How to get your SME talking

From Reads to Leads is a newsletter for B2B tech founders and marketing leaders whose marketing isn’t working. It’s about positioning, messaging, content strategy, operations, and results. If this was sent to you, subscribe here so you don't miss the next email.

In today's newsletter:

• Do your expert interviews sound like interrogations?
• Follow-up questions are the entire point
• The one question that changes everything

A couple of weeks ago I wrote about expert content. But there is one thing I didn't talk about in that newsletter. The most important thing. How to ask questions. Because when content doesn’t sound expert, it’s not always the SME’s fault. Often, it’s yours. You didn’t ask the right questions.

I’ve seen this pattern again and again: writers prepare a list of questions, get on a call with the expert, and go through the list like an interrogation. You’re checking boxes instead of having a conversation. And that’s exactly why your case studies, thought leadership pieces, and expert articles sound like everyone else’s.

I came across one study, which inspired this newsletter. After analyzing thousands of conversations, researchers found something interesting: people who ask more follow-up questions are perceived as more trustworthy. 

And when someone trusts you, they open up. They tell you the stories and insights that make your content genuinely interesting. And truly expert.

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Follow-up questions are where the good stuff lives

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The first answer an expert gives you is usually a surface-level response they’ve shared many times before. But it’s the follow-up question that makes them pause, think, and dig deeper. 

Here's how to get those follow-ups right.

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Start broad

• Walk me through your role.
• What does your typical day look like?
• How did you get into this kind of work?

You need to start broad to warm up your expert, and ask the first follow-up question. Don't move to the next question on your list until you ask the follow up.

What most writers do:

• Writer: "Walk me through what you do."
• Expert: "I'm a senior data scientist. I build predictive models."
• Writer: "Cool. So, can you explain how predictive models work?"

You just wasted a warm-up question.

What you should do:

• Writer: "Walk me through your role."
• Expert: "I'm a senior data scientist. I build predictive models."
• Writer: "What does 'build' actually mean? Like, what are you doing on Tuesday afternoon?"
• Expert: "Ha, Tuesday afternoon I'm usually cleaning messy data. Everyone thinks my job is the sexy AI stuff, but 70% of it is fixing data that's formatted wrong or finding gaps..."
• Writer: "Why is the data always messy?"
• Expert: "Because most companies collect data without thinking about what they'll actually use it for. Then they hire us to make sense of it."

Now you have context. You understand their world. And you can dig deeper into that direction.

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Move into the problem

• How do you approach [specific problem]?
• What do most people get wrong about this?
• How is your approach different from the standard way?

What most writers do:

• Writer: "How do you approach software modernization?"
• Expert: "We start with a technical audit, then create a roadmap, and execute in phases."
• Writer: "Great. Can you walk me through each phase?"

You just got a process map. Boring.

What you should do:

• Writer: "How do you approach software modernization?"
• Expert: "We start with a technical audit, then create a roadmap, and execute in phases."
• Writer: "Why execute in phases?"
• Expert: "Because the business still needs to run while you're rebuilding. If you take the entire system offline for six months to rewrite it, the client's business will just stop."
• Writer: "Has anyone actually tried to do it all at once?"
• Expert: "Yeah. We had a client who hired a different vendor before us. They convinced leadership they could rebuild the entire ERP system in one go. But the project was delayed. When we came in, half their team was manually processing orders because nothing was working."
• Writer: "So what do phases look like?"
• Expert: "We identify 'independent modules' or parts of the system that can be modernized without breaking everything else. Maybe it's the reporting layer first, or the customer portal. Something that adds value but doesn't touch critical transaction processing. Then we move to the next piece. The old system keeps running until we're ready to switch, and we can test everything in production with real users."

Now you have a story: “Why 'big bang' modernization projects fail (and what works instead)”

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Go for the tough questions

Now they trust you and you can ask the hard stuff.

That same HBR research shows people are less likely to lie when you frame questions with pessimistic assumptions rather than optimistic ones. This way, you give your SME the permission to be honest.

Don't ask:

• Does your approach work well?
• Are clients happy with your process?

Ask:

• When have you seen this approach completely fail?
• What kind of client is a terrible fit for your process?

What most writers do:

• Writer: "What's your approach to cost optimization in AI integration?"
• Expert: "We monitor token usage and optimize prompts."

Useless.

What you should do:

• Writer: "Nobody talks about the cost of AI integration. When can it become a real problem?"
• Expert: "More often than people admit. Token costs can go high fast if you don't optimize for it from day one. If you're in the PoC stage, you don't really pay attention to it, but once you start growing…”
• Writer: “Can you give me a specific example of a client whose costs have gone up?”
• Expert: “We had this startup with an AI-powered content generation tool. Launched their MVP, got some early users, but then, their AWS bill hit $8,000. They were generating long-form content for users and hadn't implemented any caching, weren't reusing context, weren't even tracking which API calls were costing them the most."
• Writer: "So how do you prevent that?"
• Expert: "You build cost monitoring into the architecture from day one. We implement token budgets per user, cache common responses, and use cheaper models for simple tasks."

Now you have something real. 

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Squeeze a framework out of them

At this point, they've been talking for 30-40 minutes. They're comfortable. They've told you stories. Now ask them to think out loud. You want to get the stuff they do intuitively but have never had to explain.

Questions that reveal how they think:

• When you look at [problem], what are you actually evaluating?
• How do you decide between [option A] and [option B]?
• What's the one thing that tells you this is going to work or fail?

Shut up and let them think.

• Writer: "When a client comes to you wanting to migrate to the cloud, what are you actually evaluating in that first conversation?"
• Expert: "Hmm..." [long pause]
• Writer: [says nothing]
• Expert: "I guess... I'm listening for whether they know why they're doing this. If they say 'everyone's moving to the cloud' or 'we need to modernize,' that's not a reason. That's just repeating what they heard at a conference. But if they say 'we're spending $50K a month on servers we only need for three months of the year,' then they have an actual problem the cloud can solve."
• Writer: "What happens when they don't have a real reason?"
• Expert: "The project can succeed technically but doesn't solve anything. They move to the cloud, pay more money, and still have the same problems because the cloud wasn't the issue."

That's a framework right there and actual messaging you can use everywhere.

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The most important question you can ask during the interview

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Can you give me a specific example of that?

That's it. One sentence. It’s how you turn vague answers into specific details. 

Vague answer: "Our process is collaborative."

Specific answer: "Every Friday, we have a session where the client's team builds the strategy with us. We put a Miro board on the screen and say 'Here's what we're thinking, now tear it apart.' Most agencies would never do this because clients might disagree. But that's the point. If they disagree now, we fix it. If they disagree after we've built everything, we've wasted time.”

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Before your next interview, do this

1. Write your prepared questions (5-7 max)
2. Order them from easiest to hardest:
   
   • Warm-up questions (role, background, day-to-day)
   • Problem questions (what people get wrong about X problem, what's the solution)
   • Tough questions (what went wrong, for whom it doesn't work, what could be better)
   • Reflection questions (how they make decisions, what's their mental model in a specific situation)
3. During the interview, commit to asking at least 2 follow-ups per prepared question.
4. Practice shutting up. After you ask a follow-up, count to 5 in your head before saying anything else.

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See you next week

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Seen our latest blog on the ugly truth about content agencies? You should check it out.

Kateryna

P.S. If we aren't connected already, follow me on LinkedIn and Instagram. If you like this newsletter, please refer your friends.

P.P.S. Need help with quality content? Zmistify your content with Zmist & Copy