I remember the first time I said “I don’t know” in a meeting. I was a newly appointed executive, surrounded by directors and founders, with no fewer than 20 people in attendance. It was, at once, the most terrifying and liberating thing I had ever said professionally.

“I don’t know,” I repeated. “But so-and-so on my team does. I’ll talk to them and get back to this group with a plan.”

I was convinced I would be fired; here I was, a new leader, admitting I didn’t know the answer to a question. About 30 seconds later—what felt like 30 minutes—a founder said, “Awesome! It’s clear you understand what we need, and you have the right people to help make it happen. Let us know.”

That’s when I realized the key to startup success is trusting people who are smarter than you, even if it means swallowing your pride. I only had the courage to be honest because the vision was so crystal clear that a vague response would only hinder us.

A clear, consistent vision, along with reliable experts, are the two essential ingredients for startup founders to achieve success—both in cyber and beyond. While this may seem straightforward, the combination often proves elusive. Why?

This challenge frequently arises from the fear that many startup founders experience when they need to involve others to facilitate success yet are reluctant to relinquish control. Danielle Laurent, CEO of Founders HR Lab, a firm offering fractional CHRO and HR consulting services for startup founders, explains that many founders simply don’t know how to implement trust in their experts because they’ve never had to before.

Danielle Laurent, CEO of Founders HR Lab.

“Trusting others is a learned skill that takes time and experience to develop. But magic happens when founders invite fresh perspectives and diverse experiences into the fold,” she said. “Trusting advisors doesn’t mean abandoning your vision; it means empowering others to elevate it. Once a founder leverages their trusted experts, they gain access to specialized skills and knowledge that can propel their business in ways they couldn’t achieve alone.”

Laurent notes that first-time founders often struggle to trust their advisors because they’ve built their businesses from the ground up, pouring their hearts into every detail.

“It can feel risky to hand over key parts of the business, especially when it’s their own ideas and innovations that have been realized,” she said. “They’ve done it all themselves, and there’s a specific way they’ve always operated. Letting go of that control can feel like losing a part of their process.”

Casey Ellis, founder and chief strategy officer of BugCrowd and a serial entrepreneur, said he “has crossed this Rubicon many times.” He’s seen the pros and cons of maintaining control versus letting go, and he’s learned valuable lessons along the way. When it comes to trusting experts, he believes it’s imperative.

“I’m a big fan of ‘mastery, autonomy, purpose’ as core intrinsic drivers for smart, motivated people,” he said. “If you hire for this but fail to enable them, you’re essentially putting the wrong kind of reins on them. At best, they’ll be quietly ineffective and dissatisfied; at worst, they’ll become disruptive and toxic.”

However, he agrees with Laurent that a clear vision is paramount:

“Trusting experts is essential, but bringing in smart people to operate without a clear vision and strong accountability results in wasted time and discontented, disenfranchised individuals,” Ellis said. “As the level of trust you give increases, so does the importance of leading well.”

This isn’t solely about trusting senior leaders; experience doesn’t always equate to wisdom. Here are some often-overlooked experts:

1. The most “junior” members of your team can offer fresh perspectives unfettered by internal or industry dynamics.
2. External consultants or agencies are specialists for a reason; they’re there to guide you, not just execute based on potential inexperience.
3. Advisors, who may be incentivized to lend their names for branding, often possess comparative insights from advising multiple companies but may not be tapped for fresh perspectives.

It’s important to note that the responsibility doesn’t rest solely on the founder or senior leadership. Downstream experts need to earn respect, which involves effective upward and outward communication that fosters trust. Additionally, gaining trust requires humility.

Casey Ellis, founder and chief strategy officer at Bugcrowd.

“Ego can be the biggest impediment on both sides,” Ellis said. “You can read every business book out there, but leading creative, high-performance people is an imprecise science, as is being a high performer under a new boss in an undefined area. The solution is to approach the situation with eyes wide open, acknowledging best efforts while being candid about imperfections and challenges, then engaging in open discussions for improvement.”

