The First Time You Heard No
Imagine walking into a shop looking for a pair of shoes.
The salesperson approaches you almost immediately.
“Sir, we have a new collection. These are our bestsellers. This model has excellent cushioning, the latest design, and a very durable sole. We also have other colours available.”
He continues explaining the shoes while you stand there, listening politely.
But perhaps you are not looking for the latest design. You might be preparing for your first marathon. Perhaps you have recently started going to the gym and need shoes that can handle your daily workouts. Or maybe you simply need a comfortable pair to wear to work because your current shoes hurt your feet.
The salesperson has given you information, but has he helped you?
Not necessarily.
Now imagine a different salesperson.
“What will you mainly use these shoes for?”
You explain that you have started running every morning. You are still a beginner, and after a few kilometres, your feet start hurting.
The salesperson asks a few more questions. How often do you run? Where do you usually run? What kind of shoes have you been using?
Only then does the salesperson begin suggesting options.
The shoes might be exactly the same as those shown by the first salesperson. The difference is that this time, the recommendation is connected to your situation.
One salesperson presented a product. The other tried to understand a person.
That difference is at the heart of selling.
Curiosity Before Communication
Many people believe that sales is about learning how to explain something convincingly. They focus on product knowledge, presentation skills, persuasive language, and the ability to answer objections.
These things matter. But they are not necessarily where the best sales conversations begin.
They begin with curiosity.
Before explaining a product, understand the person sitting across from you. Before presenting a solution, understand the problem they are trying to solve. Before describing the benefits of your offer, discover which benefits actually matter to them.
What are they trying to achieve?
What is frustrating them?
What have they already tried?
What are they worried about?
What would make their life or work easier?
And perhaps the most important question of all: what does success look like for them?
These questions sound simple. Yet, in our eagerness to convince people, we often forget to ask them.
We walk into conversations carrying our own agenda. We know what we want to sell, what we want to explain, and what we hope the other person will decide.
We prepare our arguments before understanding their circumstances.
Sometimes, we are so busy waiting for our turn to speak that we barely listen to what the other person is saying.
Curiosity changes the direction of a conversation. Instead of treating the other person as someone who must be convinced, we begin treating them as someone whose situation deserves to be understood.
And when that happens, the conversation becomes more useful for both sides.
People Don't Buy Features. They Buy What Those Features Mean to Them.
Consider a business owner who wants a website.
You could explain that the website will be mobile-friendly, have a modern design, include product listings, support enquiry forms, and offer analytics integration.
All of these might be valuable features.
But the business owner may not care about any of them individually.
What they really want is for more potential customers to discover their business. They want to look credible when someone searches for them online. They want customers to understand what they offer without having to call and ask the same questions repeatedly.
The website is the product. Those outcomes are the reason the product matters.
The distinction is easy to miss because we tend to understand our own work through its features.
A developer thinks about performance, architecture, integrations, and reliability. A designer thinks about layout, typography, colours, and visual consistency. A financial adviser thinks about allocation, risk, and long-term planning.
But the customer sees these things through a different lens.
The developer's customer may simply want fewer interruptions in the business. The design client's concern may be that their company looks less credible than its competitors. The person speaking to a financial adviser may want reassurance that they are making sensible decisions for their family's future.
The same feature can mean different things to different people.
A dashboard might mean efficiency to one customer, visibility to another, and peace of mind to a third.
A fast website might mean convenience for a visitor, fewer abandoned purchases for an online seller, or a more professional experience for a prospective client.
A reminder system might mean a useful notification to one person and the avoidance of a costly mistake to another.
This is why a good salesperson does not assume that everyone values the same things.
They discover what the features mean in the context of a particular person's life.
The Problem Behind the Problem
Sometimes, the first problem a person describes is not the real problem they need help solving.
A business owner might say, “I need a new website.”
That sounds like a clear requirement. A supplier could prepare a proposal immediately.
But what if you asked one more question?
“May I ask what you would like the new website to help you achieve?”
The answer could change everything.
Perhaps the current website is outdated. Perhaps it does not generate enquiries. Perhaps the business has expanded, but the website still reflects what the company did five years ago. Perhaps the owner has noticed competitors appearing in search results and worries that potential customers are overlooking their own business.
Each of these situations calls for a different conversation.
If the problem is outdated information, the customer might need a simpler way to update content. If the problem is a lack of enquiries, the conversation might involve the services being presented, the information available to visitors, and the path from discovery to contact. If the business has changed, the first task may be to understand its new direction.
The request was for a website. The underlying need was something else.
This does not mean that customers do not know what they want. Often, they understand their situation very well. They may simply describe their needs in the language they know, rather than in the language of the solution.
It is our job to listen carefully enough to understand what lies behind their words.
A useful question can reveal more than a polished presentation ever could. And sometimes, the best thing we can do for a customer is help them discover that the solution they initially imagined is not the solution they actually need.
Listening Is More Than Remaining Silent
There is a difference between waiting for someone to finish speaking and genuinely listening to them.
