I have a (mental) list of questions I really hate. Well maybe not hate, but certainly struggle with.

"Are you guys expensive?"

I don't know. "Expensive" is totally relative and I have no idea what you are using as a reference. I can't honestly say "Yes" or "No".

After discussing half a dozen possible project elements: "What does something like this cost?" 

First of all, I am horrible with ballpark figures. Second, I know you say you won't hold me to it- but you kind of will. And even if you won't hold me to it, I will. The number I toss out will be looking over my shoulder as I put your proposal together. Third, there are so many undecided details that any price I give is useless. There is no good way to answer this question.

"How much would it cost if I do some of the work?" 

Oh boy, this one is tough. My Uncle John used to tell people it would cost more. He would laugh, but was really only half kidding. The problem is that most clients want to take on some of the unskilled labor- removing unwanted plants, spreading bark dust, etc. These are also the kinds of things that we can do so efficiently that very little money is saved. But that is hard to explain- without sounding like a greedy control freak.

"How long will this job take?" 

This is a totally reasonable question. One that must be asked and answered. The problem is that I am really bad at answering it. Besides my own bad judgement, weather, employee health, other contractors, suppliers, vehicles, and sometimes even clients can all blow up a schedule.

"When could you start?" 

Another completely reasonable question. Most of this year the answer was somewhere between 3 and 6 weeks from now. That usually surprises, and disappoints, people. I don't like to disappoint people, especially clients! On top of that, the answer I give one day might be wrong the next. A schedule is a moving target.

Asking these questions does not mean I don't like you, or that you are a "bad" client. These are just the questions I struggle with. I am sure everyone has questions they hate. What are yours?