A prominent marketing executive-turned-VC once told me:

“The best CMOs are students of human response.”

I wish I’d said that. It’s one of those lines that’s both true and just sounds good.

Let’s say you agree with that sentiment, but you’re not quite there yet—you wouldn’t call yourself a full-fledged student. How do you get there? What work do you need to do? How should you be spending your time?

Here’s my take: You should spend more of your time studying humans. Almost everybody should.

Not markets, not segments, not “personas.” Actual people. You should pay attention to them. Make time for real conversations with them. Listen. Ask questions. And notice what they care about, what they’re trying to accomplish, what’s in their way, and how they deal with it.

Then, you should take what you’ve learned and put it to work. If you’re an aspiring CEO, CRO, CMO, or anyone responsible for finding more customers, you should use what you learn to answer the foundational questions every good go-to-market strategy is built on:

• Who should you be talking to?

• How should you talk to them?

• How do you figure out if, and how, you can help?

• How do you prove you’re worth working with?

The more time you spend in conversations with customers, the more natural these decisions become. You start to see patterns. You develop a sense for what to say and how to say it. The work gets easier - and a lot more fun.

And yet, despite this basic truth - that time spent 1:1 with real customers makes it infinitely easier to market and sell to them—most marketing out there is still pretty terrible. Unclear websites. Boring whitepapers. Pitches so dense they might as well be written in code.

There’s much crap floating around, claiming it’s enticing people to buy. And if people just did the work, it wouldn’t be that hard to improve it.

So if we all know that better marketing starts with understanding your customers better, why aren’t more people doing this work?

Why aren’t there more real students of human response out there?

What Holds You Back

One of my favorite authors, Steven Pressfield, has this quote that explains why more people don’t get to know the people they’re selling to:

“The universe is not indifferent. The universe is actively hostile.”

That’s true of life, and it’s true of getting closer to your customers. There are three invisible forces out there pushing back on you when you try to do this work.

1. The Fear of Not Knowing What to Ask

A big blocker? Not knowing how to ask good questions. Most people assume they’re supposed to get customers on a call and ask, "So, what do you like best about our product?" But as Rob Fitzpatrick explains in The Mom Test, that’s the wrong approach. People don’t ctually know what they want in the abstract, and if you ask them directly, they’ll either lie to spare your feelings or guess at an answer that won’t actually help you.

The real trick is to ask them about specific moments in their real life. Instead of, "Would you use a tool that does X?" you ask, "Last time you ran into [problem], how did you handle it?" That’s where you get the truth. Not from hypotheticals, but from straightforward accounts of their past behavior (and pattern-matching that behavior across multiple customer conversations).

The antidote for this kind of fear is borrowing good questions from other people. My two favorite sources of good questions are Rob’s The Mom Test (mentioned above), and Forget The Funnel by

2. The Hallucination Effect

Another force working against you? Your own product.

Building (or selling) something complicated does something sneaky to your brain. In the beginning, you’re focused on a real person with a real problem. But over time, without even realizing it, your perception shifts. Instead of thinking about who you’re building for, you start thinking more and more about what you’re building. The customer fades into the background, and the thing itself—the product, the roadmap, the campaign, the content—takes center stage.

Eventually, you stop seeing your product as a means to an end. It becomes the end. And when that happens, a little voice starts whispering to you:

“You don’t need to talk to customers. You just need to explain how the product works a little better.”

This hallucination effect fuels an insatiable hunger for more explanatory content. You convince yourself that if you just had another one-pager, another checklist, another battlecard, another slide in the pitch deck… then people would get it.

But that’s not what’s missing. You don’t need more content.

You need more connection.

Because every day you don’t talk to customers, you drift further away from the real reasons they buy. The best teams fight this drift. They go out and talk to real people—not to confirm what they already believe, but to make sure the story they’re telling is the right one.

3. “But isn’t this, like, a lot of work?”

The other reason people don’t do this work of connecting with customers? They think they don’t have time. And sure, on paper, it seems like a lot:

• Figure out who to talk to

• Track down the right contacts

• Figure out how to reach them

• Follow up until they say yes

• Draft an interview guide

• Take notes

• Repeat for 5-10 calls

• Analyze the notes and pull out the insights and do stuff with them

Sounds a little exhausting, right? But it’s actually not a lot of work, just a lot of steps. Like a rollercoaster, the scariest part here is waiting in line. Once you figure out what to ask and who to call, you’ll realize it’s not some monumental lift. The hardest part is starting - and the boost you get from talking to people that actually love what you’re selling is a sneaky morale boost that can last a long time.

Notes On Who to Talk To

Ok, you’re convinced. But if you’re going to study human response, you need to study the right humans. Here’s two things to keep in mind as you decide where to focus.

1. Should You Talk to Unhappy Customers?

The short answer? Nope. Not proactively at least. Unhappy customers will find you all by themselves.

Unfortunately, product and marketing teams already spend too much time talking to unhappy customers who were never the right fit to begin with. That’s useful for debugging your ICP or filling up a feature request backlog, but it won’t help you build a sharper go-to-market strategy.

The bigger risk of spending too much time with unhappy customers? Catching a case of something product positioning expert

But it’s important to remember: You don’t grow by winning over bad-fit customers. You grow by finding the ones who already love you and figuring out how to clone them.

So, when in doubt, remember this: Study happy customers. It feels better, and you’ll learn more.

2. Should You Talk To New or Long-Term-Customers?

If the person you’re talking to wasn’t involved in picking you, you’re only getting half the story. The best insights come from someone who checks all three of these boxes:

1. They were involved in the buying decision. They saw other options, considered trade-offs, and ultimately chose you.

2. They’ve been through onboarding and are now getting value. They’ve seen both the promise of the sale and the reality of using the product - and both of those experiences are recent enough that they can remember them.

3. They use the product often. They experience the value (or friction) firsthand.

If you can find someone who fits this profile, they hold the cheat codes—the insights that tell you what actually drives conversions, what messaging works, and what nearly stops people from buying in the first place.

That’s why you want to ask questions like:

• How did you find out about [product name]?

• Why did you choose [product name] over other options?

• What deal breakers would have made you walk away?

• What happened that made you feel certain this was the right solution?

• What’s the most important thing you can do now that you couldn’t before?

The answers to these questions take you out of guesswork and put you into mind-reader mode. They tell you exactly what to say, how to say it, and why it works. The key is finding the people who were there before, during, and after you got the chance to show off what you can do - and ideally, can tell that story while it’s still 1-3 years old. And the magic is in studying the whole arc they went through to eventually start working with you.

Final Thoughts

The people who are best at finding, attracting, and landing new customers don’t fixate on ICP definitions, lead scoring models, or the latest automated demandgen hacks.

They focus on the only thing that actually matters: understanding humans.

They do the work to learn the truth about what brought customers their way, how they evaluated their options, and what ultimately made them say yes.

They don’t guess. They know.

And they know because they do the work. They go straight to the only people who can give them the real answer: the happy customers they want to recreate.

When you talk to the right people and ask the right questions, everything gets easier. Your positioning stops being fuzzy. Your messaging stops feeling like a shot in the dark. The answers to what to do next stop feeling like a mystery.

You don’t have to guess anymore. You know.

And knowing feels good.