How Successful Leaders Learned What to Trust
By: Gesche Haas, Founder of Dreamers & Doers, a curated community and PR Hype Machine™ for extraordinary women entrepreneurs.
Ask any seasoned founder or CEO about the moment their leadership truly leveled up, and they won’t point to a course they took or a book they read. They’ll point to a shift, something they started doing differently that quietly but fundamentally changed the way they lead, build and show up.
Early in most founders’ journeys, the instinct is to gather more: more research, more data, more analysis, more certainty. The assumption is that better decisions always live on the other side of more information. But the leaders who’ve been around long enough know that’s only half the story. Great decision-making isn’t about eliminating uncertainty. It’s about learning which signals actually deserve your trust.
We connected with members of the Dreamers & Doers community to uncover those defining shifts. What you’ll find here isn’t a checklist of leadership best practices, but real stories from founders, CEOs, and investors who learned to cut through the noise and made that discernment a cornerstone of how they lead.
They Stopped Waiting for Perfect Information
In the high-pressure, high-stakes moments that often come with entrepreneurship, certainty can feel like the ultimate goal. Making a leap as a founder or leader is scary enough, but doing so without the “total picture” can be paralyzing. Reloveution founder and CEO Marissa Badgley knows that feeling well. Her leadership shifted when she stopped waiting for perfect conditions and started trusting action instead.
“I now choose to trust myself and have a bias toward action,” Badgley says. “When something has energy, I determine the minimally viable experiment and try to run it within hours rather than days, weeks, or never. I don’t need the outcome to be perfect to know it was worth trying. This shift has led to more ideas seeing the light of day instead of dying in my head, more creative and aligned projects, and substantially more time and energy to do the work I love.”
Kimberly Tara, who built a tax strategy tool for small businesses as CEO and founder of The Tara CPA Firm, faced an initial pull toward certainty, but she rarely had full clarity on pricing, branding, product scope, or audience. She learned to move based on what she did know and to trust that the gaps would close as she went.
“The businesses that actually grow are the ones where the founder decides and adjusts, not the ones where the founder researches forever,” she says. “It’s made everything move faster, including me.”
As a “recovering perfectionist,” Amber Chaudhry had to fight against her deeply held instincts to realize that done is better than perfect and that most decisions, even in business, are reversible.
“For a long time, decisions sat on my desk for weeks while I tried to get them exactly right,” Chaudhry says of her early days at the helm of Noori Skincare. “Making the call, even an imperfect one, almost always beats waiting. Most decisions aren’t permanent, and I can adjust as I learn.”
For leaders who want to practice trusting action over perfect information, an ability to learn and adapt is paramount. SoGal Ventures managing partner Elizabeth Galbut has extended this philosophy to her work as an investor. The leaders that catch her eye while fundraising don’t necessarily have total certainty, but a willingness to quickly adapt while maintaining clear convictions. Prioritizing this kind of leader has made Galbut a “more future-proof investor, better partner to founders and stronger long-term allocator of capital,” she says.
The best decision-makers aren’t always the most certain. They’re often the fastest learners, and realizing the power in that can prove a significant shift.
They Let Go of Assumptions and Focus on Reality
It’s important to believe in your ideas as a founder, but it’s also important to be willing to let go of them in the face of hard, specific evidence. For Tavlin Consulting CEO Allison McMillan, this meant listening to her clients instead of deciding what they needed on their behalf.
“Every conversation is data,” McMillan says. “I listen for the problems people keep raising that I’m genuinely equipped to solve, and I let that shape my offerings and how I talk about them. It keeps me anchored to real value instead of the thing I assumed was valuable.”
Linda Du also learned to trust actual customer behavior over her founder’s intuition. The Moola co-founder and CEO started running fast, lightweight experiments with actual users to pressure test her assumptions more quickly.
“That shift helped me prioritize what actually mattered and build Moola Money around genuine customer behavior,” Du says.
Founders can spend years trying to predict what will work. These leaders learned to pay closer attention to what reality was already telling them, and it paid off.
They Trusted Themselves More Than External Validation
While many leaders have learned the hard way that their intuition isn’t the only thing to trust when it’s time to make a move or decision, it still counts for something and should certainly hold more weight than outside distractions. Go To Market’s Chief Swag Officer Amanda Hofman has cultivated those internal signals throughout her career.
“I’ve gotten much better at trusting my gut when something feels off in a partnership, collaboration or opportunity,” Hofman says. “Earlier in my career, I felt like I needed a long list of reasons to justify walking away. Now, I’ve learned that paying attention to tension early usually saves everyone time, energy and stress later on.”
Values can be an important guidepost as well.
“I stopped making decisions based on what was convenient and started asking one question first: Is this aligned with my values?” says Michelle Bernier, CEO of The Right Room. “That shift changed everything, from the clients I take on, to the partners I build with, to the events I produce. When my decisions are rooted in principle rather than pressure, I stop second-guessing myself and focus on the work I actually want to be doing.”
At Unbuttoned Brands, designer Emily Dick learned to stand by her conviction to cultivate brands based on authentic identity rather than conventional formulas. For her, this meant tuning out the noise of external validation and trusting the expertise she developed while working with clients.
“I started creating brand identities based on who my clients are underneath all the social conditioning instead of things like color psychology,” Dick says. “I get to the heart of who they are by using my intuitive process to create a brand that truly reflects who they are: voice, values, quirks and all.”
To better hone her intuition, Kimberly Brizzolara waits for emotions to settle before making major decisions as founder and creative director of Brizzolara Brands. Doing so makes her intuition an even better thought partner.
“I stopped making decisions at the emotional peak,” she says. “I let the excitement crest, settle and dip, and only move forward if the clarity is still there a day later. This has saved me from every wrong ’yes’ I used to make on momentum, and it’s made my business, my book and my calendar dramatically more aligned.”
They Built Better Decision-Making Systems
When all else fails, building a system can be a powerful way for leaders to ensure it’s safe to trust their next moves. Badassery’s CEO Danielle Letayf has upleveled by more clearly designating what’s urgent in her business.
“One of the first things I ask when someone brings me a request is when they need an answer, and I work backward from there,” she says.
Integrating this basic system into her process has cleared overwhelm and allowed for better prioritization, giving Letayf more confidence in herself and the information in front of her.
By codifying decision frameworks into AI agents, Kristina Subbotina has taken a higher-tech approach, but seen similar results and success.
“I stopped trying to be the bottleneck for every operational decision and instead built AI agents that function as real members of my leadership team: a COO, CTO, and lawyer agent that run 24/7,” says the founder and CEO of Lexsy. “My decision-making frameworks are now codified rather than in my head, which made me a sharper, more intentional leader.”
Strong leaders don’t make better decisions because they’re smarter, but because they create systems, principles, and filters that help them work through uncertainty consistently and gut-check the information and sources they trust in any given moment.
All individuals featured in this article are members of Dreamers & Doers, a highly curated community and PR Hype Machine™ amplifying extraordinary women entrepreneurs and leaders through authentic connections, credibility-boosting visibility, and opportunities that accelerate big dreams. (Learn more about membership here.)
