How to Improve Client Success as an Agency: Gray Reacts to ClickUp AI's Tips
Key Takeaways
- Ask every new client to write down, in their own words, the number one problem they want solved. Keep that answer unedited.
- Run the 5 Whys on the stated problem. 'We need to get better at ClickUp' often turns out to be a profitability problem.
- You get to set the communication cadence. Then structure every update around four quadrants: what we did, what happened, what we learned, what's next.
- Sales is the sample. How you respond before the contract sets the expectation for how you'll respond in delivery.
- When something goes wrong, say so first, own it, and lay out the options. That's the moment trust gets built.
- Most work is 80% repeatable. Personalization is mostly explaining why the standard solution fits this client.
This episode has no outside guest. Kuba Grajcar hosted and interviewed Gray MacKenzie, ZenPilot’s founder and the show’s previous host. Kuba had asked ClickUp AI for “10 ways to improve client success at your agency,” found the list superficial, and read the first five to Gray: understand client goals, communicate regularly, set clear expectations, be proactive, and personalize the experience. Points six through ten were saved for a follow-up.
Start with the client’s own words, then ask why five times
Gray’s first reaction was that nobody would disagree with the list; it’s just generic. ZenPilot’s version starts with a field every client fills out when they come on board.
We have a field that clients have filled out when they come on board with us, and we keep that unedited… 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… Sometimes it’s we need to improve utilization by 20%, and it’s extremely specific… Sometimes it’s we have no documented processes.
The stated problem is rarely the real one. Gray compared it to therapy, and to the Identify step in an EOS issues list: what got written down before the meeting usually isn’t how you’d write it a second time. The 5 Whys get underneath it.
Most folks come to us and say, yeah, we need to get better at ClickUp. Why? Well, because our team doesn’t know where to find stuff right now. Why is that important? Because we’re wasting time trying to dig through all these different systems. Well, why is wasting time wrong? Because we’re not profitable. Okay, well, now we’re to a profitability problem, not a ClickUp problem.
You set the cadence, then every update covers four quadrants
On “communicate regularly,” Kuba asked how to stay regular without turning into noise. Gray tied it to expectations. One monthly meeting, a weekly call, or “call me whenever you want” are all fine, as long as you say so up front. Every update then covers four things.
The first one is what did we do since the last time we talked… Next is performance. What was the result of what we did? Hey, we launched these campaigns, we spent X dollars in ads, now here’s the results of what happened… Then the third quadrant is what do we learn from that… And so as a result, fourth quadrant, what are we doing because of that? What’s coming up next?
Kuba liked the third quadrant most. Gray’s read: sharing what you learned tells the client you’re paying attention and they can relax.
Sales is the sample
The third tip was “set clear expectations.” Gray said expectations get set long before kickoff. His phrase: sales is the sample.
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, 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, then there’s misalignment of expectations.
When a wrong expectation has already been set, own it early, lay out what’s realistic, and offer the options, including a refund. Gray also puts expectations in a written recap after the call, and uses “a lot of clients get this wrong” as a pattern interrupt before the thing that matters.
When something goes wrong, that’s where trust gets built
Kuba’s fourth point was “be proactive.” Gray joked that he’s always wanted someone to quietly build a small, consistent screw-up into onboarding so ZenPilot could fix it beautifully every time (he can’t, because the apology would be a lie). The serious version:
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… that never even happened, client doesn’t need to know. You’re way better off saying, man, we messed this up, like, that should not have wound up there.
Everyone knows something will go wrong eventually, Gray said. What clients watch for is the pattern when it does: can I trust this person, or are they hiding it and blaming me? Handling mistakes in the open also sets the internal standard: nothing gets swept under the rug here.
Personalization is mostly how you frame the standard solution
The fifth tip, “personalize the experience,” felt to Kuba like it fought with having a standard process. Gray would rather see a firm pick a lane. Truly custom work is rare (usually 20% is different and 80% is the same), and custom needs QA, margin, and higher prices. ZenPilot’s own example is its ClickUp certification, which every client team goes through.
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.
Kuba added the human side: remembering hobbies, finding common ground. Gray agreed it signals attention, and admitted he’s less warm and fuzzy himself: short, bulleted updates on what you did and learned make him feel more cared for than knowing he likes baseball. Different clients feel paid attention to differently.