In this pretty hectic and competitive world, we are often asked to work more without losing ourselves in the process. But how can we possibly do that? Gray MacKenzie from ZenPilot is right in the depths of helping people get more out of work by doing less through project management. In this episode, he joins Paul Higgins to share how their passion has led them to become one of the fastest-growing and best-featured project management platforms on the planet. Gray discusses the real advantages of using project management, such as ClickUp, for service-based business and then gives out some tips on how to deal with the changeover process and the different personalities within the business. Growth does not have to be as overwhelming as it sounds. Join Gray in this conversation to learn about some best practices to accelerate your business.

Do More With Project Management With Gray MacKenzie

Build Live Give. Mentoring with Paul Higgins

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A little bit about our guest. They’re right in the depths of helping people get more out of work by doing less. They do that mainly through project management. It’s their passion. They’re very good at it. We’re lucky to hitch onto one of the fastest growing and best project management platforms on the planet. They talk a little bit about that. They cover the changeover, which is dreaded, “What platform should I be on? Should I swap?” I also talk about how you embed and they’ve got some great things around different personalities, key users and also that dreaded one-time tracking. We’ve got some good views on that as well. What I’ll do is hand you over to Gray MacKenzie from ZenPilot.

Welcome to the show, Gray MacKenzie from ZenPilot. It’s great to have you here.

I’m excited to be here. Thanks for having me, Paul.

We’ve had several conversations around a topic that I love. I know it’s important for running a service-based business. I can’t wait to dig into it. Why don’t we kick off? When someone asks you, “Gray, what do you do for a living? How do you help people?” What is your best answer?

We’re focused on helping digital marketing agencies. I always tell people we help agencies deliver better work faster. It’s what it boils down to. It’s better, more consistent, more standard streamlined work and faster. We help them pick up efficiency improvements and deliver work with less stress.

How do you do that growth?

BLG 297 | Project Management

Project Management: An important piece in any process is training team members to know you get pre-built process templates for how stuff should be done.


We have a technology that we get found for a lot, which is ClickUp. We’re helping agencies and ClickUp is the Trojan Horse in our business model where we’re coming in and helping people streamline their operations. We go through and look at how they’re delivering work, improve the processes, document the processes and templatize them. This is where ClickUp comes into play. We build out what those standard operating procedures look like inside ClickUp, train the team, and give them insights into the operational side and client services side of the business that they haven’t had before.

The first thing is when you say ClickUp, explain what it is. Give some analogies as to what it is.

To anyone familiar with using a project management tool previously like Trello, Basecamp, Asana, or some of the big players in this space, ClickUp is a relatively new tool. They’re the fastest-growing project management tool in the digital agency space. They’re growing quickly in a bunch of different places. It raised $100 million at $1 billion in valuations in December of 2020. We’ve been partnered up with them since 2018.

Why is it going so well for digital agencies?

There’s a couple of core things that people like. The hierarchy of ClickUp works well as opposed to Asana or the simplicity of Trello, versus the Trello or Basecamp. When I say the hierarchy, in any service-based business, you’ve got clients and services beneath each client. You’ve got organizational departments. It’s not the same as running an internal marketing department where you got, “Here’s our products or our campaigns and what needs to happen beneath that.” Speaking of the hierarchy, one of the things that ClickUp contributed to space is the concept of taking the underlying data, viewing it, filtering, slicing and dicing it however you want to. That’s been a big advantage. It is now filtering out and influencing a lot of the rest of the space as well. The product improvement velocity is another big thing where they’re pushing out updates and improvements to the platform faster than what any other platform has done.

$100 million will help with doing more of those. You’re a digital agency. For a lot of coaches, consultants, service-based business owners that are reading this, project management is a bit of a love-hate. I even know within Coca-Cola when I left in 2011, we still use to manage a lot of projects out of Excel. I’m like, “We need a project management tool.” What was the default? Can you remember that terrible Microsoft product? It was ordinary. There weren’t many tools, whereas now there are lots of tools. What are the real advantages of using project management if you’re a service-based business?

