Last week, I explored how job priorities shape the B2B buyer’s mindset when it comes to purchasing decisions. The reality is that unless your product solves a problem that ranks reasonably high on your buyer’s priority list, your chances of closing deals remain slim—regardless of how brilliant your solution might be. The key isn’t just solving a problem; it’s understanding where that problem sits in your user’s priority matrix.
I used the Eisenhower matrix as a framework to map where your B2B product might land on the axes of importance versus urgency. The route to avoid is the quadrant where problems are neither urgent nor important. No matter how elegant your solution feels, that’s dead-end territory. Focus your energy elsewhere.
The good news is that the other three quadrants offer fertile ground. You might assume building in a “higher” quadrant guarantees better results, but that’s not necessarily true. As long as you’re operating in one of those three viable quadrants, you have a market worth pursuing. The approach will differ—how you build, position, and present your product will vary—but the opportunity exists.
So how do you identify your quadrant?
The answer only emerges when you step away from desk research and internal conversations to engage with the real world.
Assumptions are valuable starting points. They form the foundation of scientific inquiry and drive progress. But they must be followed by a relentless pursuit of evidence. (BTW, “relentless” isn’t hyperbole when it comes to startups and business building.)
Without getting pedantic, the following steps are enough to keep your GTM moving in the right direction.
1. Commit to regular customer conversations. Set a realistic weekly target for user interviews. You won’t manage five conversations in week one—start small, stay consistent, and build momentum. Think of it as continuously casting and recasting your net.
2. Dig deeper than your assumptions. While discussing your target problem, explore your user’s broader workflow. Understand their adjacent tasks, workplace responsibilities, and how their role fits within the larger organizational structure.
3. Map and validate priorities. Create a priority list from what you’ve discovered, then confirm with users whether your assessment reflects their reality.
Once you’ve gained clarity about your quadrant, developing the right sales approach and messaging becomes significantly easier. I’ll dive deeper into those tactics in the coming weeks.
There comes a stage early on in the B2B founder’s journey where they ask themselves: “Why aren’t people buying?”.
This usually happens after they have exhausted their base of industry friends and contacts. The ones who are happily running pilots and demos, even gushing about how good the product is. This is the initial traction that every founder so desperately wants by this point—that glimpse of validation, telling them that there is after all a market of buyers who only need to be told about the product. Anyone who fits the profile of their first users.
Which is exactly the kind of sales approach that a founder should be following at this point. As long as they remember the huge caveat that the customers they are going after at this stage can’t and won’t fit the profile of their first users, for the simple reason that they aren’t personal contacts to begin with. What happens at this stage now may well feel like having to start all over again, dashing all the enthusiasm which had kicked in after that first flavour of success with early users.
(Of course, there can be the scenario that you have a large enough ocean of friends and industry contacts to keep giving you a steady stream of revenue and growth, along with product validation, that you don’t need to worry about reaching out to the open market. I can only say two things to you—you have my unreserved envy and that you probably don’t need to read any further from here. You have already put in the hard work over the years of cultivating the right kind of network that’s needed to build a business.)
For the rest of us, let’s figure out what happens next.
The Four Stages of Startup Reality
When an early-stage B2B startup hits this wall, there are typically four possibilities at play:
Non-existent problem: The problem exists in the founder’s mind alone. No real fix for this, except talking to people and starting afresh.
Problem exists, product is crap: Not a bad place to be in. That’s where the best businesses have been born out of. Just hang out there, talk talk talk and work on the product.
Problem exists, product does the job, wrong customer: Congratulations, you have reached a stage most founders only dream of. You’re just talking to the wrong folks.
Problem exists, product works, right customer, wrong priority: This is the trickiest spot. The product works, it solves a problem, and the customer profile is correct too. So why aren’t they buying?
If you’re in that fourth category – and frankly, that’s where most promising startups get stuck – the issue isn’t your product or your market. It’s timing and priority.
The Priority Problem: When Good Products Meet Bad Timing
Here’s the thing about business problems: they don’t all carry the same weight in your customer’s world. Any business needs to get dozens of jobs done to function properly. These jobs are performed by the very people who should be using your product. But they’ll only prioritize your solution when the problem you solve becomes urgent enough to demand their immediate attention.
This is where most founders get it wrong. They assume that having a real problem and a working solution equals inevitable sales. But there’s a crucial missing piece: understanding where your customer’s problem sits on their priority ladder.
Eisenhower Matrix: The Unlikely B2B Sales Weapon
You’ve probably heard of the Eisenhower Matrix – that simple 2×2 grid that divides tasks by Urgency and Importance. What you might not have considered is how it can transform your approach to B2B sales.
When you map your prospect’s problems to this matrix, buying behavior becomes remarkably predictable:
Quadrant I (Urgent + Important): High probability of purchase, short decision cycles, willingness to pay premium prices for speed and risk reduction. These prospects have budget authority and executive attention.
Quadrant II (Important, Not Urgent): Moderate-to-high probability with longer evaluation periods. They focus on ROI, require multi-stage procurement, and involve strategic stakeholders.
Quadrant III (Urgent, Not Important): Quick tactical purchases, preference for cheap solutions or internal workarounds. Lower spend, faster decisions.
Quadrant IV (Not Urgent, Not Important): Near-zero purchase probability. Your time will be better spent in another quadrant at this stage.
What this translates into for the customer
Quadrant I (Urgent, Important)
“We have a burning issue. We need a solution now.”
