Operations
Friday Deploys and the Absent Operator
Shipped at 4:47pm. Worked in staging. Discovered the edge case at 6am Monday, when ten thousand customers found it first.
Archive
Team reality
Don't promote your best engineer
He was the strongest engineer on the team. You made him a manager. Six months later he's unhappy, the team is slower, and you've got a tier-three manager.
Growth traps
The vanity metric on the homepage
'Trusted by 12,000 teams.' Half of those teams were free users who logged in once. The number was technically accurate and strategically useless.
Money decisions
Forty percent more, and nobody approved it
Nobody opened the renewal email. The auto-renewal clause sat on page eleven. The new rate, forty percent higher, hit the card on a Tuesday.
Founder decisions
The email you drafted at 11pm and shouldn't have sent
It was clear, direct, and correct. It also cost the relationship. Being right at midnight is the most expensive way to be right.
Operations
The engineer with the runbook was over Greenland
Production went down on a Saturday. The only engineer who knew the fix was on a plane. Two hours of revenue burned waiting for him to land.
Team reality
The senior hire everyone quietly wrote off
Twenty years of experience, six months in, still asking the same questions. The hire wasn't wrong. The onboarding was.
Growth traps
Don't trust the logo on your own homepage
Their logo was on the homepage. Their quote was in the deck. They had canceled six weeks before the marketing team noticed.
Money decisions
A Full Pipeline Is Usually an Empty One
Forty-three of sixty-one open deals were marked commit. Two-thirds slipped. The CRM was a wish list with a forecast column.
Money decisions
The unit economics spreadsheet nobody opened
It lived on page four of a Notion doc, was updated quarterly, and was wrong by sixty percent. Nobody noticed until the term sheet.
Founder decisions
Why boards read your update backwards
Page nine, paragraph three, fourth sentence in. The number that mattered most was hidden where nobody would ask about it. The board found it first.
Team reality
Call the Layoff a Layoff
A reorg staged to dodge the word layoff costs more trust than the cuts. The team reads the org chart for the missing names by lunch.
Operations
Signed Thursday, Forgotten Until Wednesday
Six days of silence after the wire cleared, and a $36,000 account decided the vendor stopped caring. It looked like churn. It was a handoff nobody owned.
Founder decisions
The advisor you only call after you've already decided
He's been on your cap table for three years. You've called him twice. Both times you wanted permission, not advice.
Growth traps
The Silent Quarter
Two logos, a joint press release, and ninety days of nothing. The partnership was a marketing event that mistook itself for a go-to-market plan.
Money decisions
Stop Pretending the Discount Is a Concession
Every deal closed at twenty percent off. Two years later, list price was fiction nobody believed, and raising meant renegotiating the company's own revenue.
Team reality
The top performer who was breaking the team
His numbers were twice anyone else's. So was the rate at which his teammates were quietly interviewing elsewhere.
Operations
The OKR nobody could remember on Friday
Forty-seven objectives, two hundred ten key results, one quarterly off-site. Nobody could name their KR a week later. Working as designed.
Growth traps
40,000 Signups, No Change in Retention
40,000 signups in a weekend. Six weeks later retention hadn't moved. The spike taught the team the wrong lesson about what actually worked.
Founder decisions
Stop Postponing the Cofounder Conversation
You've been rehearsing it in the shower for nine months. The longer you wait, the more expensive the silence gets.
Money decisions
Eleven months of runway, not eighteen
He thought he had eighteen months. He had eleven. The gap was every assumption he never wrote down.
Team reality
The manager who couldn't fire anyone
He gave the same person the same feedback for fourteen months. The team learned that consequences were a rumor.
Operations
Sixty people, forty-five minutes, zero questions
They sat through forty-five minutes of updates they could have read in a doc. Nobody asked a question. The CEO called that clarity. It was resignation.
Team reality
The hire who stops asking questions is gone in nine months
A new hire who stops asking questions in week three isn't adapted. They've started running the math on leaving.