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Book more meetings by being unconventional in 2021

“Never interrupt your enemy while they are making a mistake.”

This quote has been attributed to Napoleon Boneparte since 1836, referencing his notes from a battle in 1805. Sun Tzu has also been given credit for this maxim of war.

Love ‘em or hate ‘em, they’re both unanimously considered military geniuses.

Why does this quote matter?

I spend my days helping hundreds of sellers crack cold email, phone, video, visual, and LinkedIn social selling approaches for outbound inside sales that uniquely differentiate both content and context.

What does it mean to be strategic?

Strategy and tactics are fundamentally unique, though not mutually exclusive. Air cover and ground game are both necessary for a successful approach. The best strategy is the one that is always changing and difficult to predict or analyze for patterns.

Sun Tzu put it best, “Know thy enemy and know yourself; in a hundred battles, you will never be defeated. When you are ignorant of the enemy but know yourself, your chances of winning or losing are equal.” He would have made a great VP of Sales having demonstrated insightful wisdom regarding both game theory and probability.

First Principles

To stand out, you need to break down complicated problems into basic elements and then reassemble them from the ground up. This concept is called “first principles.”

Elon Musk inspires us all to think about this practice.

He looks at a rocket and thinks along these lines: “The model is broken, so what if I deconstruct it into its simplest elements and start at the beginning?” Then came cars and solar panels.

But he first did this with a cryptographically-protected payment processing startup (big hat tip to Max Levchin, the cryptographer genius behind Affirm, a railway for point of sale lending you may have heard of called PayPal). Transferring money via email was originally and interestingly a footnote for their encryption library intended to generate revenue through a licensing model. Max found out there was no intrinsic demand for this level of security in the market, and the rest of the world was almost immediately infatuated with sending money via email.

In the Star Wars universe, the “Children of the Watch” reestablish an entire way of life called “the Way of the Mandalore” after their culture was virtually destroyed. They do this by basing their entire, new culture around wearing their Mandalorian helmets at all times.



I’m not the first to bring Guerilla and Asymmetric Warfare tactics to cold outreach and outbound prospecting. Metaphors abound as you read these profound definitions and transpose them over classical B2B mechanics:

Per wikipedia:


Guerrilla warfare is a form of irregular warfare in which small groups of combatants, such as paramilitary personnel, armed civilians, or irregulars, use military tactics including ambushes, sabotage, raids, petty warfare, hit-and-run tactics, and mobility, to fight a larger and less-mobile traditional military.”


Asymmetric warfare (or asymmetric engagement) is war between belligerents whose relative military power differs significantly, or whose strategy or tactics differ significantly. This is typically a war between a standing, professional army and an insurgency or resistance movement militias who often have status of unlawful combatants.


The initial decision to approach outbound prospecting differently shined a light on a novel approach rooted in, again, “first principles.”

Michelangelo, best known for contributions to the Sistine Chapel and the David sculpture, drills the point: “Every block of stone has a statue inside it and it is the task of the sculptor to discover it. I saw the angel in the marble and carved until I set him free.”

I saw meetings in the Salesforce haystack and set them free.

Pattern Interrupts

The Purple Cow by marketing guru Seth Godin is a simple application of the neuro-linguistic programming technique we call “‘pattern interrupt.”

Write something so bizarre that most are unlikely to forget.

This concept influences every word of my prospecting messages, concepts in branding, and sales approaches. Stu Heinecke applies this approach to contact marketing in his magnum opus, How To Get A Meeting With Anyone. He explains how he was getting a 100% response rate and setting meetings with impossibly unavailable executives by sending original cartoons via courier, inked by him on posterboards or etched into wooden planks.

If everyone is zigging, zag.

If all the brands are blue, go red.

The art and science of pattern interruption is visible in many industries. Google broke well-trodden consumer click paths by hosting a search engine with no advertisement that returned better results faster.

How can we apply these tactics to outbound sales emails and cold calling?

Studying the most common email templates in widespread circulation, it makes me uncomfortable to think about how similar they are. Even just a simple thought experiment scaling the proposed 3-paragraph “personalize, value prop, social proof, personalize, CTA” format to the point where everyone leverages the concept makes you wonder why anyone thought it was a good idea.

Same with the popular phone scripts du jour.

My techniques prove effective because short-form messaging is processed in 3 seconds whereas 3 paragraph emails take 13 seconds. We process images 60,000 times faster than text. As a kicker, it’s also out of the ordinary to open a Venn Diagram or explainer GIF (use as a reply bump to the 3 sentence sales email that cuts straight to the point. Anything other than self-worshipping product marketing language would make you double take.

Shawn Sease used to put 4 blue dot emojis in his subject lines and eventually pointed out that Best Buy started using the technique. Did Best Buy catch the wave from Shawn?

As homosapiens, our complex language skills allow for a wide range of pattern interrupts, so here are some specific and fun examples I use because I’ve seen them convert empirically:

  1. Remove pleasantry — no need to say “hope you’re doing well,” or “in these uncertain times” – we need a 10 year moratorium on these phrases
  2. Lack of formality — “Hey Jane,” vs. “Hi” or “Dear Sir or Madame” – generally speaking, colloquial speech works better
  3. Drop expected formatting — No first name, no CTA, no formatting, no capitalization (Aaron Ross classic!), no salutation, no sign off
  4. Grammar funk — Don’t even write in complete sentences, make it look choppy like business poetry – humanize and desterilize your language
  5. Just a picture with “thoughts?” – also a pattern interrupt because it’s a one-word reply email (Venn Diagrams with competitors on the outside, you in the middle work great)
  6. Hyperbole — “Would it be a crime against humanity if I asked you to spend 7 minutes with me?” This is Voss negative labeling coupled with the fact you’re not asking for 7 instead of 15 minutes. I once asked for 13 minutes and the prospect responded, “I’ll give you 12!”
  7. Humor — ”Before I start checking milk cartons, think we could hop on a zoom?” Take a risk to be funny, it converts. You can never make everyone happy but should also avoid self limiting beliefs. Talk to Jon Selig about how to write jokes in a B2B context, he had some classes going in 2020. Keep it classy San Diego!
  8. GIFs — Embedding a GIF into an email in a world where everyone else is hyperlinking. Spongebob converts; just ask Stephen Chase, the Sales Weasel.
  9. Facetime drop — can you imagine jumping in via this most personal and typically stranger-free medium?
  10. Hyper-personalization — this is the kind where you synthesize multiple insights combining both deep industry insight and references customized for the individual. Things like quoting and timestamping something from a recent podcast they were on, a previous article they were mentioned in, and tying it together with relevancy. Avoid hacky and forced personalization like, “I noticed you went to BU, go Terriers! BTW you wanna buy something?”

Make your outreach stand out.

Sharing things like really great or “needs improvement” inbound emails your team is receiving in a Slack channel or similar medium lays a great foundation for creating unique pattern interrupts. Start to build templates and touch pattern structures where pain points, themes, unique value props (UVPs), case studies and storytelling vary wildly from your competitors. Everything about your approach to speaking, tone, form and structure should be radically divergent so you have left the prospect no choice but to notice you.