Erin Lopez joined Indevtech as our Director of Growth and Partnerships. In her first months, we enrolled her in a mainland sales training program. I didn’t do it skeptically. I did it because we’d reached the point where I could no longer run new-business development on twenty-five years of institutional knowledge and winged-it instinct. Erin deserved formal training in how to do actual business-to-business sales, and I wasn’t going to be the bottleneck.

The program was structured. A hundred dials a day as the productivity bar. Non-negotiable call scripts. Cadences in business days. If a prospect said “we’re fine, thank you,” you marked them for a two-week callback. The logic: in two weeks, they’d have forgotten about you.

Erin told me she was uncomfortable with the cadence within a couple weeks of starting. Her mainland counterparts were hitting their hundred-dial numbers and getting attaboys. She was having longer conversations with fewer people, and producing what struck me as the more valuable kind of pipeline activity, but the dashboard wasn’t measuring that.

I told her: follow the training. Get what you can out of it. We’ll learn.

I already knew what we were going to learn.

She had a handful of prospects scripted for a two-week follow-up. The CRM would ping her with the reminder; she’d cringe; she’d push it out two more weeks. Then another two. Her sales coach started asking her why.

At about the eight-week mark, she called one of them back. Second time she’d ever called the number. Same lady answered. Before Erin could finish her opening line:

“Didn’t I just talk to you?”

Erin walked into my office and said, “You called it, Scott.”

“Every market thinks they’re unique”

The other rules in the program had the same shape. Disqualify a prospect if you couldn’t reach a decision maker in two or three attempts unless there was a compelling event. Applied here, that disqualifies the entire list. There is no compelling event in Hawaii. The compelling event is eventually, and the rep who gets it is the one who was already in the picture when it surfaced.

Don’t accept a first-time appointment unless the prospect is within sixty days of contract exit, because anything further out is wasted discovery — the environment will have changed by the time the deal can close.

I raised these objections more than once. The answer was always some version of: Scott, every market thinks they’re unique. You’re no different.

I can’t speak for other markets. I can speak for this one. We are an island surrounded by water. Everyone here knows someone who went to school with me. I’ve set up wireless networks in Kahala houses for CEOs of the state’s largest private institutions. Word travels fast enough that it has a name. Coconut wireless.

The sixty-day rule misreads what discovery actually is, too. Discovery is not an audit of servers and applications and licensing positions. The technical environment isn’t what changes anyway. Discovery is about the client. It’s the conversation that establishes the gap between what they have today and what they could have. That gap doesn’t depend on whether their firewall is two years old or six months from refresh. It depends on whether they trust you enough to admit where the gap is — and that’s the work of weeks or months, and in some cases years.

What we wrote down instead

That was the morning we started writing what became the Aloha Sales Playbook. None of it was new. The whole thing is a codification of how local businesses have always done business with each other. Be authentic. Be generous. Be patient. Be collaborative. Act with pono no matter who you’re talking to, because it’s all connected here, and what you do comes back around — sometimes years later, in rooms you didn’t know existed when the original good deed happened.

There’s more, and it gets more specific as it goes, but the spine of it is right there.

I don’t regret hiring the mainland company. The training Erin needed was right in front of us — but I don’t think we’d have seen it that clearly without going through the exercise of trying the other thing first. The discrepancy was the gift. The eight-week reminder was the gift. The six-word question was the gift.

Erin still works here. She does not get the question anymore. She doesn’t call from a script.