How Do You Know When It’s Time for a Leadership Coach?

Author: Cam Yenokida, Achieve Excellence

Most leaders don’t wake up one day and say, “I need a coach.” It starts smaller. Subtler. A restless feeling. A dip in motivation. A sense of complacency. The creeping thought that maybe you’re performing well… but not leading well.

You tell yourself things are fine — your team’s producing, the business is steady — but deep down, something feels off. You’re busy all the time, yet not moving forward. You’ve lost the spark that used to drive you. Every day feels like being on a treadmill, and at the end of the week, you wonder if this is really what success is supposed to feel like.

These subtle signs can build into the quiet statements you say to yourself.

“I thought I’d have it figured out by now.”
“Maybe I’m not cut out for this level of responsibility.”
“I feel like I’m carrying this whole thing alone.”
“I’m working hard but not seeing real progress.”
“I’m tired of reacting — I want to lead with intention again.” 

“I’m not sure my work reflects what I really believe in anymore.”

When seeking a leadership coach, it’s important to recognize the signs that may signal it’s time to reach out. While everyone is different, there are certainly some common themes that tend to surface.

Occasionally, there’s a feeling of, “I’m doing good, but I just have this sense that things could be better.” This often relates to executives and leaders who are finding a good level of success, yet still feel a gap between where they are today and where they want to be. Usually, these folks are a bit slower to act because they don’t perceive there to be a problem.

More commonly, this sense of “not enough” creeps into the minds of executives and many small business owners, triggering them to explore ways to improve. Because they often make decisions with little input from trusted sources, they can start to feel isolated—wondering if there’s a better way to lead their people, develop priorities, or execute their strategies.

I’d say the most common signals people should pay attention to are when they feel stuck or stagnant—stuck in a similar thought loop or unfulfilled with their progress at work or in their business.

This describes the majority of people who end up seeking support from an executive or leadership coach. They might tell a close friend that they’re tired, frustrated, or overwhelmed at work. They may be experiencing challenges in their relationship with a new boss or in getting their direct reports and teams to work effectively together.

Here’s the thing: most leaders in this position have resources. They have friends, family, and maybe even strong mentors in their lives. But at times, it can seem like a burden to rely too heavily on their network, so instead, they hold it in. They start to hide their struggles behind statements like, “everything’s fine” or “all good,” when in reality, staying in this state for too long starts to show up in unwelcome ways. It might look like avoiding hard conversations, reacting through the day instead of leading with intention, feeling drained at the end of the week, disconnecting from loved ones, or spending too much time in unhealthy habits—social media, alcohol, or other distractions.

If that’s you, here’s the truth you need to hear: you’re not broken—you’re just human.

Asking for help is not a sign of weakness; it’s actually a signal that you’re ready to match your actions with your ambition. You’re aiming to deliver even more impact in your role, business, or community. Because the reality is that there can be a real weight to leadership or owning your own business. A sense of isolation, with little room for collaboration or clarity, can lead to frustration, anxiety, and constant overwhelm.

I’ve seen incredible leaders reach tipping points throughout their journeys. They often tell me that having a trusted advisor who can dedicate space to reflect and develop strategies is critical to their growth as leaders and to the performance of their businesses.

I recall working with a business owner struggling with a potential partnership. The opportunity could have been lucrative, but something deep down didn’t feel right. I approached the conversation with compassionate curiosity, bringing their attention back to their company’s mission, vision, and values. It was an “aha” moment for my client. They ultimately decided not to pursue the partnership because it didn’t align with their values of authenticity, integrity, and service. Because of this decision, they were able to bring focus and energy to partners who believed in their mission—resulting in remarkable personal growth and profitability for that project.

I believe coaching is a process that helps leaders clarify their own beliefs, behaviors, and actions. When clients can discover that clarity and develop their own path forward, sustainable growth becomes possible. My role is to facilitate that process and serve as an active resource and positive influence on their journey. I always tell my clients that I’m trying to “work myself out of a job” by offering practical tools and strategies they can learn and apply to achieve even greater levels of success well beyond our engagement.

One of my favorite clients worked with me for just five months. He came to me feeling stuck, telling me right away, “Things are going good—I just have this feeling they could be going even better.” As a business owner of a production company, he naturally wore many hats and was constantly stretched thin. After working together, he began to shift the way he showed up in each moment—bringing focus, strategy, and enthusiasm to the most pressing priorities that would move his business forward. We uncovered blind spots together, and he developed new ways to approach relationships, clients, projects, and priorities. The results were incredible: he gained more clarity and confidence around where and how to spend his time. In that short period, he even experienced an uptick in business—always a big bonus. When we hit five months, we both agreed it was exactly what he needed to spark his continued growth. While I was sad our engagement was ending, it was the biggest compliment I could receive that he felt confident enough to carry on without me. I trust he is thriving and will continue to deliver positive, long-term results.

The truth is, many people can benefit from coaching, but so many leaders still struggle to ask for help or believe they should be able to handle everything on their own. That’s why I work hard to build trust and deliver value on their terms. You can’t push coaching on anyone—it’s about meeting people where they are and becoming a resource for those who are ready to grow.

If you’re feeling stuck or simply curious about whether coaching could enhance your leadership abilities, reach out. There are a lot of qualified coaches available, and part of the discovery process is learning about their philosophy and approach. Leadership isn’t meant to be a solo act. Whether you’re running a small business or leading a team, you deserve space to reflect and explore ways to create action out of clarity and grow. If you’re feeling that pull—that sense that things could be better—trust it. That’s often where real transformation begins.