TooManyThreadsNotEnoughContext
Here’s what always happens. We’re juggling four or five projects across Slack, ClickUp, Google Docs, and random tabs of Notion. Someone assigns a task—”Hey can you finish the client brief”—but five other messages have come in since then, and that one request gets buried in a thread that nobody reads again until launch day. Oops.
The problem isn’t people being flaky or lazy. It’s that unless the handoff instructions are isolated, labeled, and follow-up-able (is that a word? lol), they just become background noise. Threads don’t work because the original requester has to go dig back through them. DMs are better for privacy but even worse for search. Trust me, I spent an hour last Thursday scrolling through a colleague’s GIF convos just trying to find ONE attachment.
I finally created a rule for myself: if a task is handed off without these three things, it doesn’t count.
1. What exactly needs to happen (not just vague “touch base” language)
2. A location where the current info lives—Notion page, Figma canvas, Doc link
3. A way to mark it as done, that the requester will see (ClickUp task, spreadsheet checkbox, something that triggers some dopamine for both sides 👏)
Otherwise I forget it exists. Or worse, I remember it incorrectly. I once edited a doc for four hours, then found out the other person meant a DIFFERENT platform. Same name, different client. Bye bye, afternoon 🙂
TheSingleSourceTrapThatKeepsBreakingEverything
This is where my optimism becomes a liability. I wanted one place. One beautiful master database. Notion. Everything linked. Every task clickable. But the second that someone edits a description in the ClickUp version without syncing it back to the Notion one, chaos. You suddenly have two conflicting versions of the same task, with slightly different deadlines.
I didn’t even notice it at first. A teammate messaged “I added it to the checklist,” and I confidently nodded like it was going to flow perfectly. But later I realized that checklist was a Google Sheet. Separate from ClickUp. Separate from Notion. And no automations in place to tie them together.
Let me show how it played out, because it’s painful:
– I created a Notion database for all marketing tasks
– I built a ClickUp board for the same tasks, because Notion couldn’t do Gantt dependencies well
– A teammate built a priority list… in Google Sheets (fair)
– I connected some of it with Make, but I forgot to sync “status updates” backward (oops)
So now, marking DONE in Notion didn’t update ClickUp at all. I was proudly closing items and moving on, but in ClickUp, they still showed as In Progress. That meant follow-up questions like “who’s handling X?” kept popping up, and I had no idea which source they were quoting.
Eventually I added a very dramatic red badge in Notion saying: “The status shown here might be stale. Click into ClickUp to see real-time version.” Not ideal. But it’s saved me a few headaches.
SilentlyDroppedHandoffsFromZapsAndWebhooks
Here’s the one that nearly made me flip my desk. We had this super simple Zap: whenever someone clicked “Assign to Marketer” in Airtable, it would trigger a Slack DM to the marketing channel with the linked request. Easy, right? It worked for months.
Then it just… stopped. No errors. No alerts.
I only noticed because someone asked why no one grabbed their internal promo video. I checked the Airtable row—it was marked correctly. I opened the Zap—it looked fine. But no Slack message had been sent.
So I re-ran the task manually and watched it live. It ran, said “Task completed,” and… nothing happened. No message. This was weird.
Then I dug into the Zap history logs (if you haven’t done this before, click “Task History” and look at the output details). In Step 3, the Slack step, it said:
“Nothing to send, because previous step returned empty data.”
Turns out, someone had updated the Airtable column name from “AssignToMarketing” to “AssignToMarketer” but forgot to update the Zap to match. The trigger field didn’t exist anymore, so the whole path ran with a null value.
I’ve added a new habit now: anytime I change column names in Airtable, I immediately pause and open any connected Zaps or webhooks. Otherwise you’re going to lose your mind wondering what’s broken without any error messages 😛
MicroStatusUpdatesBeatBigMarkdownNotes
We used to try detailed notes. Each handoff came with a Notion page like “Here’s background, here’s the goal, here’s some links.” But nobody updated them. So they went stale in a week.
What’s worked weirdly well? Stupid simple status updates. Like a progress emoji or a tiny dropdown. Something the assignee clicks once to log progress. (No, seriously. Visuals help you pretend you’re productive.)
