A pet peeve of mine is when a development office spends all their time talking about donors and none of their time talking to donors. Has your organization ever fallen victim to this trap?
It is important that you do the needed research and you ask in the right timing. And it is also a good idea to gain input from those experts at your nonprofit that know how to ask for money and know the donor you are talking with. But do not get caught in the cycle of perpetual preparation.
Development Officers should spend a lot of their time out of the office. These individuals should be grabbing coffee with your major or principal donors. They should talk with them about why they give and call them with updates about the organization. As that relationship grows they better understand how to cultivate and steward these individuals and how to ask them for money.
If you spend a large part of your time actually talking to donors then you do not need to spend quite as much time talking behind closed doors about them. Talking to donors as a practice is much more efficient than only talking about them.