You can spend months building trust through your brand’s content, advertising, website, and reputation, then ruin all of it in a five-minute conversation.

That happened to me recently (as a customer, thankfully not as the brand). I had followed the company, watched the founder’s videos, completed the intake process, and arrived at the call genuinely interested in learning more. A few questions later, the salesperson became defensive and abruptly ended the meeting.

This experience sparked this week’s newsletter because it made me think about how quickly an entire customer experience can fall apart when the process becomes more important than the person.

Let’s dive in.

When did introductions stop being conversations?

I’ve been on the customer side of sales calls a lot more than usual this year, whether it’s because I curiously clicked a targeted ad, someone cold-outreached me, or I’d been following the founder for a while before deciding to learn more.

As a founder and a strategist, I’m regularly evaluating services, tools, and potential partners that could help me grow one of my businesses or solve a specific challenge for a client. I don’t enter every call ready to buy immediately, but I do enter genuinely interested in understanding what the company offers and whether there might be a fit.

Being on the other side of these conversations makes me pay closer attention to the experience. Like many of my peers, I’m naturally interested in how companies position themselves, address problems and communicate.

The call that ended almost as soon as it started

I had been aware of one particular offering for some time, because I follow its founder. I had started seeing their ads, watched some of the videos, visited the website, and saw enough to become curious about the service. Eventually, I decided to book a call.

That curious decision triggered a fairly elaborate process. I completed an intake form, received instructions about confirming my appointment, watched a video that was presented as mandatory, and received several reminders through both email and text message. I was also given detailed instructions on how to make sure the meeting had been properly added to my calendar. There was other content I was expected to review before the call as well.

I understand the thinking behind this. Businesses want prospects to arrive informed, prepared, and serious. They want to reduce no-shows and avoid spending time repeating information that is already available elsewhere. A little preparation can make a conversation more productive for everyone involved.

But there is a point where preparation starts to feel like homework. When someone has already spent time watching your content, filling out your form, reading your messages, and reserving space in their schedule, sending them a growing list of mandatory steps can create the opposite of the trust you are trying to build. The process starts to feel less like an invitation to a conversation and more like an obstacle course the customer has to complete.

In this situation, I was still looking forward to the call and interested in learning more. Within the first few minutes, I asked a couple of questions about the service and process. I was trying to understand the offer exactly, how it compares to other options, and how their approach might apply to me.

The salesperson seemed to interpret my questions as resistance or attitude. Rather than becoming curious about why I was asking, he became defensive.

Only a few minutes in, he made the decision to abruptly end the call.

I thought it was really odd. This company had invested effort into getting me there: It had run ads, created videos, set up forms, reminders (a ton of those), automations, and an entire sequence designed to move me toward the meeting. Yet when the actual human interaction began, the process seemed too fragile to get down to business.

After all that effort, the conversation ended before any discovery had taken place.

A question is not always an objection

That experience made me think about how easily curiosity can be mistaken for resistance.

In many sales processes, questions are treated as objections to overcome. The salesperson hears uncertainty and immediately begins trying to manage it, correct it, or move the prospect back toward the intended sequence.

People ask questions for many different reasons. They might be trying to understand the value. They might have had a bad experience with a similar service. They may be unclear about the process, uncertain about the investment, or simply trying to determine whether they trust the person sitting across from them. Sometimes they are interested but not yet convinced, which is precisely why the conversation is happening.

It could lead to a response as simple as “What prompted you to ask that?” or “Is there a particular concern you’re trying to address?” Those questions do not derail the sales process. They create the conditions for a better one.

Better sales calls I’ve been on recently have felt lighter and more conversational. The person was still guiding the discussion, but they were not so attached to their structure that a question or change in direction created tension. They paid attention to my energy, listened to what I was actually asking, and adjusted their communication accordingly.

People do not all arrive with the same mindset. Someone may be joining after a stressful day, carrying uncertainty about the decision, or feeling skeptical because of a previous experience. A good salesperson, founder, or advisor recognizes that the person on the other side of the call is not just a category in a CRM.

We’re all humans entering the conversation with our own context.

The communication style can be the deciding factor. A relaxed personality, openness, patience, and the ability to answer questions without becoming defensive can create more trust than a perfectly optimized presentation. The prospect is not only evaluating the service. They are also imagining what it might feel like to work with you once the agreement is signed and something difficult comes up.

Curiosity is the most important aspect for B2B sales

I pulled in Bryce Seto to share his experience being on all sides of this equation.

He’s a two-time Chief Revenue Officer, and I know he’s been on hundreds of sales-type calls. He also setup Seto Improv to teach the soft skills that create great leaders through executive coaching and corporate workshops.

Here’s what Bryce had to say:

Research should create understanding, not assumptions

I’ve noticed two very different approaches to preparation before this type of call. Neither extreme creates a particularly good experience.

1. In some cases, no research was done prior to the call. Of course, some information needs to be clarified or explored in greater detail. A form cannot replace a conversation. But when it becomes obvious that the form was never read, it sends a message that the prospect’s time matters less than the company’s process. The company asked for information, the customer took the time to provide it, and then the customer is asked to provide it all over again.

2. The opposite can also be uncomfortable. Some people have clearly reviewed my website, LinkedIn profile, and other content before the meeting. I appreciate that effort, but I have occasionally been met with a surprising reaction: “You seem to have this figured out already, so I’m not sure why you’re here.”

It may be intended as a compliment, but it can quickly put the prospect in the position of having to defend why they booked the call. If someone has invested enough time and interest to reach that point, there is probably a reason. They may be successful in one area while struggling with another. Their public presence may look polished while hiding a challenge behind the scenes. They may understand the strategy but lack the capacity to execute it. They may simply want an outside perspective.

