Making the big ask

I was reading Bill Hybel's book Axiom. It's full of "leadership lessons" he's learned over the years. A lot of times I'm frustrated by books like this, but (in general) I find Hybel's stuff to be really inspiring and insightful.

The second chapter hit me between the eyes. In it he says that early on as a pastor he realized that much of his job would be asking other people to do stuff. Asking someone to take on a new ministry. Asking someone to give more generously. Asking someone to become a Christian. Asking someone to fix this or that problem.

Here's my problem. I hate asking. I'd rather do it myself. I know this is a major flaw in my ministry. When I do ask, I often say "no" for the person. (Bill addresses this later in the book. I'm scared to read it.)

Bill makes a couple of helpful points:
(1) If asked properly - people should be flattered that you asked even if they choose to say "no". You ask because you think highly of them.
(2) Asking properly is the key. He says it should be clear that you've thought and prayed about asking. It should also be clear that your friendship will remain whether they say "yes" or "no". Then you just ask clearly and succinctly. After asking you invite the person to consider and pray about it with a timetable for getting back.
(3) When someone does say "no" you've got to genuinely accept it and remain friendly.

There is one thing that Bill doesn't address which is a big part of my problem. I don't WANT to contribute to people being overcommitted. So when I see people struggling to do what they've already promised, I'll often not ask. This robs them of the opportunity to decide for themselves. My problem is that some people will say "yes" to almost anything a pastor asks. They feel guilty if they say "no". Knowing this, I feel a lot of pressure when I ask. But I think it's an area I need to grow into because...

Finally (Bill doesn't make this point, but I will) at some level it's arrogant not to ask. Who thinks they can do everything by themselves? Who thinks they can do everything best?