Gray vs. AI: Client Success Strategies Based on Hard-Won Experience

Gray Mackenzie, founder of Zenpilot, talks with Kuba Greizar about what actually works for keeping clients happy. He contrasts real experience with generic AI advice, covering how to understand what clients really want, set the right expectations, and stay proactive instead of reactive.
Hello, hello, hello everyone and welcome back to Agency Journey. I am your host Kuba Greizar and with me today is Zenpilot founder and previous Agency Journey host, Gray Mackenzie. Gray, how are you doing today?
I'm feeling spicy. I'm ready to go through some lists and make some progress. Things are good?
Yeah, yeah. We've got a little bit of a fun twist to this episode. We want to talk about improving client success but for a particular lens. What I've got for you today, Gray, is I asked not chatgpt actually, but ClickUp AI even to generate a list of how did I prompt it 10 Ways to Improve client success at your agency. I looked at it. It sucks pretty much. I mean it maybe not sucks, but it's super superficial. So today to show the watchers and listeners the difference between what AI can teach you and what somebody with actual experience can teach you, I'll hit you with as many of the points on this list that we can get through in the time that we've got. And let's see how we can go deeper into each of these. Are you ready to dig in?
I hope so. I've not seen this list yet so I'm excited to hear hear what we've got.
That's even better. I think even unprompted like that, we'll get some good stuff out of you. Okay, so again, this list AI generated. I'll tell you the full list then so that you can prepare for some of these in advance. The list of 10 is brace yourself how to improve client success at your agency. Number one, Understand your client's goals. Number two, communicate regularly. Three, set clear expectations. Four. Be proactive. Five. Personalize the experience. And let's start with that five because I don't know if we'll get through the full list of ten on this episode. We can always do part two. So great. What I'll do is. I read you the first point. There's a little bit of more text there and, and then let's dig into that a little bit more and just actually I'll have you answer the how a little bit more comprehensively. So AI says the number one thing to improve client success at your agency is to understand your clients goals. Get to know what your clients really want to achieve. Ask questions and listen carefully to the answers. Awesome, great. But how, what questions to answer? What is the key to understanding your clients goals and your experience?
Yeah, I think this list is actually like there's nothing that anyone, I don't think anybody would disagree with this List. It's just very generic vanilla internally. In our account dashboard or client health tracker. We kind of use those terms a little bit interchangeably in some of our marketing to make that like the client health trackers a little more descriptive to folks who don't know what an account dashboard is. On the back end we have a field that clients have filled out when they come on board with us and we keep that unedited and then we do some other discovery around it. But it is, you know, what is the, what is the number one problem that you're trying to solve as we work together? And so in their own words, sometimes it's we're trying to migrate from Asana to ClickUp and make it work smoothly. Okay, there's a bunch of follow up questions there, but that's great. We know what your number one goal is. Sometimes it's we want need to improve utilization by 20% and it's extremely specific. We've got three months to get this done or there's some severe consequences. Sometimes it's hey, we have no documented processes and we need to get stuff together. So understanding, I think just asking customers obviously is step one towards understanding almost always. And for anyone who's done therapy or coaching, you're familiar with this. Where you start as the expressed pain or expressed problem and where you wind up after processing are usually two different things. As you dig in and understand the issue, we think of, I feel bad I need to go an episode without mentioning the entrepreneurial operating system or eos at some point. But you think of the meeting structure and the ids, like how do you work through issues? Is the IDS framework identify, discuss and solve identifying the issue. Someone's written down what the issue is going into the meeting. It's already on paper. And it turns out an awful lot of the time that when you go through that identify process, what we're actually trying to solve and what got written down are not. You would not write that the same way a second time. So that piece of understanding what understand your clients goals, is that what the question is? Right?
Yeah, that was understand your client's goals exactly.
