7 Questions Every B2B CMO Must Answer Before Starting a Positioning Project
Get the positioning pre-work wrong, and no amount of brilliant strategy will save you.
Quick summary: Seven questions most B2B CMOs skip before starting a positioning project. Get them wrong and you won't end up with bad positioning. You'll end up with no positioning at all.
Most B2B positioning projects fail before the first workshop. Not because the strategy is wrong or the market research is thin, but because nobody asked the right questions before the work began.
Bob Wright, co-founder of Firebrick Consulting, has run B2B positioning engagements for more than 300 tech companies, including GitLab, Workday, Calendly, Verifone, and Postman. Across four CMO Huddles Strategy Labs with senior B2B marketing leaders, he kept returning to the same pre-work failures. The same assumptions, skipped conversations, and expensive surprises three weeks into a process that should have been caught on day one.
These are the seven questions CMO Huddles took away from those sessions. If you can’t answer them before you start, you’re not ready to start.
1. Does the CEO know they’re about to sponsor this, not just approve it?
The question isn’t whether the CEO supports the idea of better positioning. That’s table stakes. The real question is whether they understand they are the executive sponsor, present in the room, accountable for the output, and prepared to make decisions when the team disagrees.
“Positioning is not a marketing initiative. It’s actually a company initiative,” Wright said across multiple sessions. “Marketing runs the process. But it has to be CEO sponsored.”
The projects that stall are almost always the ones where marketing got a thumbs up from the CEO and then ran the process themselves, only to deliver a story the CEO doesn’t own and the sales team won’t use. Wright’s process requires the full executive team in the room. Not because it makes for a better meeting, but because when the story is done, it belongs to everyone who built it, not just the CMO.
⚠️ If the CEO can’t commit to being in the room, stop here. A positioning project without CEO sponsorship produces a marketing document, not a company strategy.
2. What exactly are we positioning, and how far out?
“First thing I ask when we take executive teams through the process is: What are we positioning?” Wright said. “How far out are we going?”
Are you positioning a single product? A portfolio? The corporate brand? Are you building for where the company is today, or for where it needs to be in eighteen months? The scope determines everything: Who needs to be in the room, what research is required, how long the process takes, and what counts as success.
Companies that skip this question often end up weeks into a process before realizing product marketing wants a product-level story, the CEO wants a corporate narrative, and the CRO wants something they can use in enterprise deals next quarter. These are not the same thing. Pretending they are produces a positioning that serves none of them.
3. Who is this positioning actually for?
Customer? Investor? Analyst? Executive buyer? Practitioner? Every answer is legitimate, but each one shapes a different positioning. Trying to serve all of them with the same story is how you end up with something that resonates with no one.
Wright’s consistent recommendation across all four sessions: Anchor on the customer and the revenue conversation first.
“I always say lean into the customers, because that’s where the revenue growth is going to come from,” he said.
If investor or analyst positioning is also needed, it becomes an addendum. Additional slides and context layered on top of a customer-facing story that’s already solid. Wright pointed to Workday, GitLab, and New Relic as companies that used their customer positioning as the foundation for their investor decks, not the other way around.
⚠️ If you can’t name a specific person whose behavior you want to change as a result of this positioning, you don’t have a clear enough audience yet.
4. Where are you actually getting stuck in the sales cycle?
Before you can fix positioning, you need to know what it’s supposed to fix. Wright asks a pointed diagnostic in every engagement: Where do you get stuck?
Is it early (not enough pipeline, not enough awareness, not enough inbound)? Or is it late (deals that stall after the demo, procurement that turns into a feature shootout, no-decision outcomes that drag on for quarters)?
“The emphasis of your positioning depends on the answer,” he said. “If it’s a real competitive battle, that’s a very different positioning than just trying to get a buyer to raise their hand.”
The data to bring into this conversation:
- Win/loss ratio trends
- Average deal size and ACV
- Sales cycle length
- How often your team reaches an executive buyer versus a practitioner or middle manager
Those metrics tell you more about your positioning problem than any internal debate about messaging ever will.
#5 Do you have a viewpoint, or just a description?
This is the gut-check question. Worth asking in the room with brutal honesty before investing in a formal process.
A viewpoint is a market stance: A specific perspective on what’s broken, what’s changed, or what your buyers are getting wrong that your company exists to correct. A description is what most B2B tech companies have instead, a summary of what the product does and who it’s for.
