Sahin Boydas
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12 Questions to Ask During User Interviews for an AI Product

You've read all the blog posts about user research ai, but your product is still stuck. Why? Because most guides are generic and miss the point. This is the counterintuitive, step-by-step guide for founders who need to solve this problem, move fast, and get results without a massive data science team.

2024-12-075 min read626 words

You've read all the blog posts about user research ai, but your product is still stuck. Why? Because most guides are generic and miss the point. This is the counterintuitive, step-by-step guide for founders who need to solve this problem, move fast, and get results without a massive data science team.

The Counterintuitive Truth

In user interviews, the best practitioners often do less, not more.

The lesson: the market doesn't care about your roadmap. It sounds simple. It's incredibly hard to execute.

Why Most Approaches Fail

Many common approaches to user interviews are flawed at the root.

The root cause is usually one of three things:

Copying what big companies do without understanding why they do it. What works for Google doesn't work for a 10-person startup.

Over-engineering the solution when a simple approach would work better. I've seen teams spend six months building something that could have been done in two weeks.

Ignoring the human element. Technology is the easy part. Getting people to actually use it is where the real challenge lives.

The Framework That Actually Works

Here is a simple framework for evaluating user interviews. It's not complicated, but it requires discipline.

Step 1: the market doesn't care about your roadmap

This is where most people go wrong. They skip this step entirely and jump straight to execution. Don't do that.

Step 2: your team matters more than your technology

Once you have the foundation right, this becomes much easier. I've watched founders struggle with this for months when the answer was staring them in the face.

Step 3: Iterate relentlessly

Nothing works perfectly the first time. The companies that get user interviews right treat it as an ongoing process, not a one-time project.

The AI Angle

Any discussion of user interviews in 2026 has to include AI. As someone who's invested in Anthropic, OpenAI, Scale AI, and Hugging Face, I have a front-row seat to how AI is transforming this space.

The short version: AI makes good practitioners better and bad practitioners worse. It's an amplifier, not a replacement.

Some teams use AI to get far more out of user interviews. Others spend heavily on AI that solves the wrong problem. The difference comes down to understanding what you're actually trying to achieve.

This connects to broader themes around user research ai, interviewing, best practices that I've been thinking about a lot lately.

Wrapping Up

I've shared a lot here, and I know it can feel overwhelming. But you don't need to get user interviews right on day one. You just need to get started and keep improving.

Founders who do well at user interviews tend to share one trait: they're relentlessly practical. They don't chase perfection. They chase progress.

That's the mindset I'd encourage you to adopt. Start where you are. Use what you have. Do what you can. And keep pushing forward.

As always, I'm rooting for you.

FAQ

Frequently Asked Questions

Q:Are these recommendations still relevant in 2026?

Absolutely. While specific tools and tactics change, the underlying principles remain consistent. I update my thinking regularly based on what I'm seeing in the market and across my portfolio companies.

Q:How were these items selected?

Each item on this list comes from direct experience, either from building my own companies or from patterns I've observed across the 234 startups I've invested in. I prioritize practical, actionable items over theoretical concepts.

Q:Which item on this list has the highest impact?

It depends on your stage and context, but in my experience, the items near the top of the list tend to have the broadest applicability. That said, sometimes the less obvious items create the biggest breakthroughs for specific situations.

Written by

Sahin Boydas

Serial entrepreneur, #1 angel investor, author of Becoming Top 1%

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