Adaptable — The only constant in running a business is change. The market, trends, and customers are continuously in flux. As a result, leaders must be agile, ready to pivot and adjust their game plans. Sometimes that means mid-course corrections. Other times, it’s scrapping it altogether and starting from scratch. A leader must not get too fixated on the path in pursuit of the goal. Focus on the goal.

We are living in the Renaissance of Work. Just like great artists know that an empty canvas can become anything, great leaders understand that an entire organization — and the people inside it — can become anything, too. Master Artists and Mastering the Art of Leadership draw from the same source: creation. In this series, we’ll meet masters creating the future of work and painting a portrait of lasting leadership. As part of this series, we had the pleasure of interviewing Casey Clark.

Casey is the CEO and co-founder of the small business advisory firm Cultivate Advisors. He and his team have helped thousands of entrepreneurs in 160 industries grow through core business skill development and coaching. Those working with the firm for 12+ months average a growth rate of 43% in top-line revenue and 65% in bottom-line profit year-over-year. Many of Cultivate’s clients can be found on the Inc. 5000, an accomplishment Cultivate itself has made four years in a row.

Thank you for joining us. Our readers would enjoy discovering something interesting about you. What are you in the middle of right now that you’re excited about personally or professionally?

Running a small business is already a stressful endeavor. You’ve heard the stats before. According to the U.S. Bureau of Labor Statistics, nearly 1 in 5 businesses fail within a year. By the end of the fifth, about half will have gone under, with the number increasing to 70% after ten. Now add on the stressors of the current economy — rising interest rates, inflation, finding and retaining staff, and the increasing challenges of raising funds.

It’s no wonder small business CEOs are stressed out and overwhelmed. And now, because many of them work virtually, they feel isolated. They are yearning for community. In response, we are trying something new. We are holding three small outdoor adventures in Georgia, Alaska, and Montana, mixed with skill development and coaching. Each trip will include 10–20 CEOs, and along with hiking, biking, and snowmobiling, we will talk strategy and problem solve while setting goals and developing action plans. It will be a great way for our entrepreneurs to network and learn from their fellow business owners.

I’m excited about this new initiative because I’ve seen over the years that most entrepreneurs get easily bogged down by the day-to-day duties of keeping their businesses afloat. They don’t take the time to pull themselves out of the daily grind to focus on the business as a whole. And with the long hours, built-up stress, and a never-ending workload, it’s no wonder 72% say they are directly or indirectly affected by mental health issues compared to 48% of non-entrepreneurs. These trips are designed to address both these critical issues and more.

We all get by with a little help from our friends. Who is the leader that has influenced you the most, and how?

I’ve always believed that great leaders are only really good at one or two things, and then they figure out how to leverage the rest. So the leader who has influenced me the most throughout my career is really an avatar created from the best qualities and traits of about 10–15 people. There’s my father, whom I mirror my work ethic after. Growing up, he held multiple jobs, and at seven, I started delivering newspapers with him. He also taught me the importance of treating everyone with respect. There’s the boss I had who showed me the value of feedback and to always actively seek it. And right now, I am learning from our company’s COO, who has more experience than me in scaling businesses. Working with thousands of companies over the years, I’ve found a trend where you usually need a visionary and generalist to get the business off the ground, but at a certain point, you need to pivot to a specialist with entirely different skills to scale. That’s where we find ourselves now.

Sometimes our biggest mistakes lead to our biggest discoveries. What’s the biggest mistake you’ve made as a leader, and what did you discover as a result?

When I bought my first home service franchise in college, I had never managed anyone before. I thought my role was to bark orders and have everyone do what I wanted when I wanted. No questions asked.

Within one month, only one person remained on my staff out of 15. And with the phone ringing off the hook from customers asking where we were and demanding their money back, I was in trouble. I needed to act fast.

I immediately called everyone and got their feedback. With that information, I shifted my demeanor and attitude. I became open and honest in the hiring process and management of my second crew. I explained what had happened, what I’d learned, and how I wanted to collaborate moving forward. And that following year, everyone came back. Everyone. And many are still with me today at Cultivate.

