The Best Sales Reps & Operators Are The Most Urgent

First off, shout out to the first second article in Beehiiv! We recently moved here after realizing it was better for growth, although I'm sad to leave Substack.

I grew up obsessed with the Rocky series. Part of that was being a fellow Italian from the Northeast, but another part was the many lessons the anthology taught me. One scene in particular resonates differently now that I'm (back) in sales.

In Rocky III, Rocky starts getting complacent after his recent high of beating Apollo (RIP, in both real life and the Rocky movies) and becoming a national star. It’s clear he's lost that fighter's edge from the first two movies, and after a recent loss to Mr. T., Apollo Creed is training him for his re-match with Mr. T, and during an intense training session towards the end, Rocky casually says, "Tomorrow, let’s do it tomorrow." Apollo responds by straight-up scolding him: "There is no tomorrow!"

He was addressing Rocky's lack of urgency. Apollo knew that by Rocky giving it his all that day, it would make him better for the next day which eventually compounds your skillset.

I can't think of a better parallel between working at a startup, being successful in sales, and showing progress in life, especially in your early to mid-career years when the learning curve is steep.

Urgency is what most top performers in sales I’ve worked with have in spades.

A deep sense of urgency is important because it is a catalyst for growth. It means having a bias for action so deep that you feel slightly physically strained when you think things are moving too slowly, and there’s too much thinking and not enough doing, or not having enough “bias for action.”

This concept of urgency and bias for action is awesomely portrayed in “The Pottery Class” lesson in the book Art & Fear by David Bayless and Ted Orland.

In this study, a ceramics teacher divided their class into two groups: one group was told they would be graded solely on the quantity of work they produced. In contrast, the other group would be graded solely on the quality of a single piece.

Paradoxically, the group focused on quantity and ended up producing work of higher quality because they got more practice and learned from their mistakes. They could make mistakes on day 1, iterate on day 2, iterate again on day 3, and so on until they had the far superior project at the end of the study. The group focused on quality sank into the quicksand that is analysis paralysis and ended up with a lot of thinking and not enough doing, or a far worse end product in this study.

It’s human nature to measure twice and cut once; as a former accountant, I can relate here. However, I’ve come to learn that the best at sales and in their craft work fast and know that the more (thoughtful and hypothesis-driven) mistakes you make, the better you get.

I have felt a deep sense of urgency for the last four years, pretty much since my first semester at business school. The environment was extremely intellectually stimulating, and I was around many type A overachievers. It was this environment that kicked me into overdrive, and I couldn’t look away.

This wasn’t something I was ever used to, and truly felt the environment brought out this deep sense of urgency in me to want to be a top performer and keep growing.

I am unsure if it can be taught, but it can be extracted from the right environment. It’s important to find that Ikigai (what you’re good at, what you can get paid for, and what the world needs) and let action propel you into the “10,000 hours” of success and failure needed to advance your craft.

How does this directly relate to sales? Here is one: thoughtfully moving the next step as soon as possible can compound to shorter deal cycles and better qualification.

This photo above brings me to something that initially threw me off—the concept same-day follow-ups. But then I realized: If things are going well on a call (perfect fit, sense of pain to solve this, speaking to the right persona), why not anchor on something later that day (assuming you can prep/accomplish the next step by then)?

It hits on another sales skill - anchoring - a powerful tool in negotiation and sales. Start at one end of the spectrum, a bit exaggerating, so when you meet in the middle, it feels like a win for the other side (as well as yourself). By doing this with a prospect who is clearly interested in the problems you help solve, you should act on this as quickly as possible.

Urgency —> faster decisions —> faster learnings. This urgency flywheel will continue to compound, and IMO, it is such a crucial catalyst for growing in GTM.