Tips on How to Manage Difficult Employees

Difficult vs. DeterminedHow to Manage Difficult Employees

There are two basic types of “difficult” employees. The first is essentially unwilling to cooperate and probably won’t last too much longer under your employment. The second requires some guidance and proper supervision but is essentially willing to learn and wants to do a good job. You may or may not be able to keep the second type in every instance. However, knowing and utilizing some of the basics of organization and staff training will make retaining people much easier. In the long run, the “hire and fire” technique only goes so far.

Do not confuse “determined” with “difficult.” Some of the most competent people out there can be misunderstood as being difficult. They ruffle people’s feathers; they rock the boat; they have tempers; they are often perfectionists to one degree or another. The thing to look at is their intentions. Are they trying to do a good job? Are they trying to remove the barriers to a positive objective? Some of your most competent people are your least quiet. Indeed, they can get a bit noisy at times. It’s the intention that you look at.

There is no substitute for understanding people and groups. Ultimately, you want and need qualities like loyalty, longevity, familiarity, experience and competence. Achieving these things takes hard work and taking the time to work with people on a one-on-one basis. Here are some guidelines for managing employees, “difficult” or otherwise:


The first step is hiring wisely in the first place. This will save you multitudes of problems. A resume will give you some information on an individual’s education, experience and skills but not much else. Only an in-person (or perhaps Skype) interview will reveal the most salient facts about a prospective employee. You will likely note if the person is decently dressed, but that is only an initial observation. When you are sitting across from them, what are their eyes doing? Do they look at the floor or dart about the room? Are they texting or fiddling with their phone? Or do they look at you when engaged in conversation?

When you ask a question, do they answer it? How long does it take for them to answer a question? Note that I am not only referring to a “long pause.” When you ask a question, do they answer another non-existent question or bring up an unrelated subject? Are you able to get a simple question answered at all? This is important because – as a general rule – the longer it takes a person to answer questions, the more difficulty you are likely to have with this person (as long as it is a valid, legal question).

You look at education, experience and skills but that still doesn’t tell you what you need to know. Is this person inclined to create problems or create solutions? When faced with adversity, is it “someone else’s fault”? Or do they have a willingness to take responsibility for a situation? And are they at the same time able to hand over responsibility to someone else? Can they be guided and helped and do they guide and help others? All these and more are questions you should have about a person. You should be able to get some of them answered through a two-way discourse. He or she may not know what you are looking for but you certainly do. Will everyone work out? No. There is a lot more to the subject, but everything I’ve just mentioned should help you in your hiring.

Positive Communication

When you do bring someone on, there is no substitute for communication in the workplace. If someone doesn’t understand something, they should be able to ask and get their question answered without being made to feel stupid or inept. Similarly, either you or someone designated by you, should be the one responsible for helping the new hire get familiar in the workplace, know the rules, know who to see for what, etc. But it doesn’t end there. Hold meetings and make sure everyone knows the priorities and what is going on. A “difficult” employee may simply be in a complete mystery as to what is expected of him. Use positive communication so everyone is on the same page.

Standard Operation

There ARE right ways to do things. There are infinite ways to do something wrong. Some people are dedicated to doing things wrong when the right way is known and directly in front of them. They will likely not last long on your team, but keep in mind they are in the minority. Most people will make the effort to do it right when given positive guidance. Company policy that details standard operating procedures thus comes into play in a big way – especially as you grow and take on new territory. Your employees must be grooved in on how it’s done at your place of business. If an individual has a better idea they can propose it, but someone must have the final say and normally that would be the owner or board or CEO.

All too often an equal partnership goes awry because of the phenomenon of “too many chefs on the same pie.” That is not to say a democratic partnership cannot work, but it is wise to assign out specific responsibilities and specialties. The difficult employee may be in over his head in one area whereas in another he is a total pro.

Business Structure

The structure of a business is vastly more important than many people realize. If you have ten employees and they ALL answer to you directly, you will have problems. Whereas, out of those ten, if five answer to you and another four answer to a VP, then you will find your job more manageable.

The number of people who should DIRECTLY answer to any ONE executive or manager should be no more than FIVE. That is not to say a CEO does not have the right to direct anyone in the business if the need arises. It means that in day-to-day operations, a CEO, VP, departmental manager, etc. should have no more than FIVE employees under their DIRECT individual supervision. You could have five under you and each of those have five under them and so on. You could have 1,000 people in your section, but the principle is the same. This makes the job of the manager much easier as well as the job of the “worker.”

Incidentally, there is really no such thing as a “worker.” Each employee is a manager of his How to Manage Difficult Employeesor her zone of control and responsibility, from the custodian on up to the CEO.

When you have the structure worked out properly, look out for the employee who “takes orders from everyone.” Such an employee will have a tendency to do anything anyone tells them to. You cannot possibly run a business this way. They are “difficult” because they do not realize they answer to ONE person, their direct boss, not everyone in the office! There is a substantial amount of useful knowledge to be found regarding organizational structure, but these points, applied well, should smooth out many difficulties.

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