When you notice that something seems off, even slightly, then ask 'why' and keep asking until you get to the right answers. Sounds simple but it is incredibly hard to do, and most people just let things slide instead of asking questions. Here is why:

Sometimes we are afraid of sounding stupid. What if my question isn’t well informed?

While I am in discovery sessions with clients I like to start the day saying, “I need to ask for permission to ask you stupid questions, because I won't know if my question is stupid until after I've asked it and we've explored it." Maybe the question is stupid. No problem, lets move on. Maybe it is the question that uncovers the biggest piece of gold in the entire session. I have no idea. And trust me, I ask plenty of stupid questions to get to a good one.

Sometimes we are afraid of people getting defensive. Will you get tired of my incessant questioning?

I also start discovery sessions asking the client for permission to ask a lot of tough questions. Here is how I phrase it, “I’m on your side but I’m going to be asking hard questions. It doesn’t mean I don’t like you, in fact, in means the opposite. Sorry in advance if I come across as a dick." Usually the client is glad they have someone aggressively questioning them and at the end of the day the feedback is usually that they wished I had questioned more.