New Middle Market CEO Checklist: 11 Tips to Get Started as a New CEO

By Ted Skinner

What does it take to become a successful new middle market C.E.O.?

The middle market is the largest segment of the U.S. economy, representing $3 trillion in annual sales. While some companies are large enough to operate independently, most middle markets are smaller businesses that rely on other giant corporations for their supply chain or distribution networks.

As a new middle market C.E.O., you'll face unique challenges. You'll need to develop strong leadership skills, build relationships across multiple departments, and manage change effectively to succeed. Here are 13 tips to get started as a new middle market C.E.O.

Make Plans

You'll want to create a detailed plan for your business. This way, you know what you're doing and what steps you need to take to achieve success. You will want to write everything down in a word document and publish it to the entire company. A clear idea of what you're trying to accomplish can avoid wasting time and effort on projects that won't lead anywhere—balance long-term strategic planning with short-term execution planning. Additional information can be found in this popular blog post: Rhythm and Planning Cadence to Help New C.E.O.s Succeed.

Hire people more intelligent than you

You don't have to know everything about running a company. But if you run a business, you should at least understand the industry you're entering to know whether or not someone else could do a better job than you. And if they can, you should let them. There's no point in trying to learn everything yourself if you won't be able to keep up.

Look to get help

You don't need to do everything yourself. The organization has lots of internal resources from people who have been with the company for some time; they can help give you insight into how things have been done. Consider using an executive coach. Look into hiring outside facilitators to help you with your strategic planning to ensure that your organization has a solid foundation to build on. Keep focused on your expertise and bring in others to help as needed.

Advice for new CEO

Don't try to do everything yourself.

It's tempting to think you can jump right into starting a company and doing everything yourself. But unless you're willing to put in long hours and devote yourself full-time to building something, you might end up burning out and quitting before you ever really get off the ground. Instead, focus on hiring smart people who can help you build an excellent product or service.

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Keep learning

You'll always learn something new if you're running a business. Whether it's about marketing, accounting, customer service, product design, or whatever else, there's always something new to learn. And the best thing about being a business owner is that you can try different methods and techniques and see which ones work best for you.

Be honest with yourself.

If you tell yourself that you're going to be successful, you're much more likely to succeed. So stop telling yourself lies about how hard you're working, how many customers you have, how big your market is, etc. Those aren't real numbers; they're just excuses you use to convince yourself that you're already succeeding. Make sure you use the correct KPIs, quarterly rocks, and O.K.R.s (O.K.R. vs. KPI) to track your REAL progress towards your goals.


Download 5 Operating Tips for a New CEO


Have patience

Running a business the way you want takes time and may never be fully achieved. Patience is a virtue, but it doesn't mean you shouldn't expect anything to happen soon. Just remember that success comes slowly and steadily over time. Keep to your rhythm of work to make continual improvements in your business and culture, and you'll see the results over time. This isn't something that you can rush; keep putting one foot in front of the other.

Keep learning

There's always more to learn. Whether you're reading books, talking to experts, or watching YouTube videos, there's always more to learn about how to run a business. Take advantage of opportunities to learn from others. Sign up for industry-important blog posts, read the trade papers, look online and keep learning daily.  


Networking is essential. Not only does it allow you to meet new people, but it helps you gain valuable information. You'll learn a lot about the industry and what works best for them by talking to different people. What are the organizations in your industry or your town that can help you meet like-minded people? Ask around and start getting out in the community.

Stay organized

Being organized is the easiest way to stay productive. Make sure you keep track of all the details related to your business. Write down ideas, notes, and reminders. Also, use software programs to organize your files and documents. If you have revenue of more than 5 million (or smaller but growing fast), you should use strategy execution software, such as Rhythm Systems, as you outgrow your strategy spreadsheet.

Have fun!

Running a business takes a lot of hard work and dedication. However, it doesn't mean you can't enjoy yourself while doing it. After all, you're still getting paid to spend your days off enjoying yourself. So, set aside some free time each week to relax and unwind. Go out with friends, watch movies, play video games, read books, listen to music - whatever makes you happy. Just remember to balance it with some productive activities, as it is all about balance.

Rhythm Systems provides a platform for companies to engage their employees in meaningful ways. We help leaders build better teams through our unique approach to employee engagement. Rhythm Systems offers tools designed to help executives manage their time better, focusing on what matters most. Set up a time to see how we can help you.

Ted Skinner

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Ted Skinner


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