The Worst Meetings on the Internet and What We Can Learn From Them

We Ran the Worst Meetings on the Internet Through Shadow — Here’s What We Learned

Meetings aren’t broken because of time. They’re broken because of trust.

I used to think bad meetings were just part of the job, like slow Wi-Fi or awkward Slack threads.

Then I joined Shadow, an AI meeting assistant built for teams who actually want to get things done. Every week since, we’ve gotten messages like:

• “We had a 90-minute meeting just to say, ‘we’ll revisit next week.’”
• “I joined a sync where the agenda was just a Google Doc that said ‘brainstorm?’”
• “A VP once called an all-hands to announce his sabbatical. We thought we were getting laid off.”

So we did what any curious AI company would do:
We ran the worst meetings on the internet through Shadow, using Reddit threads, viral tweets, and headlines from across the business world.

We summarized what went wrong.
We unpacked what it says about remote work culture.
And we explored how tools like Shadow can help fix it.

1. “This Could’ve Been an Email”

Source: Reddit – r/chileIT

The meeting: Recurring syncs that just repeat what’s already in email.
The problem: Everyone shows up. No one contributes. Nothing moves forward.

What it reveals:

• Most meetings lack clear ownership or a decision to be made
• People attend just to be seen
• Everyone walks away confused or disengaged

What would’ve helped:

• Using async meeting tools
• Adding agendas and owners ahead of time
• Giving people permission to opt out
• Running the meeting through an AI meeting assistant like Shadow to auto-summarize and share outcomes

2. Screenshot → Policy Change

Source: Reddit – r/tifu

The meeting: A Microsoft Teams call derailed by a funny meeting transcription error
The fallout: A joke went viral. Leadership disabled transcription for everyone.

What it reveals:

• Digital workspaces carry reputational risk
• Policy overreactions hurt more than they help

What would’ve helped:

• QA tools for AI meeting notes
• Guardrails on internal sharing
• Calm, proportionate leadership response

3. Death by Calendar

Source: Vice

The meeting: All of them. This one’s about systemic overload.

What it reveals:

• Calendar bloat kills deep work
• Meetings happen because teams avoid writing

What would’ve helped:

• Org-wide meeting audits
• Async-friendly defaults
• AI productivity software that supports decisions without calls

4. Friday Surprise

Source: Reddit – r/AskManagers

The meeting: A vague Friday all-hands from a VP
The reaction: Panic. Everyone thought it was layoffs. It was just medical leave.

What it reveals:

• Ambiguity breeds anxiety
• The emotional cost of vague meetings is high

What would’ve helped:

• Clear calendar titles
• Transparent agendas
• Tools for remote team communication

5. Phones Kill Focus

Source: Fortune

The meeting: Any room where people are multitasking under the table
The rule: JPMorgan CEO Jamie Dimon banned phones, and research backs it up.

What it reveals:

• Devices destroy presence
• One distracted person can derail a whole meeting

What would’ve helped:

• “No phones” culture
• Shorter, focused meetings
• A single AI note taker so no one needs to multitask

6. “Put the Dead Cat on the Table”

Source: Business Insider

The meeting: A leadership check-in where no one says the hard thing
The advice: Dimon says: name it early. Don’t waste time with politeness.

What it reveals:

• Meetings often become rituals of avoidance
• Radical candor creates clarity, not conflict

What would’ve helped:

• Framed prompts like “What’s not working?”
• AI meeting templates for hard conversations
• Less theater, more truth

7. Dimon’s Advice Goes Mainstream

Source: Forbes

The meeting: Zombie status updates with no forward motion

What it reveals:

• Meetings don’t fix broken leadership
• Fewer calls, more ownership

What would’ve helped:

• Cutting recurring bloat
• Meeting automation using AI
• Team accountability tools to track action without constant check-ins

TL;DR — The Anti-Meeting Checklist

Before you call your next meeting, ask:
✅ Is there a decision to make?
✅ Can this be async?
✅ Is there one clear owner?
✅ Do we know the next step?

If not, don’t meet.

Use Shadow instead. It automatically:

• Summarizes meetings
• Extracts action items and decisions
• Sends async follow-ups
• Works with Slack, Notion, CRMs, and more

Want to avoid bad meetings forever?
Try Shadow, the AI meeting assistant designed for real work, not just notes.

Explore our Custom Skills Catalog to automate async standups, client handoffs, and decision recaps, all from one call.

Try Shadow Free

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