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The hiring question CEOs miss

It saves you $100K

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Off the Top

A few months ago I had a big decision to make.

I'd been at the same company for almost 8 years.

Comfortable. Good people. Knew the playbook.

But I had stopped growing.

I went back and forth on leaving for months.

Then I talked to a mentor and he told me about an idea the Marines call "The 70% Solution"

"You're never going to have 100% of the information when making tough decisions. Once you're at 70% - decide"

So I decided to quit.

Fast forward -- got lunch with my old boss Friday.

Every concern I had about growth, direction, and competition still hold true.

You're never going to be completely sure.

But a good decision now beats a perfect decision too late.

The Briefing

stories you need to know

AI fears trigger panic selling across software stocks - tech whales like ServiceNow are down 50% from its peak.

My take: Nvidia, CEO, Jensen Huang called the selloff "the most illogical thing in the world." He's right. You're not going to vibe-code enterprise software like Salesforce, ServiceNow, or CrowdStrike anytime soon. This is an emotional reaction that'll rebound (not financial advise)

The Hiring Question CEOs Miss

My company is hiring a new head of sales.

The CEO is asking the usual questions:

Can they close? Can they coach? Can they forecast?

But he's missing one question that will save him months of pain.

The #1 Question to Ask When Hiring Leaders:

When a coach gets hired in sports, the first thing they do is build their staff. The best leaders already have people waiting to follow them.

Here's how you spot it in an interview…

Ask them: "Who are 2-3 people you'd bring with you?"

The answer you want sounds like this:

“There's a guy I managed at [Company] who just hit President's Club. He's bored and underpaid. And a woman I worked with two stops ago who's been asking when we can work together again. Those are my first two calls."

If they can't answer? You're about to pay $100K+ in recruiter fees to build their team from scratch.

The Red Flags:

You'll know a bad answer when you hear one. Here's what to watch for:

"My company has a non-compete" or "My boss wouldn't let me take anyone." Great leaders figure out workarounds. They stay in touch. They know who's itching to move.

"I know lots of people." There's a difference between 5,000 LinkedIn connections and 5 people who'd quit their job to work with you again. Get specific - if they need time to get back to you, that’s fine.

If you're hearing these answers, you're not talking to a builder. You're talking to someone who's going to need YOU to build the team for them.

This Goes Beyond Sales:

Ask this for ANY role building a team - CFO, CMO, VP, Director. It doesn't matter if you're Series A or public.

One hire who brings two great people with them doesn't just fill three seats. It changes the culture and trajectory of your company.

The best leaders don't just manage talent. They magnetize it.

If they can't recruit, they can't build.

And if they can't build - what are you hiring them for?

Try This Next Interview:

Add this to your next leadership interview:

"This is a really important role. You're going to play a crucial part in building the team. Curious, who from your existing network would you try to bring with you?"

Their answer will tell you everything you need to know.

The Best Thing I Heard This Week

“If we’re all going to eat, someone has to sell”

EVERYONE is selling something.

Free Consultation:

I'm doing 10 free 30-minute strategy calls on outbound sales and partnerships.

If you're stuck on cold outreach, building an outbound motion from scratch, or figuring out partner channels - I'll walk you through what's working today.

In return, I'm using these conversations to shape a new product I'm building.

Thanks to everyone who already filled out the form. I’ll review this weekend and respond to everyone, either way.

Call start next week.

TSG

P.S. I reply to all emails.

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