OST Interviewing

Master the art of story-based customer interviews that reveal unmet needs, pain points, and desires.

Core Principle

Opportunities emerge from stories, not from direct questions.

Ask customers to tell stories about their experiences. The gold is in the narrative details, not the opinions.

The Wrong Way to Interview

Don't Ask Direct Questions

• "What do you like to watch on Netflix?"
• "What features do you want?"
• "How would you improve this product?"
• "What's your biggest pain point?"

Why this fails:

• Leads to unreliable, surface-level answers
• Misses actual behavior and context
• Gets opinions instead of needs
• Customers suggest solutions, not problems

The Right Way to Interview

Ask for Stories

• "Tell me about the last time you watched something on a streaming service."
• "Walk me through what happened when you tried to [do task X]."
• "Can you describe a recent time when you struggled with [context]?"

Follow Up Relentlessly

• "What happened next?"
• "Tell me more about that."
• "How did that make you feel?"
• "What did you do then?"
• "Why do you think that happened?"

Interview Structure

Opening (5 minutes)

1. Set context: Explain you're learning about their experience, not selling
2. Make it conversational: "This is just a conversation, not a formal interview"
3. Ask permission: "Is it OK if I take notes?"

Story Collection (40-50 minutes)

4. Start with recent behavior: "Tell me about the last time you..."
5. Let them talk: Don't interrupt the narrative flow
6. Follow the thread: Ask "What happened next?" to keep the story going
7. Dig deeper on struggles: When they mention difficulty, explore it
8. Get specifics: Ask for actual screen names, button labels, exact steps

Closing (5 minutes)

9. Thank them: Acknowledge their time and insights
10. Ask for permission: "Can I follow up if I have more questions?"

Question Patterns

Pattern 1: Recent Behavior

"Tell me about the last time you [did relevant task]."

Why it works: Recent memories are more accurate, less filtered by opinion

Example:

• "Tell me about the last time you tried to book a meeting room"
• "Walk me through the last time you filed an expense report"
• "Describe what happened the last time you onboarded a new team member"

Pattern 2: Narrative Continuation

"What happened next?"

Why it works: Keeps the story flowing, reveals the full sequence

Example conversation:

• User: "I opened the app to find a restaurant"
• You: "What happened next?"
• User: "The search bar wasn't where I expected it"
• You: "Tell me more about that"
• User: "I kept looking at the top of the screen but it was hidden in a menu"

Pattern 3: Specific Instance

"Can you walk me through exactly what you did?"

Why it works: Gets concrete details instead of generalizations

Example:

• "Which button did you click?"
• "What was the exact error message?"
• "Where on the screen were you looking?"
• "How long did you wait?"

Pattern 4: Emotional Response

"How did that make you feel?"

Why it works: Reveals intensity of the pain point

Example:

• "How did that make you feel?"
• "What went through your mind at that moment?"
• "What did you think when that happened?"

Pattern 5: Context Expansion

"Tell me more about [specific detail they mentioned]."

Why it works: Extracts opportunities from throwaway comments

Example:

• User: "I had to check three different places"
• You: "Tell me more about those three places"
• [Opportunity discovered: "I can't see all my information in one view"]

Listening for Opportunities

What to Listen For

Pain points (Struggles, friction, frustration):

• "It was hard to..."
• "I couldn't figure out..."
• "I got stuck when..."
• "I had to do X multiple times..."

Workarounds (Indicates unmet need):

• "So I just..."
• "My hack is to..."
• "I use [other tool] to..."
• "I have to remember to..."

Time sinks (Inefficiency):

• "That took forever"
• "I waste so much time on..."
• "I have to wait for..."

Confusion (Lack of clarity):

• "I didn't know..."
• "I couldn't tell..."
• "I wasn't sure if..."

Gaps (Missing capability):

• "I wish I could see..."
• "There's no way to..."
• "I can't find..."

Extract the Opportunity

Story: "Last week I was trying to book a conference room for a client meeting. I checked our room booking system and found a room available at 2pm. But when I got there with the client, someone else was in the room. Turns out they had booked it through a different system. I had to scramble to find another space while my client waited in the hallway. It was embarrassing."

Opportunities identified:

1. "I can't tell if a room is actually available across all booking systems"
2. "I risk embarrassing moments when room bookings conflict"
3. "I can't quickly find alternative space when my booking falls through"

Interview Anti-Patterns

Anti-Pattern 1: Leading Questions

• Bad: "Would you like a dark mode?"
• Good: "Tell me about a time when you used the app in different lighting conditions"

Anti-Pattern 2: Hypotheticals

• Bad: "If we built feature X, would you use it?"
• Good: "Tell me about the last time you tried to accomplish [what feature X would enable]"

Anti-Pattern 3: Asking for Solutions

• Bad: "What features should we build?"
• Good: "What's been difficult about using the product lately?"

Anti-Pattern 4: Stopping at Surface Level

• Bad: [Customer mentions issue] → Move to next question
• Good: [Customer mentions issue] → "Tell me more about that" → "What happened next?" → "How did you handle it?"

