We were lucky to catch up with Lakeya Cherry recently and have shared our conversation below.

Lakeya, looking forward to hearing all of your stories today. Can you share a story about the kindest thing someone has done for you and why it mattered so much or was so meaningful to you?

A few years ago, I attended TED in Vancouver, my first big event since the pandemic. If you’ve ever attended a TED event, you know it’s very action-packed and immersive. This particular evening, they were hosting topic-based dinners around town, and I was planning to attend the leadership one. However, I began to feel tired and considered going back to my hotel. I ran into another attendee, one of the event’s speakers, who encouraged me to attend the dinner despite being tired and to show up as my authentic self. I went to the dinner and had a wonderful time talking to those at my table about our leadership superpowers and journeys. One of the people at my table was a celebrity who was moved by what I shared. A few weeks after the conference, I was contacted by the celebrity’s assistant, who said they were so moved by what I had shared that they wanted to do something nice for me, no strings attached. I was then gifted $50,000, which ultimately gave me the additional capital/savings I sought to feel confident launching my own business. I remember crying after receiving the email and being so moved by this stranger’s act of kindness. It felt as if the universe had conspired in my favor, showing me that I had support and that it was okay to move forward.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

I’m Dr. Lakeya Cherry, an executive coach, facilitator, and consultant, and the founder of Lakeya Cherry LLC. At the heart of my work is the belief that leaders deserve support that is both strategic and deeply human. I work with executives, rising leaders, entrepreneurs, and mission-driven professionals who are carrying a lot and who want to lead well without losing themselves in the process.

My path into this work was not linear, but it makes perfect sense when I look back. I started in social work, which taught me to listen for what lies beneath the words and to pay attention to what people need, not just what they say they want. Social work is systems work, and it trained me to notice patterns, power, and the unspoken dynamics that shape people’s behavior and outcomes. That lens still anchors everything I do today, mainly when I help leaders navigate complexity within organizations.

Over time, I became increasingly drawn to leadership itself, not the polished version that looks good on paper, but the real thing. I became fascinated by what it takes to lead with clarity and courage when the stakes are high, the pace is fast, and the expectations are relentless. Coaching became the place where my love of people, my respect for systems, and my commitment to impact could come together.

Today, I provide executive and leadership coaching, team coaching, facilitation, and speaking. I support individuals who are stepping into bigger roles, leading through change, making difficult decisions, or navigating challenging team dynamics. I also partner with organizations that want to strengthen leadership, build trust across teams, and create cultures where people can do excellent work without burning out or walking on eggshells.

The problems I solve are often the ones leaders do not say out loud. Many leaders come to me when they are experiencing decision fatigue, managing constant pressure, or feeling isolated in their role. Others come to me when they know they are capable, but they still second-guess themselves, over-function, or carry more than their share. Some are dealing with conflicts they have been avoiding because it feels risky, political, or emotionally exhausting. Many are outwardly successful and internally depleted, and they want to change that before it costs them their health, their relationships, or their joy.

In my coaching, I help leaders get clear about what matters most, what they want to be known for, and what they need to stop tolerating. I help them strengthen their decision-making, communicate with confidence, and set boundaries with integrity. I also help them understand the dynamics of power and influence so they can navigate their environments without shrinking or becoming hardened. When leaders are grounded in who they are, they lead with greater steadiness and stop operating from urgency, fear, or constant proving.

With teams, I help people have the conversations they keep postponing. I help teams name what has become normalized, clarify expectations, and rebuild trust when communication has gotten messy or strained. I create space for honesty without hostility, and I support teams in moving from misalignment and frustration to clarity, accountability, and forward movement. When teams can talk about what is real, they stop guessing, they stop avoiding, and they start working together in a way that feels cleaner and more sustainable.

What I think sets me apart is the blend of depth and directness I bring to the work. I am warm, but I do not rescue, and I am compassionate, but I do not let leaders stay stuck in patterns that are costing them. I help my clients feel seen, and I also challenge them when they are shrinking, avoiding hard conversations, or over-extending themselves to keep the peace. I bring a systems lens to leadership, which means I can help leaders understand what is happening around them while also doing the inner work that makes their leadership stronger from the inside out.

