04 · Discovery
Questions to Ask
Goal: in 30 minutes, know their three biggest operational pains, who owns each, what they've tried, what it costs them, and who decides. Lead with open questions, follow with quantifying ones.
Situation - What is
Open
- Walk me through how a [common operation: project / order / route / closing] flows through your business today, from start to invoice. You're listening for handoffs, paper, and "and then we email so-and-so" moments. Each one is a candidate for the platform.
- What systems are involved in that workflow today? Get specifics. "We use QuickBooks and Excel" tells you about scope. "We have Salesforce, NetSuite, and three custom internal tools" tells you about integration cost.
- How many people touch that process from end to end? Headcount × time = cost. You'll use this in the ROI math later.
- What's been changing - growth, new locations, new regulations, M&A? Change creates the budget. A static company won't buy. A growing one will.
Pain - What hurts
Open
- If you could fix one operational thing this year, what would it be? Direct, simple, the most useful question in this section.
- When that breaks, what happens? Who has to fix it? You're identifying the firefighter - usually a senior person who hates it. They'll be your champion.
- Walk me through the last time [specific failure] happened. What did it cost you? Always make them tell a story, not a hypothetical. Stories carry numbers.
- What does your team complain about in monthly meetings? Their internal vocabulary becomes your sales vocabulary.
Cost - Quantify
Quantify
- How many hours per week does your team spend re-entering data between systems? Multiply by hourly cost × 52. ROI math written for you.
- How long does month-end close take? Quote-to-cash? Onboarding a new customer? Cycle-time numbers are the most undeniable ROI lever.
- What's the impact when [pain] happens? Lost revenue, missed contracts, fines, customer churn? If they can't quantify, the deal is small. If they can, the deal is real.
- If we cut that in half, what would that mean for the business? Plant the seed. Make them imagine the after-state in their own words.
Tried & Failed - What didn't work
Critical
- What have you tried before to solve this? Reveals their decision pattern AND their threshold for risk.
- Why didn't that work? Gold. This tells you exactly what objections will appear, and how to position around them.
- Did you build something internally? Buy something off-the-shelf? Why didn't it stick? "We built it in Access in 2018" = they understand custom builds. "We bought [SaaS] but no one uses it" = adoption is a real concern.
- What would need to be true for you to try something different? Pre-frames the close. Listen carefully - these are their actual decision criteria.
Decision - How they buy
Qualify
- If we built something that fixes [pain], who else would need to be in the room to greenlight it? Decision map. Better than asking "who's the decision maker," which gets you a polite lie.
- What's your typical procurement process for software? Is there a budget cycle? Finds out if they have a 6-month vendor onboarding before you know it.
- What does success look like 12 months after go-live? Crystal-clear success criteria you'll write into the SOW.
- If we send you a proposal next week, what happens after that? Forces them to map their internal process out loud.
The Outside-the-Box Ones
Bonus
- If you woke up tomorrow and your competition had this and you didn't, how worried would you be? Fear-of-missing-out. Often unlocks budget.
- What's the dumbest, most-manual thing your team still does? Self-deprecating, gets honest answers fast.
- If I gave you a magic wand for one workflow, which one - and what would the after-state look like? They design the demo for you. Use their words back at them in the proposal.
- Who in your industry have you seen do this well? Who's gotten it wrong? Reveals their reference points. Tells you who to study, who to avoid being compared to.
- If we don't solve this in the next 12 months, what's the cost? Cost of inaction. Most underused question in B2B sales.