Anti-Pattern 5: Batch Questions

• Bad: "Can you tell me about X and Y and how they relate to Z?"
• Good: "Can you tell me about X?" → [They answer] → "What about Y?" → [They answer] → "How does that relate to Z?"

Note-Taking Strategy

During the Interview

• Focus on listening, not writing
• Jot brief phrases, not full sentences
• Mark moments to return to with asterisks (*)
• Note exact quotes that stand out

Immediately After

• Expand notes while memory is fresh
• Write out full stories
• Identify opportunities
• Tag by experience map phase

Example Note Format

Interview: Sarah M., Product Manager, 3 years experience
Date: 2024-01-15
Context: Weekly planning workflow

Story 1: Sprint planning chaos
"Last Monday we had sprint planning. I had tasks in Jira, designs in Figma, and specs in Notion. I spent 20 minutes just gathering everything to share my screen. The engineers were waiting. One of them said 'this happens every time.'"

Opportunities:
- "I can't gather my work artifacts quickly for meetings"
- "My team waits on me to find and share context"
- "I feel disorganized when my work is scattered across tools"

Phase: Planning / Preparation

Interview Frequency

Teresa Torres recommends weekly interviews for continuous discovery.

Why Weekly?

• Keeps you connected to customer reality
• Builds pattern recognition skill
• Creates steady flow of fresh opportunities
• Prevents "big batch" research bias

Who to Interview?

• Current customers (various segments)
• Recent churned customers
• Near-miss prospects (almost bought)
• Power users
• Struggling users

Sample Interview Guide

For [Product Category]: Task Management

Opening: "Thanks for taking time to chat. I'm learning about how people manage their work, and I'd love to hear about your experience. This is just a conversation - there are no wrong answers. Is it OK if I take notes?"

Story prompts:

1. "Tell me about the last time you planned your week"

   • What happened next?
   • How did you decide what to work on?
   • Where did you capture that information?

2. "Walk me through a recent time when your plan fell apart"

   • What happened?
   • How did you adapt?
   • What made that difficult?

3. "Describe the last time you needed to share your progress with someone"

   • What did you share?
   • How did you pull that information together?
   • How long did that take?

Closing: "This has been really helpful, thank you. Can I follow up if I have more questions?"

Skill Development

Interview skill compounds with practice:

Interview 1-10: You'll miss most opportunities, struggle with follow-ups, ask leading questions

Interview 11-30: You start recognizing patterns, get better at follow-ups, notice when customers offer solutions

Interview 31-50: Opportunities jump out at you, follow-ups feel natural, you can interview anyone about anything

Interview 51+: You hear opportunities in everyday conversations, conduct interviews without a guide, extract gold reliably

Common Struggles

"They're giving me solutions, not problems"

Fix: When they suggest a feature, ask "What problem would that solve for you?" Then: "Tell me about the last time you experienced that problem."

"They're being too general"

Fix: Ask for a specific recent instance. "Can you walk me through the last time that happened?"

"The conversation feels stilted"

Fix: You're probably asking too many questions too fast. After they answer, wait 2-3 seconds in silence. They'll often fill the gap with the good stuff.

"I'm not hearing any opportunities"

Fix: You're probably not asking enough follow-ups. Every time they mention a struggle, dig deeper: "Tell me more about that" → "What happened next?" → "How did that make you feel?"

"They keep saying everything is fine"

Fix: Ask about the last time they tried to do something, even if it worked. The story will reveal friction: "Walk me through the last time you [did task], step by step."

Red Flags in Your Own Interview

Signs you're not doing it right:

• Interview is shorter than 30 minutes (not enough depth)
• You asked more than 10 distinct questions (not enough follow-ups)
• You don't have direct quotes in your notes (not capturing stories)
• You can't identify 3+ opportunities from the interview (stayed too surface-level)
• The customer talked less than 80% of the time (you talked too much)
• You left without understanding their specific workflow (too abstract)

Making It Conversational

Techniques

Reflect back: "So it sounds like you had to check three different places, is that right?"

Express curiosity: "That's interesting - I want to understand that better. Walk me through exactly what you did."

Acknowledge emotion: "That sounds frustrating. What did you do next?"

Build on their words: Use their terminology, not yours. If they say "dashboard," say "dashboard," not "home screen."

Output Artifacts

After each interview, produce:

1. Full interview notes with stories and direct quotes
2. Opportunity list extracted from the interview
3. Experience map tagging showing which journey phases were covered
4. Patterns noted if this connects to other interviews
5. Follow-up questions for future interviews

Integration with Opportunity Solution Tree

Interview insights feed directly into the OST:

1. Stories → Evidence for opportunities
2. Customer quotes → Validation of opportunity specificity
3. Journey phases → Experience map structure
4. Patterns across interviews → Confidence level in opportunities

Each interview should add branches to your tree or increase confidence in existing branches.