The big thing is keeping everyone on the same page as far as, “What are we doing? Are we getting work out the door on time?” In any of these businesses, you’re looking at whoever is ultimately in charge of client services. Probably, it is ultimately measured on what’s the lifetime value of a customer. The combination of retention, how well are we keeping clients happy, satisfied and with us for a longer period of time. How are we increasing the value of that customer through providing more of the same or different service lines?

Often, democracy rules in small businesses. Click To Tweet

Some things are honestly going to indicate whether people are going to buy more from you or be happy with you. What are the works we’re getting out of the door on time? Is it the right work? Is it done at the quality that they expect? The project management tool is the central single source of truth that we’re trying to build in these businesses. This is where it’s all measured. This is where it’s all managed. We plan and do the work all inside this one space. Everyone’s got visibility into it. We can provide those insights back to either our management team or clients.

I must admit I’m a bit of a Nazi when it comes to project management. If you want me to do something, it’s got to be in our project management software. If you want to do short comms with me, maybe we can use Voxer. I know a lot of people use Slack. What’s your experience with how people delineate where all this communication is? I’ve got clients on WhatsApp, Voxer and SMS. It feels like 100 touchpoints or comm points coming in. How does that work with something like ClickUp?

There are a couple of different pieces there. One is every agency that we’re working with, our number one rule is if it’s not in ClickUp, then it didn’t happen. We’re going to treat it like it’s our single source of truth. The outputs that we get from that data are only as good as the inputs. If we’re not adding stuff in there, we’re not going to know what’s happening here. In terms of inputs that are into it, anything that’s task-specific that’s related to an individual deliverable has to live inside your project management platform.

It’d be centralized there on the thread that it’s associated with. In high-level strategy, you are kicking around ideas, ideation, that type of stuff. Other tools are probably a better fit for some of that. Although, it’d be nice to have it all in one place. I understand each of these tools has its purpose. Voxer is super nice for quick audio back and forth, Loom for video, Slack for text. I’m not as stuck on getting all of that inside ClickUp. That’s where you have to draw the line and say, “Are we doing higher-level ideation and quick back and forth phone conversation? Is this granular? Are we getting into the nitty-gritty of what’s getting done here?”

I’ve been very fortunate that I’ve got a great team. What they do is effectively triage my inbox. One person takes 20% of the email and creates a task for me, and then I’ll do the task so I don’t have to read all the 80%. Is that something that you recommend? Is it easy to take a task out of email and put it in the ClickUp as an example?

Yes, for sure. That comes up all the time, whether it’s forwarding an email directly in for context. The team has or replying to notifications coming out of ClickUp. I think you get the same thing if you’re in client communication and you’re one of the unfortunate people who are still stuck managing that in email consistently. Everyone deals with some degree of client email. As those tasks come in, there’s some specific deliverable that those are influencing. Whether it’s updating the status, “This is approved,” go in and pull up ClickUp and update the status of that specific item, or “We would like to request this,” responding to that, adding the task quickly to ClickUp is something that we train internally. That’s what we all do for our clients.

An important piece in any process is training team members to know you can get pre-built process templates for how stuff should be done. If we’re talking and you want to add a new podcast episode, and then we’re producing a podcast for you, whoever that goes to internally knows. I don’t have to go build out all the individual steps of this. I use the template that we’ve got pre-built and add in all the tasks based on the podcast that you requested.

In digital agencies, often they’re creative people. Some would say, “Right brain is not always right,” but it’s a different rule statement. Everyone’s got their own personality, especially I find it with my teenage children. They are a lot more independent, which is fantastic than what I probably was at their age. How do you get everyone on the same page? What are some tips to help with all those different personalities and the people that say, “I want to do it my way. I don’t want to do it your way, Gray. I’m happy to do it my way?”

BLG 297 | Project Management

Project Management: We’re not saying we can’t be creative when we choose to do fewer things or be more focused. We’re channeling that creativity.


