HOW TO HANDLE A LOUSY BOSS—PART 4
Caring Enough To Confront.
As you have already learned from this series of posts, when you genuinely have a lousy boss, you must constantly make accommodations and adjustments. That is just part of the game. However, eventually you want to be a catalyst that prompts your boss to improve. That is when caring enough to confront must occur.
Regardless of how difficult, unreasonable, incompetent, or rude your boss might be, because you are a direct report, you have an ethical and professional obligation to be a force for positive change. That is implicit in the unwritten social contract you agreed to when you said yes to the job. As a professional, you want to exercise your influence for good.
Obviously, every situation is different. Therefore, here are a few factors that you will want to consider as you plan for a caring confrontation:
- Where To Start. You don’t necessarily want to go for the biggest project on the list. It could blow up in your face and only make matters worse. Identify the low-hanging fruit first. You want to go for the relatively easy wins. An early victory will be good for you, your boss, and the team. Simultaneously, it has the potential to open up your boss’s thinking to deeper discussions about bigger situations.
- Duration And Frequency. Your knowledge of your boss’s personality and psychological profile will help immensely on this one. Some people will be open to lengthy and frequent discussions aimed at self-improvement. Other folks may be more fragile. Your choices concerning duration and frequency can make or break the whole endeavor. Therefore, choose wisely. If you are unsure, then begin with something isolated and short. That will allow you to initiate action and gauge your boss’s reaction, which will inform your next step in the larger plan.
- Strategic Alliances. Although one-on-one caring confrontations are often extremely effective, some cases might be better handled with a very small group. Think carefully about whether a mutual colleague should be invited into the caring confrontation with you and your boss. Sometimes a boss who is struggling needs to hear the truth from more than just you. A wisely chosen associate can work wonders.
When you have a lousy boss, a caring confrontation can be a crucial turning point. Please stay tuned for Part 5 where I will try hard to conclude this series.

