While I hate to admit it, I sometimes make the same mistakes occasionally. I know better – but for some reason or another I do not ask the uncomfortable questions.

About a month ago, I received a call from a client who left a voicemail telling me that he/she wanted me to sell his/her apartment building. I had cultivated a relationship with this person for several years – trying to be a resource for his/her real estate goals and needs. Before putting the property on the market though, the client wanted to see what his or her 1031 exchange options would look like after the sale of the down leg.

Long story short, I saw the property on the market exclusively listed by another real estate agent a month later. If you have read my previous blogs, then you know by now that I called the client to see what I could have done differently to win the business. When I made the call, the client said his/her partner made the decision to sell the real estate and had a previous relationship with another agent. The partners had not made up their mind about the direction in which they were going with the 1031 exchange, but one of the partners decided to sell the property any way without telling the other partner about it. I realized at that point; I had never asked the client if he/she was the ultimate decision maker.

How and when do you ask someone if that person has the say-so regarding the real estate? Especially without offending them.

In my opinion, it should start from the beginning. If you can strategically AND politely ask the uncomfortable questions, you make your life easier down the road. It is not to say that this approach works for all aspects of life, but it most definitely works for real estate. It is important to consider whether the question is legitimate and needs to be addressed to effectively address the clients’ needs/goals. A couple of ways I go about asking these uncomfortable questions are the following:

1. If we can agree on price and terms today, what is stopping you from signing the listing agreement today?
2. Forgive me for asking, but who would ultimately need to sign the listing contract to sell the property?

I am sure there are many ways of asking the uncomfortable questions. It is a craft that is always being tweaked and perfected over the time. I am curious to find out…

How do you go about asking the uncomfortable questions?