Why Your "Only" Probably Isn't: Positioning Errors That Survive the Workshop

Most positioning exercises produce consensus, not clarity, and the people in the room rarely notice the difference. The best/better/only framework is one of the sharpest tools I know for finding differentiation, but it can't fix what gets poured into it. And what typically gets poured in is a mix of founder conviction, leadership assumptions, and surface-level answers that never get pressure-tested.

The result is positioning that feels right in the workshop and falls apart in the market.

The framework is sound, the inputs are the problem

The best/better/only exercise, as Stijn Hendrikse describes it in T2D3, asks three questions: what are you better at than anyone else? What can customers only get from you? And why should they care? It's simple, direct, and when the inputs are honest, it produces positioning that holds up under pressure.

I use it regularly with clients. When it works, it cuts through months of vague messaging in a single session. But when it doesn't (and I see this more often than I'd like to admit) the failure isn't in the framework. It's in at least one of four recurring errors that sneak into the room and go unchallenged.

I wrote about the first one, the founder love trap, in a previous post, how a founder's emotional attachment to a feature can distort the company's story. That's a real and common failure mode. But it's not the only one.

The leadership echo chamber

The second error is structural. In most positioning sessions, the room is full of founders and executives. The people not in the room are the ones closest to the customer (support, account managers, solutions engineers, implementation leads) who hear real objections and real reasons customers stay or leave.

Research on confirmation bias in organizations shows it becomes more dangerous in group settings, where teams grow overconfident and fail to recognize better alternatives. Add the HIPPO effect (where the highest-paid person's opinion goes unchallenged) and the workshop produces agreement, not truth.

I've seen this happen in a specific way that still sticks with me. A SaaS company I worked with ran the best/better/only exercise with their leadership team. Their "only" was a proprietary data model they'd spent two years building. Everyone in the room agreed it was unique. The problem? Three competitors had shipped similar capabilities in the previous six months. The leadership team didn't know because they'd stopped tracking the competitive landscape the way their sales team did. The AEs knew. Nobody asked them.

When your positioning inputs come exclusively from the people furthest from the deal, you're not mapping the market. You're mapping the org chart.

The "only" that isn't

This is the third error I encounter, and the most common. A team identifies their "only," genuinely believes it, and builds their messaging around it. They aren't lying. They simply don't have the visibility to know it's wrong.

Early-stage companies often operate in a small competitive bubble. They know two or three direct competitors and assume that's the field. They haven't done a thorough competitive audit, or if they have, it was a year ago. In software, a year is a long time. Features that were unique in January can be table stakes by September.

The subtler version of this is when the "only" is technically true (no one else does exactly this thing in exactly this way), but the difference is so narrow that buyers don't perceive it as differentiation. Here's the test I keep coming back to:

If you answered "yes" to more than one of those, your "only" deserves a second look.

Not climbing (or descending) the why/how ladder

Here's where I think positioning work stops too soon, and where a simple discipline can make the difference between messaging that sounds impressive and messaging that actually moves a buyer.

The why/how ladder is a framework we use at Kalungi, and it works in both directions. When you go up the ladder, you ask "why does this matter?" repeatedly until you reach an outcome the buyer genuinely cares about. When you go down, you ask "how is this actually unique?" until you hit something specific and defensible.

The pattern I see over and over: teams stop at the first answer in both directions. They write down a feature, call it a benefit, and move on. Their positioning ends up reading like a product page, not a reason to switch vendors.

Take a real example. A team comes out of a positioning session with this value prop: "Segment API compatible." That's an attribute, not a position. Going up the ladder (why does that matter?) might take you to "saves engineering teams 40 hours per integration." Keep going: why does that matter? Now you're at "the ops lead stops being a bottleneck and starts doing strategic work." That's where the buyer actually lives.

Going down (how are you uniquely API compatible?) might reveal that you support specific edge cases no competitor handles, or that your implementation time is a fraction of the industry average. That's where credibility lives.

The why ladder gives you messaging your audience cares about. The how ladder gives you proof they can believe. Good positioning does both. Very few do.

The workshop isn't the end, it's the beginning of a discipline

The fourth error ties the others together: treating the positioning exercise as a one-time deliverable.

Markets shift. Competitors ship new features. The positioning that was sharp six months ago might be blunt today, not because it was wrong then, but because the world moved.

I've worked with teams that ran the best/better/only exercise during their seed round and never revisited it after crossing $2M in ARR. By the time they came back to it, their buyer profile had changed, their competitive set had tripled, and their "only" had become their "same as everyone else." They weren't lazy. They assumed positioning was a deliverable, not a discipline.

The best teams I've seen treat positioning as a living argument.

They re-run the exercise after major product releases or after losing a string of deals. They bring different people into the room each time, a support lead this quarter, a solutions engineer the next. They ask their AEs what objections show up more often now than they used to. And they use the why/how ladder to stress-test every claim, both up and down, before it reaches the website.

If you ran your last positioning exercise more than six months ago and your product or market has changed meaningfully since then, it's probably time to do it again. Not because the framework failed, but because the inputs that fed it are stale, and nobody in the room was asking "why" or "how" enough times to catch it.

What part of your positioning would collapse if you replaced your beliefs with five recent customer conversations and an honest look at your competitive landscape?