Why Leaders Are Blind to Their Own Work
Jan 15, 2026
If you run a Series A startup (or any company moving fast enough to feel slightly unsafe), there’s a weird moment that hits you at some point.
You look up from your day. You look at your pipeline. You look at your project board. You look at your team’s “status updates.”
And you think:
“I have no idea what’s actually happening.”
Not in a dramatic, existential way.
In a practical way.
Which deals are real?
Which projects are drifting?
Which commitments were made in a thread that nobody tracked?
Which customer is quietly losing trust while your CRM says “Happy”?
Which teammate is overloaded and one bad week away from “I’m burned out”?
And the worst part is… you can’t admit it.
Because you’re the leader. You’re supposed to know.
So you do the thing leaders do when they don’t know:
You ask for updates.
The “Update” Scam
Updates are supposed to create clarity.
In reality, updates create comfort.
Because most updates are just people describing reality from memory, under pressure, in a format that rewards optimism.
“On track.” “Looking good.” “Minor blockers.” “Should be fine.”
If you’ve ever seen a project go from “on track” to “on fire” in 48 hours, you already understand the problem.
The problem is that humans are terrible sensors.
We forget.
We smooth over.
We rewrite the story in our heads.
We round up.
We present the version that sounds competent.
And when work is scattered across email, meetings, docs, and DMs, nobody even has a single place to check themselves.
So leadership becomes a game of telephone.
Except the stakes are: revenue, customers, and your company.
The Real Reason Leaders Become Blind
Most leaders assume blindness comes from scale.
Like: “Once we hit 50 people, it gets hard.”
No.
Blindness starts earlier than that.
Blindness starts the moment work becomes distributed and context becomes fragmented.
Which is basically: the moment you start growing.
In a Series A company, you’re living in peak chaos conditions:
Everyone is moving fast
Everyone is multitasking
Everyone is making promises in meetings
Everyone is operating out of inboxes and calendars
Everything important is happening in threads and transcripts
Everyone assumes someone else is tracking it
And because the company is “small,” everyone pretends it’s manageable.
It’s manageable right up until it isn’t.
The Two Kinds of “Not Knowing”
There are two kinds of not knowing.
1) Honest not knowing.
“I don’t have the full picture yet.”
This is fine. Normal. Responsible.
2) Unconscious not knowing.
“I think I know… because someone said it was fine.”
This is where companies get wrecked.
Because leaders start operating on what we call second-hand confidence.
Confidence that comes from someone else’s status update.
Someone else’s memory.
Someone else’s interpretation.
Someone else’s optimism.
And second-hand confidence is how you get blindsided.
Why This Gets Worse at Series A
At Series A, you’re hiring quickly.
Which means you’re increasing the number of moving parts while the system for tracking reality is still… vibes.
You’re also selling harder.
Which means pipeline pressure increases.
Which means “optimistic reporting” becomes culturally rewarded.
And you’re shipping constantly.
Which means commitments are made fast, casually, in passing.
“Sounds good.”
“Yep, we’ll do that.”
“Let’s follow up next week.”
And then it disappears into the thread like it never happened.
Until the customer asks again.
Or churns. Or escalates. Or you get that email that starts with:
“Just checking in…”
Which is corporate code for:
“I don’t trust you.”
The Actual Problem
Leaders are blind because the truth of work is buried in communication.
Threads. Transcripts. Attachments. Calendar events. Random promises.
And the only way to reconstruct it today is painfully manual.
That’s the trap:
Work happens in communication… But management systems track what people remember to type.
So leadership becomes:
guessing what’s real
asking for status
sitting in meetings to get clarity
hoping follow-ups happen
and being surprised when they don’t
What Changes When You Can Actually See Work
Once you can see the work picture—built from actual objects like Requests, Tasks, Events, Calls tied to Deliverables—everything gets less dramatic.
Because drama thrives in ambiguity.
When you can see:
what’s planned vs what’s done
what’s blocked vs moving
what commitments exist and who owns them
what changed since last time
what you need to ask in the next meeting
which deals/projects actually matter this week
…you stop managing the company through anxiety.
You manage it through reality.
Where Belt Comes In
Everything above describes a visibility problem.
Not a productivity problem. Not a people problem. Not a “we need better updates” problem.
A reality problem.
Belt exists because leaders shouldn’t have to reconstruct the truth of their company by:
skimming 100 emails
opening five tools
watching three recordings
asking for status
and hoping they asked the right question
Belt builds the work picture directly from where work actually happens:
email, meetings, calendars, and commitments.
It doesn’t ask people to report reality.
It observes it.
So instead of second-hand confidence, you get:
what was decided
what’s required next
what’s blocked
who owns what
what changed since last time
what you should follow up on
In other words:
the gap between what people say is happening and what is happening gets closed.
And when that gap closes, leaders stop guessing.
They stop managing vibes.
They stop being surprised.
They stop being blind to their own work.
That’s what Belt solves.
Next Article
How to Turn Chaotic Email Threads Into Actionable Tasks


