On this day, Valentine's Day, I have been drawn back again to the phenomenon that was caused by an article in the NY times by Mandy Lee Catron, To Fall in Love With Anyone, Do This and the follow up article by Daniel Jones, The 36 Questions that Lead to Love. They were based on the research conducted by Arthur Aron and his colleagues about how answering 36 questions can lead to increased intimacy (and even love and marriage) between strangers. The first is a gorgeous story to read on a day like today and the second contains the questions worth mulling over for your own relationships.

Both got me thinking.

What are the best questions to ask a client or prospective client that can lead to client intimacy? What questions gradually deepen the mutual understanding between relative strangers in a business context? What questions make you think more deeply and share more fully? What takes the conversation from a chat about the weekend's sporting or family pursuits, to a genuine exchange about business-related important matters?

Now I'm sure there's a whole book in this somewhere (and I know there are books outlining questioning techniques and types, etc.), but let's start from the ground up. What do we really, truly want to know and share? In the interests of my typical LinkedIn posts (and it's Valentine's Day and you may have better things to do than read this!), I'm going to keep it short - so 10 Questions instead of 36.

Here's my list in increasing order of intimacy. Let me know if you have others or you think these could be improved...

We've got some thoughts, but what do you want to cover off today?
We’ve done our research from public sources, [so we know, for example…] but what else can you share that we wouldn’t have been able to find publicly and might be relevant to today’s conversation?
Do you mind if I ask, what is your usual reason for choosing to use an outside provider - internal capacity shortfalls, lack of specific technical expertise or some combination?
When you review the performance of existing providers, what would the scorecard look like?
In a hypothetical sense, if you were to work with one outside firm only, what would the perfect relationship look like?
What advice would you give us to improve our chances of being invited to work with you in the future?
Where do you, personally, and your firm, more broadly, sit on the spectrum of accepting risk when it comes to complex business decisions?
What does your Board/Supervisor/Manager most worry about when it comes to our services and how does that manifest itself in their decisions about who is chosen to do the work?
If there was one concern you'd love to have the answer to, that would make your life a whole lot easier, what would the problem be?
In a very practical sense, what would we both need to do to increase the levels of trust shared by our respective businesses?

I'd love to hear your feedback.

Paul McAllister has been asking questions of himself for over 30 years, in a vain attempt to get better answers. He also asks practical questions of professionals in accounting, law, engineering and architecture that he trains and coaches in the art and science of business development to help them successfully work towards better answers.