I bump into this a ton. It’s a creative space, so I get it. We joke sometimes internally about agencies. If it’s a 10-person agency, 9 of them at least will be on the leadership team of the agency. There’s a lot of group thinking. It’s a lot of people who love running small businesses in many cases. Often, democracy rules in these small businesses. The answer that nobody wants to hear but it’s the truth is part of it has to be that there is an expectation that if you work here, you don’t get to choose. You don’t want to use ClickUp and you got use Basecamp instead for your project manager. If you’re on Asana, you don’t get to go use ClickUp because that’s what you like to do. There has to be a mandate to some degree that, “This is the expectation. This is part of working here. It’s what we do. If you want to work here, that’s part of the process.”

The other thing is it’s not all just the stick, there’s got to be some carrots for them too. It’s showing people what the outcome is. Any time that we launch a new team in ClickUp, there’s this brief trough of sorrow. That’s a week of “We’ve got more work to do. We’re already doing the work. Now we have to go. Make sure that it all gets added in.” You hit this point where the influential people on the team finally had something that they needed to go find. All context is right there. It’s in one place, or they need to plan out some work and the templates are there. It saves them time and they start to get utility from the platform. It then takes over and team members see you moving forward once you get the momentum rolling there.

There’s got to be showcasing that vision, “Here’s what life looks like on the backend of it.” Also, a little bit of retraining the mindset where some of the boundaries that we create, create the opportunity for the best creativity. Those limitations or restrictions are guidelines and frameworks to work within, where you have to unleash some of that creativity. Instead of we feel like we’re fulfilled or creative because we get to work on twelve different business types, and every challenge is a new challenge. Instead, let’s use that creativity and channel it into, “We’re solving the same type of problem for another business, but let’s figure out how we can constantly be improving it.” There’s an element there as well of this higher-level agency stuff but realizing, we’re not saying we can’t be creative when we choose to do fewer things or be more focused. We’re just channeling that creativity.

The one that I always use is freedom in a framework, which is more than the mundane stuff is done and not missed, it gives you more energy to focus on the stuff that only you can do. Use it to bring out more of your superpower rather than fighting against your superpower. Who should own ClickUp in the business? You go in. You do the implementation and it’s fantastic. Who is that owner or we used to call it the key user in my Coke days? Who’s best to do that?

With any implementation that we’re doing, we set up one person to internalize their ClickUp champion. There’s a couple of key characteristics about that person. One is they’re super detail-oriented, so they’re not going to miss the habits internally. We want somebody who is saying, “We’ve given you these rules of engagement. Someone needs to hold the team accountable for that. What’s your daily spot-check, weekly roundup, monthly review? What are the processes that we need you to follow to be successful and make sure that the system improves over time instead of degrading over time?” They need to be detail-oriented or relatively tech-oriented. They like learning new features, new tools and figuring things out. If team members have questions, “How does this work? Do you have a solution for this?” Instead of you diving in, you get their hands dirty.

This is typically not the COO of the business. That person is focusing probably more of their time on strategy than on the technical stuff, but this is equally important. It’s a different level of granularity. Often, this person will be a project manager or somebody internally. They have to be comfortable managing up and going to somebody who’s in a position that they perceive as an authority over them or realistically, to their boss and saying, “You didn’t get your tasks done. You’re falling behind. Everyone else is falling behind. They don’t know what they think. Their stuff is unblocked. They don’t know what they can do. You need to follow the same rules of engagement that we give to everybody else.” That combination of characteristics is some of the things that we look for, more than a specific job title or role.

If you never test your hypothesis, then you assume that your guesstimate is accurate or close enough. Click To Tweet

I’m going to hit two elephants in the room. The first one is changeovers. I know we’ve talked about changing from my platform over to ClickUp. I look at all of the work and I think, “This is going to be hard. Am I going to keep my data or transfer all my data?” Let’s break some myths around this that it’s very hard to change platforms.