At that moment, I learned two important lessons I’ve taken with me throughout my entrepreneurial journey. The first is that my most valuable asset is my team. Without them, I am nothing. The second is that true leaders work for their teams. My job as a CEO is to nurture, coach, and mentor them to success. Their success is ultimately mine.

How has your definition of leadership changed or evolved over time? What does it mean to be a leader now?

In the past, leadership was authoritative. Top-down. The attitude of the typical leader was, “I’m the boss. This is how we do things. I don’t need to explain why. Just get the job done. I don’t want your input. I know what’s best for the company. If you don’t like it, you can always leave.”

And despite this management style, people spent their entire careers at just one or two companies.

Today, it’s collaborative, where a true leader works in service of their team. It’s about creating a performance culture by sharing a vision, aligning goals, developing trust, and advancing those you are responsible for, both personally and professionally.

Nowadays, people change not only jobs every few years but careers too. They constantly pivot, shift and branch out. The days of putting talent in a specific, defined position are over. Roles are created around an individual’s strengths and skills.

As a result, leaders must adapt; as we all know, a company’s success is in direct relation to the success of its employees. They need to nurture, coach, and mentor their teams. Have a clear buy-in process while encouraging employees to collaborate and contribute ideas. These steps typically lead to immediate ROI with increased retention and productivity.

Success is as often as much about what we stop as what we start. What is one legacy leadership behavior you stopped because you discovered it was no longer valuable or relevant?

I go back to the lessons I learned at the beginning of my career when I tried to run my business with a top-down approach and lost my whole staff in a month. That you have to have a hierarchy — it didn’t work then, and it doesn’t work today.

In the next decade, there will be an influx of small businesses for sale as baby boomers begin to retire. We are going to hit all-time records on the number. But the sad part about this is that many of these businesses aren’t going to sell. And if they do, not at the prices many owners expect. I’m already seeing this. The reason? The hierarchical business model baby boomers used, where the owner became the company’s most important asset. Where things are done “just because” and “because I said so.” This management style doesn’t cut it anymore. Today, it’s about slowing down, having a clear buy-in process, and ensuring stakeholders are involved. It’s about sharing knowledge and delegating tasks and responsibilities. It’s about having systems in place that take the owner out of the day-to-day running of the business, which in the long term, makes the company more valuable to potential buyers.

What is one lasting leadership behavior you started or are cultivating because you believe it is valuable or relevant?

One leadership behavior that I have adopted, and that has become one of our core values at Cultivate, is to be tactfully honest. We define this as being truthful to ourselves and others from a place of mutual respect. In other words, we don’t shy away from uncomfortable conversations.

While it may seem counterintuitive initially, I’ve found these experiences to be one of the best trust-building exercises out there. When done correctly, with explicit and tangible examples, the recipient will soon see that you have their best interests in mind, having taken valuable time to address the issues thoughtfully and honestly, with a path forward and clear goals.

For example, one client we worked with needed help with a host of leadership problems, from retaining staff to scaling. After spending time with him and seeing him in action, the problem was easily identifiable. He never stopped talking. In our meeting, he spoke 98% of the time. He wanted our input and advice, but we couldn’t get a word in edgewise. It was frustrating for all parties involved. But after being

tactfully honest with him and giving specific examples of how his inability to listen and learn was at the root of all his management problems, he actually listened and learned. And while admitting it was a tough conversation, he continued to work with us, growing his business from $5M to $46M in just four years.

What advice would you offer to other leaders who are stuck in past playbooks and patterns and may be having a hard time letting go of what made them successful in the past?

Ask for feedback. The most effective leaders aren’t afraid to undergo self-evaluation. They are self-aware and recognize they don’t have all the answers. And asking for feedback is a great way to start the process.

Each year, the president of a company I once worked for would reach out to his 600 employees for a 360 review about the business and his management style. He would gather the responses (sent back anonymously), look for patterns, and put together a roadmap to address the findings on a personal and company-wide level.

