I ran my group through ashes, from sprawl wilds, recently. Sometimes they used their knowledge skills, but they never really pressed for any information. They went to the meet with no questions asked, they took the job(s) with no questions asked, and did a couple things on the side with minimal information. Coming from a mainly DND background, I think this is from a habit formed from the difference in the systems/scenarios.
I'd like to lightly encourage them to check people out, without screwing them over by ... well having them screwed over from not checking; some positive reinforcement for checking something out before rushing head long into it. Should I insert hours of time between when they need to do things? Should I weave a hint into the job offer? I'd like them to be more proactive in information gathering.
had a bit of this with new players myself, i managed it by having their contacts give them the first run and staying in contact, dropping hints and being available for questions. as the contact is assumed to be friendly/have a bond with the char already i found it gives you plenty of leeway to be over-generous with information. rewarding the right behaviours ie matrix searches with old aerial photographs of target building (thankyou google maps) but being explicit that the image is old and probably out of date, starts leading them to think of maybe doing a recce on the building for up-to-date info or trying to ask the contact if they know anyone who works there etc.
i find its all about positive reinforcement. drop the hints that they should scout out, give them plenty of time and then when they start digging, start rewarding them with useful + relevant info. it wont take long before it becomes the norm, then you can dial the assistance back a few notches.