AMA: HubSpot Head of Corporate Sales, West Coast, Sarah Mercedes (Osborne) on Discovery Tactics

First, you need to understand who your ideal customers are, what they are about, their typical challenges and what success means to them. Then, you need to understand how your product can align to address those challenges and/or support their success. It's critical that you understand who your ideal customers are, so you can articulate the value of your product in their language and within their context.

"How does solving this challenge/capitalizing on this opportunity/addressing this need impact the business overall?" It's so easy to confuse surface level challenges that often times only impact users as the actual "pain" that the company is experiencing. The C-Suite at your prospect's organization are only going to approve a purchase based on a strong business case tied to key business impact, not based on individual user inconveniences or preferences. If you don't have business pain, you likely don't have a real deal. "Why now? What is significant about solving this particular problem now?" Asking "why now" more times than not will provide you with a nugget or two that you can leverage to drive urgency later in the sales process.

If you're getting objections that early in the sales process, it's a red flag. It's critical in sales to disqualify and to do it as early as possible. Time is your greatest asset. Of course, if your prospect is asking questions or voicing concerns as part of their due diligence, answer and address, but if you are getting objections or push back, my advice would be to go negative and say something along the lines of "It doesn't seem as though this is the best fit. Would you agree?" If they do not agree and think the conversations should continue, they will tell you why and you've tied them down a bit in the process.