This is primarily just the five like it's different perspectives. First of all, who's actually involved and what are, what are, what do individuals is part of. I think the fifth tip was something around personalizing it and part of like what's your goal Kuba and what's my goal? We might be working on the same project, but we might have two different motivators or side things that we'd like to get out of it. And the five Whys is digging into, like, why is that important to you? Okay, why does that matter to you? What is it? You know, it's just going through and figuring out what's actually the core, the underlying problem. Most folks come to us and say, yeah, we need to get better at ClickUp. Why? Well, because our team doesn't know how, where to find stuff right now. Why is that important? Because we're wasting time, you know, trying to dig through all these different systems. Well, why is wasting time wrong? Because we're not profitable. Okay, well, you know, like, now we're to a profitability problem, not a ClickUp problem. And so we've got a different, different answer than we had at the beginning.
Awesome. And that is exactly the kind of stuff that I wanted to get out of you today, Gray. You know, we started with a general point of understand your client's goals. And already what I'm getting is this framework of, okay, whatever you heard here first is like an expressed need, but you have to go deeper. You have to find the underlying reason. And the Five Whys is a great framework that I think a lot of us are not using enough. I mean, it's one of these concepts that keeps coming back to me. I keep hearing about it and then, you know, I really need to make it more of a habit to use it. That's great. So I want it to be a little bit rapid fire with those. So if you don't mind, I'll move to point number two.
Yep.
Which is okay. Communicate regularly. Keep in touch with your clients often. I should do it like a robot voice, maybe not today. Update them on progress and share any challenges as soon as they come up. That's the key to keeping communication regular, but also, you know, not turning it into just noise that people end up ignoring.
Okay, I'll try and go faster for you here. First one is set the. This is tied to set expectations, which is set expectations around how and when you'll communicate. Totally fine to say to a client, we're going to do one monthly meeting and you've got access to this interface in between to send questions. Totally fine to say you can call me whenever you want. Totally fine to say we're on a weekly call together and here's who's on that call. You need to figure out obviously what's reasonable based on what they're paying you and what you can afford to, how you can afford to engage and interact with them. But you get to set whatever the Expectations are. And the key is set those expectations so that everyone's on the same page around how we'll communicate. Then in terms of how we communicate with clients, there are four main quadrants you should think about in those conversations. So the first one is, what did we do since the last time we talked? What's happened? You know, what's. This is the activity number. Next is performance. What was the result of what we did? Hey, we spent X that we launched these campaigns. We spent X dollars in ads. Now here's the results of what happened. Here's what our return looks like. You know, here's what our customer acquisition cost looks like. Those types of things. Then the third quadrant is, what do we learn from that? So, hey, based on this, we learned this campaign way outperformed that campaign. And this one that's been running is actually better than both of them. And so as a result, fourth quadrant, what are we doing because of that? What's coming up next? So this is back to our plan. Hey, remember how we had outlined this stuff? We're still doing all that except we made these two changes. We're switching this to go first and this we're bumping back because the other one's working right now. So those four really simple quadrants, the easiest way to show this is just on a ClickUp dashboard. If we're working with somebody. Here was what we did straight out of a view in ClickUp or a dashboard card. What was the performance? Integrate the recording. If it's not directly out of ClickUp, it might be a data box or something like that embedded. What did we learn? Here's the learnings. This is our text area or however we're formatting that. And then what's happening next? Again, back to the ClickUp project plan. You could do that. And I'm saying ClickUp because that's what we live in all day, every day. And I know how to do that very easily. But you could do that in a lot of other systems as well.
That's great. And of the four that you just mentioned, I think the third one is particularly exciting. I would love to work with somebody who, you know, every week or every month, they let me know what they're learning to serve me better every month. That's. That's awesome. And I have one additional. Yeah.
If I could just say this real quickly. What are you communicating? When you share what you learned, you're.
Communicating that you're trying. Wait, is this. Am I supposed to answer this?
Sorry, I should have. I should have said that non rhetorical. What do you think? What would you. So if I was reporting to you and I shared that, what would your takeaway be?
My takeaway is that they're constantly trying to improve their service.
