Agile Leadership - How do you let self organization happen in this role?

My thought is that as an agile leader you should embody the agile mindset/principle of servant-leadership while also honoring the self-managed, self-directed teams.  So in the situation you described, I would ask myself what is the best way to be a servant-leader and help them become a better team. Is the issue that the Development Team member is bringing to you something needs you to help resolve?  Could it be that they have already exhausted the options that they have and need your help?  Or is it that they haven't tried to resolve it and are trying to take the easy way?  Yes it might be easier for you to just take care of it but would that be the right thing for a servant-leader that is up a level or two to do for them?  Yeah, I know it isn't giving you a specific answer but each situation would be different. 

Part of being a PAL is helping the teams become self-sufficient.  Doing the work for them isn't always the best option. Part of building a self-managed, self-directed teams often involves letting the team fail or suffer some pain in order to work through the problem by themselves. My caveat on that is to make sure that their struggles will not have significant impact to your organization.  If you see them going down that path, step in and coach them to prevent the organizational impact. But if their path will not have significant impacts or impacts that can quickly be corrected, failure and pain are great motivators for improvement.

Thank you for your insight.  When you say letting the team fail and suffer pain, would you say the same thing for any team at any stage of maturity?  I'm thinking you would say yes because an immature team can only become mature if they fail and learn from their mistakes but I would like to hear your thoughts as well.

How do I switch to the mindset of an Agile Leader when it comes to my interaction with the Scrum Team?  If a Development Team member comes to me with a problem do I simply say "Go talk to the Scrum Master", or can I directly help with their issues without involving anyone else.

If this person approached you for help, and you were the Scrum Master for a different team, how would you proceed?

As a leader of a company do I simply set strategic goals and learn to let go when it comes to trusting my team will do the right thing.  Do I trust that they hold themselves accountable or am I still responsible for holding people accountable?

If a CEO asked you this question, as a Scrum Master what advice would you give them?

I guess what I am having trouble with is just that...the concept of a leader having to let go.

My advice would be not to assume that a different mindset is involved at all. Instead, expect the issues to remain the same along with the need for servant leadership. You must still be active without always being seen. Your organizational focus may change.

Thank you for your insight.  When you say letting the team fail and suffer pain, would you say the same thing for any team at any stage of maturity?

Yes, you answered that question just as I would have.