Five Things I Wish Someone Told Me Before I Became A CEO

They didn’t tell me that business is all about math.

I thought it was about how well I knew my functional area of expertise, which was marketing and analytics at the time. While working for corporations and at grad school, I was taught to be good at my job — functional expertise; then, as I got promoted, I became a manager without any training. When I started my business, I took it for granted that my business partner and I would be getting paid. We calculated we needed to make about $75,000 in the first year — we made $125,000. What was the tax math on that? We didn’t calculate that! What were the company’s expenses and was it higher than the amount coming in? I had to do the math!

a part of our series called ‘Five Things I Wish Someone Told Me Before I Became A CEO’ we had the pleasure of interviewing Dr. Sandi Webster.

Dr. Sandi Webster is a serial entrepreneur, author, speaker, and mentor who helps business owners select handpicked experts for their personal and business advisory boards. She focuses on sharing the knowledge accumulated from her experiences with entrepreneurs and corporate executives through her online courses and speaking with the outcome that they will operationalize their companies to get stuff off their plates.

Thank you so much for joining us in this interview series! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

Istarted babysitting when I was 10 years old and realized that I had the gift of being able to make money. I went into the corporate world while I was in college and utilized the education benefits corporations gave to complete both a Bachelor’s and MBA. While doing so, I rotated through different corporate departments so I could get the full knowledge of how a corporation ran. It benefited me after 9/11 when my corporate employer laid off my business partner and me. We immediately opened our marketing and analytic consulting company providing consultants to Fortune 500 corporations in financial services, telecom and insurance. We formed an advisory board, and they were instrumental in guiding us to scale and sell our business to a private equity company. Since then, I’ve been passionate about business owners having advisory boards. Helping them form and manage their boards is now my current business.

Can you share the most interesting story that happened to you since you began leading your company?

After about 20 years of being a business owner, I had to do all the work when I started my company. I prided myself on being a marketer but quickly realized that the marketing world had changed since I last did marketing. I was pushing paper at a desk, making strategic decisions for years, and no longer understood how to do simple social media posts! Facebook was my “go-to” social media while all the younger people moved to Instagram. I learned I didn’t need to be proficient and hired an amazing virtual assistant with functional expertise. As business owners, we must understand our role and get the help we need.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

In 2021, I was a guest speaker at an online summit. I introduced myself, told them about my business, did my presentation. Then, people started asking me weird questions about my company. It was then that I realized I had introduced myself as CEO of my old company, not my current one. I knew that elevator pitch like the back of my hand and launched into it. I had to correct myself in front of all those people. I learned to live in the “now.” I can’t get so comfortable that I forget my purpose right now.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

In the early ‘80’s, I was a young black girl working in retail for one of the top department stores. Retail was a low-paying industry and black people got paid even lower; this was no different. I took the administrative assistant job, only to realize that I was doing a bunch of jobs that didn’t include admin. I worked in customer service, learned collections, credit union, and was introduced to information management. My white male boss recognized my potential, paid me for the job I was doing and not my title. He told me that as a black girl in any corporate environment, I had to be better than everyone and have a college degree even if white people didn’t. It was the best advice he gave me because I was going to college part-time and never stopped. He moved to another company in financial services and called me about a secretarial job that was becoming available. I took the job to get my foot in the door, which was the best thing I ever did. I started again at the bottom of the ladder, but besides doubling my salary, that company paid 100% of my college tuition and I got my BA and MBA. I was one of the first secretaries to move into management and became a Director there. Between those two jobs, I learned never to give up and that I could do anything I put my mind to. I also learned that as a black woman, the standards are different and I just had to do what I could to shift that paradigm. All because someone was honest with me about what to expect from the world. I’m still grateful for that advice.

Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader?

