I SCREWED UP

"Bryan, why do you send a proposal after the first call?"

That question stopped me in my tracks.

My friend Brian asked it a few years into my business. Until then, I had never really questioned the rhythm. A first call went well, I felt some momentum, and I sent a proposal. That was simply my process.

What Brian helped me see was that I was rushing to the finish because the middle made me uncomfortable. I was proposing before I understood whether the pain was real, whether we were the right fit, or whether the person across from me could clearly see the value of solving the problem.

I was asking the proposal to do work that the conversations had not yet done.

In the early days, every sales conversation felt personal. I was not representing a product someone else had built. I was the product. I had to explain why my experience mattered, translate that experience into value, and ask someone to pay me for it, all without feeling like a used-car salesperson.

So I skipped the uncomfortable steps. I rushed toward the proposal before validating the pain, creating emotional buy-in, or helping the prospect understand the potential outcome.

Over time, I rebuilt the process around three conversations. The framework is not always black and white. There is art to it, a lot of science, and a major advantage if you have strong emotional intelligence. It also becomes much easier after thousands of repetitions.

The proposal should confirm a decision already taking shape. It should not be responsible for creating one.

A sale is a sequence of earned rights

For a business of one, sales is rarely won by one perfect pitch. It develops as trust, understanding, relevance, and conviction accumulate across a series of conversations.

Each conversation has a different job. The first earns the right to diagnose. The second earns the right to recommend. The third turns conviction into action. When those stages are compressed into one call, the prospect is forced to absorb too much before enough trust exists.

The three-call process gave me a much calmer way to sell. It also made the buying experience better because the client had time to understand us, see themselves in the work, and make a considered decision.

Conversation One: Earn the right to diagnose

The temptation on a first call is to explain everything you do. When your expertise is the product, that temptation is even stronger. You want the prospect to understand your value as quickly as possible.

But the first conversation is not a stage. It is a diagnostic room.

My goal is to speak about 20 percent of the time and ask questions for the other 80 percent.

As they say, “2 ears, 1 mouth.”

I want to understand the person, the business, what is changing, their pain, what feels stuck, and what they are actually trying to create. The more specific the questions, the more useful the data points become.

At this point, I am not trying to force our service into their situation. I am trying to determine whether there is a strategic solution we can credibly provide. That distinction matters. It protects the prospect from being sold something they do not need, and it protects us from entering a relationship that is wrong from the start.

PRO TIP  Once you find the pain, it is important to lean into the gap the prospect has expressed. A friend once told me to read Gap Selling and used a deliberately rough phrase: 'throw salt in the wound.' The point is not to manufacture pain. It is to resist closing the wound too quickly and stay with the gap long enough for the person to feel understood. You will help them close the wound, but first you have to be willing to feel it with them.

Keep the conversation moving after the call

After the first conversation, I send a short, simple follow-up with materials the person can explore on their own. The goal is to give them a useful reference point and help them begin imagining what working together might mean.

My follow-up usually includes three things:

• Materials that explain how we think and work

• Recommended reading that deepens the relevant ideas

• A deck with case studies and a clearer view of our process

An example of the materials I send after an initial conversation.

Conversation Two: Let them see themselves in the method

The second conversation is where I walk through our process and relevant case studies so the potential client can imagine themselves moving through the work. Today, I usually demonstrate it through the Arcbound process. Everything I need is already there, which creates a smooth experience and gives the person something concrete to revisit afterward.

If you are starting out and do not yet have a fully developed methodology or a deep library of case studies, create a clear document that explains whom you serve, how you work, the sequence of your method, and the possible pricing paths. The goal is to make your expertise visible and your process understandable. I wrote more about that in this newsletter on building a six-figure consultancy.

Unlike the first call, this is the conversation where I do most of the talking. The prospect should move from general interest to a much more specific realization: this can really help me.

Pricing belongs in a live conversation

Pricing can feel especially uncomfortable when you are the product. I try to determine during the first call whether the person is likely able to afford what we offer. If there is a basic fit, I carry the conversation forward and discuss pricing live near the end of the second call, once the prospect understands the method and appears genuinely interested in buying.

