Scaling Success: How Top Entrepreneurs And Leaders Delegate to Drive Growth

You don’t have to do it all—and you’re not meant to. One of the hardest but most transformative parts of leadership is learning what to hold on to and what to let go of.

In this piece, powerful entrepreneurs and leaders of the Dreamers & Doers community share the real moments when they chose to delegate, trust, and evolve their leadership. Their stories show how letting go can unlock not only growth, but also a more sustainable, fulfilling way to lead.

Founder of Triggered Academy, the clinician‑education platform certifying Pelvic Rehabilitation Fertility Specialists (PRFS™), and creator of Wyze Health, an upcoming AI‑powered fertility‑intelligence platform dedicated to democratizing women’s reproductive care.

The hardest part of letting go has been transitioning from hands-on clinician to tech founder. In my practice, I was deeply involved in every patient’s care, seeing firsthand the impact of my work. I had to shift from thinking of myself as just a clinician to truly embracing the role of a founder and visionary. Understanding that my impact could be exponentially greater if I let go of the day-to-day and focused on scaling the mission was a game-changer. It’s a different kind of impact, but one that demands a shift from control to trust, from hands-on to high-level, and from founder to leader.

CEO & Co-Founder of Onde, building AI agents to make event planning as simple as a conversation.

The hardest part to let go of were the things I’d just gotten really good at. It felt risky to hand off marketing, client experience, or product once I was finally confident in them. I worried no one else would do it as well—or care as much—as I did.

I realized my fears around delegation weren’t about the tasks but about trust. Culture, hiring, and clear team standards gave me confidence that things would be done right. Bringing in people better than me and operating in their zone of genius turned delegation into a multiplier.  It makes the ride more meaningful and lets me focus on the highest-leverage work: culture, strategy, vision, and key relationships.

Founder & Chief Visionary Officer of Alternative Coaching Methods, redefining health and wealth through plant medicine while helping high achievers transform into high performers.

Letting go of the actual coaching has been the hardest part of growing my business. My clients have come through referrals specifically because they value their time with me, making it difficult to train others to coach with my unique approach.

The pivotal mindset shift for delegating with confidence wasn’t about perfect replication of my methods, but about trust: trust in others to bring their own valuable perspectives and skills, trust in the universe that the right people would appear when needed, and—most importantly—trust in my own judgment to select and develop coaches who would honor the essence of my approach while adding their unique strengths.

Founder of L Leon Virtual Assistance, a boutique virtual assistance business helping women-led businesses scale through streamlined operations, brand visibility, and executive-level virtual support.

The hardest thing to let go of was the belief that no one could represent my brand or serve my clients the way I could. Shifting from “no one can do it like me” to “someone can do it differently and better in some areas” was game-changing. Having systems in place and hiring aligned support allowed me to delegate without sacrificing the client experience I value so deeply.

Letting go is a muscle you build. It doesn’t happen overnight, especially for women navigating entrepreneurship alongside cultural expectations of doing it all. But with each step back, I gained more clarity, space, and energy to lead, and that’s been the greatest growth of all.

Founder & CEO of LOUPN, an inclusive jewelry brand intended to encourage positivity, confidence, and love.

The hardest part of my business to let go of was social media. I had been building relationships with influencers and customers on social media since our beginnings, and it was really hard to not check every other hour and still feel connected.

Delegating slowly—training my staff on fulfillment, then customer service, and then social media—allowed me to build trust and know that I can be confident in their ability to stay positive and handle our customers with care. My team and I communicate on a daily basis, which helps me stay connected to our customers and community.

Founder & CEO of Cydnee DeToy Coaching, equipping high-achieving millennial women with the mindsets and strategies to create and thrive in the career they want through a mix of 1×1 coaching, group programs, and speaking. 

As a former executive leader turned CEO of one, I had to shift from having a team to implementing every new tool or system myself. Now, as I build back a small team of fractional support, I’ve had to relearn how to let others figure out the intricacies of a system or define a process. 

The biggest mindset shift for me was realizing that I had hired people who are much better than I am at figuring out these tools or troubleshooting various issues. Letting them work their magic was freeing and empowering for everyone involved, myself included.

Founder & CEO of Parity Lab, a global social enterprise offering trauma-informed leadership development that transforms how women leaders respond to gender-based violence by offering tools, community, and reflective spaces to help them grow their impact—while centering care, collaboration, and healing.

Letting go of Parity Lab’s original 18-month intensive program—with over 40 modules—was the hardest. While it created deep impact, it demanded immense commitment from fellows and our team alike, limiting how many we could support. Over 14 months, we had to step back, simplify, and redesign it into a more focused, scalable model that still serves fellows meaningfully without burning anyone out.

I had to accept that impact isn’t measured by program intensity but by sustainable change. When we saw that a more focused model actually increased our fellows’ implementation rates while reducing the Parity Lab team burnout, it validated that sometimes, doing less—but doing it exceptionally well—creates more meaningful and lasting results.

