I waited tables through college, I've been on the receiving end of this question. The answer is driven by the selfish pursuit of the big tip, gotta hedge your bets... but there is also personal bias and the reality of how you're feeling at that moment. The trouble is they don't have any understanding of YOU. How can anyone provide advice (large or small) that is a fit for you if they don't really understand you?
That got me thinking about the financial advice that I have asked for and taken over the years. I asked some pretty smart people. People I looked up to and respected. I was confident that I was getting really good guidance and I did get some that was a good fit for me. What I failed to realize at the time was that the advice-giver, always well-intentioned, was not perfectly equipped to make the decision for me. That falls to me, not the waiter.
Everyone has different priorities, goals and values. Everyone is at a different point on their journey. We see the world, our finances, and each other differently. There are many things that influence any advice, or coaching, that is given. When people start to assume what's important to you, or guess what you would be most happy with, good, sound advice can become misguided. It's pretty complex when I reflect back on the advice I got and how my decisions were influenced by that advice. For example, the smartest guy in the room convinced me that leasing a car at one point in my career was the way to go. I did it. I look back on that bad decision as something I should have done differently. His advice was influenced by his own situation and priorities and maybe a few assumptions of what he thought would be best for me. I didn't trust myself enough to make my own decision.
What's good for one is not good for all, no matter how good the source of the advice. You've got to listen to yourself after you've collected as much good info (research, advice, etc.) as you can. Be open to all of it but at the end of the day, you have to live with the decision. Make sure it's a good fit for YOU.
Don't leave it up to the waiter.