It’s very easy to influence people’s answers based on the questions you ask. For example, if you ask a leading question such as… So you’ll have that report on South America finished by Friday, right? Then you’ll be much more likely to get a positive (and possibly misleading) response than if you ask something more balanced along the lines of… When will the report on South America be complete? Of course, there’s a big difference between getting the superficial answer you want and getting the true, underlying data you need to make an accurate estimate or decision.
The questions you ask determine whether you will get realistic information back or not. Be careful how you phrase them. Balanced questioning can be critical in spotting potential problems early.
If you want to take it to the next level, you could probe after the initial question. When’s the earliest you’d could ever produce the report, what would cause that to happen? When’s the latest you’d get the report, what would cause that to happen? That way you can move from a single point estimate to a range of outcomes, with the latter being more reflective of the real world.