Ask for what you want - the worst is status quo

Few people are going to do anything if you don't ask. What is the worst that could happen? If you ask and they say no, you are no worse off than had you not asked in the first place.

87% of the time, Lenny, when you ask for more money, you get it.

Are you open to 450? That was really what I was hoping for. What I think I'm worth, are you open to that? Is that something we can talk about?

This is great. I want to talk about money, but before we do, I want to think about some of the things that will set me up to see succeed in this role.

If you're more in the people pleasing camp, maybe you're used to not asking at all. You're hoping that people are reading your mind. And if you're sort of more in the control freak camp, maybe you're used to ordering people around and saying, 'Go do this now.'