Name: Adriana L Cowdin

Title: CEO & Executive Coach

Organisation: Be Bold Executive Coaching

Ana L. Cowdin is a four-time entrepreneur, former corporate CEO, and one of the most sought-after executive coaches and keynote speakers in the business world. Founder of Dekaf Digital, she led the company to over 400% growth, resulting in its acquisition in 2023, placing her in the top 1% of women-owned small businesses.

With over 20 years of experience, she has successfully coached more than thousands of executives, leveraging her background as a former Chief Marketing Officer, Chief Customer Officer, and CEO in PE, privately held, and Fortune 500 companies. Cowdin’s expertise in personal branding has been featured in Forbes, Inc. 500, NY Times, Reuters, ABC News, CBS News, and many other top-tier outlets.

Known for her direct and results-oriented coaching style, she empowers executives to navigate change with clarity and confidence. Cowdin holds a Bachelor’s Degree in business management, has completed leadership and coaching courses through Harvard Business School, and has been recognized with awards such as the Trailblazer Award and the Multicultural Leadership Award.

Thank you to the 2,000 leaders who’ve generously done the 7 Questions on Leadership!

We’ve gone through the interviews and asked the best of the best to come back and answer 7 MORE Questions on Leadership.

I hope Adriana's answers will encourage you in your leadership journey. Enjoy!

Cheers,

Jonno White

1. As a leader, how do you build trust with employees, customers and other stakeholders?

Building trust starts with genuine relationships. For me, it’s about getting to know people as individuals, not just as employees, customers, or stakeholders. Trust doesn’t come from a title; it comes from consistent actions, empathy, and shared experiences.

I make a conscious effort to connect beyond the immediate work. Whether that’s asking about someone’s weekend, sharing a laugh in a virtual chat, or remembering that their kid has a big soccer game, those moments matter. They show that I value the person, not just their role.

When people know you care about them holistically, they’re more likely to trust your decisions, intentions, and follow your lead. If I don't know you beyond the confines of our work, how can I fully understand what motivates or challenges you? Relationships are the bridge to trust, and trust is the foundation of any successful collaboration.

2. What do 'VISION' and 'MISSION' mean to you? And what does it actually look like to use them in real-world business?

To me, a vision is the ultimate destination—the "why" behind what a company does. It's aspirational, inspiring, and a guiding star for long-term impact. A mission, on the other hand, is the engine that gets you there—the "how." It's tangible, operational, and focused on the actions required to achieve the vision. Together, they’re a company’s north star and compass, aligning teams, decisions, and strategies around a shared purpose. When crafting these for my latest joint venture, Kiaian, we looked at how they would relate to each other, our team, our clients, and the world at large.

We aligned on the following: Vision: To be the global leader in enhancing human potential. Mission: We deliver breakthrough solutions through behavioral science, democratized coaching, and leadership expertise, maximizing enterprise growth. In practice, this means every decision Kiaian makes should further our vision of unlocking human potential. Whether it's launching a new digital coaching platform or refining leadership strategies, the mission ensures these initiatives are actionable, measurable, and growth-focused.

In real-world business, a vision inspires stakeholders to rally around a purpose that transcends profit, while a mission keeps execution on track. For Kiaian, it looks like ensuring our product innovations aren’t just clever but genuinely empowering individuals and organizations to grow in measurable, meaningful ways. A strong vision and mission mean we’re not just delivering solutions—we’re delivering impact.

3. How can a leader empower the people they're leading?

Empowering people starts with respect—treating them as capable, intelligent adults - and investing in both their growth and the company’s success. I believe leadership is about creating an environment where people feel trusted, valued, and supported to thrive. For me, that means taking the time to build real relationships. When you know someone’s goals—both personal and professional—you can align opportunities at work to help them achieve those goals.

Whether it’s offering stretch assignments, personalized coaching, or simply listening to their ideas, the message is clear: “I believe in you.” Investing in their growth and giving them autonomy to make decisions shows respect for their abilities. When people feel respected, trusted, and genuinely supported, they don’t just perform—they excel. And when their goals align with the company’s, success becomes a shared win.

4. Who are some of the coaches or mentors in your life who have had a positive influence on your leadership? Can you please tell a meaningful story about one of them?

One of the most impactful mentors in my life was Marty, a VP I worked for early in my career, back in the late '90s. He was a military veteran, and he brought with him the discipline, teamwork, and operational rigor that defined his service. But what stood out most was his ability to balance those qualities with genuine care for people. He wasn’t just a leader—he was a great human being.

What I learned from him wasn’t just about operational excellence or leading with confidence, clarity, and conviction, though he excelled at all of those. It was the realization that you could be disciplined and results-driven while still treating people with respect and kindness. He showed me that leadership isn’t about choosing between getting results and appreciating people—it’s about doing both, and doing them well. That lesson has shaped how I lead to this day.

5. Leadership is often more about what you DON'T do. How do you maintain focus in your role?

Leadership is absolutely about focus, and that often means knowing what not to do. For me, it starts with prioritizing around the company’s strategic objectives and aligning every effort toward achieving them. Whether it’s investing in people, planning, or technology, I ensure that decisions support those big-picture goals.

At the core, though, it’s always about putting people first. If you prioritize your team, clients, partners, and stakeholders, the results will follow. Maintaining focus means filtering distractions and staying anchored in what matters most: driving impact through empowered people and a clear vision for success.

6. If you fail to plan, you plan to fail. Everyone plans differently. How do you plan for the week, month and years ahead in your role?

I plan my week on Friday mornings, setting aside time to map out priorities during a meeting-free operations day. I tackle finances first thing Monday morning—my least favorite task—so I can focus on the week ahead with a clear mind.

For annual planning, I start in August by aligning with the company's 1-, 3-, and 5-year goals. We set priorities, identify resources, and prepare for the next year’s budgets and forecasts. By November, everything is finalized, ensuring we hit January with a clear, growth-focused plan and the resources to execute.

This process has been my blueprint for over a decade, driving consistent results, including a successful exit in 2023 and strong growth for my new company in 2024.

7. What advice would you give to a young leader who is struggling to delegate effectively?

1. Don't rescue them: Let your team struggle a little—it's how they grow. Resist the urge to jump in and fix things unless necessary. Give guidance, but let them own the outcome.

2. Delegate outcomes: Instead of handing over specific steps, share the "why" and the desired result. This empowers your team to think creatively and take ownership of the process.

3. Create a "fail-safe" culture: Clearly communicate that mistakes are part of learning. Encourage open conversations about what went well and what could improve, building trust and confidence in their abilities.