Wright frames it this way: Category leaders and growth leaders all have a viewpoint. They bring buyers something they haven’t thought about. A reframe. A named problem. Something that makes a buyer say, "I never looked at it that way."
“If you’re explaining, you’re losing,” he said. “You’re trying to explain how your product works and the features and functions, nobody gets it. People get problems.”
At one of the Strategy Labs, Drew asked the room: Does your company have a genuine point of view? Fewer than half raised their hands. That’s a competitive opening for the CMOs willing to do the work.
⚠️ Most companies that think they have a viewpoint actually have a mission statement. Those are not the same thing.
6. If you set the buying criteria, would you win every time?
Wright’s competitive diagnostic it reveals whether your differentiators are real or theoretical.
“If the buying criteria was based upon these three capabilities that you have, you would win every time,” he said. “What are those? You’ve got to build a case that those are exactly the right criteria.”
If you can’t answer this confidently, you have one of two problems. Either you don’t yet know what truly differentiates you, in which case you need customer research. Or you know what differentiates you, but haven’t connected it to a named problem your buyers actually feel, in which case you have the raw material but not a story.
Either way, knowing the answer before you start tells you exactly what kind of positioning project you actually need.
7. Is the product team in the room, and do they know what they’ve signed up for?
This is the question most CMOs forget to ask, and it kills more positioning projects than any other single factor. Positioning that doesn’t connect to the product roadmap is aspirational fiction. Product priorities that aren’t informed by positioning produce features nobody can sell.
“The product leader has to be there,” Wright said.
He’s seen the failure mode firsthand: A positioning project that nailed the story, only to stall because the product team had named and scoped their releases independently, and the new narrative didn’t map to anything shipping in the next two quarters.
The harder version of this question: Does the product leader understand that a good positioning process may surface new customer problems that don’t match the current roadmap? And are they prepared to have that conversation?
⚠️ If the product leader isn’t in the room, you’ll build a story you can’t deliver. If they’re in the room but won’t engage, you’ll build a story they’ll quietly ignore.
The bottom line
Seven questions. Most B2B positioning projects skip at least four of them. The ones that skip all seven produce the most expensive kind of output in B2B marketing: A beautifully crafted narrative that changes absolutely nothing about how the company wins.
The companies that get the positioning pre-work right don’t just have better messaging. They have shorter sales cycles, higher win rates, larger deal sizes, and executive conversations their competitors can’t get to.
Bob Wright is Co-Founder of Firebrick Consulting, a B2B positioning firm. He has run positioning engagements for more than 300 B2B tech companies including GitLab, Workday, Calendly, Verifone, and Postman. He facilitated seven CMO Huddles Strategy Labs on B2B positioning in 2026.
Want more?
- For the five principles that category leaders get right, read: The 5 Positioning Pillars Every B2B Category Leader Gets Right
- To go deeper on how to own your hill, read: What Is B2B Positioning? A Framework for Owning Your Hill
- CMO Huddles brings together senior B2B marketing leaders for candid, peer-to-peer conversations on the challenges that matter most. Learn more.
FAQs About the B2B Positioning Process
The most common reason is that positioning gets treated as a marketing project rather than a company initiative. Without CEO sponsorship and full executive team involvement, the output is a story that marketing owns and nobody else uses. Wright’s observation across more than 300 engagements is that the process itself, not just the output, has to be a company-wide exercise.
Wright’s guideline is 12 to 18 months. Positioning should evolve when your buyers change, when a significant new competitor enters the market, or when a major acquisition or new technology requires a new story. What it should not do is change after every sales meeting where someone said something unexpected. That discipline has to come from the executive team, not just marketing.
Wright’s approach is to conduct analyst conversations as part of the discovery phase, not to involve them in the process itself. Analysts are useful for understanding how a category is perceived and for validating language once a story is formed. But building positioning around analyst frameworks tends to produce category descriptions rather than genuine market stances.
Wright draws a clear distinction. Branding is about experience, visual identity, tone, and corporate identity. It can last five to ten years. Positioning is about how you shape and own a category and drive revenue. It needs to evolve more frequently and has a direct connection to sales cycle performance, win rates, and deal size. The two inform each other but are not the same exercise.