[azylman]

Just giving them a few weeks at the company before asking seems like a problem. After only a few weeks, they probably don't have enough experience to answer with anything other than their own biases.

For example: you call out your Google Docs tracking system as something that should be obvious. But that's probably not obvious after only a few weeks. Some companies (especially smaller companies) can get by totally fine with that, and if you've only been at a company for a few weeks, you don't know what kind of company you're at. If they tell you that your Google Docs tracking system is bad, they're probably just reacting to it being different than what they had before.

Anyone who responds with a long list of grievances after only a few weeks is probably the type of engineer that you _don't_ want on your team: it probably means that they're unwilling to evaluate problems and solutions within the current context.