Top 5 Leadership Growing Pains Seen by This Business Coach

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PART 1 of a 5-Part Series from a Business Coach Perspective

Is there such a thing as a natural-born leader? Can leadership be taught? The answer is yes to both of those questions, but even a natural-born leader has much to learn. Your business coach is an excellent place to turn.

As a life and business coach, I work primarily (but not exclusively) with entrepreneurs positioned to grow their companies from six to seven-figure businesses, but it’s just not happening. I find my work to be gratifying and sometimes quite exciting! When a small business owner suffers and struggles, they aren’t living the life they deserve and crave. When the entrepreneur enters a successful business coaching relationship, that life reveals itself; it’s fascinating to witness how things change as their world evolves.

What many candidates for business coaching aren't prepared for is the personal and leadership growth that comes with business growth. Many of the beliefs and practices that worked well when it was just you and perhaps a couple of part-time employees won’t contribute to the future growth of your company.

There are new challenges at every bend in the leadership journey, which most often lead to enriching growth experiences. Below are some initial growing pains I commonly see in entrepreneurs seeking to build their companies into the beautiful vision that was once a dream.

Over the next few weeks, I will explore each of these issues at a deeper level. I’ll offer you my best business coach advice to equip and inspire you to grow your business to the next level. For now, here’s an overview.

1. The founder struggles to grow from employee to leader.

It’s all on you. You’ve rolled up your sleeves and done everything from answering the phones to delivering your product and services. But how can you expand your marketing, attend conferences, develop new products or services, and implement growth strategies if you’re busy doing things that are, frankly, not the job of a CEO?

It’s time to build a team and one that you can learn to trust. As you may know, trust can be a big issue for entrepreneurs, and understandably so. You’ve nurtured your “baby” all on your own, and now you’re dissecting it to share the responsibilities with others who may do things differently. They may even screw it up totally! This stage is where you’ll benefit from knowing that, at the employee level, there are very few mistakes from which your company won’t recover. Delegate and train accordingly. Only then will you have the freedom to step into the shoes of a true leader.

In the upcoming series, I’ll touch on the growing pains involved in becoming a leader to new employees and employees who “knew you when.”

2. New leaders need help to determine when and where to invest.

Money is still tight at this stage, so a misstep can be devastating. Do you hire employees, get a larger space, invest in software and equipment, or spend real money on marketing? There is a delicate balance among the choices since you must have the revenue stream to support ongoing expenditures (like payroll or rent), and there is no guarantee of that happening. This decision process involves careful planning, projections, and a leap of faith.

Entrepreneurs at this stage often believe they don’t have the money to scale. If you believe that, well then, it’s true! It’s not difficult to “find” the money to hire a contractor or two, or even an employee when the time is right. Without this support, you’ll most likely remain precisely where you are. A support team is typically the first place you’ll spend your dollars. We’ll look at that closely when I expand on this thought.

3. New leaders usually botch their company culture.

I always say,

“If you don’t build an intentional culture, it will build itself–and you will not like the results!”

company culture

One sign that you have allowed your culture to fall through the cracks is when you find yourself surrounded by customers and employees who aren’t on the same page as you are. This unhealthy environment creates stress and wreaks havoc on your business and well-being. If your stress is through the roof, it’s doubtful that an intentional culture is intact.

Honestly, most clients who begin working with me don’t even understand what culture is all about. This is one of the most exciting pieces to helping entrepreneurs achieve their long-term goals. We get to uncover your most treasured values and create the foundation upon which each building block of your business will sit. My clients learn things about themselves they’ve never realized, and the company grows to reflect its founder in the most meaningful ways.

I’ve got some great culture-building strategies and insights for you – coming soon!

4. Employees don’t always adjust well to change – tough decisions lie ahead!

This one ties into the whole culture topic for companies that already have employees onboard when they begin working with their business coach. One of the growing pains we often encounter in the coaching process is the realization that long-time employees are resistant to change and may no longer be a good fit for the organization. Ouch! You know their families—they may even be people you consider friends. In some cases, they are family!

Employees who “knew you when” often don’t adapt well when you become less hands-on. They may be more accustomed to having a say or being a part of your decision-making process. It’s not that your employees become less critical; it’s that your inner entrepreneur will surface as you grow your business (especially with a good coach at your side), and you’ll make decisions that your team doesn’t agree with or understand. Roles and responsibilities change, and we all know how difficult change is for some people. Sometimes, these facts drive a wedge that is difficult to maneuver around between the founder and the employee.

And yes, sometimes all of this means the employee leaves or is let go from the company, but here’s the good news: everyone is happier in the end. I see these past employees thrive as they enter a new stage of their professional growth. And the entrepreneurs, no longer hindered by the challenges of having a nay-sayer on board, also thrive.

5. You don’t know what you don’t know–but your business coach can teach you.

This is a big one. You’ve never done this before; how can you possibly know what to do as a leader? I believe true leaders have an innate ability to lead, but still, there’s so much to learn! And budding leaders often need “permission” to make the choices because sometimes these choices contradict everything you’ve been doing up to this point. You’ve been working non-stop, and now you’re thinking about taking a week off to go to a leadership conference in another state? Unheard of! But yes, leaders need education, inspiration, encouragement, and camaraderie.

You’ve never scaled a company to this level before, so there are countless things that you don’t know and wouldn’t ever give a second thought to unless someone brought them into your purview. The in-depth, ongoing process of building a full-blown, thriving culture might be a good example. In coaching, you’ll learn about things you’ve never even known to consider, and you’ll have the support to step into a whole new world. We’ll talk about some of those things toward the end of this series.

I hope you’ll stay with me over the next few weeks as we explore these topics at a deeper level. Questions? Is there something you’d like me to address in this series? Please feel free to contact me here or send them to me at

I look forward to supporting you during this very exciting time of growth!

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