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How to Sell With Honesty: What I Learned From Making 500 Sales Calls

The 4 strategies that help you sell anything while adding real value.

The only sales worth making are those that create value for others
The only sales worth making are those that create value for others | Photo by Renate Vanaga on Unsplash

In the span of 70 days, I made over 500 sales calls for the education consulting company I was working for.

Looking back, my first call feels like a disaster. Because, by call 500, I was having more enjoyable and genuine conversations all while getting more customers on-board and having a larger proportion of them eventually buy our premium packages (over $10,000).

The changes I’d made were simple but not intuitive. And they helped me feel like I actually add value to peoples’ lives. I never thought I’d enjoy making sales calls, but I’ve started to.

Below are the specific techniques that got me here. The techniques point to general principles for selling anything: from a product or service, to even an idea that you want to someone to adopt.

While the techniques will make you better at selling, the attitude that underpins these strategies might transform how you see your role. I describe the attitude at the end.

Let’s begin with the three kinds of people you will meet on your journey to selling something.

The Three Kinds of Leads

A lead is someone who might be interested in your product. If you’re in conversation with someone with the intent of making a sale (in-person, on the phone or via email), they’re a lead.

But all leads are not created equal. They fall into one of three categories:

1. The person who wants your product:

These are the leads that sales professionals fantasize about coming across. My fingers tingle as I write about them.

They want your product and they’re going to buy it. Unless you make it very hard for them to do so.

2. The person who isn’t sure (persuadable):

This is where you make your money. These leads don’t yet know that they want your product, but they would pay for it if they understood how much it could help them.

Persuadables need to be convinced on two counts: first, that they have need, that is, that they are facing the problem that your product is solving. Second, that they can trust your product to deliver on its promise of serving this need.

3) The person who does not want your product:

Some people don’t want what you’re selling. Your job for these leads is to simply let them know what your product is and how much it costs, so that they can refuse.

Then, you move on.


When you start talking to a lead, you don’t know which category they fall into. The techniques below help you find out and outline the best way to deal with each lead. 

To start, avoid the most common mistake in sales:

1. Don’t Start with Your pitch

When I first started sales, I was obsessed with delivering the script. At the earliest opportunity, I would rattle away the script in stiff monologues without saying anything specific about the lead I was talking to. This made for some very short phone calls.

Pitching is tempting. I get it. Your product is awesome. Thing is, nobody else cares. 

People care about themselves and sometimes they can start to care about you, but nobody you just got in conversation with, cares about your product.

Because you spend so much time with the product you’re selling, it can be easy to overlook that others don’t have the attachment to it that you do.

And, because it’s obvious to you why your product is useful, it can be even easier to forget that it is not at all obvious to others that your product is useful. You’ve seen your product in the context of the problem that its solving, your lead has not. Not yet.

Your product is the solution to a problem your lead has not even considered at the moment. And, nobody can be sold on something they don’t even know they want. 

So, starting with the solution before defining the problem is forced and counter-intuitive. It leaves the lead confused or annoyed regardless of if they want your product or not. 

So what should you do instead?

2. Ask Relevant Questions and Listen

There is only one thing that your lead certainly cares about. Themselves. So that’s what you talk about. Your job is to ask questions and then listen. But not just any questions. 

Ask your lead questions that are relevant to the problem your product is solving.

When I was selling college counselling services, I would ask parents whether they wanted their children to study abroad (because I was offering counselling for universities abroad).

This question would often get them to open up into a long conversation about their kids’ application (or the lack of it) and the problems or complications they were facing.

If it didn’t, I’d continue to ask questions: How are you deciding which universities apply to? How is the counselling system in their school? Do your kids know which major they want to study?

The results from doing this instead of pitching were amazing. Only by listening can you find out if, and how you can help a particular lead. And importantly, you learn which of the three categories your lead falls into.


Here’s what asking and listening does for each kind of lead:

For leads who want your product, asking about the problem lets them tell you that they want a solution. If the lead was genuinely in need of a college consultant, they would have told me when I asked all these questions.

For leads who don’t want your product, asking and listening allows them to gently tell you that they don’t want your product. They don’t need to reject you yet, because you haven’t offered them anything.

Not only is this easier to deal with for you, it also makes it less likely for them to feel badgered by aggressive selling. 

Finally, the persuadable leads. Here, more than anything, its crucial to ask and listen.

The worst way to persuade someone that they want something is to make it obvious that you have a vested interest in selling it to them. And this is exactly what you do if you start talking about your product instead of listening.

If you don’t take the time to find out what people want, you can never solve their unique problem. Offering solutions without first listening makes it blatantly obvious that you are more concerned with selling than finding out how to serve this particular lead.

But, by allowing people to speak about their problem, you give them the chance to convince themselves that they have a problem worth solving.

The fact is, you cannot talk people into buying something they don’t want. Only they can talk themselves into it.

If you let the lead speak, you allow them to tell you that they want what you have not even offered them yet.

Then, when you do explain your product as a possible solution, it comes across as a genuine effort to help.


By omitting the pitch and listening first, you allow your leads to become interested in you. But now that you have their attention, you have to make it count.

3. Solve Their Unique Problem for the First Time:

After your lead has spoken about their problem it’s time for you to bring up your product. But don’t make a canned pitch.

You need to offer the product as a direct solution to the problem your lead has told you about. The key is to address their concerns using their own words. 

The idea is to organically come to your product as a solution , as if you are discovering it for the first time with your lead. 

This works because this is how it actually is: Every lead is unique, and you’re solving their problem for the first time.

This shouldn’t feel like a pitch because a pitch is an ask, which frames the conversation as you asking for something that you need. You want to bring up your product as a solution to the lead’s problem: as something you are happy to offer them because you know it will help.

