Move From Tactical Founder to Visionary Leader

Recently, I sat down with a founder who’s been running his boutique services firm for ten years. He’s at that point where the company has grown yet he was still executing the day-to-day, had marginal profits, and was far from operating efficiently. He found himself grappling with a core question:

How do I get out of the weeds so I can focus on growing the business?

What stuck me most was this: here was another founder who had the courage to turn an idea into reality, to build something from the ground up, and to nurture it into a growing business that provides for their family's livelihood.

So many entrepreneurs share this struggle—in fact, approximately 65% of small businesses fail within their first ten years, often due to challenges like poor financial management and lack of strategic planning. Many founders feel stuck and unsure how to break through the bottlenecks holding them back.

As we talked, it became clear that this founder was stressed, questioning his decisions and feeling the weight of it all. He shared his concerns:

• I’m overwhelmed and find myself doing my job and others’ jobs.
• I’m worried about my burn rate and feel like I’m working too hard for the profit I’m making.
• I want to keep my valued staff, but I need to grow the business to afford better salaries and perks. Right now, I’m so busy I can’t focus on growth.

From Overwhelm to Opportunity

Despite having standardized his services, hired a small team, and built a base of loyal customers, he still referred to his company as a startup. What he didn’t realize was that he’d already achieved the hardest part: getting started. The weight he was carrying—feeling like the business depended entirely on him—was simply a natural stage of business growth.

I asked him to reflect on the following:

1. You are doing a lot. Your team is helping execute day-to-day tasks. You hired them to maintain your level of service, and if you’re bringing in new clients while they handle existing ones, that can’t be a bad thing.
2. Does the team know what success looks like? Are your team members clear on their goals and how their efforts contribute to the company’s mission? Or do they just tune into WII FM? What’s In It For Me?
3. Does your staff understand your vision? Does your team see the bigger picture—the future you’re building for everyone involved? Every relationship, including those in business, needs alignment and a shared destination that keeps everyone aligned and excited to keep building.

The answers to these questions were all no. As we dug deeper into tactics and strategy, the founder came to a simple but powerful realization: there were ways to tackle what was holding him back. But he didn’t know how to implement them, have the time, nor did he want to own the responsibility. He did identify a key employee with untapped potential—but this person also lacked the skills and experience to truly harmonize operations with strategy without help.

His epiphany? “I need to hire someone who’s been there, done that!” Almost instantly, he realized it was too early to justify a budget for a full time role. That’s when he started considering a fractional COO. Fractional COO services offer the expertise of a seasoned operator without the commitment of a full-time salary. Whether he decides to hire us or not, I got satisfaction in knowing he’s now clearer about what his company needs.

If you’re in a similar spot, here’s a checklist to consider who can help:

• A leader to organize the founder’s vision; someone to take the vision to define strategy that aligns the team, implement consistent procedures, utilize efficiency tools and embed them into daily operations.
• A strategic advisor; to provide guidance, perspective and mentorship to you and the team.
• Business acumen and experience; proven history of growing a profitable business
• Someone who fits your culture; you need a leader who can seamlessly integrate into your team and inspire others to rally around your vision.
• Someone who is entrepreneurial; who can understand your tendencies, speak your language, and provide honest feedback (manage up).
• Someone who has a history of growing and scaling profitability; experience matters. It breeds “the how” to the “what”.
• Someone that allows you to focus on growth; so you can move beyond immediate deliverables.

The reality is that this founder’s challenges are not unique. Many entrepreneurs start businesses doing what they love, only to realize running a business is quite different. They need strategic leadership to scale. It’s not about ability—it’s just a natural challenge entrepreneurs face as part of growth.

For this founder, the path forward is clear: he must either learn how to become an operational leader while maintaining his responsibility in driving the pipeline and managing the work OR hire someone who can implement the necessary structures for him. Both options can work, but the latter option can reduce the timeline and avoid him having to pay the dumb taxes. And who likes paying dumb taxes!

If you’re feeling stuck, overwhelmed, or unsure of your next step, remember: you’re not alone. You just need the right support in your corner. From someone who’s been there, done that.