Common Mistakes in Tracking Project Milestones

I see (ambitious, well-meaning) agencies fall into these 5 pitfalls every day. And all of them are related to project management. 1. There is no single source of truth for their work. Tasks and commitments are spread across Google Docs, sheets, meeting notes, calendar slots, and PM software. It’s a simple recipe for chaos. Nobody’s able to keep track of everything they committed to, or realistically assess if they can get it all done. The fix: Set up a single source of truth. (For ZenPilot and our clients, we follow a simple rule: “if it's not in ClickUp, it didn't happen”.) 2. Work is not aligned with a realistic and detailed timeline. Deliverables may have due dates, but the particular steps (or subtasks) to get that deliverable done either aren’t there, or they don’t have information on when the steps will be completed. When you don’t know when each team member will complete each subtask, you won’t know who’s overbooked = they won’t get to their subtask on time = the whole project might be delayed. The fix: Prioritize work using due dates, and layout steps/subtasks in your process so that their due date falls on the day when it will be done. (Due Dates == Do Dates) 3. Processes/SOPs live separately from day to day work. If you’ve got your SOPs in a separate wiki or a set of Google Docs, that can hurt you in the long run. You’ll have your team hunting for SOPs outside of their day to day PM system. And if they find them, they’ll be scratching their heads whether the process is up to date. And even if it is up to date, now they need to create tasks for themselves to follow the process… The fix: Make your processes live where the work gets done. Ideally, turn them into ClickUp templates. 4. Ignoring project management habits. Your PM tool setup (hierarchy, folders, etc.) matters. The way your team uses the tool every day matters 10x more. If you’re not intentional about the habits you’re building, your tasks and projects will be updated inconsistently, with varying amounts of detail—leading to unclear data about where work actually stands. The fix: Set and train the team on uniform habits and standards around how often and in what detail tasks get updated. 5. Lack of consistency + accountability in their PM system. Typical scenario: An agency owner/director leads the charge implementing a new PM tool. It works great. They move on to their next goal. Without their supervision, standards fall apart. Nobody’s accountable for checking whether the system is being maintained. Team members end up updating the system “when they get around to it” (which quickly turns to “rarely ever”), making the data in the system unusable for decision making. The fix: Appoint a ClickUp Champion. Give them the task of checking the system daily, weekly, monthly, and quarterly. Have them remind/train team members who don’t follow the system. Fix those, and you’ll be a top 10% agency.

A lot of Project Schedulers have made mistakes that tend to make project scheduling a lot harder than it should be. And I’ve unfortunately been part of this group of people 😅 Early on in my career, I made a mistake I’ll never forget. I pored relentlessly over this beautiful, colour-coded schedule for a mid-sized project. Everything was tight and ready to go. Or so I thought. Every milestone had a date. Every team member had a task. It looked perfect… until execution started. Two hours in, everything fell apart. Mind you, this was a project I had spent 2 days whole days working on😭 Why did this terrible thing occur? Because I didn’t ask the team if they had the capacity for the tasks. I built the schedule on assumptions, not conversations. Since then, I’ve seen many project leads fall into the same traps. Here are some common mistakes that make scheduling way harder than it should be: 🔷 Overplanning without stakeholder input. If your schedule isn’t collaboratively created, it’s destined to fail. 🔷 Ignoring task dependencies. One overlooked dependency can derail your entire timeline. Never underestimate dependencies. 🔷 Not building flexibility. Rigid schedules always collapse under the slightest pressure. Always give room for flexibility. 🔷 Tracking the wrong metrics. Time spent vs. tasks completed? Not the same. Scheduling doesn’t have to be a struggle, but you do have to approach it with humility and communication. What has been your biggest lesson in your project scheduling journey, I’m eager to know.

I watched a $50M hospital expansion get delayed by 8 months because of one email sitting in someone's inbox. The approval was ready. The budget was approved. The contractors were waiting. But the project manager had no visibility into where things stood. After working with 200+ organizations, I've seen the same manual workflow mistakes destroy project timelines and team morale. Here are the 5 most damaging ones: → Spreadsheet dependency for project tracking Teams lose hours updating multiple versions, and critical details slip through the cracks. One outdated cell can derail an entire milestone. → Chasing approvals through email chains Decision-makers get buried in their inboxes while projects sit idle. What should take 2 days stretches into 2 weeks. → Disconnected systems creating data silos Finance uses one tool, operations uses another, leadership gets reports from a third. Nobody has the complete picture. → Manual status reporting that's outdated before it's sent By the time you compile that weekly report, three new issues have emerged and two "green" items turned red. → Lack of structured accountability When everything is tracked informally, nothing gets tracked consistently. Problems surface too late to fix them effectively. Behind every delayed project are dedicated professionals trying to deliver value to their communities. They deserve better than being trapped in operational chaos. The solution isn't just better software. It's structured workflows that create transparency and accountability from day one. What workflow challenge is slowing down your current projects?