Hi, I’m James. Thanks for checking out Building Momentum: a newsletter to help startup founders and marketers accelerate SaaS growth through product marketing.
Most customer interviews stay surface-level. Try as you might, you keep getting polite answers about workflows, tooling preferences, and general frustrations.
You nod along, take notes, and push a little to try and extract something meaningful. But more often than not, you walk away with a wishlist of “nice-to-haves”, or the same vague complaints you already knew.
What you don’t get is the stuff that actually drives decisions.
You don’t hear about the internal tensions and the pressure to prove ROI on a new initiative. You don’t hear about the awkward leadership conversation that made them rethink their priorities, or the missed target that quietly tanked morale.
You don’t get the emotion behind the decision-making; the sense of urgency, frustration, or even fear that pushes someone to act. And without that layer of insight, it’s hard to create messaging and positioning that actually lands.
People don’t search, switch, or buy because of abstract pain points or vague value props. They take action only when something hits a nerve, and
when your story mirrors their experience.
But how are you supposed to get there?
That’s where this question comes in:
“When you’ve had a horrible day and want to throw your laptop out the window, what’s happened?”
It’s one of the most useful questions I’ve come across in customer interviews, and I first heard it from my PMM partner, Alicia Carney.
It seems simple, maybe even a bit fluffy, but the emotional weight it carries makes it a goldmine for real insight.
This question doesn’t ask about budgets or roadmaps or specific product needs. It asks about pressure and friction, the moments that tip people over the edge. It’s those emotional spikes that give you something to anchor your messaging and positioning around.
Alicia shared a brilliant example of this from her time at a climate tech startup. She was speaking to a Group Product Manager at a fintech scaleup. On paper, this was a strong buyer profile: commercially minded, accountable for revenue, working in a growth-stage company.
When Alicia asked whether a climate API would ever make it onto her roadmap, the answer was blunt: “No, this isn’t relevant to us. I only prioritise based on incremental revenue.”
She didn’t just say no, but it was the kind of response that says, “Why are we even having this conversation?” The energy shifted, and the door started to close.
But then Alicia asked the laptop-out-the-window question…
The same PM opened up.
“Some days I feel like I’m working my ass off for this company to get richer. I feel lost and under-appreciated. I love my team and want to stay to support them, but I wish I had more of a sense of meaning and purpose here.”
Same person, but a completely different story.
And that’s the point.
There’s often a huge gap between how someone initially responds to a product question and what’s actually going on underneath.
In this case, the product felt irrelevant in isolation. But when framed through the lens of purpose and emotional impact, it became something else entirely. It became a vehicle to help her champion a new initiative. To push a meaningful project internally. To find more alignment between her personal values and her day-to-day work.
That shift didn’t just change Alicia’s understanding of the buyer, it shaped how she positioned the product. It helped her move from describing a feature (a robust API) to telling a more powerful story: this is your chance to pitch something that aligns with both business growth and personal purpose.
From that insight, she built messaging and enablement that reflected both commercial value and human motivation. She reframed the product around helping customers lead new conversations, pitch bold ideas to leadership, and ultimately make change happen from within.
And all of that started with a question that wasn’t about the product at all.
If your interviews keep circling the same abstract pain points, or you’re struggling to uncover what actually drives urgency, try that question.
Don’t just ask what tools they use or what’s missing. Ask what happens on the days that break them, because that’s where the real story begins… and that’s what you build your message around.
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