CEO & Founder of Say Hola Wealth, a culturally-rooted financial education platform and community helping ambitious Latinas grow wealth with confidence, clarity, and culture.

The hardest part of my business to let go of was the belief that if I didn’t do it myself, it wouldn’t be done right. This mindset kept me stuck in hustle mode and made it hard to trust others, even when I knew I needed support to grow. Letting go meant embracing collaboration and progress over control.

Shifting from an employee mindset to a CEO mindset was key. I realized my role was to lead, not do it all. I built an SOP bank in Airtable (my favorite tool!), and now we hold monthly reviews to keep our processes clear and client care top-notch.

Founder & CEO of Aphthonia LLC, with a mission to help leaders and organizations unlock their fullest potential.

I recently transitioned from a corporate CEO to a founder and entrepreneur, which meant I  had to let go of time-consuming collaborative decision-making. Specifically, my current environment allows me to be agile and quickly pivot in decisions for the best outcome of my business.

I assessed my calendar against my skill set and service fee. This allowed me to shift tasks for two reasons, either to gain expertise or because the task didn’t garner a return on my investment.

Co-Founder of Relatable Nonprofit, helping nonprofit professionals build consulting careers so they can create impact with more freedom, flexibility, and joy.

Letting go of any part of my business has been hard. It’s my baby!  My business coach told me that “80% done for you is 100% awesome”—and that mindset shift changed everything. It helped me release perfectionism and start trusting others. I’ve also discovered that some people do certain things better than I can, which has been both humbling and freeing.

Founder of Doc Day Afternoon, a consultancy supporting business leaders in designing people-first business operations and transformational customer experiences.

As a solo founder, so much of my consulting work is built around IP and frameworks that come directly from my lived experiences and personal philosophies. When I reached a point where one part of my business clearly needed collaborators in order to scale, it felt like I was handing over something deeply personal—something I couldn’t fully control or interpret for others anymore.

Through writing SOPs and team handbooks, I began seeing my frameworks as tools for others to grow through. That shift really turned delegation from a loss of control into an invitation for shared ownership and self-actualization.

Co-Founder of Summit Chasers Network, unleashing the full potential of your business, equipping you with tailored strategies, data-driven insights, and a dedicated team to scale efficiently and profitably without sacrificing your health, family, or happiness.

The hardest part of my business to let go of was direct client fulfillment (though I’m still involved where vital) and managing day-to-day operations. It was challenging because they were the heartbeat of my early success, but delegating them was essential to scale and focus on strategic growth.

Hiring gritty, adaptable team members with the right soft skills—people who could co-create processes without needing rigid SOPs—gave me the support to let go effectively. Soft skills are often underrated when hiring, and they are crucial.

Co-Founder & CEO of CIRT, an award-winning, women-owned B-Corp delivering the all-in-one software stack for sustainable packaging. 

As a founder who thrives on big ideas, letting go of the nitty-gritty details of implementation was tough. I had to learn to trust that others could build on the vision, even if their approach was different from mine.

For me, the hardest part wasn’t about control—it was about speed and support. I’m the kind of person who jumps in when something feels stuck or inefficient, or when I sense someone needs help. But that instinct, while well-meaning, was actually getting in the way of delegation and team growth. Once I recognized that my urge to step in was rooted in a desire to protect momentum—not mistrust—I was able to reframe delegation as an investment in long-term speed, not a sacrifice of short-term efficiency.

Founder & Chief Storyteller of Austley, a communications-first marketing consultancy and coaching studio that helps startups, small businesses, and lean teams grow with clarity, confidence, and compelling storytelling—without overspending.

The hardest thing to let go of was content creation, like drafting and writing every caption, email, and client deliverable myself. As a communications expert, my voice is the product, so trusting anything (or anyone) else to capture it felt risky—but holding on to every word was also holding back the business.

Realizing I could train AI to reflect my voice—not replace it—changed everything. Now, AI acts as my first draft assistant, my editor, and my gut-checker, which allows me to move faster without sacrificing quality.

CEO of Belgian Boys, creating whole ingredient breakfast options that allow families to prep less, smile more, and indulge better.

As a founder, it was hard for me to let go of opportunities. Getting opportunities is music to a founder’s ears and saying yes is exciting because it feels like momentum, but I’ve learned that answering every opportunity is the fastest way to lose focus. At some point, I realized that saying yes to everything meant we were doing too much and not doing any of it excellently. Letting go of distractions—even good, exciting ones—has fueled our growth in recent years.

Not everything needs a yes. In fact, sometimes, the most powerful answer is “not right now.” That mindset gave me the clarity to delegate—not just tasks, but also decisions and opportunities. 

All individuals featured in this article are members of Dreamers & Doers, an award-winning community that amplifies extraordinary women entrepreneurs, investors, and leaders by securing PR, forging authentic connections, and curating high-impact resources. Learn more about Dreamers & Doers and get involved here.