Is it worth it or not? That is the question. It is hard and that’s the reality. To be clear, we focus on ClickUp. I think for the majority of agencies, for a lot of people, ClickUp is the best tool for the job, but it’s a tool for the job. It’s the last 10% or 20%. The 80% of this is, “Do you have a coherent system? Is it designed well? Does everybody know how to use it? Is there somebody who owns that success over time?” If you do that, I don’t care if you use ClickUp, Asana, Teamwork or whatever your platform of choice is. As far as switching itself goes, there’s got to be an internal champion.

You’re probably going through this with teenagers. I coach high school baseball. I’m dealing with teenagers all day. I can say the same thing that their parents say. They’ll never listen to their parents because they’re at a stage of life where they don’t care. That’s the message here and they’re going to ignore anything that comes from their parents. I can say the same thing, “Coach, that’s great advice. Thank you so much.” The only difference is who’s saying it. We’d benefit from that from the outside, in many cases, where it’s somebody else in ZenPilot and independent third-party is saying, “They’ve seen this a bunch of times. I guess we must have to do it this way.” They’ll listen to it even if it was the same thing.

In a lot of cases, it’s worth pulling in somebody on the outside, as long as it’s a trusted voice who’s got some authority, and there’s a reason to listen to them. You are not just randomly picking somebody off. There’s not some authority associated with that. Those are a couple of main things. Have an internal champion, if you can pull in somebody from the outside, and fundamentally, understand what you’re trying to accomplish. Don’t pick a tool because this is the cool new tool but figure out, “What’s the problem we need to solve here?” Hire the tool that does that job the best.

The second one is time tracking. In my last company, we used to sell software in the agencies as well. That topic used to come up all the time. Firstly, what’s your view on the topic or your experience? The second is how does ClickUp handle tracking time?

Nobody likes time track. I don’t think I have come across a person who’s super excited to do it for them. A lot of people love the concept of it but aren’t excited about it. In an agency business model, fundamentally the currency that we’re dealing with is people’s time. If you’re not measuring it, that’s the proxy for profitability in your business. I have not come up with a good way around it. I still think it’s a valuable activity to do, even if you pick it up for a while and you set it down at some point in time. I’m not convinced that it’s the thing you have to do for the rest of your agency days necessarily, but certainly for a benchmark.

It’s wild how many times we’re working with agencies, and the common thing is, “We’d love to. We know we should be doing it, but we aren’t doing it.” Implement it. Prior to implementing it is we’re building out processes. We’re setting time estimates on everything. It’s all a guesstimate at that point. We’ll say, “Here’s all it takes on the average agency based on what we’ve seen and who’s doing it,” whatever it is, a blog post or something. They guesstimate whatever they want that goes on it. They track it, go back and do a month’s worth or a quarter’s worth of data review. It’s wildly off from what they’re doing, but you don’t have those insights. If you never test your hypothesis, then you assume that your guesstimate is accurate or close enough.

You identify a lot of different areas where you should be charging more, areas where you didn’t improve efficiency, services that maybe you should cut or not offer, or you need to hire someone else to do, as well as helping individuals get into their sweet spot. What are you best at doing? I’m a fan of it. At this point, it’s also a habit. Once you get used to it, you don’t think about it, but it’s not something that I look forward to every day. I don’t think about it in my day-to-day in terms of tracking time.

I track it in another tool.

What are you using, Paul?

It’s changed names now. It used to be a Toggl. They’ve rebranded. They’ve been bought out, but if you still got a Toggl, it will redirect. I do it in 30-minute blocks. It’s a forced habit. It means that I work on one thing for 30 minutes. I’m focused instead of multitasking. At the end of the 30 minutes, I’d allocate it to what I’ve been working on. I can have a look at a client and see how much time I’m investing in a client and roughly what the activity was, but it didn’t go down to exactly 78 minutes and 23 seconds, but I find that it’s good in my business. I find the benefit is the discipline of focusing on one thing for a set period of time and trying to beat the clock. I’ll look at it and go, “I’ve got 3 or 4 minutes.” I’ll make sure I finish it off and that I’ll progress my perfection. That works well versus me saying, “I’m going to finish this task.”

