Hope this is the appropriate forum, this is a unique situation and one I haven't really had to deal with before. Background: Small growing business. About 75 employees with handle of about 1300 small business clients. Started 3 years ago, last year was first year of growth. Projected 180% growth in Year 4. I'm part of Sr. Management, a group of 6 of us. A few months ago we brought on a new employee to the Sr. Management team, the first at that level in the Marketing Department (other than myself). We would be working very closely together as he got started and in the future. We became pretty good friends (in the work environment) and he trusts me as his closest ally in the office for sure. I noticed right off the bat that he wasn't a very hard worker, but he did enough to got draw much criticism or attention at the beginning. His boss (and mine) is usually out of town and isn't a micro-manager, leaving his direct reports to be primarily responsible for their own duties and time. Recently he's been completely absent. He shows up at 10:00-10:30 (when everyone else is supposed to be there at 8 or 9) and leaves between 3 and 4 (when most leave at 5 or 6). He'll also "work from home" a day or two and do basically nothing. He largely gets away with it as he's new and most people at the company don't know him or what his hours/responsibilities are supposed to be. While it largely isn't my business, it's beginning to affect my work experience and duties. We work closely and I'll give him list of things I need help with or done and he will completely ignore or forget. We've talked about it, and he'll usually do it if I apply pressure, but our friendly relationship makes it really difficult to cross certain lines. The biggest problem however is that this person is responsible for spending a large piece of our budget this year running ad campaigns and such. A bad performance could directly reflect my job and the company. I've talked to him about having a stronger presence in the office and working more, but he always has an excuse or feels like I'm on his "team" if he didn't feel like working that day. I'm not sure how to proceed. Another conversation with him? Talk to the boss? My boss (who runs the company) and I have a great relationship, and I definitely don't want to seem like I'm trying to throw a guy under the bus or angle in any kind of way.