I spent six months building buyer personas that nobody used.
Beautiful templates with demographics, goals, challenges, and preferred communication channels. Executive summaries with stock photos and fictional names like "Enterprise Emma" and "Startup Steve." Polished presentations walking through each persona's day in the life.
Product ignored them. Sales said they were "too generic." Marketing said they already knew this stuff.
Then I took Pragmatic's PMM course and realized I'd been building personas wrong. I was documenting demographics, not understanding buyers. I was creating fictional characters, not revealing the problems people would actually pay to solve.
The Market box in the Pragmatic Framework—the foundation of everything else—isn't about knowing who your buyers are. It's about understanding the problems they have, the alternatives they're considering, and the moments when they decide to act.
Most PMMs treat the Market box like a research project. You complete it once, put it in a shared drive, and move on. That's why it doesn't drive decisions.
The Market box is supposed to be a living system that continuously surfaces insights product, sales, and marketing can't ignore. Here's how I learned to make that happen.
What the Market Box Actually Means
Pragmatic's Market box includes buyer personas, competitive analysis, market problems, and win/loss analysis. Most PMMs focus on personas and ignore the rest. That's backward.
Personas are the output, not the input. The real work is understanding market problems—the specific situations that make someone decide they need to solve this problem right now with this type of solution.
I learned this the hard way when I interviewed a customer who bought our product.
I asked the typical persona questions: What's your role? What are your goals? What challenges do you face?
She gave me generic answers: "I'm a VP of Sales. My goal is to hit quota. My challenge is pipeline visibility."
Then I asked: "What were you doing the day you decided you needed a solution like ours?"
She paused. "Our board asked for a forecast on Tuesday. I couldn't produce it because our data was in three different systems. I looked incompetent in front of the CEO. I started looking for solutions that afternoon."
That's the insight. Not "VP of Sales needs pipeline visibility"—everyone knows that. The insight is: "VPs of Sales buy pipeline tools right after they fail to deliver a forecast to the board."
That's a trigger event. That's positioning. That's a campaign. That's a sales play.
The Market box isn't about documenting who your buyers are. It's about discovering the moments when they become buyers.
The Questions That Reveal Real Market Insights
Most buyer persona research asks surface-level questions: What's your role? What are your responsibilities? What are your pain points?
These questions generate obvious answers. You learn nothing you couldn't have guessed.
I learned to ask questions that reveal behavioral truths—the specific circumstances that create urgency, the alternatives they considered, the reasons they chose your competitor.
The first question I always ask is: "Walk me through what was happening when you decided you needed a solution like this."
This uncovers trigger events—the specific moments when a tolerable problem becomes urgent.
Most buyers don't actively look for solutions until something forces them to. A new executive joins and expects capabilities they don't have. A competitor launches something that makes their stack look outdated. They get asked to produce a report they can't.
Understanding trigger events lets you position your product around urgency, not just value. It tells you when to reach prospects, what messages will resonate, and how to create urgency in sales conversations.
One company I worked with discovered 70% of customers started looking for their product within 30 days of a funding round. We built a prospecting engine around tracking funding announcements. Pipeline increased 40%.
The second question I always ask is: "What other solutions did you consider, and why didn't you choose them?"
This reveals how buyers think about your competitive landscape—which is usually different from how you think about it.
Buyers don't categorize solutions the way vendors do. You think your competitor is the other enterprise platform. They think your competitor is Excel, or doing it manually, or not solving the problem at all.
I once discovered our "competitor" wasn't the obvious platform—it was internal tools built by engineering teams. That changed everything. We repositioned around "buy versus build" economics and shortened our sales cycle by 30%.
The third question I always ask is: "Tell me about a decision you made this week where you wished you had better data or tools."
This reveals actual jobs-to-be-done in context, not abstract feature requests.
It grounds feature requests in real decisions with real consequences. Instead of "we need better reporting," you hear "Last Tuesday I had to tell the CEO whether to expand into EMEA, and I guessed because our data doesn't segment by region."
I turn these stories into use cases and messaging. "CFOs at mid-market SaaS companies use our product to make expansion decisions with confidence" is more compelling than "we have regional analytics."