That’s the hidden benefit that we hear occasionally and clear to teams as well. If you’re writing a blog post and the estimate is 30 minutes. You’re 200 out of 500 words at 25 minutes, do not crank out those less 300. It’s fine if you go over. That’s just an estimate. We just want it there as a benchmark, and then we measure against it, but there is some incentive to try to get there. It creates a little bit of a game.

For me, posting on LinkedIn is a key way of communicating value. I’ve got it down now to fifteen minutes. I got 30,000 views to the post. The quality is great. That habit of tracking the time means that I’ve reduced it over time. It used to be 30 minutes and now it’s 15 minutes. It’s a great benefit. I could honestly ask you questions forever. We might have to have your back as a guest. Before we go into the Live section, I want to know, do you have a sales machine that can get you one to three high-paying clients a month? If the answer to that is, “I’m not quite sure,” I want to help you.

If you go to, there are questions there that you can answer in three minutes. It goes against what I define as a best practice like Gray’s been talking about from his expertise when it comes to sales. I’ve listed the things that I know work for service-based business owners. You can see how many of those you have got. It’s not a mystery anymore. It becomes more of a plan. Into the Live section now, Gray. What are some habits other than using ClickUp that make you successful?

This has been our focus over the past months. You and I talked about some of the growth that we’ve gone through and figuring out how to prioritize things. In the past, I’ve been an inbox-zero-everyday type of person. I’ll work later to get stuff wrapped up. I’ll try and quickly work through things to triaged the inbox and handle it on my own. One of the key habits is the morning routine to go through and prioritize out. I know going into a day now that there are more things for sure that I would like to do than I’ll have time to get done. I’m running through our priority matrix internally to plan out where’s the time going and what are we handling during the course of the day.

BLG 297 | Project Management

Project Management: In an agency business model, people’s time is fundamentally the currency that we’re dealing with.


That’s one of the main daily habits from a sales perspective, which is where I’m spending a lot of my time right now on the growth side of the business, either doing marketing activities or sales activities. Also, operations habits. We have a daily sales shutdown scorecard. The concept of measuring stuff probably comes up over and over in the theme of what we do because we’re process nerds. It’s a daily habit at the end of each day to shut down, recap the day, what went well, what didn’t, both from numbers and also from a more, “How’d you feel about your performance today? Did I serve people well today? Did I fulfill my promises to coworkers, clients and those that I work with?”

Is that like a standup?

It’s not. It’s an actual scorecard that gets filled out. It’s a form.

The next section is the Give section. What’s a community or charity that you support and why?

This is more community than charity. I’m pretty involved in the local community. One of the things I’ve had the chance to do for years is coach high school baseball here at the local high school. That opportunity is one of the things that gives me the most life. I had this experience back in 2012 out of college, where I was coaching high school Lacrosse at the time down in Charlottesville, Virginia. I got into my car. I did a 6:00 AM pitching workout with the baseball team, then went to a couple of different practices in the afternoon. It’s a small private Christian school in Virginia. I helped out with basketball practice and then went to Lacrosse practice. I had six hours’ worth of practice on top of working that day. I got in the car and not even intentionally, I breathed down. I was like, “This is what I was made to do.” I’ve always loved coaching and I said that out loud. The opportunity to influence young lives and teach life lessons through sport is something I’m super passionate about.

For all of us as parents, when you say something, it’s hard. Being with teenagers as you are, any tips for parents on how to get more out of their job?

You’re the one we should listen to. I’ve got four young kids and it’s awesome. They’re all under six. Everyone loves spending time with me. I’m trying to cherish that time because I know five years from now, they’ll be like, “Dad, please get lost. We’ll come back and talk to you again when we’re 25.”

