What are your favorite discovery questions to ask prospects early in the sales process?

We often follow up with people who have requested a white paper or a copy of our book on sales coaching. In this case, I'll ask the question, "what prompted you to request a copy of a book (or white paper) on sales coaching?" The discussion that follows is rich.

I've created a whole workshop around this and I believe it's a huge skill gap right now. One of my favorite questions to ask is the first question, and that’s pretty much it. The first question is along the lines of, "What prompted you to take the meeting today?" or "Help me understand what's going on that led you to take the meeting now." This question is both open-ended and time-specific, which I think is critical.

For example, if I’m talking to someone on a discovery call who has come to me as a potential client, one of my favorite questions is, "Help me understand what's going on with your team right now." It’s general and allows the buyer to start talking, revealing what’s important to them. Adding the element of "Why now?" helps you understand what’s going on in the buyer’s current environment that is prompting them to spend their time with you right now, even if they’ve responded to a cold call or booked a meeting from one.

Why change at all from the status quo? You're getting by now without doing anything what is driving a look at software/your solution?

While this may seem counterintuitive it's good for many reasons, 2 listed below:

1. Get them to think through if they really would make a change? Often, to be honest, the answer is that the change will require a lot from them. Is it worth it? Secondly, they may be someone who's being nice to you and listening and engaging simply because they're a friendly person and they have no intent to buy. Best to give them an out amicably and not waste your and their time. 

2. Helps them think through what specifically they need to change, and if they agree that they need to change, they've gotten there based on their own thoughts and considerations. Not because you've called them and sold them something but because they genuinely want to do something better/differently. This is preventative of future churn if your product or service can deliver

What is the status quo - e.g. a manual process developed in house?, maybe, no process at all?, an offering from a competitor? What are the strengths and weaknesses of the current solution? What are the major drivers to considering a change? Who are the ultimate decision makers versus people who are influencers or evaluators? What is the broad timeline for getting a solution in place? Is there budget available already?

What are the biggest challenges the organization is facing that every function is accountable to solve for?