Here’s what we started using:
– A status cell in Airtable with just these options: “Waiting on Info,” “In Progress,” “Blocked,” “Done”
– A comment tag in Slack like: `@owner [Blocked] waiting on images` — that triggers a Zap to add a note to ClickUp automatically
– A small checkbox that shows when a doc’s feedback round has started (if not checked after 2 days, it gets flagged)
This way, the requester can just scan for bottlenecks without asking “what’s the latest?” 30 times.
Also highly recommend a manual reset checkpoint. Every Wednesday, we scroll through rows together in Airtable and do a 15-minute trash/pass. If something is too confusing to understand in 5 seconds, we pause and clarify. It’s like running weekly sync insurance ¯\_(ツ)_/¯
CreatingReadableHandoffNotesUnderPressure
This part is weirdly hard. You’re done with your part and want to dump it on the next person (we all do it). But quick dumping now = confusion later.
Here’s my 5-second mental checklist before I press “Assign To”:
– Is this link actually accessible to them? (Incognito test)
– Did I remove all internal-only notes or Slack screenshots?
– Did I actually state what I need them to DO? Not what I just did
– Would *I* know what to do if I saw this task after dinner?
I keep a quick Markdown template block for this. Let me paste it here:
“`
— Goal:
[X] What is supposed to happen here
— Source:
Link to where current status lives (doc, Figma, Airtable)
— Next step:
What the assignee needs to do right now
— Bounce-back:
Where to message if stuck
“`
If I can’t fill that in in 1 min, I at least leave the “Bounce-back” field obvious so people know where to ask. That alone cuts 80% of Slack wait time.
TrackingStalledTasksWithZeroAI
I know everyone wants to use AI to detect stuck tasks, but to be honest—I’ve gotten way better results with dumb conditional filters.
Here’s my current setup in Airtable (could be recreated in Notion or Sheets):
– One “Last Update” column that logs automatically (whenever Status changes)
– One “Expected Response Time” field per role (e.g. writers get 2 days, dev gets 5)
– A formula column called “Warning Needed?” which says Yes if Current Date – Last Update > Expected Time
That column powers a Slack digest every morning that tells me:
⚠️ These tasks are overdue or quiet:
• Promo Email Draft – still In Progress after 4d
• Mobile Nav Fix – no update since assigned 6d ago
No AI, no GPT. Just a checkbox and math. It works.
Someday I want a nice dashboard that lights up based on who’s gone quiet. But for now, Airtable filters + Slack reminders get me 80% there.
ThePermissionBlindSpotThatDelaysEverything
This one should be obvious but somehow isn’t. Handoffs get delayed not because the next person is slow—but because they can’t see the thing.
I had a design request get stuck for a week because the Figma file I linked said “Request Access” when they clicked. That was it. Everything else was good. But since nobody checks permissions every time, delays happen silently.
Now I do this weird habit: when assigning tasks, I click the actual link myself but in Incognito. If it says “Sign In,” I know it’s visible. If it says “Request Access,” I fix it right away. It saves such a stupidly large amount of time.
Also, for Notion, I always double-check if the page is “Workspace only” or “Anyone with link.” Those little toggles are sneaky. If you’re duplicating old templates, even worse: they keep old permissions.
PeopleDoNotReadClickUpDescriptions
This one’s for my fellow ClickUp users. You can write the most beautiful, detailed task handoff doc known to man… and nobody will read it if it’s inside a ClickUp description. I learned this the hard way.
I was wondering why certain tasks had the same questions asked over and over like “where’s the copy?” or “what platform is this for?” And I’d say “it’s in the description!” But apparently, people either don’t click to expand it or it gets hidden inside collapsed sections.
Now I add the key info as subtasks or custom fields:
– Platform (dropdown)
– Copy source (URL field)
– Reviewer assigned (person field)
These are visible at a glance, no click required. Then the description text becomes an optional deep dive. Only power users look at it, which is fine.
Also: never rely on ClickUp comments for status updates if you have external collaborators. Some clients don’t get pinged for them. We now use a mirrored Slack thread anytime external feedback is needed.
So yeah, even though I had my dreamy project tracker up and running, I discovered the hard way that visibility doesn’t mean accessibility. Or comprehension. Or even interest 😀