I think that's definitely a piece of it. And I think the other part is, like, we all want to know someone's just paying attention. I want to know that you're competent. So the outcome of what comes from that, like, are your learnings, do they make any sense to me at all? Great. But really what you're saying is, I'm paying attention. You're not just another number. And we love collecting the money from you every month. Like, I'm actually paying attention to your project and what's happening. So sharing what's being learned is the signal. Like, underneath what you're actually saying is, kuba, you can relax. I'm paying attention. I got this for you.
Yeah, exactly. It indicates that there isn't stagnation, there's an upward trajectory, you know, regarding the quality of what we do for you. That's awesome. That gets me really excited. One additional point regarding communication. You know, this is just a curveball that I think clients can throw your way sometimes is what do you do? How do you respond if you know there's agreed upon channels of communication? Let's say, you know, communication on ClickUp is okay, but via Slack, you know, we try to avoid that. What do you say to a client that consistently kind of goes beyond the boundary breaks, those rules? How do you push back against that?
Or what do you do? Yeah, so I think the natural tendency for most people is just to ignore it. Like, oh, they'll get the message if I just passive aggressive, don't respond to it. And then we get on the next call and say, oh, yeah, I kind of remember seeing that, but it wasn't in where we agreed to. And that's the worst way to handle it. So the best way to handle it is to say, hey, I saw this come through. I think if you can, if it's not a big deal, answer it there, but be super clear. Hey, this channel is not monitored. All future communication needs to go through this. And that'll get you a faster response. And just lay out the why our team. We can charge you. We don't need to keep ramping up prices because our team's got a more efficient way to handle it. You'll get a faster response, so you get your answer faster and just explain the benefits. And then ultimately, if that's a repeat offender and they won't change. Then you have a business decision to make. And it's either, you know, the most drastic version is, hey, you're not, you're not cooperating. We don't want you as a client anyways. It's normally the truth, so we're just going to fire you, or you've got a business decision to make to say and communicate clearly to them. I think the best way to do this is just to say this is beyond the scope and what we'd agreed to originally. And so you can either pay this exorbitant amount more to keep doing what you're doing, or you can get in line. And it doesn't have to be exorbitant. It might not be that big of a deal to you, and it might be a smaller. Yeah, you want to have a slack channel, totally fine. It's going to cost you an extra thousand dollars a month or $2,000 a month to do that. Does that make sense to you? Do you want to move forward with that? No, actually, I'd rather just learn how to communicate in the way that we need to. But yeah, that would be the general approach there.
It sounds like you need to be clear and firm and lean into it. We love to say it on this show and wherever we can. Clarity is kindness, right? So be kind to the client by really clearly telling them what we expect here. On the other side of that, cooperation. And actually, expectations is what point number three is all about. So let me pick your brain about that a little bit. You know, just aside from communication about expectations. First, let's hear what AI had to say. Point number three on our list of how to improve client success at your agency is set clear expectations. Make sure your clients know what they can expect from you. Be honest about what is possible and how long it will take. So that's the general advice, of course. But how do you actually, you know, communicate these expectations in a way that is understood, doesn't create, you know, a negative mood in the cooperation, so to speak. What works here?
