Cold outreach is a game of luck.

I booked a meeting from a cold email last week and had the meeting today.

Here’s what happened: The sequence

1. Saw the company on a partners website
2. Sent an email to the decision maker (I thought)
3. He went to our site looking for an integration
4. Saw we had it, forwarded my email
5. The real decision maker replied

(keep reading to learn how to create sales luck)

Reminder:

Interview once a quarter - even if you love your job.

Here's are a few observations of what regular interviewing does for your career: 1. Market Intel

You'll learn tech stack options, GTM strategies and comparative comp packages.

Good for negotiations in your current role.

The outbound sales volume trap:

Not hitting quota? Work more accounts.
Emails not converting? Send more emails.
Calls not connecting? Make more calls.

Meanwhile:
- your prospects are annoyed
- you are quickly burning out
- your pipeline still stinks

Here's what actually works: 1. Go deep before you go wide

If I could teach outbound all over again, I'd give reps 10 accounts and not let them touch a single additional one until they generate a conversation.

People are too quick to turn up the volume:
- more automation
- more accounts
- more emails

Without actually realizing what works.

You will learn more about how to generate conversations by working 10 accounts than you will 100s.

Cold calling isn't complicated it's just hard.

Here's a framework that works for my team: The Hook:

"Was on your website and had a quick question, do you have 2 minutes?"

Why it works:
- shows you did research
- not clear its a cold call
- gives them control
- sets clear timeline

Microsoft just ranked sales as the 4th most vulnerable job to AI.

1.14 million sales roles at risk.

Here’s what most people are missing: The study looked 200,000 AI chats to see how well AI can do real jobs.

They scored each job based on how much AI could handle on its own.

And it's clear where sales teams are exposed...

A couple weeks ago I was in Orlando for a partner conference.

Decided to sit through the Disney Institute training.

Best sales psychology lesson I didn't expect: Disney has a "compass tool" for customers:

N = Needs
W = Wants
S = Stereotypes
E = Emotions

Let's talk about how this maps to buyer convos.

I’m obsessed with the art of writing great cold emails.

So whenever I get an outbound email that catches my attention, I’ll save it.

Here are a few of my favorites: Day 1 Email:

This is my go to for kicking off a sequence.

Four sentences. That’s all you need.

Cold calling isn't complicated it's just hard.

Here's a framework that works for my team: The Hook:

"Was on your website and had a quick question, do you have 2 minutes?"

Why it works:
- shows you did research
- not clear its a cold call
- gives them control
- sets clear timeline

Basic cold email structure:

Sentence 1: reference a challenge (credibility)
Sentence 2: reference a problem (relatability)
Sentence 3: share a similar story (value)
Sentence 4: casual call to action (CTA)

Here's a few examples...

One day I was scrolling X and saw a post “how to make $1,000 on Upwork”

While headline was click-baity, the content was solid.

I decided to run a search for “outbound sales” opportunities on Upwork and came across a Founder that was looking for help with email copywriting.

Here’s the messaging I used to start a conversation: It worked.

A week I agreed to write a 5 email sequence for $1,000.

Here are a few opportunities you can jump on if you're looking for a side hustle in 2025...

Early in my career I was fortunate to be trained by:

- Gary Vee
- John Barrows
- Josh Braun
- Jeb Blount
- Kevin Dorsey

My favorite lesson for outbound was on objection handling... Here's a framework:

1. Use a statement like “I’d imagine”

Then give the most plausible reason why the person might have that objection. This requires subject matter expertise and empathy.

2. Say “Can I make a suggestion”

Then offer your recommendation. You want to help guide the buyer throughout the process. Not the guru that acts like you have all the answers.

3. Politely push forward

A soft and respectful ask to schedule time. Relate it back to the original objection to maximize impact.

This is the cold call scorecard I've used to train 50+ reps.

Not sure if it's "the best".

But its helped me develop and train my teams. Cold Call Intro:

1. Hits the correct tone
2. Identifies themselves before being asked
3. Uses research to build credibility
4. Empower the no

Example:

“Hey [Name] - was on your website and had a quick question, you got 2 minutes? If it’s not relevant you’re free to hang up on me.

Here’s a secret:

If you want to get your resume in front of the right person, don't just apply on the website or LinkedIn then wait.

Find a hiring manager and do this:
(this applies to any role) Job application template:

Common objection right now is "lets talk in 2025"

Here's a framework you can steal:

1. use a statement like "I'd imagine"
2. say "can I make a suggestion"
3. politely push forward

This is what it sounds like: Objection 1 = "let's talk in 2025"

Talk track:

“I'd imagine you don't have budget left for this year. Can I make a suggestion... what if we give you a preview of how we can help with XYZ to see if this should even be on your radar for next year?"

I’m often asked “when should I pitch on cold calls?”

My answer: once you’re able to answer these 3 questions: 1. What’s the problem?

If there isn't one, they’re not taking another call.

My favorite talk track for this is:

“Typically when I talk to other VPs they are struggling with X, Y or Z. Sound like your world at all today?”

A thread on B2B outbound tech selling 101: There are 3 ways to find companies for outbound:

1. Buy a list
2. Pay someone to build a list
3. Build a list yourself

My recommendation is option 3.

Here’s a secret:

If you want to get your resume in front of the right person, don't just apply on the website or LinkedIn then wait.

Find a hiring manager and do this:
(this applies to any role) Job application template:

Cold emails should be less than 100 words.

- personalization will get you opens
- relevance will get you replies

Here's a cold email checklist: 1. Subject Lines = Relevance

No more than 3 words.

Convey the main reason for why you’re reaching out.

Example 1: "reports for [boss]"
Example 2: "hiring SDRs"
Example 3: "quick question"

I spent 3 years training remote BDRs on how to cold call.

Here's my favorite role play exercise: Each rep is assigned a part of the call.

Rep 1 = Intro
Rep 2 = Objections
Rep 3 = Close

As the Manager / Team Lead works through the call, queue in the next rep to join the conversation...

AE on our team just hit $1M in sales this year.

I asked what's working and he said "socratic questioning."

Rarely hear sales questioning framed this way in trainings and liked it: Socrates developed the technique to engage in philosophical conversations.

Hence the name "Socratic" questioning.

The practice involves 4 types of questions:

1. Clarifying
2. Probing
3. Evidence based
4. Implications & Impact

Here's what it sounds like...

One of the most powerful words in selling:

"Typically"

- sets expectations without overpromising
- demonstrates expertise and credibility
- helps frame next steps

Here's 3 examples you can use 👇 1. Establish credibility and expertise

"Typically other VPs I talk to are struggling with [Problem 1], [Problem 2] or [Problem 3]. Sound like your world at all?