Business-to-business (B2B) marketing teams are running more channels, more data, and more reporting than they were three years ago, usually with fewer people to do it. The result is a particular kind of executive frustration: the strategy reads well in the deck, the campaigns ship on schedule, and the pipeline still feels soft. The instinct in that moment is to push harder, add a channel, buy a tool, or demand another dashboard. Tiffany Lyman Otten, Principal of The Otten Collective, argues that this instinct is exactly backward. The problem is rarely effort. It is drift, the slow separation between what a go-to-market (GTM) strategy was built to do and what the business now needs it to do, and no amount of additional activity closes that gap. “Drift is hard to catch from the inside,” Otten says. “It’s like being one degree off on a compass. You don’t feel it at first, but a few miles later, you’re nowhere near where you meant to go.”
Interrogate The Assumptions Before You Fix Anything
The costliest mistake in a struggling GTM motion is solving the wrong problem quickly. Teams under pressure reach for execution because execution feels productive, and the calendar fills with work that generates motion without generating clarity. Otten’s counter is deliberately slower and deliberately uncomfortable: run the “five whys” on the issue that is not working, and keep running it past the point where the answer sounds reasonable. “Most teams jump straight to solutions and end up with more activity, not more clarity,” she says. “The messaging isn’t landing. Why? You get an answer. Why is that true? Keep going. By the fifth “why,” you’re usually staring at something very different from where you started.”
What makes this more than a workshop exercise is where Otten applies it. She treats the “five whys” as a default operating habit rather than a diagnostic reserved for crises, and she points it at the assets most teams treat as settled: pain points, value propositions, and positioning. The method forces a team past the feature list and past the benefit statement to the impact a buyer actually feels, which is the only layer that changes behavior. Most B2B messaging stalls one or two “whys” short of that. It describes what the product does, gestures at why that is useful, and stops before it reaches the consequence the buyer is living with. “When you don’t know where to start, start here,” Otten says.
Go Talk To People, Not Dashboards
Analytics tell a company what happened. They are structurally incapable of telling it what almost happened, what a buyer refused to say out loud during a negotiation, or what nobody thought to instrument in the first place. Otten’s prescription is blunt and unfashionable in a function that has spent a decade investing in measurement infrastructure. “The truth lives with your closed-won buyers, your closed-lost buyers, and your sales reps,” she says. “Five honest conversations will surface more than a quarter’s worth of analytics work, because you’ll hear things nobody thought to track and things nobody would tell you mid-negotiation.”
The sales team is the underused asset here, and Otten offers a specific way to mine it. Ask reps what they spend the most time educating buyers on, then keep asking until a trend emerges. That trend is a messaging gap hiding in plain sight, and it is fixable immediately, while the deeper strategic work continues. The logic is simple: if a rep has to explain the same concept in every call, the market is not arriving with that understanding, and the marketing function has quietly outsourced a job it should be doing at scale. Few leaders think to ask the question, which is why the same explanation gets repeated, deal after deal, at full human cost.
Build A Strategy Small Enough To Run
Clarity, in Otten’s framing, is a subtraction problem. A strategy that lists everything the team could do is not a strategy, it is an inventory, and too many competing priorities means there is no priority at all. She proposes three filters that function as a pass or fail test. For each ideal customer profile (ICP), can everyone name the buyer, the problem solved, and the value in one sentence? Does every motion connect to a real decision the buyer is making? And is there one thing the team could stop doing this quarter that nobody would miss? That last filter carries a sharp follow-up question: if something can be dropped without consequence, why is it still being done?
The final sharpening step is about people rather than tactics. Otten maps the resulting priorities against what she calls the team’s superhero quadrants: identifying who is genuinely good at a given motion and energized by it. Those are the initiatives that get executed well, which makes them the ones to act on now. The rest can wait. Running through all three moves is a single idea that reorganizes how a leadership team looks at its own numbers. The point is not to optimize the selling process. It is to find the friction in the buying process. “Not your selling process,” Otten says. “How they buy, or don’t.” Most GTM reviews measure the company’s activity and call it diagnosis. The sharper question is what makes it hard for a buyer to say “yes,” and that answer rarely appears in a dashboard.
To learn more, book a discovery call or follow Tiffany Lyman Otten on LinkedIn for more insights on B2B GTM strategy, messaging clarity, and revenue-focused marketing.
