🏈 THE SIDELINE

Michael Dell took his first vacation in 9 years.

It was 1993 and he lasted 8 days.

His team couldn't make basic decisions without his approval. And it spanned everything from supplier contracts to pricing changes, hiring, and more.

Understandably, he came back from vacation furious. Not because of his team, but because of himself. How could he have built a $2B company that depended completely on him?

Dell was a Quarterback: the execution powerhouse of his company.

→ Decisions piled up waiting for him

→ His team got used to seeking his approval instead of ownership

→ Growth and work capped at his capacity and time

The Quarterback trap isn't obvious: your competence is what's made everyone else dependent.

Dell decided to do something about it.

Over 12 months, he went from being a Quarterback in his business to a Head Coach.

And his team knocked it out of the part. They went from needing him for every decision to making 47 decisions independently during his 2-week vacation. He agreed with 43 of them.

Here are 5 lessons from how he did it:

FROM THE FILM ROOM
🌎 Expand your thinking

• A16z on AI adoption by industry. Banking and financial services are reaping the productivity benefits of AI, but adoption is still ~20% according the latest Census data. How can you apply AI in your finance function? (Link)

• John Seiffer on how to find CEO time. (Link)

• Steven Cravotta on how to steal your customer’s profitable ads (Link)

  

• Deo on how long it takes to close by deal structure (Link)

  

• How buyers find businesses to acquire, ~23% were brokered and never went to market. 44% were through direct discussions with business owners. (Link)

  

🛠️ Tool Stack of the Week:

• Blaze AI - produce marketing materials faster

• Clay - I use this for enrichment, faster than than doing manually work

• Saner AI automatically shows what to prioritize each day

• Grammarly to fix grammar on the go

BUILDING A WINNING PROGRAM
LESSON 1: If your company can’t survive two weeks without you, that isn’t fun

In the early 2000s, Dell was already a multibillion-dollar public company. From the outside, it looked institutional. Inside, it wasn’t. When Michael Dell tried to take time off, the company came to a halt in <10 days.

The business was big, but it was dependent.

Your move: Schedule a two-week vacation 90 days from today. Tell your team now: “The business will run without me. Our job is to make that possible.”

If the idea feels reckless, it might be the right thing to do.

LESSON 2: Your team needs to know how you make decisions

When Dell stepped back the first time, leaders kept calling with questions he thought they should already know how to answer. How to price products, what suppliers to pick, or how to manage customer requests.

He’d spent years making good calls, but never shared how he weighed tradeoffs.

So he started documenting decisions.

Your move: Track the decisions you make for a week. "Here's what I decided, here's why, here are factors I considered, here's when to escalate."

That’s how your judgment scales.

LESSON 3: Be specific about decision rights

Dell had “strong leaders” in place, but they constantly escalated anyway. Authority was limited to an org chart.

“Owning finance” was meaningless when a $300K vendor decision could still blow back on them.

Dell responded by defining decision rights with thresholds.

Your move: Of the decisions you make this week, is there a natural owner? Can you define a dollar amount or risk level they can own without escalating? Under what conditions should they escalate?

Share the doc with your team, “if it’s not listed here, assume you own it.” If they still can’t pick up the ball, they might need more info or some encouragement and support to take full responsibility.

LESSON 4: You are the team’s role model

Dell noticed leaders would bring up problems, never solutions.

He’d conditioned them to defer to his judgment.

So he changed one habit:

He stopped answering first.

Your move: Next time someone ask you a question, respond with:
“What do you think we should do?” or “What’s the downside if we try that?”

You’re building judgment, not obedience.

LESSON 5: Your vacation is rehearsal for due diligence

After all these changes, Dell finally took two weeks off.

His team made 47 decisions and he agreed with 43.

That was the moment he knew the company could not only survive without him, but that if a buyer came into the mix, his transition and the transaction would go way smoother.

Your move: After you've explained how you make decisions, given your team the power to make decisions, and taught them to think on their own, it's time to see how it all works by taking some time off.

Ask your team to keep a list of every time they felt like reaching out to you, why they wanted to, how they solved the issue, and who made the final decision. Review decisions when you get back.

Would you have made the same ones? Why or why not? Target 80%+ alignment over time and you’ve got a transferable business.

THE FOURTH QUARTER
IF YOU'RE A QUARTERBACK:

Stop answering every question and start building decision playbooks.

Stop being available 24/7. Start assigning clear decision rights.

Stop jumping in to "just handle it." Start testing your business by disappearing.

The shift feels like going from being needed to being unnecessary.

It's uncomfortable. It challenges not just your ego, but your identity.

But it's absolutely necessary for growth.

Dell spent 12 months on this transformation.

Start this week.

FINAL WHISTLE
Not sure if you're a Quarterback?

Take the 3-minute quiz at 👉 Ownerquiz.com 

Discover if you're a:

→ Quarterback (you're doing the work, team waits for you)

→ Linebacker (you're protecting against risk, reviewing everything)

→ Offensive Coordinator (you're chasing opportunities, changing direction often)

→ Head Coach (you've built systems that work without you)

Cheering for you,
Kinza