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In the fast-paced, high-stakes world of entrepreneurship, trying to do everything alone can be a costly mistake—especially when the road ahead is uncertain. According to Tiffany Dufu, President of the Tory Burch Foundation, the smartest move an entrepreneur can make during challenging times isn’t pushing through alone—it’s asking for help.

Why Asking for Help is a Power Move, Not a Weakness

Tiffany Dufu knows firsthand that seeking guidance can accelerate your growth and avoid costly detours. Through her work at the Tory Burch Foundation—an organization that provides women entrepreneurs with access to capital, community, and education—Dufu has seen a clear pattern: entrepreneurs who aren’t afraid to ask for help often make faster, smarter decisions.

“Asking for help is a leadership muscle,” Dufu explains. “It’s not a weakness. The more chaotic the environment, the more essential it becomes to lean into vulnerability.”

Research backs this up. A Harvard Business Review study found that employees who sought advice from experienced peers not only performed better but were 42% more likely to solve difficult problems effectively. In a world where innovation and speed are everything, reaching out can mean the difference between stagnation and breakthrough.

From Startup Struggles to Smart Scaling: Dufu’s Personal Lesson

In 2018, Dufu founded The Cru, a peer-coaching platform designed to connect women navigating professional and personal growth. Two years in, she faced a big question: how to scale the business with a subscription-based model targeting corporate clients?

Instead of wasting time on trial and error, Dufu tapped into her network of investors and mentors. One introduction changed everything—a seasoned entrepreneur shared their exact playbook for launching a B2B subscription service. No fluff, no gatekeeping—just real, actionable steps.

“You don’t need to reinvent the wheel,” Dufu says. “There’s always someone who has already done what you're trying to do.”

The result? Within the same year, The Cru was acquired by Luminary, a New York-based networking platform. While the acquisition price wasn’t publicly disclosed, the success story speaks volumes about the power of mentorship and collaboration.

Taking Initiative Doesn’t Mean Going Solo

One of the most common misconceptions in business is that "taking initiative" means doing everything alone. According to Dufu, true initiative lies in proactively seeking the best path forward—including asking others for guidance.

This mindset shift is crucial. A study by McKinsey & Company found that 80% of top-performing entrepreneurs credit mentors for helping them avoid major setbacks early in their careers. Yet, fear of looking incapable often holds people back.

“There’s nothing I’m facing now that someone else hasn’t faced already,” says Dufu. “And the sooner I find them, the sooner I can move forward.”

The Psychology of Asking for Help

So, why don’t more people ask for help?

According to research published in Psychological Science, people consistently underestimate how willing others are to help. In one study, participants expected only 48% of strangers to agree to assist them—but in reality, 76% said yes.

Leadership expert Simon Sinek echoed this during the Brilliant Minds 2024 conference:

“We wrongly associate asking for help with weakness. But in truth, it builds trust. People respect those who are honest about what they don’t know.”

In business, trust is currency. By asking for help, you’re not only solving problems—you’re building meaningful relationships that can lead to partnerships, referrals, and future opportunities.

How to Ask for Help Like a Pro

Here’s a quick framework, inspired by Dufu and other top leaders, for making your asks effective:

1. Be Specific: Don’t just say, “I need help.” Clarify what you're working on and what kind of insight or support you're seeking.
2. Do Your Homework: Show that you’ve done some legwork already. This demonstrates commitment and respect for the other person’s time.
3. Follow Up: If someone shares advice or resources, circle back. Let them know how their input helped you—it keeps the relationship strong.
4. Offer Value in Return: Even if you’re just starting out, share what you can—feedback, connections, or your own expertise in another area.

The Bottom Line: Collaboration is the Future of Leadership

As the global business landscape grows more complex, the old image of the lone-wolf entrepreneur is being replaced by collaborative, connected leaders.

In fact, data from SCORE (a nonprofit supported by the U.S. Small Business Administration) shows that mentored businesses are more than five times as likely to survive past the five-year mark compared to those without guidance.

Whether you're launching your first startup, pivoting in a crisis, or scaling rapidly, one thing remains constant: you don’t have to do it alone.

Smart entrepreneurs don’t just hustle harder—they ask smarter questions to the right people.

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