I don’t even have to think about it. It was in my previous company. The financial crisis happened in 2008 but didn’t hit us until our contracts ran out in 2009. We were a million-dollar company and our biggest client was in financial services. The phone stopped ringing. We had no contracts, and I was the COO with HR reporting to me. My business partner and I agreed we had to let people go. We learned this technique on how to decide which team members were the most expendable, meaning someone else could add their job to their role. Unfortunately, the expendable person was an older lady who really needed the job and everyone liked her. She begged me not to let her go, but I had to for the health of the company. I fired people without qualms in the past, but letting someone go whom I liked and doing a good job was difficult. I went into the ladies’ room and cried — and I don’t cry! She never spoke to me again. It was a tough decision, but as a leader, I made a tough decision based on what was best for the company. Thankfully, we ran very lean and turned around the company even in a down economy.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

As the key decisionmaker, the buck does stop with the owners or the leader. Good leaders manage the strategic planning side of the business, while others are in charge of the tactical efforts to execute the strategy. We also have to keep ourselves on the pulse of all the different areas of the company. Leaders have to be the main cheerleader for the company even in bad times because people are following our lead. If the head of HR makes a bad hire, the company doesn’t fall apart. If a leader makes a wrong decision or a bad hire for his team, it impacts the entire company. Leaders carry the weight of the company on their shoulders.

What are the “myths” that you would like to dispel about being a CEO or executive? Can you explain what you mean?

One myth I must let go of is that the CEO should be able to do everything. I can’t know everything. I hire functional experts who can do the job better than I. Women business owners, in particular, need to ask for more help than we do. Another myth is that CEOs get paid a lot — maybe in a large corporation, but not in a small company. We tend to pay employees before we pay ourselves. We use personal dollars to keep the company going. Employees will look for another job!

What is the most striking difference between your actual job and how you thought the job would be?

I thought I would build the course, and they would come. I decided to create this course in 2020; however, it was completed in 2021, when everyone was doing events online and the market quickly saturated. I thought my job would be speaking at events and creating courses; however, I spend a lot of time creating marketing material, including social media. I’m also back to being the tech person, the printer fixer, checking emails, etc. It is more tactical than strategic.

Do you think everyone is cut out to be an executive? In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive? Can you explain what you mean?

Not everyone is cut out to be an executive or leader, and not all leaders have the same traits. I think an effective executive is a successful executive. I’m taking this section straight from Harvard Business Review’s 2004 article by Peter Drucker.

An effective executive does not need to be a leader in the typical sense of the word. Peter Drucker, the author of more than two dozen HBR articles, says some of the best business and nonprofit CEOs he has worked with over his 65-year consulting career were not stereotypical leaders. They ranged from extroverted to nearly reclusive, easygoing to controlling, and generous to parsimonious. What made them all effective is that they followed the same eight practices:

1. 1. 1. They asked, “What needs to be done?”
      2. They also asked, “What is right for the enterprise?”
      3. They developed action plans.
      4. They took responsibility for decisions.
      5. They took responsibility for communicating.
      6. They were focused on opportunities rather than problems.
      7. They ran productive meetings.
      8. And they thought and said “we” rather than “I.”

If you love having your hands in the day-to-day, then you shouldn’t become an executive. You can have a business, but hire someone to be the visionary and strategic person.

What advice would you give to other business leaders to help create a fantastic work culture? Can you share a story or an example?

To have a fantastic work culture, you must think about your employees first. You must understand what makes them happy to come to work every day and give it to them. Some companies note that their people like to take a break to have fun, so they give it to them. Whether you see the employee in person or have virtual ones is irrelevant.

My company had about 200 virtual employees around the country. Projects were really important to them and the company. I gave them assignments that challenged them. Some wanted short-term assignments while others wanted long-term ones — that’s what we gave them. We had quarterly meetings to keep everyone on the same page. We also had Christmas parties in different regions of the country so they could have in-person meetings. Domestic group activities, like the breast cancer walk, brought them together. Most importantly, most employees were moms with children and wanted benefits that were meaningful to their families, like good healthcare and paid time off. This flexible and caring culture gave us a low turnover rate.

How have you used your success to make the world a better place?

My success has given me the freedom and ability to share my knowledge with other business owners. In addition to coaching business owners at different revenue levels, I mentor high school and college entrepreneurial programs, like Virtual Enterprises, that holds business contests. During the pandemic, free of charge, I helped churches, business owners, and students set up virtual spaces for productivity. I also taught them Zoom classes. I served on the advisory boards of non-profits that are geared toward entrepreneurs.

Read full interview here.