Qualifying with Questions

💡 Key Idea: The first 5-10 minutes of a sales call aren't for selling - they're for diagnosing. Your only goal is to find out if the person on the other end has a real, painful problem that you can actually solve.

✋ Permission Slip: You have permission to disqualify people. Your goal isn't to convince everyone to buy your product. It's to find the small group of people who are a perfect fit. Be willing to politely tell a prospect you don't think they're a good fit, and why. Your time is your most valuable asset.

📊 Outcome

By the end of this section, you'll have a small set of powerful, open-ended questions and a simple framework to confidently guide the first 5-10 minutes of any sales call.

🛠️ Resources

• Sales Call Notes & Qualification Template
• Optional: A call recording tool (Fireflies, Fathom, or Fyxer)

🎯 The Founder's Advantage: You're Not a Sales Rep

Lean into the fact that you're a founder. You're not a coin-operated salesperson running a generic playbook. You're the person who's most obsessed with the problem you solve. Use that to your advantage.

Your superpower is genuine curiosity. When you ask questions, you're not just qualifying a lead - you're also building trust and credibility, and gathering mission-critical product research.

✅ Qualification Framework: The Scrappy Six

You don't need a long list of questions. You just need a few good ones to get the conversation rolling and uncover the truth. Let's use the example of selling Loom (the video messaging tool) to a product design team.

1. The "Current State" Question

This is your opener. It's broad and gets them talking about their world.

"Walk me through how you [do the relevant process] today."

Example (for Loom):

• Q: "Tell me a bit about how your team gives and receives feedback on design mockups today."
• A: "Usually, the designer will post a screenshot in Slack. Then, a bunch of us will leave threaded comments, or if it's complicated, we'll just schedule a 30-minute meeting to review it live."

2. The "Pain" Question

Once they've described their process, you need to find the crack in the system.

"What's the most frustrating part about that process?"

Example (for Loom):

• Q: "How do you like the current process with Slack threads and meetings? Does it work well or could things improve?"
• A: "Honestly, the Slack threads get messy and lose context. But the meetings are a huge time sink. It can take a full day to get feedback that should have taken 10 minutes."

⚠️ Try not to lead the prospect. Here's a bad example of a question:

"Where does that process with Slack threads and meetings feel slow or clunky?"

By asking the question this way, you seed in the interviewee's mind that the process might be slow or clunky, when in reality, it may not be.

3. The "Impact" Question

A problem isn't real until it has a business consequence. This question connects their frustration to a tangible cost (time, money, risk).

"How does that [pain point] impact your team/goals?"

Example (for Loom):

• Q: "You mentioned feedback can be delayed by a day. Does that cause any issues for your sprints or engineering handoffs?"
• A: "It slows down our entire sprint. A one-day feedback delay can push a feature launch by a week if we miss the handoff to engineering."

⚠️ Don't assume impact. A bad example is:

"And what's the downstream effect of that delay?"

This assumes there is a negative effect. Asking "Does that cause any issues?" is more neutral and allows them to say "no," which is also valuable data.

4. The "Past Attempts" Question

This helps you understand how motivated they are and what they've already tried.

"Have you looked at other solutions for this in the past?"

Example (for Loom):

• Q: "Is this feedback bottleneck something the team has tried to address before?"
• A: "We haven't found a great solution. We just kind of live with it. We tried another recording tool once, but it was too complicated to use."

⚠️ Ask broader questions.

Asking "Have you looked at other tools?" is okay, but it's a closed question that limits the answer. Asking "Has the team tried to address this before?" is more open-ended and might reveal they tried to solve it with a new process, not just another tool.

5. The "Desired Future" Question

This is your bridge to the demo. You're getting them to articulate exactly what they want, so you can show them just that and nothing more.

"In a perfect world, what would this look like for you?"

Example (for Loom):

• Q: "Setting aside your current process for a moment, if you could design the perfect feedback system for your team, what would it feel like?"
• A: "If I could just point at the design, talk through my feedback for two minutes, and send a link... that would be a game-changer."

⚠️ Encourage big-picture thinking.

A bad example is: "If you could improve one thing..." This can limit the prospect to incremental improvements. Asking them to redesign the process invites transformative answers and uncovers the true scope of their ambition, which is exactly what a founder needs to hear. It's then up to the founder to distill, through additional questioning, which aspects of that new process are need-to-have vs. nice-to-have.

6. The "Active Priority" Question

This is a crucial pre-demo check. It helps you distinguish between a problem they have and a problem they're actively trying to solve.

"How high on your list of priorities is fixing [the problem] this quarter?"

Example (for Loom):

• Q: "Where does fixing this feedback process fall on the team's list of priorities right now?"
• A: "It's becoming a real bottleneck. We have a goal to ship features 20% faster this quarter, and this is one of the main things slowing us down. So yes, it's a priority."

⚠️ Don't assume it's a priority.

A bad example is: "How high on your list is this?" This assumes it's already on their list. Asking "Where does it fall?" is a neutral question that allows them to say "It's not on our radar," which is critical information for you.

🔍 The Post-Demo Check-In

After you've shown them how your product solves their specific problem, it's time to gauge their actual intent to buy. These questions help you understand if this is a real opportunity or just a "nice-to-have."

"Have you set aside a budget for a solution like this?"

(A simple way to bring up the topic of money.)

"What does your process for evaluating and purchasing new tools look like?"

(This uncovers the path to a real "yes".)

🤫 The Most Important Skill: Shutting Up

Your job is to ask a good, open-ended question and then be quiet. Let them talk. The awkward silence is where the truth comes out. Don't jump in to fill the void. Listen, take notes, and ask a thoughtful follow-up question. That's the whole game.

✏️ Assignment

1. Practice the Scrappy Six questions with a colleague or friend about any process they use
2. Prepare your version of these questions tailored to your specific product and customer

🚀 What's Next

Now that you know how to qualify prospects with questions, we'll move into the demo phase. You'll learn the "Show, Don't Tell" approach that lets prospects experience your solution rather than just hearing about it.