Operations
Your Support Team Is Hitting Every SLA and Failing
Every SLA held: first response, resolution, CSAT. The open queue still doubled in a year, because none of those metrics measured backlog.
Archive
Team reality
When Everyone Passes, the Review Failed
Forty-seven reviews. Forty-three 'meets,' four 'exceeds,' zero 'below.' The cycle was a calibration exercise that had stopped calibrating.
Growth traps
Category creation is usually vanity
They named the category, ranked first for the term, and the term drew eighty searches a month. The category existed in the deck and nowhere else.
Money decisions
The marketing spend with no attribution
Six hundred thousand a quarter, four channels, clean CAC on the dashboard. The dashboard was wrong — it took a Series B investor and a holdout test to prove it.
Founder decisions
The customer call you stopped doing
Year one he took five customer calls a week. By year three he was down to two a month, and the roadmap had drifted without anyone deciding to let it.
Operations
The internal tool nobody used
Six months of engineering. Three demos to leadership. Logged into twice in production. The tool was a project nobody had asked for.
Team reality
Your best people don't quit over money
She didn't leave for a raise. She left because she'd spent a year and a half working around one person, and the math finally stopped working for her.
Growth traps
The persona you invented to explain a slow quarter
Pipeline was light, so marketing introduced a new ICP. The new ICP didn't exist. The deck had a name for it anyway.
Money decisions
The collections call you should have made in March
By July the invoice was 120 days old. The customer was still polite. The receivable was already gone.
Founder decisions
The pivot you delayed by a year
The signal shows up in spring. The pivot happens the next winter, after months of burn and the best people leaving. Most of the delay is identity, not data.
Operations
Same Three Problems, Every Six Weeks
Thirty-one action items over six retros. Four done. The retro was a ritual that mistook complaint for improvement.
Team reality
The skip-level you stopped doing
He ran them every quarter for two years, then stopped because he was busy. Three resignation letters later, he saw what the skip-level had been buying him.
Growth traps
The international expansion before product fit
The board said go global. The product still didn't work for half the US customers. London opened in March. By December, it was a tax.
Money decisions
The bridge round you didn't realize was a down round
Same price per share. New terms in the legal language. The founder found the down round in a footnote eight months later.
Founder decisions
The acquisition offer you didn't take seriously enough
It came in at $40M when the last round said $30M, and he laughed it off. Eighteen months later, the company took a $12M down round.
Operations
Eight engineers, fifteen minutes, zero re-plans
A standup that never changes anyone's plan has stopped coordinating and started reporting to the manager. Kill the format; ask one question instead.
Team reality
The rockstar who wouldn't write a doc
He shipped twice as much as anyone. He documented none of it. Two years in, the company couldn't onboard anyone without his calendar.
Growth traps
Two thousand scans, one deal
A $40,000 booth scanned 2,000 badges and closed one deal. The revenue at a conference shows up at the dinner, not the ten-by-ten carpet.
Money decisions
The customer concentration you didn't name on the deck
One logo was 42% of revenue. The slide said 'enterprise customers,' plural. The investor asked the number anyway, fifteen minutes in.
Founder decisions
The investor you took money from for the brand
Their logo opened doors. Their partner showed up to one board meeting in two years. The check was real. The relationship was vapor.
Operations
Stop telling new hires to scroll back
When the wiki is empty, Slack becomes the wiki — and Slack is the worst filing system ever shipped. The five-line decision log is what actually survives.
Team reality
The PIP Nobody Believed
Sixty days of check-ins and three signed documents produced an outcome the team called on day one. The plan wasn't improvement — it was a record for the file.
Growth traps
Put More Friction in Your Free Trial
Signups up forty percent, conversion down sixty: the trial worked perfectly for people who would never pay. A trial is a selector, not a funnel widget.
Money decisions
The cash collection cycle nobody owned
Invoices went out on the first. Money landed somewhere between day forty and day ninety. Nobody could explain the gap because nobody was watching it.