I would say the first question is "Why should I work with you" and the second question is "Will you give me a list of referrals I can call."
The questions will vary depending on whether you're seeking a buyer's agent, or a listing agent. In either case, asking them to produce their MLS statistics may be helpful.
For a buyer's agent:
* How many houses of the type I am looking helped to purchase in the last 6 months / year?
* What was the list/sale ratio of those sales (that'll help identify their negotiation skills)?
* Will you help me strategize when it comes to negotiations?
* How many homes do you think it will take to find what I'm looking for... how long should it take?
* What is the average list/sale ratio in our area?
For a listing agent:
* How many homes of my type have you listed in the last 6 months/year?
* What was the list/sale ratio of those homes
* What was the average days on market for those homes
* Please describe your marketing strategy for my home
* Describe your strategy for price reductions, and timeframe
* What is your recommendation for price, for a quick sale, moderate sale, squeezing-every-dollar-outta-the-house sale... and which do you recommend and why?
That should start the conversation.
Get a good feel for the agent... leave some "silence" in the room, and allow them to fill it (we agents love to talk about ourselves)... ask them to describe the overall experience of a recent purchase or sale.
WOW, did you get some great responses. Some here in The City and others from a great distance. They all put out some perfect questions but the common theme is one of "comfortability and trust". The best way to get this in a short period of time is to interview a couple/few and ask for a list of people that you can talk to. Be careful with this list because any agent should be able to pick people to give them positive referrals.
I liked the Grenier groups answer coupled with Deborah's answer. However, I'd also include some questions surrounding the ideas of Tenants Rights, TIC/Condo, Mulitple Offers and basic neighborhood knowledge of the areas your interested in.
All in all, a very good question/response session.
Why are you the best agent to represent me in the search and purchase of my next property? (Buyer)
The agent needs to know a little bit about you and your goals in order to provide a meaningful answer. An agent who is able to ask about your needs, listen to your feedback and direct and advise accordingly will use their knowledge and skills and be focused on you.