Finding and developing context in your conversations AND Asking the right questions

Entrepreneur Mastery Lab - Finding and developing context in your conversations

Finding and developing context in your conversations is at the heart of the biggest riddle anyone in sales can face….what are the right questions to ask? Asking good questions is an art form. Speak to any master salesperson and in today’s world, it’s not about slick talk, it’s about meaningful questions. Ask someone a meaningful question that gets them thinking and you may just open their eyes to a problem they didn’t know exist, or at the very least, key in on the true issue at hand and the real problem that needs to be solved.

In Humble Inquiry, Edgar and Peter Schein attempt to provide us with a guide to asking good questions. As someone in sales that has always wanted to know what the ‘right’ questions were, this was an incredibly helpful book. After all, how many books out there really train you on how to ask good questions? It’s generally not the most popular topic people are talking about.

It may end up being one of the most important books to read as a business owner, however. In a day and age where sales has evolved from being an offensive game to one of collaboration and partnership, asking good questions is the ultimate consultant move. To be clear, this isn’t to say I loved the book, that would be a lie. It felt and read a little too clinical and technical for my taste. Still, there were some tremendous insights in the book that are worth sharing, especially around context.

Context is brought up in the book from many perspectives, and, rightly so! Here are the primary areas of context that are especially helpful to a service-based professional or business owner.

1. Why am I asking this?

It’s easy to ask questions. We’ve been doing that since we were kids. Asking the right questions that will elicit an informative response from our clients and prospects is an art form. The first step in gaining expertise in the art of question asking is to ask yourself first! Yup, that’s it, right there. The very first question to ask is internally, to yourself. Why am I asking this? If your answer is internal and not external (about you and not about them) you need to pause and re-think whether it’s the best question to ask.

2. Why are they asking me this?

What’s really behind their question. Is it what they are asking? Often times the questions we are asked to respond to are not the questions that will address an issue at hand. Technical questions are a great example of this. Most of the time the technical information being asked for is easily accessible, who doesn’t have google, after all? Answering here will still help address something directly, you just need to consider what’s the driving force behind the question and is that really a technical issue or is it something wholly different and greater that needs to be answered.

In short, the Schein brothers ask you to ask ‘why?’ In a world where it’s very easy to speak fast and barely listen, it’s time to step back and consider the context of why we are asking a question and why a question is being asked of us.


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