Instead, you might ask, “You already seem to have a strong foundation. What are you hoping to improve or unlock from here?” That question respects what the person has already built while still leaving room for them to explain why they reached out.

Research can make the conversation more relevant. Bring what you have learned into the conversation with curiosity.

Why founder-to-founder conversations feel different

Some of the most valuable conversations I’ve had have been directly with founders.

I know this is not always possible. As a business grows, the founder cannot personally handle every sales conversation, and building a team is often necessary.

Still, founder-to-founder conversations tend to have a different feel. Often, there is less performance and more transparency. I’ve found we can speak openly about where our businesses are, what we have tried, what has worked, what hasn’t, and what we are trying to build next. The conversation can then become less about placing someone into a predefined category and more about understanding whether there is a meaningful way to help each other.

Founders are also often able to adapt the conversation more naturally because they understand the thinking behind the service, not only the sequence used to sell it. They can explain why the process works a certain way, where it can be adjusted, and what might need to be tailored. This flexibility makes the solution feel connected to the person in front of them instead of something designed for an imaginary average customer.

There is also a sense of mutual learning. Even when the service is not a fit, I may leave with a better understanding of their approach, and they may learn something about my needs or the market. The call does not feel wasted simply because it did not end in a transaction. A genuine relationship or future referral can still emerge from it.

That has been especially noticeable when the founder is the person featured in the company’s advertisements and content. There is an expectation created when one person is presented as the trusted voice of the business, but the prospect is then passed through a screener, handed to a separate salesperson, and perhaps moved to another person after that. By the time the customer reaches someone who can answer the deeper questions, they may feel several steps removed from the person and promise that attracted them in the first place.

A company does not need to hide the fact that it has a team, but the experience should feel connected. I think whoever handles the conversation should understand the founder’s perspective, the company’s values, and the customer’s context well enough to continue the relationship that the marketing started.

 Have we optimized away the most important part?

Modern sales processes are designed around efficiency. Companies want to qualify leads, protect their calendars, reduce no-shows, shorten sales cycles, and improve conversion rates. Those are reasonable goals, particularly for small teams with limited time.

Every additional form, video, reminder, screening call, and mandatory step creates friction. Some friction can be useful because it helps ensure that both parties are taking the conversation seriously. But too much can communicate that the customer must prove they are worthy of the company’s attention before the company has done anything to earn their trust.

This is especially important in B2B and professional services, where the person booking the call may already be managing a business, leading a team, serving clients, and making several important decisions at once. They do not need to be spoken to like a student who has failed to complete an assignment. They need enough information to arrive prepared, followed by a thoughtful conversation that respects their intelligence and time.

What is the purpose of a discovery call if everything has supposedly already been “discovered”?

• A form can collect facts, but it cannot fully capture context.

• A video can explain the offer, but it cannot respond to someone’s uncertainty.

• An automated sequence can prepare a lead, but it cannot sense when the person needs reassurance, clarification, or a different pace.

That is what the conversation is for.

Of course, a business should protect its time and avoid taking calls with people who are clearly not aligned. But the language around this can sometimes become strangely self-focused. Companies talk about preventing prospects from wasting their time, making sure only serious buyers get through, or refusing to speak with anyone who will not follow the exact process. That mindset may improve efficiency on paper, but it can also create an adversarial relationship before the conversation has even begun.

The person on the call is not there to serve the sales system.
The system should help the company serve the person.

What the customer remembers

Looking back at these recent experiences, I do not remember every feature that was presented or every claim each company made. I remember how I felt.

I remember the people who made the call feel comfortable and open. I remember the ones who answered questions directly instead of avoiding them or forcing the order of the call. I remember the conversations where I felt they had taken the time to understand my situation without assuming they already knew the answer.

The other types of calls (and there’s fewer of these, to be fair) seem like weeks or months of content and marketing to build interest, and one short conversation to end it. That’s the part of the customer journey that can be easy to overlook:

The greatest opportunity isn’t another funnel, script, or sequence but simply becoming better at having conversations (and we can all benefit from this, myself included). That can look like:

• Listening without immediately preparing a response.

• Asking why someone is uncertain instead of treating uncertainty as an inconvenience.

• Being honest about what the service can and cannot do.

• Adapting the conversation to the person instead of forcing every person through the same performance.

The calls that I’ve appreciated the most didn’t always lead to a purchase (sometimes we simply realized that the timing or fit was not right). But I left feeling positive about the business because the person treated the conversation itself as worthwhile.

When that happens, as a customer, you may come back later, recommend someone else, or continue following the company because trust was built without pressure.

As businesses become more automated, those moments of genuine human attention may become even more valuable.

The systems can help us get people into the room, but they should never become more important than what happens once we are there.

What can we do about this?

Before adding another step, script, automation, or mandatory video to your own sales process, it may be worth experiencing it from the customer’s perspective. A few questions to ask yourself if you’re selling:

• Does this step help the customer, or does it mainly protect our own time?

• Are we using the information people provide upfront?

• Does our research make the conversation more relevant, or are we using it to make assumptions?

• Can we respond with curiosity when the conversation moves away from the script?

• Would a thoughtful prospect feel comfortable asking difficult questions?

• If the call does not result in a sale, will the person still leave with a positive impression of the business?

Try to pay attention to how people may feel while they are talking to you (I know not everyone shows it). A sales process should create enough structure to support a good conversation, but not so much structure that the conversation can no longer breathe.

The system may get someone onto the call, but the human experience determines what they remember afterward.

So much talking about talking. If you read this far, I invite you to have a conversation with me. No pressure, no questionnaire to get through or videos to watch first. Whether we’ve spoken in-depth before or not, let’s chat 🙂