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Every sales organization has its own set of comfortable lies. These are the assumptions that live in the space between what everyone knows and what nobody says out loud. They survive in quarterly reviews, strategic planning sessions, and coaching conversations because questioning them feels dangerous. After all, if you’ve built an entire go to market strategy on a foundation that might be cracked, admitting doubt seems like professional suicide.
But here’s the thing about comfortable lies: they’re expensive. They cost time, money, and the kind of organizational energy that could be spent actually winning deals instead of pretending everything is fine. The most successful sales leaders aren’t the ones who never question their approach. They’re the ones who ask the uncomfortable questions early enough to do something about the answers.
So let’s talk about three questions that your sales team probably isn’t asking, even though these questions might be the most important ones standing between your current results and the ones you actually want.
Question One: Are We Selling to People Who Can’t Actually Say Yes?
There’s a peculiar kind of theater that happens in modern sales organizations. Your team fills pipelines with opportunities. They have conversations that feel productive. Decision makers nod along in meetings. Everyone agrees the solution makes sense. The prospect even says things like “this looks really good” and “we need to move forward on this.” And then nothing happens.
Month after month, these deals sit in your pipeline like houseguests who won’t leave. They’re not dead enough to remove, but they’re not alive enough to close. Your salespeople provide updates that sound like progress but feel like Groundhog Day. “They’re working on budget approval.” “They’re building consensus internally.” “They’re waiting for the right time to present to leadership.”
Here’s what nobody wants to admit: in many of these situations, your team isn’t selling to decision makers. They’re selling to people who have some influence, maybe even strong influence, but who lack the authority or political capital to actually make something happen. Your salespeople have optimized for access rather than power.
This happens because real decision makers are hard to reach. They’re busy, they’re protected by layers of organization, and they often don’t take meetings until someone else has done the groundwork. So your team does what feels natural: they work with who’s available. The problem is that working with available people creates the illusion of progress while almost guaranteeing mediocre results.
Think about it like this. Imagine you’re trying to get a new policy adopted in a large bureaucracy. You could spend months crafting the perfect proposal, building consensus among middle managers, and creating detailed presentations. All of that activity would feel productive. It would generate meetings and emails and feedback. But if the person who actually decides policy never sees your work or doesn’t care about the problem you’re solving, all that activity accomplishes nothing.
Sales teams do this constantly. They work deals that were never really winnable because they never got to the person who could win them. The truly uncomfortable question isn’t whether your team is working with decision makers. It’s whether they even know how to identify real decision makers in the first place, or whether they’ve learned to mistake organizational access for actual influence.
The intellectual challenge here is recognizing that decision making authority is contextual and political, not just structural. Someone might have VP in their title but lack the trust or credibility to champion new initiatives. Someone else might be a director who has the CEO’s ear on specific topics. Your org chart doesn’t reveal these dynamics. Only careful questioning and pattern recognition can.
But asking this question forces you to confront an uncomfortable reality: if your team has been spending months or years selling to people who can’t say yes, what does that say about your sales process? About your coaching? About how you’ve trained people to qualify opportunities?
Question Two: Does Our Product Solve a Problem People Are Willing to Pay to Fix Right Now?
Most sales teams operate on a seductive assumption: if we can just explain our value clearly enough, people will buy. So they invest in better messaging, sharper positioning, and more compelling presentations. They create detailed ROI calculators and customer success stories. They train their teams on objection handling and value based selling.
And yet, deals still stall. Not because prospects don’t understand the value. They get it. They agree it would be helpful. They might even genuinely want it. But they don’t buy, or they don’t buy now, because understanding value isn’t the same thing as feeling urgency.
This is where most sales strategies run into a wall that nobody wants to acknowledge. Your product might solve a real problem, but solving that problem might not be urgent enough to overcome organizational inertia, budget constraints, or the simple fact that people are already overwhelmed and your solution adds complexity before it delivers relief.
Think about personal productivity apps. There are hundreds of them, many quite good, all promising to make you more organized and efficient. People download them with genuine enthusiasm. They see the value. They want to be more productive. But most abandon them within weeks because the pain of being somewhat disorganized isn’t acute enough to sustain the effort of changing behavior. The problem is real, but it’s not urgent.
B2B sales faces a similar dynamic, just dressed in enterprise clothing. Your solution might genuinely improve efficiency, reduce costs, or mitigate risks. But if those improvements are incremental rather than critical, and if adopting your solution requires budget approval, implementation effort, change management, and political capital, the honest answer is that most organizations will choose inertia.
The question your team needs to ask is brutally simple: are we solving a problem that causes enough pain right now that someone will spend political capital, budget, and time to fix it? Not six months from now when they’ve built a business case. Right now. Because if the answer is no, you’re not in a sales execution problem. You’re in a market timing problem, and no amount of better selling will fix that.
This is where the intellectual honesty gets uncomfortable. If your average sales cycle is nine months and involves multiple stakeholders, there’s a good chance you’re selling to people who agree you’d be nice to have but don’t think you’re essential to have. That’s not a positioning failure. That’s a fundamental mismatch between what you’re offering and what the market urgently needs.
