Hey there,

If your buyer could find the answer to your question on their own website, you've already lost credibility.

Situation questions are the most misused part of discovery. Most sellers treat them like a checklist, rattling off questions about team size, tools, and process without doing a single minute of research first. The buyer checks out, gives you surface-level answers, and you walk away thinking you had a "great discovery call." You didn't. You had an interview that went nowhere.

Last week, we introduced the SPIN framework (if you missed it, catch up here). Today we're going deep on the S - Situation Questions - and specifically how to use them without sounding like you're reading from a script.

Let's get into it.

In order to run a discovery call that actually moves a deal forward, you need to walk in with context. Situation questions aren't only about gathering basic facts, they're about demonstrating that you've done your homework and earning the right to go deeper.

Here's how to make them count.

This is non-negotiable. Before you ask a single situation question, spend 10-15 minutes researching the company's size, tech stack, recent news, and anything publicly available about how they operate. (Steal this AI prompt to help)

Why? Because the fastest way to lose a buyer's trust is asking something you should already know. Your situation questions should build on top of your research, not replace it.

Instead of "How big is your team?"

Try:

"I saw you've grown the team by about 30% this year, how has that changed your process?"

Same category of question. Completely different level of respect.

The best discovery calls feel like conversations, not interrogations. The funnel technique gets you there.

Start broad: "Walk me through your overall process from end to end."

Then narrow: "How does your team handle the initial evaluation step?"

Then get specific: "What criteria are they using at that stage?"

Then probe: "How consistently is that applied across the team?"

Each question builds naturally on the last. You're going deeper without it feeling forced.

And bridge phrases like "That's helpful context, building on that..." keep the conversation flowing instead of making your buyer feel like they're being cross-examined.

Here's what most sellers miss: situation questions aren't just about gathering information. They're a diagnostic tool. Your buyer's answers tell you how to run the rest of the deal.

High-readiness signals - like standardized processes, clean data practices, and a track record of successful technology adoption - mean you can move quickly to problem and implication questions. You've got a buyer who's ready to act.

Low-readiness signals - like inconsistent processes, underutilized tools, or competing priorities - mean you need to slow down. Spend more time understanding their constraints before you push toward a solution. Misreading these signals is how you end up with a proposal that never closes.

That's it.

Here's what you learned today:

Situation questions set the table for everything that follows. Get them wrong, and you're building your entire deal on bad information.

Your action step this week: Before your next discovery call, spend 15 minutes researching your buyer. Write down what you already know, then craft your situation questions to go beyond that. Notice how differently the conversation goes when your buyer realizes you've done your homework.

Next week in Part 3: We'll tackle Problem Questions: how to surface the pain your buyer has been living with so long they've stopped noticing it.