How to Approach Uncomfortable Situations in the Workplace


We all dread uneasy situations at work. Whether it be giving negative feedback on a project, confronting a coworker’s annoying habits or talking to a supplier about past due bills, there are ways to help get you through these tense exchanges. As the head of a commercial collection agency, I’ve become an expert in handling difficult conversations and situations. Below are five ways I handle uncomfortable situations or conversations in the workplace.

Be Honest

Your mother said it, your first-grade teacher said it, you’ve said it to your own kids – honesty is the best policy. Being direct and honest with people may feel uncomfortable at first, but it can help prevent more difficult situations. If you’re late shipping an item, don’t make excuses, explain the situation to your customer. If your co-worker’s constant phone calls are an annoyance to you, politely tell him or her. Developing a reputation for honesty and aboveboard communications makes people much more likely to trust you, forgive you and want to work with you.

Get Ahead of a Situation

If you’re having trouble paying a bill, talk to the person you owe. Let them know what the problem is and work together to find a solution. If an employee is not performing up to standards, don’t wait until a performance review to spring that on them; talk to them now and let them know while there’s still time to fix the problem. Oftentimes people try to hide a difficult situation and hope the other person doesn’t notice. This rarely works. Being the first person to bring up a problem or sensitive situation can actually give you a head start in a negotiation.

Respect the Privacy of Others

When you have a difficult or sensitive situation in an office, it can be tempting to ask others for their opinion. However, doing so exposes more people than necessary to sensitive personal or business information. In some cases, soliciting opinions can also have legal consequences. For example, an employee could sue you for revealing confidential health or other personal information.

Keep Records

If you’re dealing with a sensitive or uncomfortable situation, chances are there will be some disagreement about what was said or decided. Keeping good records of who said what and which conclusions were reached may be helpful in future conversations, or if need be, legally. Good notes can also help diffuse a tense conversation. People’s memories are often faulty when they’re upset or worried – taking good notes can help ensure things are remembered correctly.

Stay Calm

Yelling never helps. Whether you’re the person at fault, you feel wronged or you’re a manager who has to deal with someone else’s mistake, the best way to handle a difficult situation is to stay calm. Emotions are easily read in tone of voice and physical mannerisms. If you feel anxious or angry about the situation, the other person will know. Attempting to bully or strong-arm someone will never help solve a difficult situation in the long run. Before talking about a situation, consider creating a game plan, writing out your feelings and thoughts, or even role-playing the conversation with someone outside of the office, but keep in mind privacy concerns.

Too often when dealing with business relationships we concentrate on the “business” side and forget that we’re dealing with actual human relationships. Keep in mind the need for honesty, directness and calm. Dealing with work situations as you would a personal relationship will go a long way towards ensuring that you can handle even the most uncomfortable situation smoothly.
Dean Kaplan is President of The Kaplan Group, a commercial collection agency specializing in large claims and international transactions.  He has 35 years of international business experience, traveling to over 40 countries to negotiate over $500 million in mergers and acquisitions and other business deals.  He previously owned a manufacturing firm that counted Disney, Warner Brothers, Macy’s, Hard Rock Casinos as customers.  He has provided business planning and other consulting services to a wide variety of businesses including farms during his career.


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