Here in Australia, you’ve got to do 120 hours before you can get your license. That’s a lot of time to spend with your teenager. Cherish that moment. Makes sure that you’re helping them to save their lives and the lives of others by driving. It’s a brave way to connect with your children because you’ve got to spend 120 hours next to them. Look for that one. That’s pretty much what you do. I support a charity called The Purple House. It helps indigenous Australians get access to dialysis, which being a kidney transplant patient, it’s very important to me. If you want to check out more about that, you can go to The last section is a Rapid-fire section. Other than ClickUp, what’s another piece of technology which is essential for running your business?

HubSpot is the first one that comes to mind. There’s a handful of other ones that we use. One is called the MPS Platform. We use them to measure Net Promoter Score for our clients and also for the agencies that we’re working with.

The next is a sales tip. You’re spending a lot of time on sales. That scorecard idea was fantastic, but what’s another tip you can give us around sales?

To a lot of coaches, consultants and course creators, I’m sure someone’s talked about having breaking down and doing a foot-in-the-door type of offer or a lower-tier offer so people don’t have to bite the full bullet all at one time. That has been working super well in our business. This holds true from the agency days where we break out. Right now, we’re selling ClickUp audit if someone’s already been in ClickUp. We get a lot of agencies or teams who have been in ClickUp for 1 or 2 years, and they feel like it’s a mess. They’ll come back to us looking for a last-ditch effort before they jumped ship out of ClickUp. We’ll do a ClickUp audit and go through their entire project management, process documentation, and ClickUp usage. It’s been tremendously valuable to agencies, but it’s also been a great way to accelerate the sales process and streamline that this isn’t a full commitment all at once. It’s a smaller initial commitment to work with us.

Relationships matter most. Click To Tweet

What’s your best source of ideas?

Internally, we have a channel. We use Slack for our internal comms in addition to ClickUp. We’ve got a channel called Discovery. It’s a cool place for team members to share new things that either they’re thinking about or have discovered online. That’d the number one place I’d go. My kids are the second place. They’re constantly coming up with new ideas and grill me.

What impact do you want to leave on the world?

This question reminded me of a question that my wife’s grandfather asked the first time I ever met him. We were having lunch together. We have just graduated from college and weren’t married at this point. We were just dating. The first question he even asked over lunch, “Gray, what’s the biggest lesson you learned during college?” What I said was, “Relationships matter most.” The impact of the place and the thing that I want to be known for is the relationships that I’m building and genuinely caring for people where they are. Loving people well is the one main focus of every day. Can I serve the people who are in front of me well? I can’t control fully who that audience is or who those people are, but the people who are around me. Are they living their life better than without me here?

The fact that you’re so heavily involved in baseball, I know some of your clients that I was referred to speaks very highly of you. I think that rings through. I’m no better than practicing what you preach. It’s been wonderful having you on. I could ask you a squillion more questions on this topic, but it’s important. There are two key things. You can go to You can try the ClickUp app. If you do get a ClickUp account, you can go to The whole onboarding process is one that you can get from Gray and the team at ZenPilot. It’s wonderful having you on, Gray. I look forward to talking with you again soon.

Thank you, Paul. I appreciate the opportunity

I loved that interview with Gray. I’m very supportive of project management, not because it’s a tool. It’s because of the outcomes when everyone’s working in the same direction. Your creativity is freed up by the fact that you’re not worrying about things you’ve missed or what you’ve got to do. It makes it nice and easy. You can grab that demo at If you’ve got the ClickUp demo, then you can also go in and get their onboarding templates in Also, if you believe that your sales machine isn’t capable of getting you 1 to 3 high-paying clients a month, please go to Please take action to build, live and give.

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About Gray MacKenzie

BLG 297 | Project ManagementGray MacKenzie from ZenPilot has gone under the hood of over 1800 digital agencies over the past 8 years in search of the best way to build and lead healthy teams and deliver better client services.

Gray is a bona fide process nerd and today helps agencies streamline their operations inside a project management platform called ClickUp.

You can learn more about Gray and read his definitive guide to ClickUp for Agencies at

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