How Waiting Tables Prepared Me to Be a CEO

Whether you're serving lunch or pivoting your business, you're paid to deliver results in a chaotic environment where you really don't control much.

learn more about Jason Wesbecher

By Jason Wesbecher

Opinions expressed by Entrepreneur contributors are their own.

For three summers in college I waited tables at a Washington, DC "power lunch" establishment. As anyone who has ever worked in a restaurant will tell you, it's a cash-rich but grueling job. You spend eight consecutive hours on your feet while balancing the demands of finicky customers with an often boorish and profane kitchen staff. Pulling that off each day while maintaining a stainless shirt and crisp smile is immensely challenging.

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A friend recently asked what prepared me to be a first-time CEO of a start-up. I hesitated. Nothing was the first word that came to mind. Most of my previous professional experiences could be described as linear. Which is to say, I could focus without distraction on the objectives ahead of me. Being a CEO is very non-linear. It's about embracing the unpredictable each day and soldiering through the chaos. Which, upon reflection, reminded me precisely of my days waiting tables. As it turns out, there are a number of similarities between the two jobs.

Staying Out of the Weeds

Waiters and kitchen staff have their own vocabulary. One of my favorite phrases is in the weeds which means that one is overwhelmed with activity and cannot keep up. As a waiter, I had to devise lightning quick organizational routines to help pull myself out of the weeds when, for instance, the hostess would simultaneously seat three tables in my section. In practice, this meant bringing water to all three tables at once, rather than sequentially, while keeping an eye out for coffee refills at my other tables.

This is exactly what any given day as a start-up CEO is like. It's difficult to adhere to a set schedule because a customer issue or software gremlin is perpetually lurking around the next corner. You have to deal with multiple crises in parallel while also accomplishing your day job. All while keeping your cool.

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People first

Being a start-up CEO is first and foremost about people. Evaluating them, motivating them, reading them. The four major constituencies that you must serve to be successful in this role are your employees, your customers, your investors and your family. If you can't engender trust and excitement across each one of these groups, it's only a matter of time before you are an ex-CEO. Waiting tables isn't any different.

Waiters are often incorrectly labeled as food service workers. Waiters aren't in the food business; they're in the people business. They have to read the body language of each table to figure out who wants to engage in a dialogue and who wants to be left to their conversation. They have to be prepared to instantly reinvent themselves every few feet as they move to the next table. Seating after seating, night after night, waiters must bring a mental sharpness to how they interact with their patrons and kitchen staff to have a shot at making money.

I believe online interaction is just as important in the business world, which is why my company, Docket, helps users communicate and evaluate what resonates in email.


Being a waiter taught me how to delegate. To be the best server to my guests, it often meant not doing every single task personally. I relied heavily on bussers, back-waiters and even managers to deliver the best service experience to diners. They would help deliver water, bread, drinks, you name it. In turn, I would tip them generously at the end of my shift. Everybody, including the customer, wins in this model.

Good start-up CEOs also carry with them a strong ability to farm out important projects to team members and mentor them through the completion of the assignment. It's key for CEOs is to recognize that they are no longer measured against personal contributions or accomplishments. Instead, they are measured against the growth of their company. Achieving this takes every single employee rowing at the same cadence, in the same direction.

In many respects, waiting tables was like getting a degree in entrepreneurship. I ran my business (albeit small) across my five or six tables. I worked closely with all parts of the organization to ensure a quality product was delivered at exactly the right time, while I obsessed over the whims, desires and attitudes of my customers.

If I couldn't get these pieces to work in harmony, I wouldn't make money. These were the very simple "street" economics of the job. Perhaps most importantly, I learned that when it all falls apart and you end up getting crushed by circumstances beyond your control, there's always another shift tomorrow.

Related: Magic and the CEO -- Applying Lessons Learned From the Stage

Jason Wesbecher

Executive VP, Sales/Marketing, Corel

Jason Wesbecher is executive VP of sales and marketing at Corel, the provider of ClearSlide, CorelDRAW, MindManager and WinZip. He leads global field operations across sales, retail, OEM, marketing and enablement to support clients and partners using Corel software to transform how teams do work.

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