When we are preparing to sell, our minds are often occupied with what comes next. We hear a problem and immediately search our memory for the feature that solves it. We hear an objection and start constructing a response. We hear a question and prepare an explanation.
We may appear attentive while mentally rehearsing our pitch.
Genuine listening requires a different kind of discipline. It asks us to put our own response aside, at least temporarily, and pay attention to what the other person is actually communicating.
Sometimes, the most useful information is not in the words themselves.
A customer might say that the price is too high. That could mean they genuinely cannot afford the offer. It could mean they do not understand the value. It could mean they are comparing it with a cheaper alternative. Or it could mean that they are interested but uncertain whether the investment will deliver the expected result.
The words are the same. The circumstances are different.
Responding immediately with a discount might solve one situation and make another worse.
Instead, we could ask, “I understand. Is your main concern the budget itself, or would it help to understand more clearly what you would be getting for the investment?”
That question does not guarantee a sale. It does something more fundamental: it creates an opportunity to understand the concern accurately.
Listening also means paying attention to what people do not say. Hesitation, uncertainty, and repeated questions may indicate that something remains unclear. Rather than treating these signals as obstacles, we can use them as invitations to explore the conversation further.
Of course, we should not pretend to know what another person is thinking. A pause does not always mean doubt, and a short answer does not always indicate disinterest. We can observe, but we should ask rather than assume.
The goal is not to become a mind reader.
The goal is to become a better listener.
Questions That Open Doors
Not every question is equally useful.
Some questions are designed to move the conversation towards a decision we have already made. Others genuinely help us understand the person.
Consider the difference between asking, “Would you like to buy this package?” and asking, “What are you hoping to improve in your business over the next six months?”
The first question asks for a decision. The second invites a conversation.
Both may have their place, but the second can help reveal what a meaningful solution would look like.
Useful questions are often open-ended and specific enough to encourage a thoughtful answer.
Instead of asking only, “Do you have a problem with your current system?” we might ask, “Which part of your current process takes more time than it should?”
Instead of asking, “Would you like to grow your business?” we might ask, “What is currently preventing you from reaching more of the customers you want to serve?”
Instead of asking, “Is the price acceptable?” we might ask, “How are you evaluating whether this investment makes sense for you?”
And instead of assuming that we understand the answer, we can reflect it back.
“So, if I understand correctly, the main challenge isn't getting enquiries. It's following up with them consistently. Is that right?”
That simple sentence gives the other person an opportunity to correct us.
It also demonstrates that we have been paying attention.
The best questions do not make people feel interrogated. They help people think more clearly about their own situation.
There is a subtle but important distinction here. Asking questions merely to uncover an opportunity to sell is still a form of interrogation. Asking because we genuinely want to understand is a conversation.
People can often sense the difference.
Understanding Before Offering Advice
There is a temptation, especially among people who are good at what they do, to offer solutions too quickly.
A friend describes a problem, and we immediately suggest what they should do. A colleague shares a difficulty, and we explain how we would approach it. A prospective customer mentions a challenge, and we begin demonstrating our product.
Our intentions may be good. We want to help. We want to show that we know what we are doing.
But advice offered too early can miss the point.
Imagine a business owner who says that sales have been declining. You might immediately suggest advertising, a new website, better social media content, or a customer relationship management system.
Yet the real issue could be that the business is attracting the wrong customers. It could be a problem with pricing, customer retention, delivery, or the way the product is positioned. It might even be that the owner has too many enquiries to handle effectively and needs a different kind of support.
Without understanding the situation, every recommendation is partly a guess.
Expertise is valuable, but expertise becomes more useful when it is guided by context.
This is true beyond business. A manager who wants to help an employee perform better must understand what is getting in the way. A teacher must understand where a student is struggling before choosing how to explain a concept. A doctor must understand the patient's symptoms and circumstances before deciding on an appropriate course of action.
In each case, the quality of the solution depends partly on the quality of the understanding that comes before it.
Sales is no different.
The more consequential the decision, the more important it becomes to understand before recommending.
People Are Not All Motivated by the Same Things
Two people can look at the same offer and see completely different things.
One customer may value speed. Another may value reliability. A third may care most about cost. Someone else may be willing to pay more for personal support because they do not want to manage the details themselves.
Some people want independence and control. Others prefer guidance. Some are excited by growth and new possibilities. Others are primarily concerned with avoiding risk.
None of these motivations is automatically right or wrong. They simply reflect different circumstances, priorities, and experiences.
Consider two small business owners evaluating the same service.
The first has just started a business. Cash is limited, and every expense matters. They want something affordable that will allow them to establish a credible presence without making a large upfront commitment.
The second has operated a business for fifteen years. They already have customers and a steady income. Their biggest frustration is the amount of time they spend managing routine tasks. They may be willing to pay more if a solution reduces that workload.
Offering both customers the same explanation may not be effective.
The first might need reassurance about affordability, flexibility, and getting started. The second might want to understand how much time the solution could save and how easily it would fit into existing operations.
