Picard,

First off, kudos on coming here and asking the question. It's often not easy to to that.

Many here have already hit upon some great suggestions. And this is one of those subjects that have lots of paths to success. But my experience training leaders over the years has crystalized a few thoughts you might find helpful...

#1 - Assertiveness is a habit. That means it can be learned just like shyness was. That's important to remember.

#2 - Like all habits, repetition is key. At times it will be uncomfortable. Be prepared for that and accept it. You are learning a new way to act so by definition you are out of your comfort zone.

#3 - Start by helping people. This may sound counter-intuitive at first until you understand it. Instead of starting out by asking for things for yourself, many people find it easier to start being assertive by doing for others. Go into a meeting/situation looking for who you can help. Who's situation can you improve? Which person at the table can you make more successful? Who can you help win? By helping others win, you will find that you most often get what you need. Or at the very least, it will give you the "right" {in your own mind} to ask for what you need.

#4 - Continue the win-win strategy by offering options that YOU shape. Asking yes/no questions can be scary at first. That fear of rejection or closing down the options can paralyze people. Instead, craft options that are win-win in nature. You will find it much easier to be assertive. For example... instead of asking the boss additional resources (yes/no), craft options YOU can live that help HIM/HER win. "Mr Bossperson, I know there is always a lot of pressure to get the monthly report published. And it's a visible project. There are a couple of options that might help. We could either move submission deadline up to Tuesday or maybe publish via website instead of paper. Which of those do you think would work better?"

The key for #4 is the format. State issue and how you are helping that person. Offer two options that will work and you are comfortable with. Leave the decision to them. This format leaves "authority" with the other person, but you are in fact the one driving the solution. It preserves egos and is easy to do.

I hope this helps and good luck. And if you are interested in discussing more of this, send me a PM.