I don't see the need to talk to him.<p>For one thing, it sounds like your satisfaction there will boil down to your personal agenda. If you are trying to build a world-class IT shop, you'll struggle. If you are trying to help the non-profit do their work, which will clearly entail sacrifices in IT, you'll be fine.<p>Also, if further prying did not give more info, then they expect you to make decisions based on what they told you. If you need more info, you may have differences in communication styles that will lead to problems down the road.