Questions Sellers Should Ask Themselves

Reading Time: 5 minutes

If you’re not interrogating your own approach, your buyers certainly will. Salespeople are often praised for the questions they ask their prospects. But the best sellers I know turn that curiosity on themselves just as relentlessly. In an environment where buying committees are growing and confidence in vendors is falling, success lies not in finding clever ways to overcome objections, but in asking harder questions — of yourself.

Gartner’s latest research notes that B2B buying decisions now involve an average of 10 stakeholders, each with their own priorities and risk tolerance. It’s no wonder the number one competitor most sellers face isn’t another supplier — it’s the buyer doing nothing at all. In that context, your product knowledge is table stakes. Your ability to self-interrogate is the differentiator.

Here are five questions every seller should be asking themselves — not once, but constantly. They’re not designed to soothe. They’re meant to sharpen.

Do I really understand how this buyer buys?

It’s easy to talk in generalities about your ICP or your vertical. But unless you’ve mapped the internal politics, procurement process, and emotional drivers of the specific organisation you’re selling to, you’re still operating in the realm of assumption. And assumptions, in sales, are where good deals go to die.

Understanding how a buyer buys is not the same as asking who signs the PO. It’s about knowing who influences the decision quietly, what internal deadlines matter more than yours, and where the resistance to change is coming from. It’s about knowing whether this is a budgeted project or a back-of-a-napkin idea someone’s been championing for six months. It’s about asking yourself whether your proposal fits into an existing buying motion — or whether you’re asking them to invent one.

According to a 2023 Korn Ferry survey, nearly 80% of sellers still rely on outdated personas or generic messaging when building their pitch. Unsurprisingly, less than a quarter of buyers say they feel truly understood in those conversations. If you’re still leading with “how we help companies like yours” instead of “how you’ve made similar decisions before,” you’re still outside the building.

Am I making it easy for them to buy — or just easy for me to sell?

There’s a dangerous comfort in perfecting your pitch, refining your deck, and rehearsing your objection-handling. It makes your process feel smooth. But what about theirs?

Too often, we assume that because a buyer is interested, they’ll naturally find a way to navigate the internal roadblocks. That’s a fantasy. B2B decisions are high-stakes, high-friction, and often politically fraught. Most buyers aren’t looking for the perfect solution. They’re looking for the safest bet.

Gartner found that 77% of B2B buyers described their last purchase as “complex” or “difficult.” That’s not because they were dealing with bad salespeople. It’s because the systems they operate in are labyrinthine, risk-averse, and allergic to ambiguity. The seller’s job, then, is to act as a guide — not a guest.

Ask yourself: have I made the next step obvious and low-effort? Have I equipped my champion with the language, tools and proof they need to lobby internally? Have I removed the ambiguity around what comes next? Or have I simply handed them a proposal and hoped their enthusiasm will carry it through the maze?

Am I chasing deals or building momentum?

Revenue is the outcome everyone’s measured on. But the input that really matters — and that most forecasts ignore — is momentum. Deals don’t close because someone liked your pitch. They close because a series of small, well-timed actions created continuous motion. When that motion stops, so does your deal.

Too many sellers become obsessed with the late-stage drama of closing, and forget to nurture the early signals of progress. A second meeting secured, an additional stakeholder brought in, a procurement question asked unprompted — these are the true leading indicators. Momentum is quiet. But it’s measurable. And it’s usually invisible to the seller who’s focused solely on the dollar signs at the end of the quarter.

McKinsey’s research into high-performing sales teams shows that they monitor pipeline velocity as closely as they do pipeline value. In other words, they measure how deals move, not just how many exist. Because a stuck deal is a dead deal. The question isn’t “Can I close this by end of month?” It’s “Has this moved since last week — and if not, why?”

Momentum isn’t always dramatic. Sometimes it’s just a nudge: a relevant case study, a thoughtful follow-up, a hard question asked with care. But over time, those nudges compound. And in a world where trust is built in inches, not miles, that’s what turns interest into intent.

What do I actually sound like to the buyer?

It’s a strange exercise, but an essential one: record your next call, and play it back with the question, “Would I buy from me?” Not based on the words you used, but the tone, rhythm, pace, and intent behind them.

Do you sound calm, informed, and curious — or urgent, transactional, and rehearsed? Are you responding to what’s being said, or merely waiting for your chance to redirect? Are you adapting your energy to theirs, or bulldozing through a script?

Gong’s data tells us that top-performing reps speak nearly half as much as their average counterparts, and ask more open, layered questions — the kind that start with “Help me understand” or “What’s behind that?” The best sellers don’t just gather information. They demonstrate presence. And presence, in a buying process that’s often political and emotionally loaded, is everything.

Buyers are highly attuned to what’s unsaid in a conversation. They’re listening for signs of desperation, impatience, defensiveness. They’re reading between the lines for cues about whether you’ll be a partner or a pest. If your tone doesn’t match the weight of their decision, no amount of features will save you.

Why should they change — and why now?

This is perhaps the hardest question to answer — and the most important. Because no matter how good your product is, if you haven’t made the case for change, you haven’t made the sale.

Sellers often leap too quickly to the pitch, assuming that if they just articulate the benefits clearly enough, the buyer will lean in. But that’s rarely how it works. In most cases, buyers are trying to protect themselves — from risk, from politics, from scrutiny. The idea of changing suppliers, tools, or workflows is fraught. It threatens the status quo. And most people would rather live with a known problem than invite a new one.

Forrester’s research suggests that in nearly 60% of lost opportunities, the buyer didn’t go with a competitor — they simply stuck with what they had. Not because it was better. But because change was too hard to justify.

So the real sale isn’t for your solution. It’s for the need to act. Have you shown them the cost of inaction — not just in financial terms, but in missed opportunities, declining relevance, internal frustration? Have you connected your offering to something they already care about — a strategic objective, a board-level priority, a personal win?

Urgency isn’t about being pushy. It’s about being precise. The most powerful sales conversations are the ones that reframe the buyer’s world — where the pain of staying still becomes sharper than the risk of moving forward.

What You Do Alone

Salespeople love to talk about mindset. But too often, that conversation stays superficial — a quick quote, a bit of Monday motivation. The real work is quieter. It happens when no one’s watching. It happens when you sit down after a call, close the laptop, and ask: “What did I miss? What could I have done better? What’s really going on here?”

Because in a profession full of noise, the sharpest sellers know the most powerful questions are the ones they ask themselves.