Inevitably the leader faces difficult choices and the difficult conversations that emerge from those choices. The most difficult for me as a leader were the ones that had personal implications for staff. One that comes immediately to mind is those conversations around under-performance. I don't think anyone enjoys these conversations. The temptation is strong to understate the degree of under performance so as not to confront the real shortcomings of the employee. I once had a young woman who was attempting a role that was new and foreign to her prior experience. After much coaching and feedback she wasn't getting any better....she just didn't have the aptitude for the kind of work we were doing. I knew her performance conversation would be difficult because she wanted to succeed at the new role so badly and had tried so hard to be successful. It was, as expected, a difficult and emotional conversation. She had a huge emotional stake in being successful in the role and confronting failure was difficult. The easiest thing that would have avoided the difficult conversation would have been to "soft sell" her shortcomings, thereby implicitly encouraging her to continue. Had I chosen that course of action we would have had the same conversation six months later. This is what I mean by the easy way out usually leads back in...failure to confront a challenge only delays the conversation and makes for an even more difficult conversation later.
Performance conversations issues aren't the only difficult choices a leader has to make. There are choices about resource allocation, priorities, organizational reporting relationships, promotions, competitively selected positions....all of which can have significant personal impact. Experienced leaders intuitively know the right thing to do and also know it's a more difficult course of action. Forcing yourself to do the harder right thing rather than the easier wrong is a key element of effective leadership.