Answer:

There can be only one reason you are hesitating to step in and help your boss solve this problem: his previous behavior must be telling you he won't receive your input well. Otherwise this shouldn't be an issue. If he hasn't demonstrated that he's defensive, perhaps you are over-sensitive about being assertive.

In any event, the best way to approach your boss is as a partner not an "expert." There is a possibility that this situation is different from the one you were exposed to before, and you don't want to come across as a "know-it-all."

For example, you could say, "How is that xyz issue coming...? (Listen for details and ask specific questions that will tell you if your solution idea will work.)...You know, this problem sounds a lot like something I worked on before in my last job. I wonder if that solution would work on this problem...Maybe it would be worth it to spend a few minutes talking about how that problem is similar to this one. You're closer to the problem and could tell if this idea would work."

In this way, you've opened the door without sounding pushy. As you talk about the problem, listen carefully for the differences between this problem and the other situation. Sometimes we wed ourselves to a solution we've used before because we fool ourselves into thinking the issues are the same. Another trap some people fall into is constantly talking about their former place of employment until their boss and co-workers want to say, "If it was so great there, why don't you go back!"

After you've listened carefully, and if you feel that the solution you've used before is the right approach, talk about the benefits as well as the risks and negative consequences. This will build your credibility as a thoughtful problem-solver who can be relied upon to provide a balanced view of all sides of the issue.

If your boss is smart, he will recognize how much you have to offer and will seek out your opinions and expertise as a matter of course. Start making your boss look good and you'll look good, too.