Hey!

Welcome to Social Files—your no-BS guide to generating demand for your B2B product using social & content.

Hope you’re having a great Wednesday. It has been a week. We just hired our SVP Operations at Compound (she starts Monday). I’m wrapping up my second week in NYC, and finally settling in. Also, still chipping away at my debut science fiction novel, The Shattered Planet.

Been busy!

Now, what you're here for: marketing & content. Today, I’m sharing some field notes on how to run effective content interviews. I’m talking to more and more marketing leaders who want to try running exec content, and while I’m biased towards Compound, I think there’s benefit to trying this motion internally. This piece should help.

If anything, it will help you understand what to screen for when vetting agency partners to support your Executive Content motion. **

Shall we?

🔎 DEEP DIVE

How to run better Content Interviews

5 lessons from 500+ Content Interviews with B2B founders & execs

When I first started doing exec ghostwriting, I thought the writing was the most important part of it all. I was wrong.

No hook lever, no turn of phrase, no formatting style will save your LinkedIn growth if the raw material was never there to begin with.

So, if you want to stand up an Executive Content motion, you’d better be damn good at Content Interviews.

Before we go any further, let’s define Content Interview.

This process looks vaguely similar across writers and agencies. This is what it looks like at Compound. Every two weeks, we sit down with the executive we’re writing for, usually over a video meeting. We’ll come with a list of questions prepared based on what we believe will perform well on LinkedIn. We’ll use the interview time slot (usually 45 minutes) to run through the questions, kind of like a podcast interview. The transcript we end up with is the raw material for the 3-5x LinkedIn posts the founder sees cross their desk in the next week.

Simple enough, right?

Eh.

It wasn’t until I tried to train this skill that I understood the amount of nuance that goes into conducting an interview where you (1) get the material you need and (2) make the interviewee feel good in the process. The second is arguably as important as the first.

This is teachable, though. I wasn’t born with it. All it took was 200+ episodes of a fitness podcast nobody listened to, 50+ episodes of an esports podcast slightly more people listened to (but not many more), and…I don’t know, maybe 500 Content Interviews with high-level execs over the course of four years to get to a point where this stuff is mostly easy.

What I’d like to offer you today are 3 high-leverage ways to get more out of your next Content Interview. This will also show you how our team approaches the interview flow, should you want to work with us instead of cobbling together an Exec Content motion.

(1) Mirror the exec’s energy.

When I train new Content Leads and Strategists on the interview flow, I find they’re usually married to a specific style of interviewing. Usually, this is their default personality. Someone more bubbly will present that way on an interview. A more introverted, reserved Lead might come off quiet.

The problem is not any particular style. Content Interviews are not an extrovert’s game. You can be introverted and excel in Content Interviews (case in point: yours truly).

You do, however, need to understand how to modulate your tone and energy.

Dissonance in energy levels and speaking cadence—in either direction—is grating for the executive, and will hinder your ability to extract good material.

Last year, we worked with an early-stage founder who was very reserved. His answers in interviews rarely exceeded one sentence. Yet, I had paired him with a Content Lead who was particularly bubbly, and still learning the skill of tonal modulation. The Content Interviews were rough, and it was this client who drove this point home for me. I hadn’t realized that I acted as a chameleon in the interviews I ran.

Simply put:

• If the executive is higher-energy, bring yours up to match (aim for ~20% increase).

• If the executive is lower-energy, bring yours down to match (aim for ~20% decrease).

‘Mirroring’ also applies to word choice.

For example, say you're interviewing a founder who you notice uses the phrase ‘clock speed’ when describing what they look for in new hires. You’ll want to use that when speaking to them instead of an analogous phrase like ‘horsepower’ or ‘processing power.’

This seems neurotic. Perhaps it is. But, it’s all in the interest of ending up with winning content.

(2) Your ultimate goal is to extract material.

Rookie interviewers focus too much of their energy on ‘keeping the client talking.’ This stems from a place of nerves. You’re not confident enough to direct the conversation, and so you allow the executive to ramble. Then, you end the call feeling proud of yourself before reviewing the transcript when you finally sit down to write, and realize you spent 41 of the 45 minutes on two prompts—hardly enough for 5x posts.

You must be able to discern between rambling and a valid thread. There is a difference. Even when you are on a valid thread, you must have confidence in pacing the interviews so that you get through enough prompts to fill out your content calendar.

The same can happen in reverse.

We have one long-term client who struggles with vague answers. He’s a growth-stage founder, and I can tell his mind is often stretched thin when he comes to interviews. If I were to accept the surface-level answers and move on, the interview might feel easier, but we’d end up with worse content.

In my experience:

Sacrifice the ‘rhythm’ of an interview for the sake of getting a take or a nugget or an anecdote that will take the finished post to another level.

(3) Tweaking interview prompts for better outcomes.

Executives require varying levels of specificity in their Content Interview prompts.

Think of it like a spectrum.

On one end, you have founders who don’t even need a prompt. They show up to the Content Interviews ready to yap, and often have their own content ideas.

Far to the other end, you have founders who struggle in live settings. They need post ideas spelled out for them, and often have to prep before the Content Interview.

You must know which type of exec you're working with, and tailor your Content Interview prompts accordingly.

I’d recommend erring toward specificity. Better to provide it and not need it then need it and not provide it. Also, even for more charismatic executives, the structure helps make sure you end up with workable material.

(4) Map Content Interview times around the exec’s energy levels.

You won’t at all be surprised to hear this, but running a Content Interview when an exec is swamped, tired, angry, or otherwise not in the best state of mind is a recipe for disaster.

If LinkedIn content is a priority, slot the interview time during a window where energy is high.

So, if you are working with a ‘low-energy’ founder, you want to try and catch them during the thin window of their calendar where they maintain a sliver of charisma.

This is a minor tweak with major upside. Try it.

(5) Executives enjoy conversations with peers.

Busy founders and executives don’t want their already-slammed calendar filled with even more pointless meetings.

Few things, in my experience, annoy a founder more than being on a mandatory call with someone who couldn’t even take the time to understand their product or industry.

You must know the exec’s category well enough to hold your own in conversation with them. You must know the terms they use, and be able to speak in a language that doesn’t make you sound like an obvious novice. This makes the interview more enjoyable, and enables you to get a layer deeper—so you can walk away from the Content Interview with better material.

This, of course, also helps you write better content.

The ‘Mirroring’ concept from earlier also helps you achieve peer status faster.

Okay, so what do I ask them?

Good question.

I wrote a bit more in-depth about our full Content Interview workflow here. You can find some of my favorite interview prompts here, and even more in this template pack I put up for a few bucks.

Hope this piece was helpful.

🗃 FILE CABINET

Here’s my favorite marketing and business content I bookmarked this week.

• Still haven’t read or listened to much business stuff, if I’m being real. My entire podcast rotation has been overtaken by The Rest is History. I’m 100% OK with that. I just finished their mini-series on WW1.

BEFORE YOU GO…

As always, thanks for allowing me into your email inbox every week.

More from Social Files:

• Read the rest of my essays

• Work with my agency in 2026

• Steal my founder-led content templates

Talk soon,

Tommy Clark