When I was a junior in-house lawyer I had an irascible New York attorney as my line manager. He'd say "You Limey lawyers are so passive and reactive; you've gotta go out there and grab the deals you're working on and take charge." He'd urge us to be more commercial, to understand the business better, to regard ourselves as part of the business, not remain standing apart from it as a legal adviser. It was good advice, although I wish it had been delivered in a more constructive way. In fact my younger self would have benefitted from reading this short piece by Barrett Avigdor which perfectly encapsulates what that guy was talking about in a clear, straightforward, practical and positive way.
The courage comes in when you make recommendations or offer opinions that are more than just legal advice. When the CEO turns to you and asks, "What do you think we should do?", it takes courage to go beyond the legal advisor role and offer business advice. You could be wrong, or you could be telling the CEO something he does not want to hear, but it is in exactly that moment that you distinguish yourself from all other lawyers and enter the realm of business advisor. Of course, to become a trusted business advisor, you need to be right more often than not, and you need to be clear and honest in your communications. Being a yes man (or woman) or pontificating for minutes on end will not win you a place as a trusted business advisor.