Once a coworker was trying to sign a prospective client. Our boss constantly had to check in with him to see what progress was being made, and the work simply was not getting done at the pace the boss wanted. There was a significant risk that we would lose this big client. I did not want to overstep any boundaries, but I offered to help my coworker with the research. I think my coworker was a little too prideful to outright ask for help, but I could tell he was grateful for the help, and we ended up splitting the commission when we landed the client.