The Competitive Intelligence That Actually Wins Deals
Pragmatic's Market box includes competitive analysis, but most PMMs do it wrong.
They create spreadsheets comparing features: we have X, competitor A has Y, competitor B has Z. Then they wonder why sales doesn't use the battlecards.
Feature comparisons don't win deals. Understanding why buyers choose competitors does.
The best competitive intelligence doesn't come from analyzing competitor websites—it comes from interviewing customers who didn't choose you.
Every quarter, I interview 10-15 customers who evaluated us and chose a competitor.
Most PMMs avoid these conversations because they're uncomfortable. I used to. Then I realized these are the most valuable interviews you can do.
The question that reveals everything is: "Walk me through the moment you decided they were the right choice."
Not "Why did you choose them?"—that gets you generic answers like "better fit" or "easier to use."
"Walk me through the moment" forces them to reconstruct the specific conversation, demo, or realization that tipped the decision.
I learn the exact message competitors use that resonates, and I steal it. I learn the specific capabilities that matter in bakeoffs, and I prioritize them. I learn the objections to our product that sales isn't surfacing, and I fix them. I learn the positioning angles competitors use successfully, and I counter them.
I learned more about our biggest competitor from five loss interviews than from six months of monitoring their website.
One customer said: "They showed us how much time our ops team would save. You showed us features. We bought time savings."
That one sentence changed our entire demo strategy. We stopped leading with features and started leading with time-to-value. Win rate increased 15%.
Making Market Problems Actionable for Product
The Market box includes "Market Problems"—understanding the specific problems buyers need solved.
Most PMMs document this as a list of pain points: "Customers struggle with X. Customers want Y."
Product ignores these lists because they're not actionable. "Customers struggle with reporting" doesn't tell product what to build.
I learned to map problems to impact and frequency instead.
For each market problem, I document the specific situation buyers encounter—not "reporting is hard" but "Sales leaders can't forecast pipeline because data is in three systems." I document the business consequence if unsolved: "Missed forecasts lead to board scrutiny, budget cuts, and job risk." I document how often buyers encounter this: "Weekly for 60% of sales leaders, monthly for 30%." I document the evidence: "10 of 15 VP Sales interviews, March 2025."
This format makes problems actionable. Product knows what to build. Sales knows which problems create urgency. Marketing knows which messages resonate.
I started presenting market problems this way and product roadmap conversations changed overnight. Instead of debating whether a problem exists, we debated whether it's frequent enough and high-impact enough to prioritize.
One problem I documented—"Finance teams spend 40 hours per quarter reconciling data across systems"—became our top product priority and biggest competitive differentiator within six months.
Making Market Research Continuous Instead of Quarterly
The biggest mistake PMMs make with the Market box is treating it like a project. You do buyer persona research in Q1, deliver the report, and don't update it until next year.
By the time you finish the research, it's already outdated.
Markets move fast. Competitors launch new capabilities. Buyer priorities shift. New alternatives emerge.
The Market box only works if it's a continuous system, not a quarterly project.
My rhythm became weekly: interview 2-3 customers, prospects, or churned users. Bi-weekly: update the market problems doc with new insights. Monthly: share competitive intelligence brief with product and sales. Quarterly: synthesize themes and update buyer personas based on pattern changes.
The system works because the time commitment is small—4-6 hours per week. Continuous insights prevent staleness. Product and sales see value because insights are timely. You catch market shifts early instead of six months late.
One quarter, I noticed three customers mention the same new competitor in win/loss interviews. I updated our battlecard within a week. Sales was prepared when that competitor started showing up in deals the next month.
If I'd waited for the quarterly review, we would have lost two months of deals because sales didn't know how to position against them.
The Persona Format That People Actually Use
After years of building personas that nobody used, I finally figured out the format that product, sales, and marketing actually act on.
Demographic-heavy personas with fictional names, stock photos, and "day in the life" narratives don't work.
What works is problem-based personas organized around trigger events, evaluation criteria, and objection patterns.