This all starts in the sales process. So the sales is the sample. Common phrase to go back to. What someone experiences from you in the sales process is a sample of what they're going to expect to feel from you down the road. If you are unresponsive in the sales process and it takes them three pokes to get back from you. Like, that's the anticipation for what the level of service is going to look like later on. Conversely, if you call them two minutes after every email they send in the sales process and you don't do that in delivery, there's different. Then there's misalignment of expectations. So the first thing from the sales side and all the way through from your marketing, all the way, all the way through till a client's done and moved on. There should be consistency in those expectations that get set. So you can't set the expectation that we're going to do something totally unrealistic in marketing and sales and then get in. And it's super hard to reset expectations now in the wrong expectations of a set. Now when that does happen, and the truth is for almost every business there's times where that happens. You need to be as again, clarity is kindness, like as open and honest as early as possible. Own whatever your fault in that process has been. Lay out what the options are moving forward from there. Hey, we are not actually going to be able to double your SEO traffic in 30 days even though somehow our new salesperson told you that was going to happen. That's totally our fault for doing that. And so we think we could grow by X amount or we could do these things which is give us the highest probability of getting the best long term outcome and you can continue with that at this price or we can refund your money and we can do whatever, we can refund this X amount of money or whatever that looks like you're trying to be exceedingly open and fair in those conversations. So yeah, I think that's. And the other tip with expectation setting is you want to have that shared by the different stakeholders. That gets really, really hard the larger an organization is. And if you can't get to decision makers, one, I think you've got to question your, your, your sales process or your, you know, wherever that falls. But two is it, it gets a lot harder if you're playing the game of telephone to get clear expectations set up and down the chain and so recording that. So if you're on Zoom or Riverside like we are right now, have it recorded. Here's what the expectations are and then ideally, and I would recommend this to everybody, put that in writing as well and just document it and have it in an email chain. Hey, we agreed to xyz. I think there's an art to call recaps in email. And so now I think we've gotten away from that a little bit more with the Avomas and the gongs and the choruses and the ways to have stuff supported but be super clear and have a, have a trail of what those expectations were at the beginning and then all the way through.
I want to fish for something here. I mean, you might have something like that. You might not. But when you want to really clearly set expectations with a client or anybody in the conversation, really, is there a particular phrase or tactic that you turn to to really get them to pay attention and to. Is it as simple as saying, okay, just to set expectations XYZ as possible, this other thing isn't. Or is there a phrase you turn to?
I don't know. I'm sure there is a phrase, because I think we all have patterns. I don't have a good catchphrase for you. I do have a kind of, like, pattern interrupt is probably the best way to try to say it. So let's just take us as an example. We're talking about you working with Zen Pilot. And, hey, I want to be super clear with you, because this is something that a lot of clients get wrong, and I'm just trying to set the expectation. Like, you got to listen up, because a lot of other folks have gotten this wrong before. Yes, it seems expensive. This. This project that we're looking at. This is a $50,000 project that we're talking about doing together. And you're looking at the financial side. What a lot of clients miss is the time investment from their team that's needed as well to really adopt these habits and these processes and, you know, get the most out of this. And so I want you to be. I want you to go with both eyes wide open in terms of what this will look like. Um, and same thing. Conversely, you know, sometimes that's. Hey, a lot of clients think that they have to do xyz, and actually, here's why that's not important, or here's what we do to make that super easy for you. So it could be very positive or very negative, but I'll often use that, like, a lot of folks get this wrong as a way to make. Nobody wants to be in the wrong crowd. We all want to think, oh, no, I'm the person who can pay attention and get to it. So that's a. I'm sure there's room for improvement there, but that's what I often use.
Perfect. That's phishing attempt successful as far as I'm concerned. A lot of clients get this wrong. That definitely would make me perk up if I were in that kind of conversation. Thank you. All right, I think we're good to go into point number four here to keep things rolling. So point number four to remind you is be proactive. And the AI goes on to say, don't wait for problems to happen. Look ahead and try to prevent issues before they start. Okay, that's obvious enough. How do you do it? How do you foresee the future here and be proactive.
