A Founder's Dilemma: What is my role in this growing company?

A Founder's Dilemma: What is my role in this growing company?


As your business grows, the roles and relationships you’ve established up to that point will inevitably change. If you fight against this, you’ll stand in the way of its potential success. But what happens when you feel your role begin to change?

Many founders talk about the struggle of building systems and processes when scaling, but that's not what is really keeping them up at night.

Instead, it's...

"Where do I belong in my growing business?"

As soon as your company finds success, this question must be addressed by its founder, especially if there are multiple founders.

Traditionally, once this realization has come, the founder begins discovery through the lens of what they want. Asking a series of questions such as:

  • What do I want to do?
  • What title do I want to have?
  • How can I maintain power?
  • What gaps are there in the company?
  • What am I not comfortable hiring for?

Those are the wrong questions to begin asking.

Here are 5 questions you should ask for a clear answer:

1. Moving forward, what will the business need objectively by way of management to keep winning?

To know these needs, answer this question: What does the company need to be great at to win? Your primary responsibility is always to the company. Running your management through your lens of comfort and ego first is the wrong process. The business is bigger than its founder. With this first question, you take a step back and objectively look at what the business needs, not what your ego needs. This is difficult to do, and I recommend having a coach or advisor to challenge your biases.

2. Which needs of the business could I make the promise to meet and perform exceptionally?

This is more than what you’re good at, it’s where your gifts lie. To confidently answer this, you must believe that there is no one in the world you could hire who could do this job better than you. A good way to determine this is the areas you focused on to get the business where it is. If you look back on your experience scaling it, which areas provided the steepest learning curves, and which did you do comfortably and confidently? Learning curves steepen in rapid growth, so odds are the company has outgrown you there. Does it mean you can’t learn it? No. It means there is a greater risk of you leaning into an area where your gifts are not magnified.

3. What do I really enjoy and believe in doing?

Gifts inform passion, so you should enjoy this. But I acknowledge there are more complexities to a business, like who you’re working with, the organizational skills required to thrive, and who steps into your shoes to own your current role and responsibilities. The answer may be to stay the CEO, because it is where you thrive and you love it. But every CEO has a strength and a weakness, which is why we ask the first two questions.

4. What am I willing to spend years of my life on?

When entrepreneurs with a bucket full of ideas ask me which idea is the right one, I tell them, “The one you’re willing to work the hardest on.” This rings true for what your next step is as well. If you want to continue being the CEO who has the most "bosses" in the company (customers, partners, boards, and employees 😉) then lean in and crush it. If not, and you are willing to work tirelessly in product development, finance or sales, then do that.

5. Is this a critical contribution?

If your superpower is culture, but you only have 5 employees, perhaps that isn’t a full time, critical contribution. If this is the case, you may need to continue to leverage other strengths you have until the company scales into other areas. Ensure the role you think you are best suited for is one that has a substantial contribution to the collective success of the business.

A few bonus notes:

  • If you’re bad at managing people, don't be discouraged, most people are, but scaling is about building through people, so you can’t hide from that. You're going to have to learn it if you want to grow.
  • I’ll re-emphasize - this is not a playbook to remove yourself as CEO. If you want to be CEO, then go for it, but perhaps use these questions to determine who you need around you to allow you to be a CEO that leans toward your gifts.
  • I highly recommend outside counsel when going through this exercise. We aren’t great at identifying our individual strengths, and other people who know us may see things in us in a more positive light than we see in ourselves. They will also combat impostor syndrome, which every successful person deals with.

These questions were inspired by Peter Drucker, who is my most admired teacher in business management and leadership. If you want help going through this exercise, you know where to find me (hint: links below)

With purpose,

KC Holiday


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