The contrarian insight here is that sometimes the best sales strategy is admitting who you shouldn’t be selling to. If your solution genuinely shines in specific high urgency scenarios but you’re trying to sell it broadly because you need volume, you’re training your team to push rope. You’re teaching them to overcome objections that can’t actually be overcome because the objection isn’t about your product. It’s about urgency, and urgency can’t be manufactured through better sales technique.
Question Three: Are Our Top Performers Succeeding Because of Our System or In Spite of It?
Every sales organization loves its top performers. These are the people who consistently exceed quota, close the big deals, and make leadership look smart. They’re held up as examples in team meetings. Their approaches get documented and turned into best practices. The organization assumes that if everyone else just did what the top performers do, results would improve across the board.
But here’s a question that keeps smart sales leaders up at night: what if your top performers are succeeding not because of your sales methodology, but despite it? What if they’ve figured out workarounds, developed relationships that bypass your official process, or possess natural abilities that can’t be taught or systematized? What if everything you think is working is actually just survivorship bias dressed up as strategy?
Consider what this looks like in practice. Your top rep closes huge deals by building deep relationships with executives over months of patient cultivation. Your sales process, meanwhile, prescribes a standardized approach with specific stages, required activities, and forecasting milestones. The top rep nods along in coaching sessions but basically ignores most of it because they’ve learned what actually works. When leadership asks how they do it, they translate their intuitive approach into the language of your official methodology because that’s what everyone wants to hear.
Meanwhile, average performers follow the system more faithfully because they don’t have the confidence or experience to deviate. They complete the required discovery calls, fill out the qualification criteria, and move opportunities through stages at the prescribed pace. And they get mediocre results, which leadership interprets as execution problems rather than system problems.
This dynamic exists in every field where skill and intuition matter. Think about cooking. Recipe books provide structure and guidance, but the best chefs don’t mechanically follow recipes. They understand the principles behind techniques well enough to adapt in real time based on ingredients, equipment, and taste. If you tried to turn their cooking into a repeatable process, you’d end up with something that worked okay but lost what made it special.
Sales methodology faces the same challenge. The best salespeople are pattern matchers who read situations and adapt their approach based on subtle cues. They know when to push and when to back off. They sense political dynamics that aren’t visible on org charts. They build trust in ways that feel natural rather than tactical. None of this fits neatly into a CRM workflow or a seven step sales process.
The uncomfortable question is whether your entire sales infrastructure, your training, your tools, your management cadence, is optimized for average performers following a system rather than for developing the judgment and skills that actually drive results. And if that’s true, you might be institutionalizing mediocrity while your best people succeed by ignoring you.
This doesn’t mean methodology is worthless. Structure matters, especially for complex sales with multiple stakeholders. But there’s a difference between providing a framework that supports good judgment and mandating a process that substitutes for it. Most organizations drift toward the latter because it’s measurable and manageable. You can track stage conversion rates and forecast accuracy. You can hold people accountable to activities.
But you can’t easily measure whether someone is building genuine trust or just completing trust building activities. You can’t track whether someone truly understands a customer’s business or just asked the required discovery questions. So organizations measure what they can and hope it correlates with what matters. Often it doesn’t.
The truly scary version of this question is even more direct: if you lost your top three salespeople tomorrow, what would happen to your revenue? If the honest answer is “we’d be in serious trouble” then you don’t really have a sales system. You have talented individuals who are kind enough to let you claim their success belongs to your organization.
Why These Questions Matter
Notice what these three questions have in common. They’re not about tactics or execution. They’re about foundational assumptions that shape everything else. Whether you’re reaching actual decision makers determines if your sales activity can ever convert to revenue. Whether you’re solving urgent problems determines if the market timing supports your growth goals. Whether your system enables or constrains your best people determines if you’re building a scalable organization or just benefiting from individual talent.
These questions are uncomfortable because the honest answers might require significant change. Not tweaking your pitch or adjusting your commission structure. Real change. Like redefining your ideal customer profile. Like admitting your market isn’t ready for what you’re selling. Like rebuilding your sales approach from the ground up.
That’s why most organizations avoid asking them directly. It’s easier to focus on execution, to believe that if everyone just worked harder or followed the process more diligently, results would improve. But this is the organizational equivalent of rearranging deck chairs. It creates the appearance of action while avoiding the fundamental issues.
The best sales leaders ask these questions not because they enjoy discomfort but because they understand that unexamined assumptions are expensive. Every quarter you spend selling to people who can’t say yes is a quarter you could have spent elsewhere. Every deal you chase without real urgency is energy that could have gone to better opportunities. Every process that constrains your best people is potential you’re leaving unrealized. None of this is about being negative or questioning for the sake of questioning. It’s about intellectual honesty in service of better results.
So here’s the real question: is your sales organization brave enough to ask uncomfortable questions and follow where the answers lead? Because the competition that’s willing to ask them has an advantage that better CRM systems and more aggressive goals can’t overcome. They’re playing a different game, and they’re probably winning.