Karen Daniels is president and COO of Charter School Business Management, an Entrepreneurs' Organization (EO) company founded by Raj Thakkar of EO New York. The company empowers charter schools with financial knowledge, accounting services and back-office support. As a company leader with a vested interest in executive education, we asked Karen what she learned in a recent professional development opportunity. Here's what she shared.

As the second-in-command for Raj Thakkar, an entrepreneurial CEO with a skyrocketing business, I have my work cut out for me. One challenge that every second-in-command can identify with is Founder's Syndrome. That's the tendency entrepreneurs have to micromanage aspects of the business that are arguably better left to the talent hired to perform those jobs.

At its best, Founder's Syndrome can elicit nostalgic feelings from the company's early days. At its worst, it undermines the authority of valued employees and halts the forward progress of critical projects.

The key to solving Raj's Founder's Syndrome was a professional development program called Master Key Executive (MKE). It basically teaches a company's second-in-command how to become an invaluable asset to an entrepreneurial CEO. Through the program, I gained a nuanced understanding of how entrepreneurs think and learned how to keep Raj in his lane of highest and best use for growing our company.

Here are five steps I took that helped cure my CEO's Founder's Syndrome:

  1. Ask, "What Keeps You Up at Night?" Entrepreneurial CEOs are a unique breed. They founded the company--it's their baby--and they don't think anyone else cares quite as much as they do about its success or failure. Here's the thing: As the second-in-command, you're the someone else who cares that much. The MKE program recommends weekly meetings to discover what's keeping your CEO up at night and what you can do to end that incessant worrying. By sharing his concerns with me and tracking the progress as we work toward solving those issues, I help him feel heard.
  2. Upward communication. Entrepreneurs require communication about the items they worry over. If they don't receive an update, they assume the very worst. From my perspective, this was a trust issue. If you know and trust me, you know things are handled. But from Raj's perspective, he needed updates around certain worries. A shared Google doc listing the projects that caused him concern was the answer. I update it regularly as items move forward toward resolution.
  3. Transparency. The communications pathways we opened through MKE enhanced my understanding of the entrepreneurial mindset. Though we always had a very strong working relationship, we've now taken it to the next level. By discussing business challenges thoroughly, I've gained a window into his strategic thinking that helps me see issues in a whole new light. It's enabled me to know where to focus my energy and where to delegate. Knowing what's important to him allows me to play to my strengths and leverage the strengths of others.
  4. Today Matters vs. Tomorrow Matters. As an entrepreneurial CEO, Raj is our visionary. His highest and best use is strategizing how to grow the business and forming the relationships that will get us there. Those are "tomorrow matters"-- the forward-looking vision of the company. But when he gets bogged down in "today matters"--the daily running of the company, the tomorrow matters suffer. It took a dramatic event to make this happen, but he is now squarely focused on tomorrow matters and leaves the today matters to me.
  5. After Project Review. After big projects or incidents, we conduct an After Project Review assessment. This helps us capture and discuss what lessons we learned, how to see them from a positive standpoint, and pinpoint how they will help us grow stronger in the future.

Our moment of truth

About a year after I finished the MKE program and implemented the steps above, we signed our largest client ever--a company 10X the size of our other clients. What a moment!

But then it happened: Raj learned that his mother had late-stage cancer. He disengaged from the company for four months to be with her. His departure was sudden, and those four months of running the company without him were intense.

I don't think I could've gotten through it without the support of our leadership team. It was an abundance of sleepless nights, stressful days, ongoing challenges--and some wins. Knowing that Raj was at peace leaving everything with me gave me the confidence to get it done and figure it out, and that's what we did.

It was an incredibly strengthening journey--a trial like that either makes or breaks you. Raj was extremely grateful for everyone's hard work. Our whole team grew stronger.

Assessing the outcome

When Raj returned, he had a momentary feeling that he was no longer needed. Nothing is further from the truth. However, our After Project Review revealed that roles evolved during his absence. As an outcome, we've examined everyone's responsibilities to make sure we're applying our talents to their highest and best use.

Now that he knows the company can not only survive but also continue to grow in his absence, Raj no longer micromanages anything. He remains completely in the lane of his highest and best use: Focusing on tomorrow matters to grow our company. Implementing the lessons and methods I learned through the MKE program proved to be extremely valuable. This outcome underscores our strong belief in the importance of investing in education--at every stage of life and business.

It was a trial by fire and a lot of work, but that's how MKE helped us discover the cure for Founder's Syndrome!