Picture yourself preparing for a presentation coming up in two weeks. You are preparing to present to a senior level decision maker and you are working with a coach or contact to better understand that person. You are building a profile of the things you need to know about that person, such as their background o both professional and personal o their objectives, strategies, hot buttons, issues, and concerns. Other things on your mind may be more personal than that. For instance, you may be wondering how they like to spend their time when they are not working. It could be that they have a hobby, avocation, or association that would be helpful to understand. How do you ask the question "How does this person spend their time when they are not working?" and when do you ask it.

First of all, we are safer when we can ask that question of a good coach. We can tell a good coach "I would really like to understand how this person spends their time when they are not working. I'm curious as to whether there are any interests we have in common." That will sound absolutely fine to a good coach.  A contact, on the other hand, may not understand that positioning. If you think the contact is open, go ahead and ask it, but err on the side of caution. Downplay the importance of your request. We don't want to be perceived by anybody as trying to "dig up the dirt".

Lastly, if we don't have a good coach or a contact we are comfortable with, let's not ask the question at all. There will be time later in the selling cycle for us to gather that information.