Small-company edition:

When pressured on the business by employees, CEO always starts with, "I need you to stay focused on..."

You have more than one MBA on the team.

You have a Chief Strategy Officer.

Your CTO just came out of a Phd program.

Your CEO sells instead of listens.

You have a launch party, and no customers attend.

Customers hate the product and vision, so the sales guy is fired.

You are not told the terms of the last funding round (5x liquidation preference?)

You never hear how much cash you have in the bank or see board meeting notes.

You complain about how the customers "just don't get it" and aren't "visionary."

Your CEO says revenue is coming in in two weeks, just after he gets a meeting with the buyer, negotiates price, gets it approved, agrees on terms, writes up up contracts, negotiates them, signs them, and invoices the customer on net 30 terms.

You add features because board members want them.

Your CEO calls himself a "visionary" in his bio.

The CEO keeps everything secret because, "that is how Apple does it."

The CEO approves all of the design decisions because, "that is how Apple does it."

You are selling a platform.

Co-founder agrees to bring in experienced execs but thinks they will report to him.

You are selling to schools, hospitals, or non-profits.

You are commercializing a technology.

Your value proposition is that you help workers break down organizational barriers and work cross-functionally.

Your business model assume you will become one of the 7 websites that the average user visits every day.

Your site is going to be ad-supported, and you have 1500 users.

CEO avoids eye contact.

It gets really quiet.

You get free lunch but have no customers.

Your free lunch is taken away.

You get asked, "how much do you really need to live on?"

You get a pay cut. Your co-worker disappears.

Your CEO still doesn't make eye contact.

You get laid off and become a creditor to the company because they didn't reimburse your last 5 expense reports.

The company declines to buy your unvested shares back.

The liquidation yields 5 Aeron chairs and an espresso machine, and Ashton Kutcher's stock is senior to yours.

via What are telltale signs that you're working at a "sinking ship" company? - Quora.