Along with providing a wealth of important insights he otherwise might have missed, the exercise created a corporate culture where we employees felt valued and invested in its success. Our opinions and ideas mattered.

I’ve done this several times in my career, on a smaller scale, when I feel I’m in a rut. I’ve always found the feedback valuable, transforming my perspective and how I was working at the time.

Many of our readers can relate to the challenge of leading people for the first time. What advice would you offer to new and emerging leaders?

One of the most important pieces of advice I give to new and emerging leaders I work with is don’t become the answer hotline. Don’t become the leader who has to sign off on everything, the one who has to have everything run by them. Many businesses struggle with owner dependency and, as a result, aren’t able to successfully scale or sell at top dollar. If you are constantly answering questions, there is no time to strategize and plan your business’s long-term goals.

I tell first-time, and many experienced leaders too, that it’s crucial to put systems in place and train your employees to manage most of the day-to-day variables that come with running the business. Sure, there will be times when the owner has to be brought in. But by removing themselves from many recurring tasks with established procedures, most businesses see an immediate increase in efficiency, productivity, and value.

Based on your experience or research, what are the top five traits effective leaders exemplify now? Please share a story or an example for each.

Relationship Oriented — We work with people every day. As a result, as a leader, you must make decisions from a relationship standpoint. If you don’t put those relationships on equal footing with the business, you’ll have difficulty getting people to buy into initiatives and follow you to the end goal and beyond.

Introspective — The most successful leaders consistently self-evaluate to help them perform more effectively in their roles. Their ability to be reflective allows them to identify their blind spots and, as a result, make better decisions.

Tactful Honesty — Leaders today are afraid of having hard conversations. They struggle to share feedback, which is vital to an employee’s development and the organization’s growth. But done correctly, with preparation, tact, honesty, and guidance, the employee should come out of the meeting with well-defined goals and the understanding you want them to succeed.

Adaptable — The only constant in running a business is change. The market, trends, and customers are continuously in flux. As a result, leaders must be agile, ready to pivot and adjust their game plans. Sometimes that means mid-course corrections. Other times, it’s scrapping it altogether and starting from scratch. A leader must not get too fixated on the path in pursuit of the goal. Focus on the goal.

Accountable — Accountability is about ownership and initiative, developing a culture in which all employees are responsible for their actions, performance, and decision-making. That includes you as a leader. If you don’t hold yourself accountable, how can you expect your team to do the same? Often people think a thriving company culture is all about the fun and perks, and that’s part of it. But it’s also about performance. The best way to build a successful culture is to make sure performance is a reality, which requires your ability to hold both yourself and your team accountable.

American Basketball Coach John Wooden said, “Make each day your masterpiece.” How do you embody that quote? We welcome a story or example.

Entrepreneurship is inherently anarchy. Without a boss telling you what to do and when to do it, days blur by, and there’s always another deadline. In all this chaos, it can sometimes feel like nothing is getting done.

All leaders set goals to manage their businesses, but often the focus is on the long term. And while these are important and necessary to the success of any enterprise, they often feel overwhelming. As a result, I’ve made a point of breaking down these larger macro goals into daily mini-ones. These micro-goals keep me accountable and focused on the more significant, future-facing priorities needed to scale the business while also giving me a sense of accomplishment at the end of the day. They also build upon each other and get you closer to your intended results.

What is the legacy you aspire to leave as a leader?

I believe the legacy of any successful leader should be determined in the aftermath of their departure. When they leave, it’s a smooth and seamless transition for all — from employees to customers to vendors. My goal for my legacy is to have the people and systems in place at Cultivate so that when that day comes for me, it’s a non-event because of how well the organization was built.

How can our readers connect with you to continue the conversation?

I’d love to stay connected and hear from your readers. Please visit our website at, connect with me on LinkedIn, and follow us on Facebook, Instagram, and YouTube.

Thank you for giving us the opportunity to experience a leadership master at work. We wish you continued success and good health!