We were lucky to catch up with Kaaryn Nailor recently and have shared our conversation below.

Kaaryn , thanks for taking the time to share your stories with us today To kick things off, we’d love to hear about things you or your brand do that diverge from the industry standard

While most leadership coaching follows a traditional playbook of fixing what’s “wrong,” I’ve flipped the script with a neuroscience-backed approach that puts your natural talents in the spotlight. Instead of dwelling on weaknesses, I amplify what a client already great at and strategically bring in resources to handle the rest. This isn’t just about faster growth – it’s about working smarter, not harder. I’ve seen this make all the difference for entrepreneurs who want to stop being trapped in the day-to-day of their business and start having their business fuel their creative vision. As we navigate this fascinating era where AI and human creativity intersect, this approach helps visionaries craft concrete strategies to reclaim their time and design a life that matches their ambitions. Because let’s face it – no one starts a business to be chained to a desk.

Kaaryn , love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

My consulting practice specializes in helping diverse leaders navigate those crucial moments of transition – whether they’re corporate executives seeking their next big move or entrepreneurs ready to scale. One of our newest offerings, Unleash Your Best Idea, is a 10-day intensive that helps people transform their business dreams into concrete plans. I designed it specifically to break down complex business concepts into bite-sized pieces, making it work for everyone.

Before launching Kaaryn Nailor Consulting, I managed a team at Columbia Business School that helped NYC’s small and medium-sized businesses generate over $1 billion in economic impact. Add in my background in intellectual property law and years of leadership development work, and you’ve got the perfect storm of experiences that shaped my mission: making strategic business guidance accessible to all kinds of leaders, especially those who might not fit the traditional mold.

What gets me excited every morning is our holistic approach. We don’t just look at spreadsheets and strategies – we look at the whole person behind the business. I especially enjoy partnering with Fortune 500 companies to support their suppliers from underrepresented communities, combining practical business development with group coaching. It’s about creating opportunities for entrepreneurs who might otherwise get overlooked in traditional business settings.

In this field, I’ve learned that success isn’t just about having a brilliant idea – it’s about having someone in your corner who understands both the business landscape and your personal vision. Whether I’m working with a solo entrepreneur or a corporate leader, my goal is to help them turn their ideas into reality while staying true to who they are. Because at the end of the day, the best business strategies aren’t just profitable – they’re sustainable and aligned with the life you want to create.

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?

The biggest lesson I had to unlearn? Perfectionism – and trust me, as a former attorney, that was no small feat. In law, there’s no room for error. Every comma matters, every word is scrutinized, and that perfectionist mindset became part of my DNA. When I first transitioned into consulting and coaching, I brought that same exacting standard with me. I’d spend hours obsessing over presentations, rewriting emails, and fine-tuning programs until they were “perfect.”
Here’s the plot twist: that perfectionism I’d worn like a badge of honor? It was actually holding me back. I remember sitting at my desk one night, agonizing over a training document, when it hit me – I was so focused on making everything flawless that I was missing opportunities to make real impact. My clients didn’t need perfect; they needed present. They needed someone who could adapt, pivot, and meet them where they were.
These days, I’ve embraced what I call “strategic imperfection.” Instead of trying to do everything perfectly, I focus on where I can make the biggest difference for my clients. Sometimes that means delegating tasks to amazing collaborators who can do them better than I can. Other times it means sending that email without reading it fifteen times first. It’s freeing, and honestly? My work has gotten better. Turns out, letting go of perfect opened up space for something more valuable: being genuinely helpful.
The irony isn’t lost on me – I had to become a “less perfect” consultant to become a better one. And that’s a lesson worth sharing.

How’d you build such a strong reputation within your market?

Looking back, I’d say my reputation has grown through what might seem like a counterintuitive approach in the consulting world – I keep it real, I keep it measurable, and I keep it accessible.
Let me break that down: First, I’m obsessed with actual results. In a field where success can sometimes feel vague or theoretical, I make sure my clients walk away with concrete wins they can point to. It could be a small business owner finally stepping out of day-to-day operations, or an executive successfully navigating a major career transition – but every win needs to be tangible.
Then there’s the relationship piece. I learned early on that the most powerful business transformations happen when clients feel truly seen and supported. Not just as business owners or executives, but as humans with complex lives and dreams. Word spreads when people feel that level of support – most of my clients come through referrals from others who’ve been through the journey.
But what I’m most proud of is making business strategy accessible to everyone. Business success shouldn’t be limited to people with MBAs or fancy corporate backgrounds. That’s why I created Unleash Your Best Idea – it breaks down complex business concepts into practical steps that make sense whether you graduated from trade school or a career-changer from a professional discipline. This commitment to speaking plain English (not consultant-speak) and meeting people where they are has become a big part of my brand. Because at the end of the day, good business strategy shouldn’t feel like rocket science – it should feel like a conversation with someone who gets you and wants to see you win.

Contact Info:

• Website: https://www.kaarynnailor.com
• Instagram: Kaaryn_Nailor
• Linkedin: https://www.linkedin.com/in/kaarynnailor

Image Credits

Nick Nelson