Yes, you’re in sales (even if you hate the idea of selling)
August 4, 2026
Five insights to help any leader sell with more confidence and authenticity
You might not want to hear it, but I’m going to say it anyway.
If you’re a leader, then you’re in a sales role.
I’m not saying you’re cold calling and looking at quotas all day.
But you are trying to get people on board with your ideas. To pitch a big vision. To make your case for a new hire.
And how well you do those things has a major bearing on how far you go in your career.
Allan Thygesen, CEO of Docusign, put it directly when he joined me on How Leaders Lead:
“You can’t be successful in any organization unless you’re selling to others.”
For some people, that’s no problem. Sales comes naturally.
But if it doesn’t for you, that’s OK. You don’t have to become a different person to get better at sales. Here’s what some of the world’s best leaders have figured out about selling — and why it might not be as uncomfortable as you think.
1. Reframe sales as service
A lot of people balk at the idea of sales because they feel like it’s inherently self-serving.
Guy Raz has spent years reframing that feeling.
As the host of NPR’s How I Built This, one of the most successful business podcasts in the world, Guy is essentially always selling. He’s pitching guests, attracting sponsors, and building an audience.
As he told me, “What helps me ‘sell’ is to think about what I do in service of others.” His show, as he sees it, is a free business school course for entrepreneurs who don’t have access to the founders he interviews.
When you stop thinking about what you’re trying to get and start thinking about what you’re trying to give, selling feels completely different.
Whatever you need to sell—whether it’s an idea, a product, or a service—think deeply about how it will make someone’s life better. Lean into that, and the selling takes care of itself.
2. Lead with genuine passion
For a lot of people, selling is nerve-wracking. You start feeling the pressure, overthinking your pitch, and wishing you knew more “sales strategies” that would make you more persuasive.
But here’s what UNTUCKit founder Chris Riccobono has figured out: the most persuasive thing you can bring into a sales conversation is genuine enthusiasm for what you’re selling.
Chris still does much of his own marketing and selling because he believes nobody can tell his story better than he can. When he talks about his product, people feel that he genuinely believes in it. That passion is disarming.
The same applies to you. When you’re selling a vision to your team, making a case to your board, or pitching an idea to a potential partner—let your belief in it show.
Passion is persuasive, and it can give you confidence when you need it most.
3. Play to your strengths
It’s easy to conjure up a stereotypical salesperson—loud, charming, and buddies with everyone. But if that’s not your style, you might easily assume you’re not cut out for sales at all.
HubSpot CEO Yamini Rangan had the same fear when she moved from engineering into sales. Her colleagues figured she’d wash out within a year.
Instead, she embraced her background: “I approached sales like an engineer,” she told me. While other salespeople might play golf or be great at sports banter, she knew she was great at analysis. She could get customers talking about their businesses. So that’s what she leaned into.
At the end of her first year, she crushed her goals.
You don’t have to sell the way anyone else sells. Figure out what you bring to the table—analytical rigor, deep expertise, genuine curiosity, natural charisma—and build your approach around that.
Your version of selling might look nothing like the stereotype. But when you find the version that feels natural to you, the work of selling will feel more natural, too.
Watch Yamini’s full episode on YouTube
4. Teach, don’t pitch
If there’s one mindset shift that can transform how you feel about selling, it’s this: stop pitching and start teaching.
Bobbi Brown built one of the most beloved beauty brands in the world. She was also a regular beauty consultant on The Today Show for 14 years, but she never mentioned her products by name. Instead, she taught women about beauty and makeup, empowering them with information.
As she told me, “I was the teacher. That’s just who I am. I don’t want to be the person hawking my products.”
But every time she appeared on the show, customers flooded the counters. She had taught them something useful, and they trusted her enough to buy from her.
The same principle applies in any leadership context. When you want to persuade someone, start by sharing what you know. Help people understand something they didn’t before. Make it valuable.
When people feel like they’re learning rather than being sold to, you can create deep trust and strong relationships. And that’s most of the hard work of selling, already done.
Keep learning from Bobbi Brown
5. Don’t see rejection as the end
I know what you’re thinking. All of these reframes are helpful, but they don’t take away the scariest part of sales: what if they say no?
I get it, and that’s why I want to share what Kendra Scott has figured out after building a billion-dollar jewelry brand: “no” is just the beginning of the conversation.
As she told me in my very first episode of How Leaders Lead, “If you’ve pitched somebody and they’ve told you no, guess what—now you’re talking to them at least. ‘No’ could be the beginning.”
Kendra sees rejection as a starting point—a chance to stay in touch, to send a handwritten note, to find another angle.
Rejection is a part of the process, but it’s not the end of it. Every “no” you get is practice. Every “no” is information. And sometimes, a “no” is just a “not yet.”
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Whether you like it or not, selling is a part of every leader’s job.
But I hope these insights show you that you don’t need natural charisma or a slick pitch deck to be great at it.
Those things can help, but the best salespeople do exactly what we’ve covered here.
They serve others. They show their passion. They add value. They lean into their strengths. And through it all, they don’t let rejection stop them.
How do you approach sales? Drop a comment and share your wisdom with the rest of us.