Conversation-Driven Development
Why Cursor, Windsurf, and Bolt need an “Interview Mode”
Writers dread staring at blank white pages.
Developers, and now vibe coders, face empty black screens.
Both writers and developers encounter the same fundamental challenge.
It’s hard to translate nascent thoughts into something meaningful.
Knowing how to translate your ideas into prose (and running code) is only going to become more valuable. There's still friction here though because, well, writing is difficult. What makes the process easier?
Effective prompts.
Not from you but questions from a system directed at you.
We need to simulate organic conversations.
There's a reason your brain is flooded with ideas after discussing a topic you're passionate about with a friend.
Great ideas always emerge from great conversations.
It's easier to brainstorm when presented with a question.
Better yet, a series of questions that adapt based on answers provided.
Your imagination struggles in an empty space. You have too many choices and micro decisions to make. Analysis paralysis shows up. Great questions are guardrails on your roaming mind, and these constraints can spark creativity.
What if all you had to do for a first draft or a minimum viable product was engage in a conversation that closely matched human dialogue?
Where Current AI Development Tools Fail
Add the prompt below to Cursor, Windsurf, or Bolt.
It’s intentionally not that great (more on this later).
"Help me build a product requirements document for a Hacker News clone. Start by interviewing me."
The response will be something similar to this:
I'll help you create a product requirements document for a Hacker News clone. Let me ask you some key questions to understand your vision better.
First, what are the core features you want to include in your Hacker News clone? The original Hacker News has:
Story submissions
Comments
Upvoting
User accounts
Basic moderation
Would you like to keep all of these, or are there specific features you want to modify or add?
What's your target audience? Are you building this for:
A specific community/niche?
A general audience?
A particular industry or topic?
Do you have any specific design preferences or requirements?
Keep the minimalist HN style?
Modern UI/UX?
Mobile-first approach?
What are your scalability requirements?
Expected number of users?
Expected number of posts/comments per day?
Any specific performance requirements?
Are there any specific features from other platforms (like Reddit, Twitter, etc.) that you'd like to incorporate?
Please share your thoughts on these questions, and I'll help you create a comprehensive PRD based on your responses.
How many questions did you count?
The questions are fine, but the UX is terrible.
There are way too many questions presented at once. In a real life conversation, a friend wouldn't drill you like this. It's overwhelming and kills momentum.
What these tools need is a refined interview mode that:
Asks one focused question at a time
Adapts follow-ups based on previous answers
Offers suggestions to assist users who are stuck
Gradually builds complex structures from simple responses
There needs to be an "interview mode" here.
And here.
We need single‑question progressive interviews baked into these tools.
Think of your mind like a juggler.
There's a natural limit to how many balls can stay in the air at once. When Cursor bombards you with a dozen questions simultaneously, it ignores fundamental principles of human cognition and conversation.
Interview Mode
The most effective interviews, whether conducted by humans or AI, respect four key dynamics of information processing:
Cognitive load: Humans comfortably juggle 2–4 chunks of info. Twelve simultaneous questions is a bit much.
Incremental clarity: Each answer refines the mental model before the next decision.
Socratic momentum: Each question sets up the next, preventing analysis-paralysis.
Error-correction loop: Tiny steps surface misunderstandings early, saving thousands of wasted tokens.
Here’s a refined interview mode:
We need to rethink the interaction model between developers and AI-powered editors. It's not simply about having AI ask questions, it's about creating a continuous flow state where each exchange builds momentum.
When properly implemented, CDD doesn't just avoid blank pages, it changes how we externalize and refine complex ideas.
Me: I want to build a tool that analyzes my writing and identifies overused phrases.
Agent: That's an interesting project. What type of writing do you want to analyze first?
Me: Mostly blog posts and essays.
Agent: So we're focusing on longer-form content. What would you consider "overused" in your context? Number of occurrences, proximity, or something else?
Me: Probably words or phrases that appear multiple times within the same section.
Agent: That makes sense. Would you want to detect exact matches only, or also similar phrases with slight variations?Notice what's happening:
Each question addresses a single decision point
The agent acknowledges my answers before proceeding
Questions build on previous responses
When I reveal uncertainty e.g. “probably” the agent explores options instead of demanding a definitive answer
This creates a natural progression that produces a more accurate spec.
Going back to my Hacker News Clone, here's a more effective prompt:
"Help me build a product requirements document for a Hacker News clone. Start by interviewing me. Only ask me one question at a time. I might want to ask for recommendations based on each question if I don't have an answer."
The first question is the most important.
What are you trying to accomplish?
More importantly, why are you building this?
You can safely say I don’t know, which would kick off a generative conversation.
The Future of Creative Work
The most successful tools won't just offer powerful models, they'll transform how we approach the blank page problem.
By embracing conversation-driven development, we can make the software development process more natural, productive, and human.
Whether you’re building software or drafting an essay, there is so much power in a great question and conversation.
Wasting time sucks.
You can burn thousands of tokens going down the wrong path.
I've done this countless times. Prompting my way to an underwhelming result.
When this happens, it's easy to blame the tool or "AI" for not being worth your time.
It's likely that you should have just asked for an interview.
— Daniel
Been using Bolt a lot recently. I would appreciate an interview mode, and you can ask it questions, but I also need a way to take the code and put it into an actual website builder once I get it to a place of my liking. AI can only take me so far.