I am proud of the transformations I have witnessed through this work. I have coached leaders through promotions, pivots, first-time executive roles, and seasons of uncertainty. I have watched people reclaim their voice, stop performing confidence, and start embodying it. I have seen teams move from resentment and misalignment to clarity and shared ownership, and I have seen leaders step into greater authority while remaining grounded, values-led, and human.

I am also proud of building Lakeya Cherry LLC from the ground up. I started my business in 2020, and I have grown it by staying committed to excellent work, meaningful relationships, and the long game. Entrepreneurship has stretched me in all the ways leadership stretches us, and it has pushed me to let go of perfectionism and stop equating overwork with worth. I have learned how to build a model of success that is sustainable and aligned, and that lesson has made me a better coach and a better leader.

The main things I want people to know about my brand and my work are that I take leadership and people seriously. I believe leaders can be influential and compassionate at the same time, and I believe results matter, but not at the expense of someone’s well-being or integrity. I help leaders build the internal capacity and the practical skills to lead with clarity, courage, and steadiness. If you are in a season when you are being asked to rise, I will help you do so in a way that aligns with who you are, not just with what the world expects.

What’s been the best source of new clients for you?

The best source of new clients for me has been referrals from friends, colleagues, and former clients. Even after five years in business, referrals remain my number one source of new leads, and I see that as a reflection of trust and results.

At the same time, I have learned that I cannot assume people fully understand what I do, who I serve, or when I have capacity for new work. I used to think that if I were doing great work, the referrals would keep flowing. The truth is that relationships are powerful, but they still need clarity. I have had to get more intentional about communicating my offerings, naming the kinds of engagements I am seeking, and making it easy for people to connect me with the right opportunities.

Any stories or insights that might help us understand how you’ve built such a strong reputation?

When I think about what has helped me build my reputation, a few things stand out.

First, I did not enter this work as a “new” leader. I came into coaching and facilitation after nearly a decade as the CEO of a nonprofit focused on strengthening and mobilizing diverse social impact leaders through education, leadership development, networking, and community-building. In that role, I helped build the organization’s brand, expand its reach nationally and internationally, and design and lead leadership experiences at scale, including conferences, summits, fellowship and mentorship programs, and long-term leadership development initiatives. That experience shaped how I show up today. I understand what it means to lead real people in real systems with real constraints.

Second, I have built trust by consistently delivering excellent work and being the kind of partner leaders want in the room. I bring both warmth and rigor. I create spaces where people feel safe enough to be honest, and I also hold the line on clarity, accountability, and follow-through. Over time, that combination has led to repeat work, long-standing client relationships, and strong word of mouth.

Third, my partnership with Evolution has been a significant factor in my credibility growing. For the past five years, I have had the opportunity to coach and facilitate across a wide range of sectors and organizational contexts, often in partnership with other senior coaches and facilitators. That exposure has sharpened my craft, expanded my perspective, and strengthened my ability to meet leaders where they are, whether they are in a high-growth company, a mission-driven nonprofit, healthcare, education, or the public sector.

Fourth, I have been a Brené Brown Certified Dare to Lead Facilitator since 2019, and that work has been foundational to my reputation. I have facilitated numerous Dare to Lead experiences in both public and private settings, including cohorts specifically for Black women and women of color, as well as offerings for universities, schools, nonprofits, and other organizations. People know what they are going to get with me. They know it will be meaningful, practical, and honest.

Finally, I have been intentional about staying visible and staying connected. I maintain a consistent online presence, and I communicate with my community through a monthly newsletter. I share real insights, real reflections, and real tools, and that has helped the right people find me and trust me over time.

If I had to sum it up, my reputation has been built through lived leadership experience, strong delivery, long-term relationships, and a commitment to doing work that creates real change for people and teams.

Contact Info:

• Website: https://lakeyacherry.com/
• Instagram: https://www.instagram.com/lakeyacherry/
• Facebook: https://www.facebook.com/lakeyacherryllc/
• Linkedin: https://www.linkedin.com/in/lakeyacherry/
• Twitter: https://x.com/lakeya_cherry
• Other: https://www.threads.com/@lakeyacherry

Image Credits

Danielle Finney