- How do you approach opportunities?
- How do you view the progression of an opportunity? How do you know if you're in a strong position to win or there's a need to adjust?
- What are the primary challenges and obstacles that you face in connecting with prospects and customers?
- What aspects of the sales process do you feel are more difficult than they should be?
- Why do you win business? Why do you lose business? Why do you lose business that you should win?
A Note on Deep Dive Conversations
Deep Dive conversations are designed to get your thinking started, so the agendas will be fairly loose at times. We'll know we have a good deep dive if the meeting is conversational in nature. We will allow the conversations to dictate the questions, as the greatest insights often come from the 3rd follow-up question that we hadn't expected to ask but asked because of something said.