The two dollar skill
Forwarded this link? Subscribe here for more.
I was nine years old when I closed my first deal.
It was the summer school holidays in Australia. I'd convinced five kids from our neighbourhood to raid their parents' garden sheds for tools - rakes, clippers, a wheelbarrow with a wobbly wheel - and go door to door pitching the elderly residents on a simple proposition: we'll leave your garden better than we found it.
We weren't pretending to be landscapers.
We knew we were kids. And we knew the residents couldn't do it themselves or afford a real gardener. So we showed up, earnest and honest, and assured them we'd be responsible.
When they said yes, we got to work. And we did what we said we would.
We earned $20 each per day. At a time when pocket money was $2 a week.
I didn't know it at the time, but that summer I learned the most important skill in business, the one that isn't taught in any MBA program, the one that drives most CEOs to the top and the one that almost nobody wants to be associated with.
Sales.
Somewhere along the way, we decided that selling was beneath us.
We trace it back to a bad experience. The used car salesman who wouldn't stop talking. The pushy store salesperson. The cold caller who couldn't take a hint. We felt manipulated, pressured and even conned.
And in those moments we made a quiet decision: I never want to be that person.
So we buried the word. We replaced it with friendlier terms. We don't sell, we shape, influence, convince, pitch, align stakeholders, build consensus.
We created an entire vocabulary to do exactly the same thing without the discomfort of calling it what it is.
And in doing so, we lost something important.
Because here's what we miss when we anchor to the used car salesman and refuse to identify with selling: We forget how prolific the need to sell actually is.
Every meaningful thing you've achieved in your career required you to sell.
You sold a hiring manager on taking a chance on you.
You sold a team on following your vision when the path wasn't clear.
You sold investors on writing a cheque based on a story and a spreadsheet.
You sold a board on a strategy they weren't sure about.
You sold a partner, a spouse, a friend on why this next chapter of your life mattered.
If you're a CEO, you are selling every single day. Vision to your team. Confidence to your investors. Culture to candidates. Credibility to partners. Calm to your board when markets shift.
The CEOs who resist that reality (who think selling is someone else's job, something that happens in a different team) are the ones who struggle to scale.
Because the skill that compounds faster than any other in leadership isn't strategy or finance or operations.
It's the ability to move people to action.
And business schools don't teach it.
The message hiding in plain sight
There's a phrase you hear constantly in medium and large companies: "You need P&L experience to move to the next level."
Leaders hear this, especially those who've spent years managing budgets in government, consulting, or large-scale operations, and assume it means they need to go run a business unit. And to some extent, that's true.
But the deeper message hiding inside the P&L requirement isn't about managing costs.
It's about generating income.
It's about proving you can create revenue, that you can take something to market and convince people to buy it.
In other words, you need to sell.
Look at the resume of almost any CEO.
The sales experience is there.
Sometimes it's explicit. They ran a sales org, they closed enterprise deals, they built a GTM function from scratch.
Sometimes it's disguised. They "led commercial strategy" or "drove revenue growth."
But it's there. And it's that experience, and the objective results that came with it, that preceded their reputation.
That's why my advice to anyone transitioning from the military, consulting or from a core operations function who wants to pursue senior leadership is always the same: learn to sell.
Not because selling is the only skill that matters. But because it's the one that proves you can create value in the market and that proof opens every door that follows.
So if selling isn't what we saw in that used car yard, what is it?
At its core, selling is meeting needs. That's it.
The best salespeople in the world, the ones who build careers, companies, and legacies, are driven by one thing: the pursuit of delivering more value to the person in front of them than anyone else in the market.
That's why the hallmark of a truly great salesperson is that you don't feel like you're being sold to.
Their first mission is to add value.
And they can't do that if they don't understand your needs. So they'll be more curious than almost anyone you've ever met.
They'll ask questions that surprise you. They'll listen (actually listen) in a way that makes you feel like the only person in the room.
They'll also be forthright.
If there's not a fit for what they sell, they'll tell you. They'll thank you for your time and mean it.
But it won't stop there.
They'll keep you in mind. And if they find a product or service that is a fit, even if it's not theirs, even if they stand to make nothing from the introduction, they'll make the connection anyway.
Why?
Because while they have quotas and targets to hit, they understand something deeper.
Word of mouth is a powerful force. And by being the person who leads with curiosity and consistently delivers more value than anyone else in market, they're setting the scene for the compounding effect that no amount of advertising can create.
