Competitive Discovery Question Set

24 questions across 8 categories. Weave 2-3 naturally into a call — never read the list top to bottom.

1. Opening the Door (low-friction)

1. "Where are you in the process of looking at options — just starting to look around, or already got a shortlist?"
2. "Besides us, who else is on your radar for this?"
3. "Is this the first time you've tried to solve [problem], or have you been through an evaluation like this before?"

2. Status Quo / "Do Nothing" Competitor

1. "If you did nothing and kept things exactly as they are today, what happens to [specific consequence] six months from now?"
2. "What's stopping the current way of doing this from being 'good enough'?"
3. "Who internally would be fine with things staying exactly as they are?"

3. Named-Competitor Surfacing

1. "When you say you're 'looking around' — is that a formal RFP, or informal conversations like this one?"
2. "Which vendors have you actually had a call with, versus just requested pricing from?"
3. "Is there a clear front-runner right now, or is it genuinely open?"
4. "Who put [Competitor] on your radar — inbound from them, or did someone on your team bring them in?"

4. Perception & Sentiment (how they REALLY feel)

1. "What's your honest reaction after talking to [Competitor] — impressed, underwhelmed, somewhere in between?"
2. "What's the one thing [Competitor] said that made you go 'hm, not sure about that'?"
3. "If [Competitor] weren't in the picture at all, would your shortlist look any different?"
4. "On a scale from 'just doing due diligence' to 'genuinely torn between us' — where's this at?"

5. Incumbent Vendor / Renewal-Specific

1. "What's working well enough with [current vendor] that we'd need to match or beat to earn this?"
2. "What's the actual trigger for looking elsewhere now, versus renewing on autopilot like last time?"
3. "Does [current vendor] know you're evaluating alternatives — and if so, what have they offered to keep you?"

6. Evaluation Criteria & Weighting

1. "When you sit down to actually compare us, what are the 2-3 things that will make or break the decision?"
2. "Of those, which is non-negotiable versus 'nice to have'?"
3. "Who on your team is most skeptical of change, and what would it take to win them over regardless of vendor?"

7. Red Flags / Losing Ground

1. "Has anything come up in these conversations that's made [Competitor] look better than expected?"
2. "If you had to bet today, who wins this?"

8. Late-Stage Confirmation

1. "Before we go further — is there anything about [Competitor]'s offer we haven't addressed that's still sitting in the back of your mind?"
2. "What would need to be true for us to be the easy, obvious choice by [decision date]?"

Rules for Using These

• Never disparage a named competitor — ask sharp, fair questions instead of making claims about them yourself.
• Ask one competitive question at a time, woven into the natural flow of the call — never stack them into a block that feels like an interrogation.
• After any sentiment question (11-14), stop talking. The honest answer usually comes in the pause, not the first sentence.
• If a prospect won't name a competitor directly, questions 4-6 and 18-20 still surface the comparison indirectly without requiring a name.