It's a lot about how you say things, not what you say. The most important thing is to advise not direct. Ordering entrepreneurs around won't work. If they wanted to take orders, they'd be working at some big company taking orders from someone else. It's also critical to soft pedal the advice. Coming from an investor, it's going to have an impact anyway, so I find it best to say something like, "have you thought about", as opposed to "that's not the way to do it".I couldn't agree more that it's of critical importance that a Board Member know how to coach & guide while keeping a CEO upbeat about what he/she has already accomplished. Obviously, this is Management 101, but I've found several VC's and Board Members who tend to forget the basics of management & motivation. No matter how good the CEO, people are people and they need to be treated with respect & recognition. Just like anyone, CEO's appreciate words of motivation & validation.
If you have something to say, think carefully about how to phrase it...