Don't Program Your Kids
I've had a lot of experience working with young professionals, both as young Associates at venture firms as well as working with business school students in various projects, such as an i-Team at MIT's Deshpande Center. These are smart, high-achieving individuals who have great potential to do a lot in the future.
However, I have been frustrated and amazed sometimes when I see that many of these people have a hard time making decisions on their own. In many cases, these people have followed a program from the time they were young. Their parents, teachers, and advisors have laid out a plan for them, have given them lots of additional resources, and have shown them the recipe for success. I often have been asked by them "tell me exactly what I have to do to get promoted or to get the project done." My reaction was that I wanted to throw them into the deep end of the pool and say "swim".
I think that it is critical for entrepreneurs to figure out what to do on their own and to not be afraid of making mistakes. Many of these young people have never faced a setback. They are terrified of failing and think that the consequences are monumental. They need to learn that failing is part of learning. Also, you can ask for advice and integrate that into a strategy without having someone tell you exactly what to do.
As a Board member, I try to do the same thing. I advise the CEO and rarely, if ever, tell them what to do. Most CEOs want to gather input from many sources and insist on finding conflicting inputs so they can understand all sides of an issue before they make a final decision. As an investor, I need to trust the CEO to make an intelligent decision based on understanding all sides of an issue. If I lose that trust, it's probably time to make a CEO change.
As a parent, I am conscious of this with my young kids. I want to give them access to every resource and opportunity, but I don't want to dictate what they do. I'll keep them from making really big mistakes, but they need to learn to blaze their own path and make their own decisions about what is important to them. I certainly don't want to insist that they follow a program that meets my needs (but probably not theirs). Instead, I'll throw them into the deep end of the pool (but will watch to make sure they figure out how to swim).