As you try to get me talking about my problems, demonstrate your sensitivity. I do not respond well to someone who asks me right up front “What are your problems?” That’s too assertive and you haven’t yet earned the right to an answer. Similarly, don’t ask “What’s not going well?” I’m not going to answer that. But I might answer “What don’t you have time for?” I can answer that without feeling uncomfortable.

While I am unlikely to tell you my problems, I may be willing to acknowledge problems you already know about. For example, ask me why we do things the way we do, why we haven’t tried certain options. Instead of asking “What problems do you have with that way of doing things?” say “Some of our other clients who do things the way you do have had to contend with the following issues as a result. What have you done to deal with those consequences?” That question gives you an opportunity to show you are familiar with my type of situation, and it doesn’t confront or challenge me.

Excerpted from ‘Managing the Professional Service Firm’ by David Maister, page 117