There’s a piece of advice nobody hands you when you start a business.

Not in business school. Not in the entrepreneurship books. Not in the mentor conversations over coffee where everyone’s talking about vision and culture and hiring the right people.

Here it is: You are not just the CEO. You are also the closer.

And most founders are good at one and genuinely terrible at the other. For me, I still need a little bit of help in leadership and operations. Turns out, being the eldest child of an Asian family is not enough, haha! 

Two Roles, One Person

Leadership and sales feel like completely different worlds, and we’ve been conditioned to treat them that way.

Leaders build trust. They cast vision. They hold the room through uncertainty, through setbacks, through the long stretches where nothing seems to be working. Great leadership is about making people believe in the mission, in each other, in what’s possible even when the evidence is thin.

Salespeople do something different. They create urgency. They handle objections in real time. They read the room, adjust on the fly, and know how to guide someone from “maybe” to “yes.” Great sales is about making people act, not just feel.

Different skills. Different mindsets. Different moments. And yet, as a Founder, you need both. Sometimes in the exact same conversation.

The Story That Explains Everything

Every time I get on a sales call with a prospect, I come prepared to close. I know the offer, I know the objections, I know where I want the conversation to go.

(photo of me closing a sale or a Zoom call with a lead)

But something interesting happens, and it happens more often than you’d think.

The prospect starts talking. Not about my services. About their team. Their hiring nightmares. The freelancer who disappeared halfway through a project. The “cheap VA” who ended up costing them more in mistakes than they ever saved in fees. The frustration, the exhaustion, the quiet feeling that nobody they bring on actually gets it.

And somewhere in the middle of that, I make a decision most salespeople never make. I put down the close entirely.

I stop thinking about the deal and start thinking about the person sitting across from me. I ask deeper questions. I try to find the real issue underneath the surface complaint, because it’s almost never actually about the freelancer. It’s usually about something harder. A difficulty letting go and trusting someone else with a business they’ve poured themselves into. A pattern from early in their career where they didn’t get enough support or mentorship. An honest reckoning they’ve been avoiding about where the last bad hire actually went wrong.

I sit with them in that. I help them think it through. I’m not performing empathy here. I genuinely stop caring about the sale and start caring about leaving them better than I found them.

Here’s what almost two decades of doing this has taught me: they almost always come back and hire me anyway. Not because I closed them. Because I led them.

You’re Always Selling Something

Walk through a typical week as a Founder and look at what’s actually happening beneath the surface.

You’re rallying your team around a new direction. That’s leadership. You’re pitching a potential client on why you’re the right partner. That’s sales. You’re posting content to build your audience and attract inbound opportunities. That’s also sales, whether you call it that or not. And yes, a lot of the tactical execution around content and marketing can be outsourced to the right people. But the Founder’s voice and perspective? That part stays with you.

You’re recruiting a senior hire who has three other offers on the table. Sales. You’re in an investor meeting explaining why right now is the right time. Sales. You’re trying to convince your best employee to stay during a hard quarter. That one is a blend of both, and you’d better be ready to move between them without missing a beat.

The mistake most Founders make is thinking these are two separate jobs, roles you can eventually hand off as the company grows. And yes, you can hire great salespeople. You can bring in someone who runs circles around you in a discovery call. You can build a strong team around you.

But if you can’t sell your own vision, to clients, to talent, to the market, you will always be dependent on someone else to carry that weight for you. And that dependency has a ceiling you’ll eventually hit.

The Switch Is the Skill

The real competency here isn’t just being a good leader or a good salesperson in isolation. It’s knowing which mode the moment calls for, and being able to move between them fluidly, sometimes within a single meeting.

You open with leadership. You build rapport, establish trust, make the other person feel genuinely heard. Then the conversation shifts, an opportunity opens, and you need to close. The founder who can’t make that transition fumbles the moment. They stay in “cast vision” mode when the client is ready to sign. Or they push for the close when the person across from them needs to feel understood first, and they lose the room entirely.

The most counterintuitive thing my own sales calls have taught me is this: sometimes the best close is not closing at all. Sometimes the most persuasive thing you can do is put down the pitch, ask the harder question, and trust that genuine leadership will do more than any technique ever could.

However, that only works if you’ve built both muscles. If you’ve never developed the sales instinct, you won’t recognize the moment to use it. If you’ve never developed the leadership instinct, you’ll push when the moment calls for patience, and you’ll wonder why the deal slipped away.

Almost Two Decades, One Core Lesson

The realization didn’t arrive all at once for me. It built slowly, conversation by conversation, a gradual accumulation of moments where I started to notice what actually moved people versus what just moved a conversation forward on paper.

The Founders who scale well aren’t always the sharpest operators or the most brilliant strategists. More often, they’re the ones who figured out how to do both things: hold the room and close the room, inspire people and move people to action, and know, in any given moment, whether leading or selling is what the situation actually needs.

It’s easy. You want to make your business profitable, so you SELL. 

Now you became so good at selling, so you need to hire more people. Now you have to be a LEADER. 

Then you spent time in operations and leadership, you have to bring back sales up again. So you start SELLING again. On and one.

If you’ve been telling yourself that sales isn’t really your thing, or that leadership is something you’ll figure out later, I’d encourage you to reconsider. You don’t have to be world-class at either. But you do have to be genuinely competent at both, and you have to know when to switch.

Learn both. Master the switch. It’s one of the best pieces of advice I’ve carried through almost two decades of building businesses, and I wish someone had told me sooner.

From the desk of: 

Karla Singson 

CEO, Proximity Outsourcing 

P.S. Check out my best video about sales, and going from 0 to $1M in a year without ads. And also, check out this video about my best leadership investment.