• Walk me through your last three roles. (a) Why did you accept the role / what were you looking for? (b) What was the nature of the sale (size of customer, size of deal, # of stakeholders involved, sales cycle)? (c) What was your biggest accomplishment in the role? (d) What was your biggest mistake and what did you learn? (d) Why did you leave?
• Walk me through the most complex deal that you closed in the last year. Share step by step how it got done.
• As an AE, what data are you looking at daily/weekly to know how you’re performing?
• Tell me about a time you lost a major deal. What went wrong? What did you learn?
• If you’re getting ghosted a lot in deals, what does it mean and what do you do?
• What is your sales superpower?
• What are you not good at / need coaching on? How would your last boss answer the above questions?
• Tell me about a customer you signed in the last year or two that you’re still in communication with today.
• As one of the first sales hires, you won’t have access to a ton of collateral or supporting material. How do you overcome this?
• At our stage, we are sometimes selling customers on our ability to deliver on features promised in a roadmap. How do you think about selling roadmap items? How do you manage customers’ expectations?
• Can you explain [industry] to me? What types of customers do you think we’re a great fit for? Who are the big players in our space?
• On a scale from 1 - 4 how would you rate your technical savvy-ness and why?
• What’s a technical objection you’ve gotten in a previous role and how did you overcome it?
• What’s the oddest thing you’ve ever done to get a partnership across the line?
• What’s your biggest concern about taking this job?
• If you were to start tomorrow, what’s the first thing you would do?
• Tell me about the last thing you learned at your company, and how you went about learning it?
• Tell me about a time something wasn’t going well at work.
• What are you passionate about?