Sometimes the person decides on the spot. More often, they need time to think. By this point, however, they have seen the process, heard the pricing, spent at least an hour or two with me, and have enough context to make a real decision.

For a business of one, the economic model can take many forms: a retainer, board advisory work, speaking, investing, or some combination. If this is your core business, I believe the ideal state is usually a recurring offer.

One piece of advice from Tom Brady's book agent, Jim Levine, stayed with me: get enough repetitions at a price point the market can say yes to, do excellent work, and raise the price as the value becomes clearer. That worked well for us for years, until we changed our economic model in the past year to fit our long term business strategy.

The Strategic Maneuver: Reflect the client back to themselves

Once I have validated the pain, determined the fit, and believe we can genuinely help, I usually spend one to three hours writing a personal note to the person I spoke with after both calls.

The note reflects what I heard: where they are, where they want to go, what is getting in the way, and how our work could help close that gap. It is not a generic recap. It is not AI slop. It is specific, considered, and personal.

The note does more than follow up. It demonstrates that I listened, that I can synthesize complexity, and that I understand the heart of the problem. In many cases, that is the clearest preview of what it will feel like to work together.

My mom used to tell me growing up, "The extra mile is never crowded." This is an email that IS going the extra mile. It takes care, a bit of heart, thought, and time.

Conversation Three: Turn conviction into action

By the third call, the prospective client usually arrives with final questions. This is where we address the remaining objections and make the decision. The call is often much shorter, sometimes only 15 to 20 minutes, because the real work has already happened.

As Blaire on my team often says, the contract is not closed until the person signs.

Once we receive a verbal commitment, we intentionally schedule the first kickoff or onboarding call. Current demand makes that useful for us, but it also makes the experience easier for the client. Busy professionals live by their calendar and email. Putting the kickoff on the calendar anchors the decision and removes the friction of another scheduling exchange.

Friction can quietly kill a yes

At the beginning of this year, we ran into a good problem. We were closing great clients, but moving them from yes to signed was taking too long.

Our contract was 36 pages, built from seven years of lessons, edge cases, and hard-earned experience. It protected the business, but it also created friction. Even committed clients were taking 72 hours or more to sign.

In one of our meetings, Timothy Springer helped us rethink the experience.

We kept the substance of the agreement but simplified how it was presented: a clean order form connected to a Master Services Agreement. We preserved what seven years had taught us while removing the burden from the customer experience.

Since making the change, our average signature time has dropped from 72 hours or more to less than 24 hours in some cases.

The lesson for me is that complexity naturally accumulates as a business evolves. But sophistication is not the complexity itself. It is knowing how to preserve what you have learned while making the experience simpler for the customer.

Sometimes the next stage of growth comes from removing the distance between a decision and action.

I have never learned so much from someone in 12 months.

Before clients experience the work, they experience the conversation

For a business of one, the sales process is part of the product. Before a client sees the full quality of your work, they experience how you listen, what you notice, how clearly you frame their problem, whether you remember the details, and how thoughtfully you follow up.

Every conversation is a small sample of the relationship you are asking them to enter.

That is why no single call needs to carry the entire sale. The first conversation creates understanding. The second creates relevance and conviction. The strategic follow-up creates personal resonance. The third creates a decision. A simple contracting experience turns that decision into action.

You do not need a perfect pitch. You need a sequence of conversations that makes the right decision easier to see.

Community Notes

1. I have been learning a ton about the physical AI space from a new client of ours, Devan Capur. He is a fascinating fellow with a book coming out called HUMANOIDS. It is a beautiful exploration of elderly care, aging, and the role humanoids and physical AI may play in the transition ahead.

 Preorder HUMANOIDS on Kindle. You will not regret it.

2. The Challenger Sale by Matthew Dixon and Brent Adamson is an important read for anyone trying to lead a stronger customer conversation. Idea here is to hold your POV

3. Gap Selling by Keenan is especially relevant to the idea in this newsletter: understand the gap between a customer's current state and desired future before rushing toward a solution.

4. In the last newsletter, I shared the wrong link to Anton Langer's story about why he gave blood on his birthday. It is a meaningful piece, and you can read it here.