It's natural to want people around you who are supportive and positive. I get that. Trust me, I get it! However--and this is a big however, if your squad consists of a bunch of "yes" people, be careful. "Yes" people will try to convince you that average is good enough. They'll have you believing that mediocrity is the norm. They're uncomfortable with telling you the truth. "Yes" people will have you out here looking...foolish.
Having supportive and positive folks in your circle is a must! Make sure you have genuine people who have your best interest at heart also. People who will tell you the brutal, honest truth when everyone else is stroking your ego. People who aren't afraid to tell you flat out, "Dude, you're f***king up." People who will look you square in your eyes and say, "I disagree with you and here's why...."
I recently finished a major project and shared it with a close friend/mentor for feedback. This friend is wickedly talented and very successful. I respect his opinion and I know he cares about me. After reviewing my work, he gave it a 7.5 out of 10. Ugh! My heart sank. It was tough to hear, but you know what? He was right.
I carefully reviewed his feedback, examined my work and made some adjustments. And now? My project is much better and scheduled to launch this summer (Yes!).
Anywho...the moral of the story is this: Be cautious of folks who only tell you what you want to hear ("Yes" people). Be open to constructive criticism. Be 'OK' with being wrong sometimes and make changes if necessary. And always surround yourself with people who will push you to be your best.