People remember how you made them feel. And they tell other people.
Think about that for a moment.
Curiosity. Value. Honesty. Follow-through. Generosity.
Even when there's nothing in it for you.
Does that sound like a used car salesman? Or does that sound like the kind of leader you'd follow anywhere?
The irony is that the qualities that make someone exceptional at selling are the same qualities we celebrate in exceptional leaders. We just refuse to use the same word for both.
Here's what I've learned coaching CEOs over the years.
The ones who scale fastest aren't the ones with the best strategy decks or the most sophisticated financial models. They're the ones who can walk into a room, a board meeting, a customer call, an all-hands, a difficult conversation with a co-founder, and move people.
Not through manipulation.
Through clarity, conviction, and a genuine desire to create something worth believing in.
They've embraced that selling is their job. Not a part of their job.
The job.
And the ones who struggle? They're often brilliant operators who believe their work should speak for itself. That the product, the numbers, the track record should be enough.
Sadly, it never is.
Because every inflection point in a company's life requires someone to stand up and sell.
A new direction.
A hard pivot.
A round of funding when the metrics aren't perfect.
A partnership that changes the trajectory.
A hire who had three other offers.
None of that happens without someone who can sell.
I think about those summer days a lot.
Six kids with borrowed tools and zero credentials, knocking on doors with nothing but a genuine offer to help. We didn't have a pitch deck. We didn't have testimonials. We didn't even have a company name.
What we had was a simple understanding: these people need something, we can provide it and if we do good work, they'll trust us to come back.
That's selling. That's always been selling.
The question is whether you're willing to call it that.
The bottom line
Sales is the most important skill in business. It drove your career more than you probably admit. It's what your organisation needs from you every day. And the reason most people resist it is because they're anchoring to the worst version of it instead of aspiring to the best.
The best version?
Curiosity. Value. Honesty. Follow-through.
That's not a used car yard. That's leadership.
So let me ask you this: What's the best sales experience you've ever been part of either as the buyer or the seller?
Email and tell me. I read every email.
Thanks for reading, I appreciate it.
The Partnership Playbook Podcast
Here are this week’s podcast episodes for your walk, commute or workout.
LEADERSHIP MOMENTS
EP 160 - 12 min: How “great deals” quietly destroy growth (and what GTM leaders can do differently). What if the deals your team celebrates most are quietly undermining your growth and leadership credibility? This episode reframes how strong leaders evaluate deals without becoming blockers or sounding negative. Listen on Apple Podcasts | Spotify
EP 162 - 12 min: Why strong CEOs are always closer to the numbers than you think. Are you leading with conviction or quietly hoping your numbers don’t get tested? In this episode, you’ll learn how knowing the right numbers strengthens leadership and fuels sustainable growth. Listen on Apple Podcasts | Spotify
CEO INTERVIEW
EP 161 - 1 hr 8 min: With Christiana Brenton. What if your revenue playbook was slowing your growth? Christiana thinks differently, starting with curiosity, empathy, and humility. From scaling Flight Studio to rejecting a $100M offer, this conversation flips traditional thinking on partnerships and performance. Listen on Apple Podcasts | Spotify
When you're ready, there are three ways I can help you:
1. CEO Coaching: For CEO’s who want to lead with clarity and grow their business without sacrificing what matters most. A tailored 12-session experience with three interconnected elements: scaling you as a leader, elevating how you lead others, and creating conditions for sustainable business growth.
2. The Partnership Lab: A 6-week experience for founders, CEOs, and GTM leaders who are done with slow growth and stalled conversations. Learn to rapidly qualify and prioritise high-value partners, Install a system that turns conversations into contracts and capture outsized returns from partnerships that scale. Apply to join the first 2026 cohort today!
3. Leadership Events: From Cochlear and Lifeblood to military leaders, I have shared inspiring stories and practical frameworks and insights that shift how leaders leverage partnerships for growth. Book me to speak at your next conference, offsite, or leadership event.
Looking for something different? Send me an email.
Businesses don’t scale faster than the leaders running them
Each Wednesday, I send a letter with thought-provoking, deeply practical insight to help you:
→ Lead with clarity
→ Create leverage through partnerships
→ Bring real meaning to your team
Subscribe and get immediate access to my Frameworks Vault, the essential tools CEOs and GTM leaders use to grow with confidence.
