You can be on Entrepreneur’s cover!

3 Red Flags to Identify a 'Smooth Operator' Before Hiring One Since nobody is perfect, anybody who seems perfect is suspicious.

By Michael Mamas

entrepreneur daily

Opinions expressed by Entrepreneur contributors are their own.

skynesher | Getty Images

Several years ago, my company needed to hire a contractor to construct a new building for our business. Since it was quite a large project, and I didn't want to take any chances, I assembled a committee to conduct interviews with me. Every builder we interviewed appeared knowledgeable, experienced, down-to-earth and personable. Finally, one guy came in who stood out head and shoulders above the rest. He displayed no inadequacies, even offering some excellent suggestions that the architect had not considered. He was clearly very intelligent.

We spoke with him for a long time, much longer than the other candidates. Clearly everyone in the group, including those with a great deal of experience in construction, was impressed. We were all ready to turn the project over to him, quite confident that he would just take over and alleviate our burden. After the interview was over and the contractor walked out, we all turned to each other and said, "That's our guy. He's perfect."

Related: The 3 Most Common -- and Costly -- Hiring Mistakes

Then the nightmare ensued. He was a disaster, cutting corners to make a buck, denying any responsibility for things that were clearly his mistake, overcharging and even invoicing for products and services we never received. If that wasn't bad enough, once we hired an attorney, his true colors came out when he said, "I know the laws backward and forward. There is no way you can touch me. I can out maneuver any attorney."

Of course, you can always ask for references, but the problem with references is the candidate only gives you people's names who are part their alliance. It is certainly a good idea to get a solid contract, but the laws are so convoluted (as most attorneys will tell you), there is no such thing as an airtight contract. Furthermore, the people you need an airtight contract with tend to be the smooth operators who know every loophole.

After experiencing him and other smooth operators, we have gotten better at identifying them. Based on that experience, provided below are a handful of red flags you should watch for when hiring employees or contractors.

1. Turning over your power.

It's common to want someone who can just handle things for you. Smooth operators seem so responsible and knowledgeable that it is easy to believe they will be able to take on your responsibilities with no problem. That can range from a small department to the total management of all your finances. Smooth operators can convince you that they are able and willing to do anything for you. They offer tremendous relief, telling you that they'll handle it, and you don't even have to think about it anymore.

Related: How Entrepreneurs Can Resist Shiny-Object Syndrome

No matter the size of your project or what type of service you need, stop looking for a person who will handle everything for you. And certainly, never allow yourself to be convinced by anyone that such a person actually exists. Keep on top of what is going on at all times. Ideally, never make anyone indispensable. Always be ready to walk away from the person if you start having concerns.

2. The perfect person.

Smooth operators come across as being in control, confident, sharp as a tack, fully knowledgeable, highly experienced and ready to take over the reins with no identifiable inadequacies or problems. They are brilliant bamboozlers. Without realizing it, you are charmed. It's as if a spell has been placed upon you. When you find them, it's often accompanied by a sense of relief, if not even euphoria. It is as if your wish has been fulfilled.

When that happens, it's time to take a step back, take a cold hard look at reality, and double down on due diligence -- references, visiting their office and spending more time with them to observe how they function. It's time to start reading between the lines, and look for what they might be hiding. That can become evident through their behavior -- like how they talk about other people when you are just hanging out with them. As you befriend the person, you start to get a sense of their real attitude towards other people. They will think they are convincing you that you are on the same side of the fence with them. Just don't forget that in their world, you're actually on the other side of the fence.

3. The controlled contract.

One thing you'll commonly find is that smooth operators are highly knowledgeable when it comes to contracts. It's only when you sit down to actually write the contract that you realize the person is very particular regarding specific details and wording that must be included. Unfortunately, by the time it comes to writing the contract, most people have already decided they are hiring the person. That's a big mistake. You often find out more about a person by how they go about writing a contract than through interviews, references, etc. Be ready to walk away.

Related: When Opportunity Presents Itself, Will You Be Ready?


If you should find yourself hooked by a smooth operator, don't judge yourself. It happens to the best of people. Move on. Certainly don't try to salvage the relationship.

Don't bury your head in the sand when the red flags start appearing. It's not always easy to come to terms with something we don't want to admit. We all have our dreams and would love to think the next interviewee will fulfill it for us. Be ready to cut your losses, and put a stop to the relationship immediately if you get suspicious that you are dealing with a smooth operator. Hopefully, this information will help you be aware of the signs so that you don't get caught in a contractual or human relations mess.

Michael Mamas

Founder of The Center of Rational Spirituality

Dr. Michael Mamas is the founder of The Center of Rational Spirituality, a nonprofit organization dedicated to the betterment of humanity through the integration of ancient spiritual wisdom with modern rational thought. From personal issues to global trends, Mamas helps individuals and organizations develop a deeper understanding and more comprehensive outlook by providing a "bridge" between the abstract and concrete, the eastern and western, and the ancient and modern. Mamas has been teaching for 35 years and writes on a variety of subjects on his blog,

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Business News

A Look Inside the Company That Is Making $500 Million a Year Serving Italian Beef Sandwiches Made Famous by 'The Bear'

Portillo's CEO Michael Osanloo shares his secret to keeping hungry customers coming back again and again. (Hint: It requires a lot of napkins.)

Business News

A Non-Profit Newspaper Published a Column Criticizing Facebook. Then Meta Blocked All of Its Posts.

Facebook's communications chief said that the posts were removed because of "a mistaken security issue."

Business News

Walmart Shoppers May Be Eligible for $500 After Settlement

Walmart shoppers who purchased weighted goods or bagged citrus in the U.S. or Puerto Rico from late 2018 through early 2024 might be eligible for a share of a $45 million settlement.

Business News

Elon Musk Reveals When Tesla Will Release Its First Robotaxi

Tesla's CEO says the fully autonomous Tesla taxi is arriving soon — in 122 days.

Business Ideas

63 Small Business Ideas to Start in 2024

We put together a list of the best, most profitable small business ideas for entrepreneurs to pursue in 2024.

Business News

Total Solar Eclipse 2024 Live Feed: Where, When and How to Watch the 2024 Eclipse

Here's what to know about the total eclipse 2024 and a live stream from NASA.