The Bigger the Cheque, the More It Runs on Trust

Marketing writers like to divide buying into rational and emotional. In my experience the line that matters in an expensive decision is simpler than that: do I trust the person on the other side? If I do, I move fast. If I don’t, every claim needs proof.

I know this best from my own decisions as a buyer.

With someone I trust: minutes

In October 2021 a real estate developer I had been meeting with for nearly two years sent me a new investment opportunity at 4:30 in the afternoon. I replied eleven minutes later that I was in, with a couple of questions and a request for a call that day. (Networking Is the Follow-Up tells how that relationship was built.)

What I had was nearly two years of history with him, and that history did most of the work.

Trust is not the end of the checking, though. A year later I asked for one change to the investor updates:

can we please get an update on the timeline as well in these reports? A small section that would indicate that we are ahead of schedule, on schedule, or behind schedule….

Trust gets you the yes. Transparency keeps it.

With a stranger: proof I can visit

In 2025 I was choosing a contractor for a high-end apartment fit-out. One firm’s proposal was promising, but I had no history with them. My reply asked for a completed checklist with specifications, a revised bill of quantities, a timeline with milestones, payment terms and warranty details, and a meeting. And this:

Share 2–3 completed reference projects that we can visit that are most relevant to this scope of work, so we can better understand your capabilities in delivering high-end finishes and integrated systems.

I told them why:

This is a premium, detail-oriented project requiring transparency, craftsmanship, and technical competence.

With no shared history to rely on, the proof had to do the work that trust did in the first case.

The same instinct is in the 90 days I asked for on a domain purchase in 2019: “I have to make sure everything passes the smell test, before closing on the property.”

What that means when you are the seller

If that is how I buy, it is how my customers buy too. So on the selling side, the bigger the account, the more I want my people in the room.

In May 2024 I told DMA’s head of business development:

Arrange travel plans with Vibhu; go see customers that pay 5k+ or will pay 5k+ with him. And go see past customers that want to meet you guys that paid 5k+….all these numbers are monthly numbers.

A proposal can describe the work. Only a relationship makes a buyer comfortable committing tens of thousands of dollars a year to it, and relationships at that size are built face to face.

What I still believe

For small purchases, the offer and the price do most of the work. For large ones, the buyer is really deciding whether to trust you. Either you already have that trust, from a history of doing what you said, or you have to make up for its absence with proof the buyer can check: references they can visit, milestones they can measure, terms they can hold you to.