well, and that's one of the, the benefits of having a system like that is to just keep your tasks on track and know where your milestones are, you know, and there's thousands of them that are there.
Yeah, and, and that's honestly a good point too, making sure that you're organized inside your organization, because how can you expect your clients to feel and be organized if you're not, right?
So yeah, so you know, you set that expectation of next Wednesday, they don't deliver, and if you don't follow up on that, they're gonna be like, well, they're not keeping up with it, why should I?
Right, exactly.
For sure. Now on the last little part, when we know we have clients that are in the retail space, right, and we're talking about difficult clients, Your experience has been in retail in the past. What about those clients that come in and you just, you kind of like, or customers, I guess we'll call them that, they walk into the store and you're just like, oh no, like they're back again, that kind of thing.
Yeah.
Or they're, they're trying to always like push the boundaries of, you know, sales and promos and that type of stuff. How do you deal with those type of people?
Yeah, so I guess first off, a bit of background. I worked retail 4 years. I was in a management position, which it entails not only running a sales floor or whatever, but also coaching employees. So that can even be young teenagers who are really uncomfortable with those difficult clients. But you often hear the cliché of the customer is always right, and I never, ever, ever abided by that. I think my philosophy still to this day and what I taught my employees was acknowledge, but don't, you know, acknowledge that it's correct or that they're right. Just make sure that they feel heard. And, you know, that's really all that people are looking for. Like, if you think about, you know, somebody who comes into the store and is like swearing at you because they're so upset about not getting the 20% off because it's you know, 2 days too late, they're not really only upset about the 20% off, right? They want to feel heard and they want to be acknowledged. And then you can do everything that you can. But, you know, at the end of the day, there are boundaries and, you know, there are expiration dates on coupons for reasons, right? So do everything that you can to make sure they leave happy and, you know, make sure even though they can, you know, get on your nerves beyond what you thought possible, make sure that you're keeping in mind that they have a voice to everybody that is in their social network, and so they can spread a big message, right? So just doing your best to be able to say that, you know, that customer left happy, but also never— and, you know, acknowledging them, but the customer isn't always right, and we know that.
So yeah, for sure. And I think that's great advice. So I mean, the takeaways from this are setting those expectations, with the client, make sure they understand them, um, and, you know, keeping up with, with those different, you know, different steps along the process, making sure you're following up, make sure that the things are there, um, there, and don't let yourself kind of fall into that slump of, of being lenient with everything. So I think this is, this is a better version of this show, right? Version 2. And I just confirmed it did record, so we're good. If you're listening to this, obviously it did record. So thank you for listening, and, um, you know, if you want to reach us, you can go to bluecowmarketing.ca, and we'd be happy to have a conversation with you.
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