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Lessons Learned from Our Mistakes

In the book, Outliers, best-selling author Malcolm Gladwell theorizes that it takes 10,000 hours of “practice” to achieve mastery in a field. Whether it is learning to play an instrument, hit a 95-mile-per-hour fastball, or run a catering company, 10,000 hours of practice, (also known as “work”) is the magic number.

Gladwell also concludes that natural talent played only a minor role in the results of his study. Practice trumped everything else. At some point along the way, elite performers fell in love with their practice and wanted to do little else.

Armed with this information, the natural tendency is to start pounding numbers into whatever device you are strapped to and figure how much time 10,000 hours equates to. I have done the math for you, and the answer may be a surprise. Ten thousand hours is about five years of full-time work. 

Full disclosure, I have not read the book—yet. I have been in the catering and restaurant industry for 30 years, however. There is no way I had “achieved mastery” after five years.  

Perhaps Gladwell knows something I do not. Perhaps I should have read his book 30 years ago (or 60,000 hours of practice) when I was starting out (although that would have been a bit tricky as Outliers was published in 2008).  

Trial & error

Hindsight can be a unique learning tool. With “practice” comes experience. With experience comes expertise. I do agree with Gladwell that the more you practice, the better you get. Occasional luck always helps. Pro golfer Gary Player coined the great line, “The harder you work, the luckier you get.”

The knowledge, information, and teachable skills I share today in writing this column, speaking at conferences, coaching clients, and providing tips for efficiency and profitability on our website are the results of decades of trial and error. Here are a few examples of situations of lessons learned from our mistakes. As always, let my pain be your gain, and apparently, Malcolm Gladwell has proved that practice does indeed, make perfect!

Situation: Hiring staff.

What we did then: Interviewed potential employees once (sometimes very briefly) and if all appeared good, we signed them up! 

What we do now: Bad hires cost time and money. No one is hired until we meet with the candidate twice (which is a good weeding-out process because half the people do not show up for a second interview). If I am looking to fill a management position, I usually meet with candidates three times.

I like hiring “thinkers.” For those people who are randomly applying, “because I need the money,” we created a list of open-ended questions, such as: 

• What was a mistake (the bigger, the better), or bad decision you made at your last job? How did you handle it? What did you learn from it?  

• Tell me about someone you had a serious conflict with in your past work history. Were you able to resolve it? If so, how? 

Lesson learned: A job interview is similar to a first date. Everyone is on their best behavior, presenting themselves in the most positive light. When we hire an hourly employee, we say, “We will sit down again after two weeks and decide if this feels like a good fit on both ends.” Today we always check past work references. It’s true that the best indicator of someone’s future performance can be gauged from their past work history.


Situation: An unhappy customer reported, “Your delivery person was 30 minutes late and didn’t even bother to call me!”

What we did then: Gave the delivery driver an earful for “being 30 minutes late and not calling the customer” even when the driver said, “I was like 10 minutes late, and I did call before I was scheduled to be there.”

What we do now: Calmly ask delivery drivers for their side of the story.

Lesson learned: When two people have different versions of the same event, the truth often lies somewhere in the middle. Don’t respond until you collect all pertinent information and make a determination as to what happened. (This fact-finding mission revealed that the driver was 15 minutes late and had left a voice mail 10 minutes before the scheduled delivery time, as they are trained to do.) 


Situation: Missing equipment. We were continuously purchasing new airpots, Cambros, warming bags, chafing dishes, and carts to replace the ones that had vanished from our clients’ offices.

What we thought then: “It’s the cost of doing business.”

What we know now: Equipment is expensive to replace. Our clients need to assume responsibility for the equipment we provide them.

Lesson learned: It was amazing how we suddenly began getting all our equipment back when we added this to the menu and website: “Client will be responsible for the cost of any unrecoverable equipment.”


Situation: Managing your accounts receivable.

What we thought then: We provide catering services for reputable, well-run companies. We’ll bill them for our services, and they will pay us on time.

What we know now: LOL! If only it were that easy. Once you start billing, you will always be owed money. As your business grows, your “past dues” will increase. It is critical to have an organized system for tracking every dollar that you are owed.

Lesson learned: While most corporate accounts get billed once and pay on time, chasing money is a reality of any business. Someone in your operation needs to be responsible for regularly monitoring your accounts receivable. When an account becomes past due, call and ask to speak to the person in the department that handles vendor payments. Try not to get your customer involved. It may make them feel uncomfortable ordering if there is a past due balance. Set up a database with the contact information of who handles paying your bills and document your interactions.

Suggested opening dialogue: “Hi [first name], this is Michael from The Corporate Caterer. I’d like to check on some open invoices that are showing in our system. 


Whether it takes 10,000 hours or 60,000 hours, my mantra to the members of our website, is  “Always think of your business as a work in progress.  Commit to doing one thing—anything, as long as it is something that will make your operation a tick better every day. Those ticks add up.” 

It’s the same philosophy I share with my staff. “Let’s agree there is always work to be done that can result in better services for our members and clients and will make us a more profitable business. There is no finish line. Our work will never be done.”

 Michael Rosman can be reached at 781-641-3303, [email protected], or on his membership website,


Michael Rosman

Michael Rosman

Owner/Founder, The Corporate Caterer, Boston, MA

Michael Rosman has over three decades of experience in the catering and restaurant industry. His career began in the management-training program with Creative Gourmets in Boston, where he spent five years working in different corporate dining facilities and catering venues throughout the city. He then purchased an existing café in Boston’s financial district and eventually took ownership of a nearby pizzeria. During this time he began creating the infrastructure for a corporate drop-off catering operation and five years later, he sold his client list to the largest independent catering company in the city.

As Director of Corporate Catering with Via Lago Café and Catering in Lexington, MA, he built an almost two million...


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