People will hardly ever speak up if you ask, “Are there any questions?” – How many times have you been in a meeting (or, worse, leading one) when, after all the presentations, someone asks, “Are there any questions?” and the response is crickets. That’s because most people are never going to step up and ask the first question in front of a room.
As humans, we tend to feel a bit stupid when asking questions. If you think back to your school days you were made to feel that asking questions meant you didn’t understand something and so you would hold back on asking too much to avoid looking stupid in front of your peers. Of course, no one wants to feel stupid and it is always easier to remain silent than risk feeling embarrassed.
Again, that’s especially true when there is a lot going on and a lot of change. If you really want to know what people think (and you should), don’t ask, “Are there any questions?” Instead, ask “What are we missing?” or “What’s going on that we need to pay more attention to?” If you really want to grease the skids, pose one of those questions and then give people ten minutes to talk about it in small groups and then ask for some spokespeople from each group. You’ll almost certainly get better information that way.
Summing-up: The best way to encourage questions is to create a “question-asking environment“. You must encourage questions constantly by allocating some time for the audience to reflect on the content and have them proactively brainstorm some questions in pairs or smaller groups.