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How to manage a Productive, Profitable, and Successful Team in ClickUp

Tom recently got to chat with Gray MacKenzie, he’s a self-professed bonafide process nerd. Together with co-founder Andrew Dymski, they created ZenPilot. A go-to for agencies to set up, implement and streamline their operations inside the project management platform, ClickUp.

These guys love solving problems; figuring out the pros and cons of complex issues and then translating and transcribing their expertise. So that others can comprehend and take action. In fact, to date, they have staggeringly helped over 2,300 agencies deliver better client services. Since forming an initial partnership with ClickUp in early 2018, ZenPilot has become ClickUp’s largest implementation partner!

What’s more, Gray is one of our very own Paperless Movement Partner Experts! If you aren’t aware, in the community we have a range of verified tool specialists. They provide exclusive in-depth videos to get you started in no time. All on the tool/platform/school of thought that they are experts in. Listening to the podcast, you will discover that Gray is extremely generous with his knowledge and loves sharing his expertise. He does this to help other businesses grow. ZenPilot specializes in supporting digital agency use cases. But, their philosophy applies to any form of business. So, whether you are an agency or not, an experienced ClickUp user or a ClickUp newbie. Maybe even a ClickUp wannabe. Gray has some super insightful, well-researched points we can all benefit from.

Hit play to listen to the Podcast! Take it all in digest the full blog post below!

Why ClickUp

A good project management tool allows for planning, executing, and monitoring project progress smoothly. Having all aspects of your project centralized in real-time means data can easily flow across to people. It can move freely within their teams so that everyone knows who is doing what and when.

Andrew and Gray spent 6 months researching project management tools. They did this to find out which one would deliver the requirements and needs of agencies. This is because as you presumably already know, there are a lot of project management apps out there!

We bet on the right horse with ClickUp.

Gray MacKenzie

They evaluated 71 different project management platforms. With ClickUp being the ultimate winner as the best fit for scaling up, and meeting the objectives across a whole range of metrics and categories for digital agencies.

Despite Tom’s initial reservations with ClickUp, Tom shares his reasons for choosing ClickUp. Tom uses ClickUp for his Paperless Movement team. There are many people in the Paperless Movement Community that have a real desire to use ClickUp. The technical infrastructure that ClickUp offers is great but it also requires some guidance on how best to use the platform.

How to manage a Productive, Profitable, and Successful Team in ClickUp

It’s Not the Tool

If you use ClickUp and you do the work, yes, you can become more productive. But, fundamentally it’s not the tool. Instead, it is crucial to define how you use your tools and know what your priorities are. ZenPilot does just that, they “Take The Mystery Out Of Agency Operations”. They follow a proven playbook to fix your systems, processes, and project management, so you can scale your business.

Always ask yourself, what would you do if your favorite platform you are currently using stopped working? What if the company went bust? Could you easily migrate your current workflow or system using another tool?

The ClickUp Potential

Tom shares his experience of transitioning from Asana back to ClickUp. In fact, he has shared on many occasions how he struggled to find the ‘right’ project management tool, for him and his team. It has been an experiment and a challenge. Yet, despite it being a complex tool, he has chosen to stick with ClickUp. He chooses it for its flexibility and potential to scale i.e. its ability to grow with his budding business, growing team, and thriving community.

Gray and Andrew decided to double down on ClickUp, first for themselves. Then as it became clear that it was the right fit for their agency-specific needs, they used it as the core platform for the agencies they worked for.

With ClickUp’s drive and philosophy, Gray believes, this platform has a greater chance of sustaining momentum for a longer time period. So far, that early bet on ClickUp has paid off in spades. They’ve rapidly emerged as a major force in the project management space, mainly due to ClickUp’s:

  • Consistent product development velocity
  • Unique deep hierarchy structure
  • Aspiration and ambitious reputation
  • Drive to be better than the rest
  • Customer service responsiveness

Understand the Process

A core message of our ICOR® Mastery program is the importance of it being tool agnostic. Success and productivity are not based on your chosen tool, it’s all about having a system and one that works for you. We have all seen the offerings of tool templates and blueprints that work for a specific individual or business. The con is, they make you believe you can use it too. However, when it comes to using it, your lack of knowledge of the tool means this glorified template is now made redundant or at best limited.

