Over the years, I've led several groups and had a hand in discipling many girls. Early on, I told myself that if God wanted me to have hard conversations for the sake of character growth, that I would do it. I would risk "being liked" because I didn't want to miss the opportunity.
I think it's easy to chicken out for the sake of not wanting to step on toes, but when your heart is right and you don't make it about you, it's amazing the value (not judgment) the other person feels.
We all know Paul spoke so boldly that it ended him in prison sometimes. He wasn't scared to risk that for the sake of obedience. I would have loved to witness the reaction of the church as they read Paul's letters. Were they offended, shocked, grateful? All I know is that God is not about religion. He's about the state of your heart and for that I'm definitely willing to risk speaking boldly.
Scripture reference : Romans