You might not think of your daily conversations as scripted, but tacit expectations drive most exchanges. In any workplace or business meeting, there’s usually an unspoken agreement about who holds the most leverage, and where to draw the line between an acceptable ask and an unreasonable one.
But Daniel Lubetzky, the latest billionaire to become a Shark Tank judge, has made it a habit to respectfully test those hidden boundaries. The entrepreneur first gained fame building Kind Snacks, a granola and nut bars brand that he sold to Mars for more than $5 billion in 2019.
At Kind, Lubetzky would instruct his team members: “‘Make sure you ask them for something that they are going to say ‘No’ to,’” says Miguel Leal, Kind’s former chief marketing officer who later co-founded Mexican food brand Somos with Lubetzky. Executives would huddle before every confab with a store buyer or supplier and decide what far-afield question they would pose, anticipating rejection. Could they ask for a lower price? Faster service? Superior shelf placement?
The strategy is simple. Ask a question no one expects to hear and there’s always a slim chance that they’ll surprise you with a yes. A bold question might also open the door to a compromise, getting you closer to a deal that hadn’t even been on the table before. Perhaps most importantly, the simple act of forming the inquiry, and practicing how you’ll frame the question, is a useful exercise for clarifying your aspirations.
Don’t be a “maximalist”
Lubetzky confirms that he pushed Kind employees to make big, nearly verboten asks this way, explaining to Fortune that he codified this habit so that everyone would, like him, keep pushing themselves and the company.
But the advice, comes with a big caveat. It’s “not about just being a maximalist and blindly asking for more,” he says. That kind of thinking can lead to poor decisions and wreck relationships. Instead, the goal is to have everyone take ownership. Lubetzky backed that up by giving meaningful amounts of equity to everyone on staff.
Leal has kept up the tradition at Somos, where Lubetzky is a board member. Not long ago, Leal asked a partner an out-there question about “slotting fees,” or the cost of adding shelf space, and saved the company more than $100,000 in costs at a big box retailer. Looking ahead at 2025, Leal says, Somos’ team also plans to ask all of its retail partners for the “endcap” or the display at the end of a grocery aisle in time for Cinco de Mayo. More than 80% of the shops will say no, Leal predicts, because Somos is considered too small of a brand to take over such valuable real estate.
Getting it right
To be sure, Lubetzky’s dictum is similar to the old truism: it can’t hurt to ask. But it turns that mentality into a habitual action. One rule of thumb for anyone who experiments with the strategy: If you’re yielding a lot of yeses, then you’re probably not stretching far enough. Leal also says he prefers to ask the unexpected question during in-person meetings, but he’ll settle for a phone call, or even an email, if that’s all he can do.
Following this advice doesn’t come easy, and Leal recalls a time he backed out from asking a pre-planned “No” question at a meeting in his early days at Kind. At the end of the conversation, Leal tried to work up the courage to ask about cutting into a major competitor’s shelf space, but he felt paralyzed with fear, despite his years of success marketing for big established brands. He later had to explain what happened to his peers. “I am a people pleaser, and I don’t want to disappoint people, and I had a lot of fear of rejection,” says Leal.
“What I realized is that it’s just a muscle. It’s something developed,” he adds. “There is nothing to be afraid of, because the downside is basically where you are today, and then the upside is unlimited.”