I've never been devious enough to do this, but I've always wanted some. Somebody should quietly do this on the Zen Pilot team and then not tell me about it later so I don't have to have a guilty guidance. But I think we would have even more loyal customers if we, as part of our process, had something that we consistently screwed up in the onboarding phase or very early in an engagement and had a process to then go back and say, oh, we messed this up. I'm so sorry. Here's what happened. Here's how we're fixing it so that doesn't happen again. And here's how, like, we've already handled it for you first. That would be a lie if we said, you know, I'm fixing this so it never happens again. So that's why we can't actually do it. But when things go wrong, that's the opportunity to build trust. When everything's going right, of course, you keep doing what you're doing. And this is where we all mess up, is we want to hide. What, like, just sweep that under the rug? That that never even happened. The client doesn't need to know. Or actually, you're way better off saying, man, we. We messed this up. Like, that should not have wound up there. And we posted on the website, here's what we messed up in our QA process. Here's how we've changed the process as a result of that. Super sorry. Here's what we're going to do about it. And now you've got somebody who knows stuff. Everyone knows something's going to go wrong at some point. And so what we're all looking for is the pattern of what happens when things do go wrong. Can I trust this person? Are they on my side? Or they try and hide what went wrong, run from what went wrong, blame it on me when it goes wrong. So I think that just reframing in our minds, something goes wrong, we all feel the stress reaction to that, and that's totally natural. But the best customer service folks realize very quickly they go from that stress to, whoa, this is an opportunity. Like, I can go fix this. Yes, it might cost us something, it should probably cost us something, but I can go fix it and I can build a deeper relationship if this person's willing to give me that shot and some folks aren't. And also on the service provider side, I'd rather know that early this person has zero tolerance for us to ever make a mistake that's not going to end well. Like, at some point in time, somewhere along the way, someone's going to make a mistake.
Okay, awesome. So AI says to quote them again, try to prevent issues before they start. What I'm getting from you is almost look forward to issues happening because they give you this unique opportunity to demonstrate how issues get handled and to actually exceed expectations in that respect. That makes a lot of sense to me. Although planting that in a deliberate way in advance. Yeah, that might be a touch too far. I do understand why you might want that. Right.
Yeah. I should not belabor the point. But handling those issues super publicly as well, acknowledging it to clients, the hidden benefit to that is it sets a totally different standard for your internal team. We don't sweep stuff under the rug here at Zen Pilot. Oh, wow. Like, Gray did not sweep that under the rug at all. He just went and told the client exactly what happened. We didn't have to do that. So I guess that's not what we're about here. Instead, we're about pulling it up early. And so you. What happens then is. And that's embarrassing for him to have to go do. So I bet he doesn't want to live through that again. I don't want to make him live through that again. Like, I'm going to take that at a different level of. I attribute a different level of gravity or seriousness to resolving that and proactively solving it so it doesn't happen again. Because I know what we're going to. We're going to embrace the short term pain when it happens. And so nobody really likes the short term pain.
Yeah, that's. That's really what you want in a partnership, right? Of any kind. You don't want things to be swept under the rug. But go through the short term pain, like you said, and address the issues as they happen before they grow into even bigger issues. Awesome. Okay, so we're ready to talk about point number five and then decide if we go into the rest of the list. I'm thinking we're going to keep things pretty short and sweet for this episode. Maybe tease it for another one. So the last one is personalize the experience. AI says treat each client as unique. Customize your services to fit their specific needs. I'm sensing that it's kind of an. I mean, I'm Feeling tension between this and also having like a standardized process. Right. To ensure the quality of service. Tell me about personalizing the experience. What's the key here?
Yeah, think back to like mass customization in the E Commerce or apparel world. Neogwi produce these different variations that fit, you know, fit people differently or are slightly customized. But the core stuff is all the same. I don't have a strong. So I think I just much rather see a firm go one way or the other. We're totally custom when we're totally custom and we're solving totally new problems every single time that we take on a client. If that's really the case. That's very rarely the case. It's usually, hey, there's 20% of this that looks different, but 80% of the stuff looks exactly the same as stuff we've done before. But let's just say it's totally custom, that's totally fine. But you need to bake in that you have a QA process that you're understanding where the issues are. You know, you just have to build in more margin and higher that translates to higher prices is what that means for that customization. Because we need to make sure it gets caught. The opposite side, the much more productized route is, hey, we already have a system for that. And you can take and built to sell by John Warlow has a great example of this. Like, you know, there's the totally custom agency and then there's the productized agency is basically what he sets up and walks through why the productized agency has success, but also how to personalize how that feels. So in our example, everyone who works with us is going to go through the ZenPilot ClickUp certification that is not customized to them. There's some customization that we'll still do on top of that, hey, there were 10 commandments for how you operate in the day to day and ClickUp in that and in your firm there's actually an 11th one that's super important and it's XYZ. So there is some personalization here. But the flip side of personalization is making if I just tell you with no other context, I have a certification. Everybody's got to get it on your team. Is it custom to you? Not at all. It's the same exact thing that thousands of other people have gone through. Aren't you excited to do it? I don't even know if I want this or why this pertains to me. And so the personalization is really helping you understand why this is actually the exact solution for what you need. This has been tried and tested. This is proven out by tons of other teams. Your team can actually. This is exactly what you need. You know what, what you're struggling with is everyone's done thing. They're done things their own way and it's spiraled into all this crazy spaghetti mess inside your project management system. Wouldn't it be really nice if everybody had one coherent system and all worked off the same ground rules and expectations? That seems like the perfect personalized solution for you, right? Yeah. Okay, well, here's how we're going to get there. And this course is a part of it. And so part of it is just the framing of the solution is a big piece of that personalization.
