A common issue I see creeping into company cultures is a constant always-happy-go-lucky attitude. The permanent “everything is awesome” mantra and the total avoidance of any negativism is as damaging as an overly negative culture.
In an effort to create a “can-do” attitude, I see too many companies going to far and banning all criticism from their internal debate.
I think this is dangerous as it prevents you from seeing the full picture, identify pitfalls and faults early on and make sure that whatever you build works — and does so very well.
A healthy dose of negativity should be equal part of your conversation. Figure out why something might not work. Look for the flaws in your assumptions. Think through the ways how something could fail.
Good and bad. Positive and negative. Success and failure. All parts of the equation which the best entrepreneurs take into account. And then move forward with conviction and gusto.