Jul 8, 2026
For celebrity entrepreneur Robert Herjavec, landing a big deal has little to do with charm or persistence — it’s about understanding people. In a recent Instagram post, the former Dragon’s Den panelist explained that his “whole trick” for closing big contracts wasn’t actually a trick at all — but rather, it was making sure people never felt like they were being sold to.
For anyone who works in sales, runs a side hustle or simply dreads the moment a conversation turns into a pitch, that idea points to a bigger question we all face at some point: How do you ask for the sale without breaking the trust that got you in the room in the first place?
The psychology behind Herjavec’s approach
In the post, the Croatian-born, Toronto-based entrepreneur pushed back on the common advice that once you spot an opportunity, you should move straight to finalizing the deal. In his view, jumping to close the moment someone opens up sends the wrong signal — it tells the customer you care more about the transaction than about them.
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He described the risk of putting the client in an uncomfortable spot — someone who shared something personal, only to feel that openness is now being used against them. To avoid that, Herjavec said the better approach is to listen first and offer something genuinely useful. “You always want to close from a position of helping, not selling.”
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Is ‘helping first’ just a feel-good sales pitch?
Herjavec’s advice sounds appealing, but it can also seem out of touch. The public image of a Shark or Dragon is someone who moves in for the kill, not someone who slows down to build trust.
So does this softer approach actually hold up in the real world of sales? Canadian data suggests it does — and that trust, more than any single tactic, is often what keeps a customer coming back.
A September 2025 trust survey by Toronto-based marketing and research firm dNovo Group found that 26% of respondents cited dishonesty or misleading information as the top reason they would cut ties with a business — ahead of poor product or service quality (21%) and privacy violations (12%). The same research found that word-of-mouth recommendations from friends and family remain far more trusted than online reviews, social media or AI-generated suggestions when Canadians decide where to spend their money.
Global research points in the same direction. According to HubSpot’s 2025 State of Sales Report — a survey of roughly 1,000 sales professionals worldwide — 42% of respondents said understanding a customer’s goals is a major driver of repeat business and upsells, while another 30% pointed to building trust as a key factor. When HubSpot looked at what separated top-performing salespeople from the rest, the answer wasn’t a closing technique — it was people skills: 40% of respondents identified building an authentic rapport as the most effective way to upsell or cross-sell.
Helping doesn’t look like a sales pitch, which is likely why it works so well. Salespeople who apply Herjavec’s approach tend to focus more on understanding the problem than on rushing toward a solution. When you care more about the other person’s outcome than your own commission, he suggested, the sale tends to take care of itself.
Soft skills may be the strongest advantage in an AI-driven economy
You don’t have to work in sales to take something from Herjavec’s approach. As automation and artificial intelligence (AI) make technical know-how easier to find, human skills — listening, empathy, patience — may be the biggest advantage left.
Fluency with AI tools might get someone in the door. But it’s curiosity and a genuine interest in solving another person’s problem that tends to keep that door open, whether you’re closing a business contract, negotiating a raise or building the kind of reputation that brings repeat clients.
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At the end of his post, Herjavec returned to the same idea: A customer’s trust is the most valuable thing a salesperson builds, and it’s worth protecting over the long run rather than trading away for a single sale.
Lessons for Canadians managing money and building a business
Herjavec’s advice doesn’t require a TV deal or a storefront to apply. Here are a few practical takeaways for Canadians who sell, freelance or simply want to negotiate better:
- Ask before you pitch. Herjavec’s method starts with understanding what the other person actually needs before proposing a solution. Try opening your next negotiation — whether it’s a client contract or a salary conversation — with a genuine question instead of a pitch.
- Treat trust like a financial asset. Canadian survey data shows a single instance of dishonesty is the fastest way to lose a customer for good. Protecting your reputation is as important to your long-term income as protecting your credit score.
- Let word of mouth do some of the work. Since Canadians say they trust recommendations from friends and family more than any digital channel, investing time in relationships can deliver better results than paid marketing, especially for self-employed Canadians and small business owners.
- Watch the soft-skills gap. As routine sales and customer-service tasks get automated, the ability to listen is becoming a real edge for anyone earning income through sales, freelancing or client work in Canada.
Bottom line
Herjavec built a career closing million-dollar deals — and his biggest insight is surprisingly simple: People can tell when you care more about the sale than you do about them. And the data backs him up — Canadian and worldwide research all point to the same conclusion: Trust is what wins repeat business, and losing it takes only one dishonest move.
For Canadians who sell, freelance or negotiate for a living, that sentiment is a practical takeaway, not only a feel-good idea. Ask before you pitch, listen before you close. And as AI takes over more of the routine parts of sales and customer service, the ability to truly connect with people may be the most valuable skill you can build.
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Eric Esposito is a freelance contributor on MoneyWise who loves making financial topics accessible and understandable to readers. In addition to MoneyWise, Eric’s work can be found in publications such as WallStreetZen and CoinDesk.
Managing Money • Jun 12