Quadrant II (Important, Not Urgent)
“This matters strategically, but we can wait.”
Quadrant III (Urgent, Not Important)
“This is a recurring problem that needs fixing without asking for too much.“
Quadrant IV (Not Urgent, Not Important)
“Nice to have, but no time or money.”
Where Should You Aim?
Q1 is where you would ideally like to be, but getting there requires a combination of the right timing and event triggers. During early stages, the best place to target is Q3. Once there, you can start building your move towards Q2, the place to be for B2B legend status.
Here are a few examples of businesses in each of these quadrants to give you a better sense.
Quadrant I (Urgent + Important): This is where you want to be when prospects have budget and authority. Think PagerDuty during system outages, Zoom during COVID lockdowns, or Slack when email became unbearable. But you can’t manufacture these moments – you can only be ready when they happen.
Quadrant II (Important, Not Urgent): This is the sweet spot that SaaS startups should aim for. The place where they achieve nirvana. Salesforce owns Q2 for CRM, HubSpot for marketing automation, Notion for team productivity. These companies built sustainable, predictable revenue by making themselves essential to long-term strategy. The challenge? It takes time and perfect product-market fit to get here.
Quadrant III (Urgent, Not Important): This is often where you’ll start and get initial traction. Calendly began solving the “urgent but small” problem of scheduling conflicts. Loom started as a quick way to record screens instead of typing long explanations. Typeform tackled the immediate pain of ugly surveys. The key is using Q3 as your wedge into Q2.
The interesting thing about problems is that they don’t remain confined to any quadrant, but keep moving between them. This can be seen in how some businesses have achieved greater success as their customers transitioned.
Slack: Started as a gaming company’s internal tool (Q3) → became essential team communication (Q2) → now critical business infrastructure (Q1 during outages)
Zoom: Video calls were “nice to have” (Q3) → strategic remote work enabler (Q2) → mission-critical during pandemic (Q1)
Take your recent calls and assess where their problem sits. If most are in Q4, you’re wasting time. If they’re mostly Q3, you might have a business. This exercise will change how you qualify leads.
Keep a simple spreadsheet with columns for Prospect, Problem Quadrant, Trigger Events to Watch, and Last Priority Ranking. Review it weekly. You’ll start seeing patterns that transform your hit rate.
The beauty of this approach is its simplicity. It doesn’t ask for anything dramatic, while giving you greater insight into your buyer’s mindset to align it to your product and sales approach. That’s usually all you need at this stage.
Conventional wisdom suggests founders should step back from sales as quickly as possible. This approach misses a fundamental dynamic: the founder’s unique advantages in B2B sales environments.
Academic research demonstrates that founder-led companies consistently outperform their peers, particularly in the critical early-stage sales process. Not necessarily because of superior sales technique, but because of their position as a problem-solver invested in customer success.
Strategy 1: Leverage Authentic Passion as Social Proof
Research on emotional contagion reveals that genuine enthusiasm spreads unconsciously between people. Founders communicate with what’s “authentic credibility”—prospects perceive reduced agency risk when a CEO stakes their reputation on a solution.
This dynamic becomes particularly powerful in B2B environments where buyers must justify decisions internally. The founder’s presence inherently validates the purchase decision, providing social proof that extends beyond product features to encompass organisational credibility.
Strategy 2: Master the Consultative Paradox
Founders possess a unique advantage: they can afford to be genuinely consultative, even when it means walking away from revenue. This “costly signaling” demonstrates trustworthiness through actions that appear contrary to immediate self-interest. Research shows prospects develop deeper trust when salespeople acknowledge limitations or suggest competitors might be better fits.
This authenticity paradoxically increases close rates by positioning the founder as trusted advisor rather than vendor, fundamentally altering the buyer-seller dynamic.
Strategy 3: Transform Product Roadmap Discussions into Strategic Partnerships
Customer co-creation research reveals that involving buyers in product development significantly increases purchase likelihood and retention. This approach creates “psychological ownership” through the IKEA effect—people value things more highly when they’ve contributed to their creation. When founders invite prospects into product development discussions, they’re creating this psychological ownership that significantly influences purchase decisions.
Strategy 4: Weaponise Intellectual Humility
Social psychology research reveals that admitting uncertainty in non-expertise areas actually increases credibility in expertise areas. Founders who acknowledge gaps in their sales process or market understanding create “authentic leadership presence” that paradoxically strengthens their authority when discussing technical solutions.
Research on founder personality suggests successful entrepreneurs exhibit high intellectual humility, adapting strategies based on market feedback. This translates to more effective discovery conversations and stronger prospect relationships built on mutual learning rather than one-way pitches.
Strategy 5: Create Asymmetric Value Through Vision Sharing
Transformational leadership research shows vision-driven narratives create stronger emotional connections than feature-focused presentations. Founders possess exclusive access to the origin story—the authentic “why” behind their solution that hired salespeople can only approximate.
Research on entrepreneurial narratives demonstrates that founder-led stories about company purpose create “meaning-making” for prospects—connecting solutions to broader organisational goals. When founders share their authentic problem-solving journey, they provide prospects with compelling stories to champion internally, creating advocates within the buyer organisation.
The Founder’s Competitive Edge
These strategies work because they leverage inherent founder advantages. Each strategy represents a foundation for deeper exploration—from emotional contagion neuroscience to consultative selling behavioural economics providing a robust framework for understanding why founders can excel as chief sales officers. Much of which comes down to understanding founder weaknesses and using them counter-intuitively as sources of strength.