By keeping it organic and conversational, you help the lead feel like they’ve arrived at the solution along with you. If possible, you should nudge the lead to come up with the particular product they want on their own completely.

People are far more likely to agree with your solution if they feel that they have discovered it for themselves. That’s why this approach gets the desired outcome for each kind of lead:

If your lead is persuadable, then bringing up your product as a solution to their problem gives you the best possible chance of convincing them.

Because of the reasons discussed above, coming to the solution organically brings you one step closer to convincing the lead that your product will actually deliver on their need.

If your lead does want the product, then they will agree with your presented solution. You’ve made a sale!

If you find that your lead does not want your product, then you might not be able to offer them any solution at all. You can still bring it your product gently, but don’t be pushy. These leads are not to be converted.

The best thing you can do with here is to make the lead feel good about your conversation while letting them know of your product. This way, you leave open the possibility of their becoming future customers and referring others to you.


So, you’ve convinced your lead they have a problem. You’ve made your solution sound pretty good too. But why should they trust your solution? It feels too good to be true. Unless, you tell them that it’s not.

4. Acknowledge the Flaw

All this time you’ve been talking to a lead, but now, you’re about to make a friend.

See, every product has a catch. Maybe its personalized but expensive. Or its cheap but not durable. Or something else. Whatever it is, products have flaws by design, since trade-offs are essential to a competitive product.

Your product can only be a great value proposition for one kind of client if it is ordinary or unhelpful for another.

Now, it’s tempting to avoid bringing up the drawback of your particular product. This is the biggest missed opportunity in sales.

I used to sell a product that was the best in its class, but also the most expensive by far. I was conscious that the price would be a turn-off for leads. So I didn’t bring it up at all while talking up the product. 

This was a mistake. Leads just got more suspicious about what the catch was with all these personalized services and performance guarantees. The longer I spoke, the less they trusted me.

But, when I started acknowledging that our product was the most premium service on the market, and it was like this because we offered unrivaled performance, our conversations transformed. Leads started trusting me.

Of course, some clients were still uncomfortable with the price. But now, I was on their side: they could trust me to tell them about the good and bad parts of the product. 


You win trust and lose nothing by bringing up your product’s flaw. Leads and customers will eventually find out the catch anyway, but they shouldn’t have to ask for it. If the lead ends up having to coax the flaw out of you, they’ll never know if you’d have volunteered that information yourself.

By sharing with them the drawback of the product voluntarily, you build rapport and show that you are keen to help. The effect is enormous. 

Your honesty about the drawbacks of the product displays supreme confidence in its value. After all, you couldn’t be sharing this if you were afraid to lose the client.

You could only share the product’s flaws because you’re confident its value outshines its drawbacks, or you already have too many clients. Either way, your product looks very attractive.

At this point, you’ve already sold to the people who want your product since they don’t care about the drawback. Those who don’t want your product are already out.

With those who you can persuade, being vulnerable about your product is the clincher. They know all about the problem already. But, by acknowledging the products drawbacks, you come across as the person who they can trust to guide them to the right solution. 

So now, they believe you when you say that this product will solve the problem you’ve identified together. If they could be persuaded, they will be. 

The General Principles

The above are the four steps to selling to anyone. And they can be generalized to principles to do any kind of convincing. If you’re trying to convince someone of the importance of climate change say, these same principles will hold you in good stead:

The Four Principles For Selling Anything:

a) Don’t over-commit or reveal what you want.

b) Let the other person speak so they can commit and clarify their position.

c) Come to a solution mutually. Make it feel organic.

d) Build trust in the solution by revealing your own uncertainties.


But the techniques also point to the single most important selling attitude you can take away from this piece: 

The Attitude: Your Job is to Create Value for Others 

You are selling to create value for people. Your getting something in return is the happy accident. In the long term, you get value from selling only if you have created value.

It’s easy to get caught up in the numbers and want to convert every lead there is. This is a terrible strategy. If the person you are selling to isn’t going to get value from buying your product, they’ll soon leave, share their dissatisfaction with others, and cost you in customer service.

If you have to trick or pressure your lead into buying something they won’t use, its not worth it. In the long term, it will hurt you.

This is immense. It takes the pressure off you as a salesperson because now you’re qualifying your lead just as much as they’re qualifying you.

Your job is not to find every customer there is, it’s to find the customers that you can help the most.

When you take on only the best customers, you can create an astonishing amount of value for them. This is amazing for company morale and every delighted customer brings in more customers.

A handful of quality customers served by quality employees is far better than several unhappy ones being poorly served by several poorly trained employees. That’s why good businesses get huge, while great businesses stay at the size that allows them to create amazing value for each customer.

Flipping this switch in your head changes the dynamic of your interaction. Selling is usually difficult because we approach with neediness — which is an ugly emotion that pushes people away. 

But when you enter the conversation from the perspective of creating value for the right people, you go from being needy to being ambitious to help.


Why This Matters

This matters because without genuine value-creation, selling becomes the thing that people hate about sales: it becomes parasitic.

We are surrounded by products that prey on our weaknesses and addictions; products that steal our attention, energy and independence; products that have been catastrophic for our health and our environment.

These products are not worth selling.

Because there are simple sufferings to be mended, and small joys to be sparked by an odd, clever, or beautiful product. There are also social goods to be fairly distributed and political injustices made right from selling important ideas.

To actually help people, these ideas and products might need the inspired salesmanship that only you can conjure.

So, go ahead, and sell responsibly if you can. Sell what you believe in and what you’ve found valuable.

Do it because when you sell what you love, all the effort you’ve put in pays for itself the moment your first customer smiles. That is, long before a single dollar comes into your account.