ClickUp Review for Small Remote Teams in 2024

Table of Contents

Setting up ClickUp for the first time

When I first tried to set up ClickUp for a small async team, I honestly expected it to be one of those platforms that takes a day just to invite people. It actually wasn’t too bad, except that the default workspace feels overwhelming. The sidebar has Everything, Spaces, Folders, Lists, Views, and honestly I got lost in there like opening too many doors in a house I barely just moved into. My trick was just to delete half the default stuff and start as lean as possible. One Space called “General” with one Folder called “Projects” and inside that I threw a few Lists. If you try to impress people day one with a complex workspace, it backfires. Someone always asks, “Wait, where do I put the notes for our client meeting?” and then you realize nothing actually makes sense.

Using the invite flow: you send team members an invite from settings and they get an email. Problem is, one of my teammates kept saying, “I clicked accept, but then nothing happens.” I had to tell him to open the email link in Chrome, not Safari Mobile, since ClickUp doesn’t always load the full workspace on phones. That was one of those frustrating bug moments where I said, “Okay, let’s just use desktop until this platform catches up.”

Managing tasks without creating chaos

ClickUp gives you like 7 different ways to view tasks. The problem is, the first time you open Board view, you feel like you’re looking at a messy garage. Everything gets thrown into cards and unless you add custom statuses, it just says “To Do,” “In Progress,” “Done.” My approach was to rename those statuses into words that made sense to us as a team of contractors. So “To Do” became “Idea,” “In Progress” became “Doing,” and “Done” stayed the same. Simple, but makes your board feel like your own.

The thing that tripped us up was subtasks. If you click the little arrow to expand subtasks, they show up like a new list inside your list. Sometimes, though, when my coworker checked off a subtask, it disappeared from Board view but didn’t mark as complete in List view. I thought it was some sync issue, but after testing twice, I realized it was just a setting buried three menus deep that says, “Show Closed Subtasks.” For beginners, that’s the stuff that drives you nuts — tasks don’t seem to exist unless you toggle the right setting.

To actually keep ourselves sane, we also limited “Assignees” to one per task. Otherwise, no one feels responsible. You can technically assign everyone to everything, but guess how that ends: people shrug and the work doesn’t move ¯\\_(ツ)_/¯.

ClickUp chat versus Slack

You can chat inside ClickUp, but it feels like talking in an abandoned mall food court. People peek in, but nobody hangs out. I tried telling my team, “Let’s move all conversation threads into ClickUp comments so everything lives with tasks.” What happened was that two people forgot, messaged in Slack, and suddenly we had duplicate conversations. I then had to copy Slack screenshots back into ClickUp so it didn’t look like I ignored comments. Personally, I still think Slack is better for live banter and ClickUp comments are best for context right on the task itself.

One thing I did like: you can assign action items directly from a comment. Somebody wrote, “We still need the logo in higher resolution,” and I highlighted that text and turned it into a new task. Boom. That only works well, though, if they typed it properly. When people write stuff like, “uh can someone maybe upload logo???” the auto-task creation looks hilariously awkward.

Docs and knowledge storage in ClickUp

ClickUp Docs feels like its own secret app inside the app. If you click the little paper icon in the sidebar, you can make documents that multiple people can edit together. We used it for onboarding checklists. But again, the navigation is clunky. If you don’t pin a Doc into a Space, it gets lost. I once wrote a two page SOP about payment processes and then literally could not find it two weeks later. The search pulled up six results for “Invoices” and none were it. Eventually, I found it buried under “Private Docs.” Super frustrating.

Docs also let you embed tasks directly inside. So I made a workflow doc that literally listed each ClickUp task inline so contractors didn’t have to switch tabs. It felt powerful in theory, but in practice, people kept editing the doc instead of actually moving tasks along. I guess that’s the balance here: too much flexibility and people get lost.

Time tracking when no one wants to track time

ClickUp has built in time tracking where you can hit Start and Stop on a timer. But let’s be real: almost nobody wants to remember to press timers while they work. My team found out the hard way because someone left a timer running overnight and it said “19 hours editing thumbnails.” 😛 At least it gave us something to laugh about.

Instead of forcing timers, we just made a rule. At the end of each day, people type however many hours they remember into the task. The reporting is less exact but we avoid absurd system logs that look like “User idle time exceeded limit Error Code 40599.” If you’re billing clients by the hour, you probably want a separate actual time tracking app anyway. There are integrations with tools like Toggl and Harvest — those are way safer than relying on ClickUp’s built-in.

ClickUp automation experiments and dead ends

Automations in ClickUp sound cool. “When status changes to Done, move task to Archive folder.” But half the time, it didn’t trigger how I expected. Sometimes I’d mark a subtask as done and the parent task would suddenly close too, which nobody asked for. Another time, I tried setting up “When due date arrives, post comment reminding assignee.” Instead, it dumped the comment twice. I double-checked logs and it literally said “Action fired at same timestamp.” Yep. Classic automation bug.

I tried connecting ClickUp to Zapier for more advanced things. That meant creating Zaps like “When task is created in ClickUp, send Slack DM.” It actually worked, except my coworker screamed that he got spammed with ten DMs because I forgot to add a filter. Lesson learned: always test with your own account first so you’re the one who gets spammed, not your team. They forgive one mistake, but after three, you’ll be back in Slack apologizing with memes :).

Pricing considerations for small teams

For a tiny team like ours, pricing actually wasn’t the problem. There’s a free plan that honestly goes a long way if you keep things simple. The moment you want guest sharing with permissions or advanced dashboards, though, you bump into the paywall. We ended up paying about $5 per person per month. Not terrible, but when you realize half the features collect dust, it feels like paying for premium seasoning you forgot to use on dinner.

The tricky part is scaling. At five people, it feels affordable. At twenty people, you start to question if the per user cost is worth it or if something like Trello with addons might be cheaper. Still, ClickUp includes tasks, docs, goals, and reporting all in one, so even if some of it is clunky, you do get that all-in-one feel.

Best way to introduce ClickUp to your team

The first week I rolled out ClickUp, I dumped everything at once: docs, automations, chat, dashboards. That was a mistake. Everyone stared at the workspace like it was an airplane cockpit. The smarter approach is baby steps. Step one: use it only for tasks. Step two: once tasks feel natural, add Docs. Only after a month should you touch automations. Trust me, going slower makes it stick.

What helped us was making a simple table right inside a Doc:

That way, nobody panics about where information lives. Clarity, not complexity, wins here. That applies especially when teams are remote and working across time zones — it takes one lost document to waste a whole day.

Final thoughts on using ClickUp daily

ClickUp is powerful but messy. It’s like a toolbox where half the tools are hidden behind secret panels, and sometimes the hammer just vanishes from the drawer for no reason. Small teams can absolutely make it work, but you’ll need to babysit the system at first and be quick to simplify whenever chaos creeps in.