Laurent encourages employees to focus on becoming trusted experts within their teams by consistently delivering results, actively learning, and expanding their knowledge to maximize their contributions. She emphasizes that this type of performance helps build trust.

“Communicating your progress, sharing insights, and being proactive not only benefits the team but also fosters trust with your manager,” said Laurent. “When you show that you understand how your work drives overall goals, you create a relationship where your manager can trust you more, ultimately giving you greater autonomy to grow and contribute.”

For anyone to succeed, there must be a clear and effective vision, which fosters both trust and autonomy.

“If I were coaching managers, I’d encourage them to lead with confidence in their ability to set a clear vision and guide their teams toward meaningful outcomes. It’s about creating an environment where everyone understands the direction, how they fit into the bigger picture, and what’s expected of them,” Laurent said. “Managers should set inspiring, organized goals and ensure everyone knows their role in achieving them.”

Laurent notes that ongoing feedback and structured check-ins help hold the team accountable, but the balance of direction and trust enables individuals to take ownership and excel. Managers must actively trust their teams by providing space for autonomy, recognizing contributions, and encouraging growth. This proactive approach fosters accountability and motivation within the team.

“With that foundation, people know where the company is headed and how their work fits into those goals,” she said. “This clarity allows them to act with confidence, take initiative, and help move the company forward. Real success occurs when there’s enough structure to guide people, combined with the trust to let them work in ways that bring out their best. When trust is built on a solid foundation, things get done faster, problem-solving improves, and people feel empowered to do impactful, meaningful work.”

This approach fosters a trusted culture, which is essential for the financial success of a business. Yes, that culture must be grounded in clear, confident, consistent strategy—but it also requires trusting people to do their jobs and valuing their input based on why you hired them.

“When done well, trust fosters a culture of humility, intellectual honesty, and psychological safety,” Ellis said. “When a smart, diverse team is aligned under these conditions, things can move fast.”

Conversely, you’ll notice a slowdown when this culture is lacking, often because it’s fractured.

Ellis explains a concept known as “Conway’s Law,” which states that a company’s output (product, platform, community, service, etc.) is inherently reflective of its organizational structure.

“I believe it’s also a reflection of the culture, values, and internal vision of the organization,” he said.

This dynamic has its flipside. I recall one organization I worked for long ago that placed blind faith in its leadership without providing clear vision or measuring outcomes related to that vision, causing the company to falter. Allowing anyone to operate without quantitative and qualitative measures poses significant business risks. I’d argue that sometimes the qualitative gut instinct of an expert can take you further than data, which can be manipulated to present a desired narrative.

I asked Ellis, as a serial entrepreneur and successful founder, why it’s often difficult to step aside and let others lead—whether that means managing those below you or allowing someone more experienced to take the helm. What can help them help themselves?

“The founder role is unique because your company will always carry your DNA, regardless of how much control you feel you have,” he said. “Secondly, ‘startup parenting’ shouldn’t be taken lightly; diligence and leadership are always vital. However, as a company matures past its reliance on the founder for survival, it becomes critical to consider where it’s wise to step aside.”

“When founders truly trust their experts, their entire world opens up. They can focus on what they do best without getting bogged down in the details or feeling the need to master new disciplines,” Laurent said. “Instead, they can channel their energy into scaling the business, knowing their trusted advisors are managing complexities with care, integrity, and strong intuition.”

With that trust established, founders are free to dream bigger, think more strategically, and act on opportunities that propel the company forward.

“Leaders who invest in building trust create a workplace where innovation is genuine for every role, not just a buzzword,” Laurent said. “You see it in action: people bringing fresh solutions to the table, tackling challenges head-on, and contributing in ways that advance the business. When trust is reinforced through ongoing communication and accountability, the entire organization operates more efficiently, with fewer obstacles and greater success.”

Related: Hacker Conversations: Casey Ellis, Hacker and Ringmaster at Bugcrowd