Okay, awesome. Awesome. That was a lot in the short time frame. What comes to my mind here too. And at the risk of sounding a little bit cringe, I'm going to add one thing to what you said. A little bit of a different aspect to it. When I look at Personalize the experience. Aside from the issue of whether your service is totally custom or built out of predetermined elements or more or less a similar process for everybody, what stands out to me is just the person part and personalize the experience. And when I think about working with Zenpilot, okay, the process, there are certain elements to it that are unlikely to change from client to client. What really makes our cooperation stand out with any kind of service provider is just the personal approach and the personal touch. I can feel that I'm getting great treatment and that I'm being valued as a client, just because when I mention something personal, it gets remembered, it gets referred to. We find common hobbies between myself and the service provider, and I think that that makes a ton of difference. I know it's a bit of a. It's very much a different point than, you know, service customization versus productized services. But I just wanted to throw that in there because to me, that makes all the difference. You know, are you a fun crew to hang out with? Is there a culture fit that contributes a lot to making this point a success and to, you know, client success in general? Does that track with your experience?
I think it does. I think my nature is like, I'm just a lot less warm and fuzzy. So what you're really doing when you do that, exactly what you're saying is like, hey, pay attention to your hobbies. I know that you play the bass. I know that, you know, you're into this or that or whatever. It answers the Same question I mentioned earlier. Like it just is a signal that hey, you're paying attention and so I can trust you a little bit more because I know that you are paying attention to me. I would just say different clients, different people will feel paid attention to or feel that love differently. So I need, if you're a service provider, to me, I need very little. It's great that you know that I like baseball or I've got four kids and I love being outside with them or you know, whatever else. But what would make me feel even more loved is if you are on top of your stuff and I'm getting super short bulleted updates on here's exactly, you know, what we, what we did, what we learned, we can go faster. So the personalization is even personalizing your approach a little bit to what does this person need? What's their love language?
Exactly. It reminds me of a LinkedIn post by Maggie Kernarans from our team where she was talking about love languages and client service provider partnerships. We should lay that out. We should have an infographic about that. That's totally a framework that we can, that we can talk about. Alrighty. So Gray, not to keep you too too long for this particular episode I mentioned, we have a list of 10 pieces of advice that ClickUp AI had on how to improve client success points 6 through 10. I'll just leave for a follow up episode that somebody can listen to at a later date or binge it if it's already out. Just check the Agency Journey feed. Was there anything else that you wanted to add in the general point of improving client success? You know, another key that comes to your mind or just another, you know, one last tip before we say goodbye here?
No, I think I would step on six through 10. I don't know what they are so I don't know what to avoid.
Ah.
So no, I'll leave it as I've got 10 different things floating around in my head. But nope.
Okay, so we'll do 6 through 10 AI edition next time and then maybe even more from Gray for another episode about that. But this one short and sweet. It's over. Thank you so much everybody for listening to Agency Journey today. And that's it for today. We'll see you in the next one.










