Selling like a human
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I closed my first deal at seven.
It was summer. I knocked on a neighbour’s door and offered to fix her garden. She said yes. Certain I couldn’t complete the task on my own, I found three other kids on our street, “borrowed” their parents’ tools, and turned up the next morning as a four-person crew. We weeded, we raked and when the job was done, we returned the tools.
By the end of that summer I’d made more money, in real terms, than I would until I left school.
Here’s what I didn’t understand at the time. The gardens needed doing. But that wasn’t what people were paying for. They were paying because something about watching a group of kids organise themselves, knock on the door, and get after it made them feel something. They weren’t buying gardening from children. They were buying the feeling of it.
I’d sold them something human. I just didn’t have the language for it yet.
I’m worried we’re losing what it means to sell.
Not me. My sales are fine. I mean the world.
I think we’re quietly forgetting that selling is a human skill, and treating it instead as a function you automate, script or outsource. And I think that’s a mistake we’ll feel for a long time.
Sales has a bad rap
Sales feels sleazy when the person doing it has stopped caring about your needs. You’ve felt it. It sounds like the predictable script that’s being read, the urgency that’s manufactured or the person across the table who’s not listening to you but instead, desperate to insert their line. That’s not selling. That’s desperation wearing a smile.
Here’s what great salespeople do instead.
They get curious before they get persuasive. They ask questions and then sit with the answers long enough to work out what you need, which is often not what you said you wanted. And then they build something with you that feels less like a transaction and more like being understood.
When you strip selling back to what it is, it’s deeply human. Understanding a need. Staying curious about a person long after the easy questions are done. Building enough trust that someone will hand you a problem they haven’t solved themselves. Knowing how to bring it to a close without forcing it. The quiet satisfaction when a deal lands. And the slower, deeper pride that comes months later, when what you sold has done what you promised it would.
And that last feeling matters more than I think most people realise. Sadly, few get to enjoy that feeling because of how we’ve designed the reward of selling.
For decades we’ve paid salespeople on the signature. When you close the deal, you trigger the commission. It’s clean, it’s measurable, and it works well enough that nobody questions it. The signature is the moment we decided to celebrate.
But watch what that does inside an organisation.
It rewards the moment of sale, not the value the sale was supposed to create. A deal can close, the commission can clear, and the customer can still be no better off twelve months later.
We paid for the signature, not the outcome.
And it draws a line down the middle of the company. On one side, we have people whose contribution is visible, objective and celebrated at the end of the quarter. On the other, everyone whose work makes the sale deliverable, the people who turn a promise into something real, and whose contribution is divorced from the commission that’s been paid.
I’ve watched this play out time and time again in companies I work with. The salesperson hits the number and rings the metaphorical bell. The team charged with delivering what was sold watches on as the bell gets rung and over time, corrosion appears. It tells one half of the company that they create value and the other half that they merely support it. This ‘othering’ is as subtle as it is culturally dangerous and it lives in who gets the dinner, who gets the recognition, whose name gets praised in the all-hands.
You can feel the resentment build even when everyone’s acting as a professional.
Rewarding a different moment
Most experienced CEOs know the role they have as cultural architect of their organisation. They also know the impact of this reward system.
So, what if we rewarded a different moment?
Think of it as two that work together.
First, move the trigger.
Reward value delivered, not value sold. Tie a meaningful part of the reward to whether the customer got what they paid for, measured at the point it’s been delivered and proven, not at the point the contract was signed. This changes what your best salespeople optimise for. They stop chasing signatures they’ll never see the consequences of and start selling things that hold up.
Second, widen who shares in it. If a deal creates value, the reward shouldn’t stop at the person who closed it. Let it reach the people who made the value real. You don’t have to do this evenly, and you can’t do it for everything. But the principle resets the idea that value creation is a team sport, and the compensation model should say so out loud.
I know what some of you are thinking, ‘That sounds good, Phil, but I can’t touch my comp plan. I’d lose my best people, and I wouldn’t know where to start.’
That’s fair. Let me show you how two high profile companies made this change.
Hubspot
When HubSpot was scaling its sales team, it paid reps a simple bounty for every new customer. Customer count exploded. So did churn. The instinct was to blame the customer success team, until they looked at the numbers and found the problem sat in sales. Sales reps were chasing anyone who would sign, including customers who were never going to stick.
So HubSpot changed what they paid for.
First, they added a clawback. If a customer cancelled inside the first four months, the sales rep gave the commission back. The finish line stopped being the signature alone, instead it became the customer staying.
