One of my clients has a boss who hoards information and responsibility and doesn’t give him the support he needs to do his job.
Naturally, he wants to influence his boss to lead him better—that is, he wants to lead his boss. You have to see people as people first and positions on organization charts second, take responsibility, and lead them if you want to influence them. The first step I advise in leading anyone is awareness—in this case, understanding the motivations of the person you want to lead. If you don’t understand their motivations, you’ll have a hard time influencing them.
As common as his boss’s behavior is, everyone’s motivation is different. Until he knows his boss’s behavior, trying to influence him will likely end up worse than taking pot shots. When you try to influence someone without understanding them, you risk

• showing you don’t understand them
• implying you know their job (and life) better than they do
• implying you’re meddling
• implying you’re trying to impose your values on them

all of which discourage the person from listening to you. Those risks damage your ability to influence enough with anyone. When the person is your boss, they’ll likely make your boss think “That’s why I’m your boss. Because I know what I’m talking about and you don’t.”
His boss wasn’t sharing his motivations with him though.
As we role-played and discussed the logistics of motivating his boss to open up, my client kept having trouble seeing how to ask his boss effective questions. He kept trying to tell the boss what he wanted. As important as communicating your situation is, if it precedes the other person feeling understood, they’ll hear your talking about your needs as neediness and self-interest.
If you say

“Boss, to do this project well, I need some support from you.”

no matter how you sugar-coat it, your boss will hear these parts of your message

• I’m needy
• I’m asking you to do something for me
• I’m valuing my time over yours
• I’m imposing on you

Great bosses will listen through that, but I don’t recommend counting on it.
My client’s problem was that when he asked his boss for support, his boss would always reply “Well, what do you think?” and when my client answered, his boss would say “That’s what I was thinking too,” or some variation that never led to getting new information or support.

The solution

Finally I said to my client

“You have kids, right”

“Yes.”

“How old?”

“A son who is 10, …” [I don’t remember all four ages. I just wanted to make sure at least one was old enough]

“Imagine your son came home with a bad grade for the second time after telling you he’d do better but wouldn’t share with you the reason. You know there’s a reason. You wouldn’t accept him holding back. But unlike him not doing a chore, you can’t force him to get a high grade. You have to motivate him to learn. You also have to convey to him that you aren’t doing this for yourself but for him. You wouldn’t accept him not answering, but you wouldn’t threaten to punish him if he didn’t either. You’d have to understand him and influence him.”

This approach seemed to make sense. Simply saying to your son “You’re my son so you have to improve your grades” won’t likely work. Nor will saying “You’re my boss so you have to help me” or any variation of “You’re supposed to help me” or “You should help me.” If you treat people like positions on organization charts, which you do when you don’t treat your boss like a person first, they’ll learn to stay formal with you and not share. They’ll sense you’re trying to help yourself, not them.
I suspect you’d say something to a child like

“This is the second time you got a low score. Last time you said you would do better, but you didn’t. You’re not saying what the problem is, but we’re going to have to figure it out. I’m not doing this for my sake. I’m doing it because it’s my responsibility to raise you as best I can. The better you do in school, the better you’ll do in life.”

You would then respectfully but firmly work with him or her until you understood the situation and got their participation. You might say something to your boss like

“I’ve asked you for help before and haven’t gotten it. I’m not asking for my sake. It’s my responsibility to do this job as well as I can and the job needs some project management. The better I do this job, the better you’ll look.”

The point is to make sure of the same three things you would with a child

• You are acting out of responsibility for the job
• Working with you will help them
• You are putting their interests before yours

Treating a boss with kid gloves treats them like they aren’t human. Why would you be surprised by them responding in kind?