This perspective is echoed by many of our Partner Experts and guests. Despite many of our guests being tool specialists, a common thread of their philosophy is that there are multiple reasons to use each tool, but the tools themselves aren’t the reason for your success nor are they the reason for your poor business outcome. The tools can only help and assist you accomplish the outcome you desire to achieve. The tool isn’t the magic wand that chooses your business. Instead, structure, systems, vision, and knowing how to execute your workflow are the key components you need to focus on.

When to hire a consultant to build your productivity setup

As tech-savvy as Tom and Gray are, they recognize that not everyone has the motivation or the skillset to learn these protocols, or perhaps they don’t have the knowledge to get the data into their chosen platform. This is especially the case with ClickUp, it is known to be clunky and not ideal for those who want to just get started.  ClickUp requires some initial work to onboard the whole team and set up the workflow, time to understand its many views and settings. Plus, there are no pre-built dashboards or templates. ClickUp’s power is that you can build whatever you want, but, the downside is you have to also know what it is you’re designing. That’s why ZenPilot exists, to show you a way forward.

The ZenPilot Approach

As a ClickUp consultant, it may surprise some people that Gray believes the expertise about your own project management system and processes needs to come from in-house. He believes it is wise for teams to access external support and expertise, hiring experts to come in to build the infrastructure that will provide you with a basis to scale from. However, understanding why the system is built in a certain way, knowing what needs to be done, making sure you maintain workflows and team accountability, and ensuring ongoing improvement, are all aspects that need to come from within your business. This is an area that SHOULD NOT be outsourced.

Expertise has to come from in-house, you can’t outsource it…..You need somebody internally who knows how to keep your system running.

Gray MacKenzie

Team Training and Team Enablement

When businesses are looking for a project management tool, it is so typical to get preoccupied with the new technical features and believe the marketing spiel that this new app is the system that will make us super-efficient. Ideally, every single task that can be automated is automated, we have one hundred percent team compliance, and our whole company is working exactly the way they’re supposed to work. But let’s face it, in reality, this isn’t the case, we’re humans after all!

Successfully introducing new software to your team can be a challenge. In order to convince and encourage your team to adopt new technology, by helping them gravitate to the tool in the same way you do, expectations and systems need to be made clear from the get-go. Having external help, like ZenPilot, or another trained team member design a system that functions for everyone should be one of the first steps you make. It is imperative that all who use the system have been sufficiently trained to use the new tool or software. One of the key components to ZenPilot’s success has been their approach to team training and team enablement.

As highlighted, the success of an agency or business is not reliant on the chosen project management tool. Rather, it’s the coherent operating system around how they actually operate. It’s also having a team that is well-trained, competent as well as confident in the system.

Making the tools work for you

Every tool has to have its designated place within your system. As Gray, explains, if you’re using Slack, there has to be a clear expectation set around what and how you use it. For example, if teams are using Slack for conversations or ideation this makes sense for it to live and stay in Slack. However, in cases where it’s something task-related or deliverable and is connected to a specific project then that has to happen in the comments thread within ClickUp. This enables cohesion, transparency, and ultimately there is a clear record of why that decision was made.

When we have the conventions, expectations, SOPs and we have our Single Source of Truth, we are able to measure, scale-up, learn and grow.

Tom Solid


It’s easy to get lost with ‘shiny object’ or ‘new app’ syndrome and believe that a single product can solve everything for us. In truth, the tool will be useless unless you write down your process map and create SOPs, strategies, and conventions. As a result, Gray has witnessed how organized and efficient businesses can become successful with the right tools as well as processes. ZenPilot provides a thorough and truly thought-through package that can help you understand your own end-to-end system, if you want to find out more, do book a call with ZenPilot. If you want to take away the guesswork with using ClickUp for operations and creating workflows, Gray also shares a thorough deep-dive in mastering ClickUp, in our Community.

It’s been an insightful chat with Gray and hearing about his business success. Also how ZenPilot is helping thousands of agencies all over the world use a proven playbook to enable them to empower their team and scale profitably. But, also how their philosophy is incredibly aligned with our very own ICOR® Mastery ethos; design your workflow and get your systems and protocols defined first, your chosen tool will naturally follow.

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