For VP of Sales at mid-market B2B SaaS companies with 50-200 employees, I documented trigger events—when they start looking. Sixty percent start looking after the board asks for a forecast they can't produce. Twenty-five percent start after a new CRO joins and expects capabilities they don't have. Fifteen percent start after missing a quarter due to pipeline visibility gaps.
I documented evaluation criteria—what they care about. They want time to first value with wins within 30 days. They care about sales team adoption because they've been burned by tools reps won't use. They need integration with existing stack because they won't replace Salesforce.
I documented common objections. They say "We can build this internally" even though they actually can't, but engineering says they can. They say "Too expensive for our stage" because they're comparing to doing nothing, not to the cost of the problem. They worry about change management risk because they've been burned by failed rollouts before.
I documented competitors they consider. Eighty percent evaluate Clari or Gong as primary alternatives. Thirty percent consider internal tools built by engineering as secondary options. Fifty percent compare against status quo and Excel.
I documented why they choose us: speed to value, ease of adoption, specific workflow advantages. I documented why they choose competitors: more enterprise features from Clari, better AI capabilities from Gong, lower upfront cost from internal tools.
I added evidence: based on 20 customer interviews and 15 win/loss interviews from Q1 2025.
This format is actionable. Product knows what to build—address objections, match evaluation criteria. Sales knows what to emphasize—trigger events, differentiation. Marketing knows what to message—trigger events, objection handling.
I shared this format with sales and heard: "This is the first persona doc I've actually used." That's when I knew it worked.
Learning From Common Market Box Mistakes
After watching dozens of PMMs struggle with the Market box, I started seeing patterns in what made them fail.
The first mistake was only interviewing customers who love you. They only talked to power users and promoters. They avoided at-risk accounts and losses. Selection bias meant they missed the insights from people who struggled, almost churned, or chose competitors. The fix was interviewing a mix every month: happy customers to learn what's working, at-risk customers to learn what's almost working, churned customers to learn what's not working, and losses to learn why they chose competitors.
The second mistake was asking what people want instead of watching what they do. They ran surveys asking "What features do you want?" and built based on responses. People are terrible at predicting what they'll use. They say they want feature X, you build it, nobody uses it. The fix was asking "Show me the last time you tried to accomplish this job" and watching what they actually do. Build based on observed behavior, not stated preferences.
The third mistake was treating personas as a one-time deliverable. They spent six weeks on persona research, delivered a report, never touched it again. Markets change. Buyer priorities shift. Competitors launch new capabilities. Last year's personas are outdated. The fix was making persona research continuous. Interview customers every week. Update personas quarterly based on pattern shifts.
The fourth mistake was doing competitive analysis from websites, not from buyers. They analyzed competitor websites, pricing pages, and demo videos to understand their strategy. What competitors say doesn't tell you why buyers choose them. The fix was interviewing customers who evaluated you and chose competitors. Ask: "Walk me through the moment you decided they were the right choice." That reveals their real positioning and strengths.
The Market Box Is Your Foundation
Everything in the Pragmatic Framework builds on the Market box.
You can't do positioning (Focus) without understanding competitive alternatives (Market). You can't do pricing (Business) without understanding buyer priorities (Market). You can't do launches (Programs) without understanding trigger events (Market). You can't do enablement (Readiness) without understanding objection patterns (Market).
Most GTM failures trace back to skipping the Market box.
Your launch failed because you didn't understand buyer priorities. Your positioning isn't landing because you don't know the competitive alternatives buyers actually consider. Your pricing seems too high because you don't understand the business impact of the problem you solve.
The uncomfortable truth: Most PMMs skip the Market box because it's hard, slow, and involves talking to people.
It's easier to jump straight to tactics—write messaging, build sales decks, plan launches. Those feel productive.
But without Market work, you're guessing. You're building campaigns for buyers you don't understand, positioning against competitors buyers don't consider, and messaging problems buyers don't care about.
I learned to spend 20% of my time in the Market box every week. Interview customers. Talk to prospects who didn't convert. Analyze win/loss patterns. Update competitive intelligence. Document trigger events.
That foundation makes everything else faster and more effective.
I've watched PMMs spend six months relaunching the same product because they refused to spend two weeks on buyer research.
Don't be that PMM. Do the Market work. Everything else gets easier.