The product may be identical. The conversation should not be.
Understanding people does not mean placing them into rigid categories or manipulating their emotions. It means recognising that their priorities may differ from ours.
We should not assume that a person wants what we would want in their position. We should discover what matters to them.
Empathy Is Not Manipulation
Understanding another person's motivations creates influence. And influence brings responsibility.
If we discover that a customer is worried about losing business, we could use that fear to pressure them into buying something they do not need. If we learn that a person values status, we could make them feel inadequate without our product. If we know that someone is under pressure to make a decision, we could use that urgency to push them towards an unsuitable choice.
These tactics may produce a sale. They do not necessarily produce a good outcome.
There is a difference between understanding a person's concerns so that we can help them make a better decision and understanding those concerns so that we can exploit them.
The first builds trust. The second spends trust.
A good sales conversation should make the decision clearer, not make the customer feel trapped. It should help them understand whether the offer fits their needs, what it can reasonably deliver, what it cannot do, and what alternatives they might consider.
Sometimes, that conversation will lead to a sale.
Sometimes, it will reveal that the product is not the right fit.
And sometimes, the most useful thing a salesperson can say is, “Based on what you've told me, I don't think this is what you need right now.”
That might seem like a strange thing to say when the objective is to sell. But a sale is only one part of a relationship. The way we behave when we could have sold something but choose not to can matter just as much as the way we behave when a customer buys.
Trust grows when people realise that we are not interested only in what they can purchase from us.
We are interested in whether we can genuinely help them.
The Courage to Discover That You May Be Wrong
Curiosity requires humility.
When we believe strongly in our product, we may unconsciously assume that everyone should want it. We know how much effort went into building it. We understand its strengths. We can imagine all the ways it might help someone.
But our enthusiasm is not evidence that the product is right for everyone.
A customer may have a different priority. They may already have a solution that works well enough. They may not have the resources to make a change. They may need something we do not offer.
Their decision does not necessarily mean that they failed to understand our product. It may mean that we have not understood their situation, or that there is no meaningful fit between what they need and what we provide.
This is an important lesson for founders, especially those who have invested months or years in building something.
It is easy to fall in love with a solution and then search for people who will validate it. It is harder, but often more valuable, to understand the people first and remain open to what we discover.
Sometimes, their answers will confirm that we are solving a real problem. Sometimes, they will reveal a gap in our offering. Sometimes, they will show us that we have been solving the wrong problem entirely.
All three outcomes are useful.
Curiosity is not a technique we use only when it supports our existing beliefs. It is a willingness to let the conversation teach us something, even when what we learn is inconvenient.
The Conversation Changes When the Person Comes First
Think back to the salesperson in the shoe shop.
The first salesperson wanted to explain the product. The second wanted to understand the customer.
The distinction may appear small, but it changes the entire experience.
When people feel understood, they can explain their concerns more openly. They can ask questions without feeling that they are interrupting a pitch. They can evaluate a recommendation in the context of their own needs.
And the salesperson gains something equally valuable: a clearer understanding of whether the product can genuinely help.
This principle applies whether we are selling shoes, software, financial advice, a service, or an idea to our colleagues.
A founder pitching a business should understand what matters to the person considering the investment. A job candidate should understand what the organisation needs, not merely recite their own achievements. A consultant should understand the business challenge before proposing a solution. Even in an everyday disagreement, we are more likely to make progress when we try to understand the other person's point of view before insisting on our own.
None of this requires us to abandon our objectives.
We can still want the sale. We can still believe in our product. We can still communicate confidently and ask for a decision.
But our objective should not prevent us from seeing the person in front of us.
Perhaps the most important shift is this: instead of entering a conversation thinking, How can I convince this person?, we begin by asking, What do I need to understand before I can help this person make a good decision?
That question does not guarantee a successful sale.
It does something better. It gives the conversation a meaningful starting point.
Before You Explain, Understand
We often measure a salesperson by how well they speak: how clearly they present, how confidently they respond, how persuasively they describe a product.
But perhaps we should also measure them by the questions they ask, the assumptions they challenge, and the attention they give to the answers.
The best salespeople are not necessarily those who can talk about a product for an hour. They may be the ones who can listen carefully for ten minutes and then explain, in a few sentences, why a particular solution makes sense for that particular person.
They know that a conversation is not an opportunity to deliver everything they know.
It is an opportunity to discover what the other person needs to know.
Understanding does not replace product knowledge. It gives product knowledge direction. It does not eliminate persuasion. It makes persuasion relevant. And it does not guarantee that every conversation ends in agreement. It helps ensure that the conversation is about the right things.
Before presenting the solution, understand the problem.
Before describing the benefits, understand which benefits matter.
Before trying to change someone's mind, understand how they arrived at their current point of view.
And before deciding what you want to say, listen to what the other person is trying to tell you.
Sales is not simply about getting people to understand what we offer. It is about understanding people well enough to know whether what we offer matters to them.
