3 Red Flags to Identify a 'Smooth Operator' Before Hiring One

Since nobody is perfect, anybody who seems perfect is suspicious.
3 Red Flags to Identify a 'Smooth Operator' Before Hiring One
Image credit: skynesher | Getty Images

Grow Your Business, Not Your Inbox

Stay informed and join our daily newsletter now!
Founder of The Center of Rational Spirituality
6 min read
Opinions expressed by Entrepreneur contributors are their own.

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.

More from Entrepreneur

We created the SYOB course to help you get started on your entrepreneurial journey. You can now sign up for just $99, plus receive a 7-day free trial. Just use promo code SYOB99 to claim your offer.
Jumpstart Your Business. Entrepreneur Insider is your all-access pass to the skills, experts, and network you need to get your business off the ground—or take it to the next level.
Discover a better way to hire freelancers. From business to marketing, sales, finance, design, technology, and more, we have the freelancers you need to tackle your most important work and projects, on-demand.

Latest on Entrepreneur