Then they went further. They ranked sales reps by the churn rate of the customers they brought in and paid the lowest-churn quartile up to four times the commission of the highest. The culture evolved to sell customers who stay, earn more, sell customers who leave, earn less. Churn fell sharply.
Notice what they did, and what they didn’t do. They didn’t blow up the model or strip anyone’s earnings. The best salespeople still earned the most, often more than before. What changed was the definition of best. It stopped meaning most signatures and started meaning most customer value.
You don’t have to copy HubSpot. The principle matters more than the mechanism. There are a variety of tactics. A clawback window, a retention multiplier, a bonus that pays when the customer renews or a slice of the deal that flows to the team who delivered on the customer promise. Pick the one your business can carry and start there.
And for what it’s worth, the fear of losing your best people usually has it backwards. The people you lose are the ones who only ever wanted the signature. The ones you keep are the ones who wanted to sell something that matters and those are the people you want to hold onto anyway.
That’s the trigger. Here’s an example of widening who shares in it.
Southwest Airlines
Southwest Airlines started sharing its profits with employees in 1973, the first airline in the United States to do it and has done it every year since. Across four decades it has paid out close to six billion dollars this way.
In one recent year the figure was 667 million, around 12% of each eligible employee’s pay, better than six weeks’ wages. It doesn’t go to the people who sell the seats. It goes to everyone who clears the hours, the gate agents, the ground crew, the people who turn a ticket into a flight that lands on time.
And here’s how this approach shows up in the culture. A difficult customer once pulled rank on a Southwest gate agent, demanding to know whether the agent realised she was a shareholder of the airline. The agent looked at her and said, “We all are.”
That line is only possible because the company made it true. When everyone shares in the value, the line down the middle of the company isn’t there to draw. There’s no half that creates or half that supports. There’s one group of owners, and they know it.
You don’t need an airline’s balance sheet to borrow the principle. You could consider a pool that pays out when a delivered deal performs. It becomes a share that reaches the people who delivered the customer promise. Importantly, the figure matters less than the message it sends about who counts as a value creator.
And here’s the part that makes me an advocate for this change in strategy. Rewarding value delivered doesn’t just heal the divide. It re-humanises the selling itself. When your reward depends on the customer being better off, you can’t afford to stop listening. Curiosity stops being a nice-to-have and becomes the job. You’re back to understanding needs, building trust, taking pride in what you delivered, the human factors that made selling worth doing in the first place.
We built comp models that treat the sale as a transaction and then we wonder why selling started to feel transactional.
A framework to help you sell
I really enjoy selling and when I’ve earned someone’s attention, there is a framework I keep in mind to ensure their attention is rewarded.
The best way to remember it is to say to yourself, ‘Call in the cavalry’. C-A-V. Three questions I ask of myself in the moment.
CAV
Am I being Curious enough?
Am I being Authentic?
Am I able to deliver real Value?
That’s it. Three questions, and they deliver two big benefits.
They pull me into the moment. Whatever else is going on in my day, those three questions put me back in the room with the person in front of me.
And they’re felt on the other side of the table. People can tell when you’re genuinely curious about them rather than waiting for your turn to talk. They can also tell when you’re being straight with them. And they can tell whether you believe you can make them better off, or whether you’re just trying to get to yes.
Run CAV honestly and you can’t sell the sleazy way, because the sleazy way fails all three questions. It isn’t curious, it isn’t authentic, and it isn’t built to deliver value. You’d catch yourself before the other person ever felt it.
And it costs nothing. You can use it in a sales meeting, a board conversation, a tough conversation with someone on your team or at your own kitchen table. The cavalry is always available. You just have to call it in.
Remember that seven-year-old?
Nobody paid that seven-year-old a commission. I got paid because people could see something being built in front of them and wanted to be part of it. The money came after the value, not before it.
I think we knew how to do this once.
So, here’s what I’d ask you to sit with this week. Look at how your organisation rewards its people. Then ask yourself an honest question.
Are you paying for the signature, or for the value? And does everyone who creates that value know they’re seen?
Work with Phil
CEO Coaching — For CEOs who want to lead with clarity and grow their business without sacrificing what matters most. A tailored 12-session experience across three dimensions: scaling you as a leader, elevating how you lead others, and building conditions for sustainable growth.
I've spent 20+ years leading, building and recovering businesses and coaching CEOs doing the same. I work with a small number of people at a time. If the timing is right, let's talk.
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