5 Tough Situations You’ll Eventually Face When Managing People

5 Hardest Parts of Being a Manager

As a business owner, managing people is by far the toughest responsibility of all. Every person is different, unpredictable, and motivated by a unique set of factors. And while good hiring practices will mean smooth sailing most of the time, every business owner will eventually encounter tough situations. Knowing how to respond will help you avoid making costly mistakes.

Be Prepared for These 5 Management Situations

Between 2003 and 2013, RainmakerThinking, Inc. interviewed 37,419 managers from 891 different organizations and asked them a simple question: “What is the hardest thing for you about managing people?”

Instead of presenting multiple choice answers, which often waters down responses, they actually collected verbatim responses to the open-ended query. While there were thousands of unique answers, 87% of the responses fell into one of 10 common challenge categories. They are as follows:

  • Not enough time (or too many people to manage) – 24 percent
  • Giving negative feedback – 19 percent
  • Different personalities – 6 percent
  • Interpersonal conflict – 6 percent
  • Balancing being the boss with being a friend – 6 percent
  • Employees with bad attitudes – 5 percent
  • Dealing with pressure and shifting priorities from my own boss – 5 percent
  • Cumbersome and lengthy firing process – 5 percent
  • Insufficient authority and discretion to reward high performers– 4 percent
  • Managing people in remote locations – 4 percent

In other words, the management challenges you’re facing in your own business probably aren’t unique. You’re dealing with the same points of friction as business owners all over the world. And while this may not make things any easier on you, it’s at least encouraging. It also means there’s a lot of great advice and helpful resources out there to guide you along.

Keeping the groups above in mind, there are specific situations within these categories you’ll eventually face when managing people. By preparing yourself for them in advance, you can develop a framework for how they’ll be handled in your organization.

Hardest Parts of Being a Manager

Here are five specific situations to be ready for:

1. Firing an Underperforming Employee

Managers of large and small companies alike rank firing employees as one of the most difficult responsibilities they have. In fact, some major corporations actually hire termination companies to come in and handle this undesirable process for them. But if you’re going to be a good manager, you have to learn how to fire an employee in a firm, appropriate manner.

“The first and most important step in the firing process is to make sure your employee can see the train coming, long before it arrives,” says Tye Deines, the Director of Human Resources for one of the country’s largest human service organizations. “This is part of your job supervising your team. If your staff isn’t meeting your expectations, it’s your responsibility to let them know immediately—not months later.”

If you’ve done a good job providing expectations, correcting employees when they don’t meet these expectations, and giving them opportunities to regain your trust, then the termination process becomes much easier.

When it comes to the actual firing, you have to be firm. Cut straight to the case, explain the reasons for termination, and quickly transition into the logistics of how the termination will work. It’s okay to show empathy, but don’t let the employee control the conversation. You’ve already made your decision, so stick to it.

2. Supporting a Grieving Employee

There’s nothing sadder than walking alongside an employee who has just lost someone close to them – such as a spouse, child, parent, or dear friend. You have to provide space for grieving, while also making it clear that the employee must eventually return to a productive role with the company.

When you first learn of your employee’s loss, send a sympathy gift basket to their home with a note that lets them know you’re thinking about them. Encourage them to forget about all work-related responsibilities for the next few days and give them room to mourn.

After a few days have passed, you can begin to press in a little bit and encourage a gradual return to work. If you aren’t a naturally empathetic person, you may want to have a coworker who is close to the employee handle the process.

After the employee’s return to work, be vigilant of their behavior. “Watch for warning signs of prolonged grief and ongoing performance issues, such as poor grooming, severe withdrawal, substance abuse, or other uncharacteristic behaviors might be warning signs,” employee wellness expert Julie Ferguson writes.

3. Handling Conflict Between Multiple Employees

Few things are more frustrating than conflict between employees in the workplace. Not only does conflict impact productivity, but it also threatens to compromise the healthy workplace culture you’ve worked so hard to cultivate over the past few months or years. Conflicts don’t just involve the participants – they indirectly involve everyone else.

While you shouldn’t feel the need to immediately jump into the middle of every conflict, there does come a point where a manager needs to get involved. And when you do get involved, be sure to listen more than you talk. It’s through listening that you’ll understand the heart of the matter and be able to bring in some sort of resolution.

“Conflict resolution doesn’t necessarily have to end in agreement. Sometimes, it’s best to agree to disagree, respectfully,” HR expert Megan Moran admits. “When that happens, employees should acknowledge there is a difference of opinion or approach, and come up with a solution together on how to move forward.”

The outcome of every quarrel will vary, but your approach should be the same. You want to develop a culture in which employees understand how to communicate in peace and conflict. If you have an employee who repeatedly exhibits an inability to communicate and/or reach resolution, it may be time to discuss parting ways.

4. Dealing With a Dishonest Employee

When you hire an employee, you do so with the assumption that the individual will act with the company’s best interests in mind. Unfortunately, this doesn’t always end up being the case. If you’re in management long enough, you’ll eventually encounter your fair share of dishonest employees.

A dishonest employee may be someone who physically steals from the company (taking cash, products, or supplies), commits intellectual theft (taking ideas away from the organization), or misleads management (cheating on a resume, lying about hours worked, etc.).

The primary objective is obviously to prevent dishonest behavior from occurring in the first place. You can do this by making sure employees understand what behaviors are acceptable and what are against company policy. But even with the correct policies in place, you’re still going to have some issues on occasion.

When you notice dishonest behavior, you must active decisively. If you try to tiptoe around the issue, you’ll end up getting taken advantage of. Step up, implement the appropriate reprimand, and move on. There should be no enabling on your part.

It’s also important that you use dishonest behavior as a teaching opportunity. Employees learn through experience and they’re much less likely to repeat the behavior of a coworker if they’ve seen the consequences played out in real time.

5. Persuading an Employee to Stay

While we’ve discussed the challenge of firing an employee, the opposite is true as well. It’s sometimes even more difficult to hang on to an employee who is looking to accept a position with another company.

In most cases, employees leave for one of the following reasons:

  • More money
  • Better benefits
  • Greater responsibilities
  • Career change/pivot
  • Relocating to a new city

While you can’t do much if an employee wants to switch careers, you have some room for negotiation when it comes to money, benefits, and responsibilities. You may even have some options when it comes to relocation.

“In the past, location was probably the biggest objection that companies couldn’t overcome. If a spouse moved to another state it was inevitable that the employee would quit and move as well,” CoWorx Staffing Services explains. “In today’s ultra-connected world this doesn’t need to be the case. If the long commute is a problem talk about flexible work hours that can help. You could also arrange for a remote working relationship that will continue their employment even if they move away.”

Learn From These Challenges

It doesn’t matter how good your idea or product is – the only way to be successful on a large scale is by involving people. And when you involve people, you can bet they’re going to present some management challenges that are uncomfortable, troubling, and stressful. But they’re also going to make your life a whole lot easier by offering help, guidance, time, and labor.

The key is to anticipate major challenges, tackle them head-on, and learn from your successes and failures. By letting challenges shape your management style, you’ll eventually grow into a better manager who is capable of handling a variety of situations.

Photo via Shutterstock


Larry Alton Larry Alton is an independent business consultant specializing in social media trends, business, and entrepreneurship. Follow him on Twitter and LinkedIn.

2 Reactions
  1. Thanks for posting this Article. Great points.

  2. It happens because people have different agendas. People are the hardest to deal with. They are also very unpredictable.