Believe it or not, there are some bosses who like confrontation and argument. They like their ideas to be challenged and can quickly adopt better ideas and plans when they hear them. You don't need any advice to work with a boss like that, except to make sure you can support your suggestions with strong arguments.
But lots of bosses see disagreement as a threat to their authority. They might be insecure in their position and uncertain of the contributions they are making. It is always a mistake to confront a person like that, because they will immediately become defensive and feel like they have to 'win' the argument, even if they are wrong.
It's important to surface your disagreements at the right time. In a large group, in a client meeting, or in front of your boss's boss are definitely wrong times.
You should review the material on handling difficult people, because we'll use the same techniques on a defensive boss. For example, let's say your boss is proposing an utterly too optimistic project schedule for a new client. Don't march in to his office and say "This schedule is ridiculous. There's no frickin' way we can deliver on time. I'm not working weekends just because you don't understand how complicated this project is..."
Here's an alternative:
- First find something you agree with - Start out by agreeing with your boss. "This project for Fenster Corp is going to be challenging, but it's a great opportunity for our department and the company. I'm excited about working on it."
- Transition to the impacts of what you don't agree with - Don't make personal attacks "...you don't understand...". Instead, use facts and questions. "It seems to me it took us 5 weeks to complete the first task alone on our last contract. Is there someway it is going to take less time for Fenster Corp?" "There were 10 people working on the previous project; how many will be working on the new one?"
- Surface the issues - Sometimes decision you disagree with is the result of issues you may not be aware of. Perhaps your boss is being pressured by the client or his own management to complete the project sooner. It's ok to ask "Are there other factors we haven't talked about that need to be considered in developing the schedule?" These may or may not be legitimate in your eyes, but don't dismiss them. They have to be dealt with if your boss thinks they are important.
- Collaborate, don't confront - By using a questioning approach, you convey a collaborative approach to shared problem-solving. It's also respectful because you are asking the other person to support their assumptions, rather than confronting them with (perhaps) a poor decision. You may find that your understanding or knowledge of the facts was flawed. If so, admit it. On the other hand, you may be able to reach a negotiated compromise, or at least have your views acknowledged.
