Groundwork Is the Fastest Way to Find the Real Story

The information you need to position your company well already exists inside your organization. It's just sitting in the wrong rooms, with the wrong people, and nobody with a title is asking for it.

I've written before about positioning errors that survive the workshop, how leadership bias, echo chambers, and shallow questioning produce messaging that feels right internally and misses externally. This post is about what to do instead. And the answer isn't a better framework or a more expensive consultant. It's groundwork.

Leadership has experience, operations has evidence

There's a natural hierarchy in how companies treat information. The founder has the vision, the VP has the strategy, and somewhere further down, a customer success manager just got off a call where a client described, in plain language, exactly why they almost left for a competitor. That insight will probably never make it to the positioning conversation.

This isn't about disrespecting leadership experience. Founders and executives carry pattern recognition that's genuinely valuable. They've seen market cycles, they've made bets that paid off, and they understand the product at an architectural level that nobody else does.

But there's a difference between understanding the product and understanding what the market does with it. The people in operations (support, CS, sales engineering, implementation) hear the unfiltered version every day. They know which features get praised in demos and never touched again. They hear the objections that show up in the last two weeks of a deal, the ones that never make it into the CRM notes.

When I ask a founder why customers buy, I get the story they want to be true. When I ask an account manager, I get the story that's actually happening.

That gap is where positioning goes wrong. Not because founders are dishonest, but because the closer you are to the product's creation, the further you tend to be from its daily reality.

Get out of the corner office

In 2021, Uber CEO Dara Khosrowshahi did something unusual. Under an internal initiative called "Project Boomerang," he spent months driving for Uber and delivering for Uber Eats in San Francisco. He got tip-baited by passengers, struggled to find apartment complexes for food deliveries, and experienced firsthand how unnecessarily complex it was to sign up as a driver.

The result wasn't a PR stunt. He came back and told the Wall Street Journal that the experience forced him to reexamine every assumption the company had made about the driver side of its marketplace. Uber revamped its driver app, reworked onboarding, and shifted its internal language around how it treated the supply side of the business.

Howard Schultz did something similar at Starbucks, not once, but across multiple tenures as CEO. When he returned in 2022, his first move wasn't a strategy deck. He gathered small groups of frontline baristas in conference rooms across the country and asked them what was broken and what they'd change. He reportedly visited around 25 Starbucks locations per week during his time as CEO.

These aren't feel-good leadership stories. They're evidence of a specific principle: the closer you get to where value is delivered, the more accurate your understanding of the business becomes. And that principle applies directly to positioning. If your value props were written in a conference room by people who haven't sat in on a support call in months, you're working with a dated map.

Interview your customers, especially the ones who left

Talking to your own team is the first layer. The second is talking to your customers directly, and doing it frequently enough that it's a habit, not an event.

Current customers will tell you what's working. They'll name the feature they can't live without, and that's useful for confirming what you think your strengths are. But the real signal is rarely in what happy customers praise.

The sharpest positioning insights come from the people who left.

Churned customers will tell you things that active customers won't, because they have no reason to protect your feelings. They'll name the competitor they switched to and explain exactly which promise from your sales process didn't hold up. It's almost never the moment you think it is.

A comprehensive survey on churn analysis by Klue found that churn interviews are one of the highest-ROI research investments a company can make, not just for retention, but for competitive intelligence and product direction. Every churned customer carries specific intelligence about what your messaging got wrong.

The discipline isn't complicated. Run five to ten customer interviews per quarter. Make sure at least a third are with customers who left. Ask open-ended questions and resist the urge to defend. Record them, transcribe them, and share the patterns with whoever is responsible for positioning and messaging.

The information is already there, you just need a system to surface it

This is the part that frustrates me the most. In every company I've worked with, the raw material for great positioning already exists. It's buried in Gong recordings and support ticket patterns that nobody outside of CS ever reads.

The problem isn't a lack of data. It's a lack of circulation. The people generating the insights don't realize they have positioning gold, and the people writing the positioning don't know where to look for it.

I've started recommending a simple practice to every client: once a month, the person responsible for messaging sits in on two live customer calls, one with a current customer and one with a prospect or at-risk account. No agenda, no interview guide. Just listen. You'll learn more in those two hours than in any workshop.

Combine that with the why/how ladder I wrote about in the previous post. Take what you hear from the ground floor and stress-test every claim. Go up: why does this matter to the buyer? Go down: how is this actually unique? If the answers hold up against real voices from the field, you've got positioning that can survive contact with the market.

If they don't, you've saved yourself from shipping a story that only makes sense inside your own building.

The best positioning I've seen doesn't come from the smartest person in the room. It comes from the person who listened to the most people outside of it. Who are you listening to?