Dealing with Difficult Situations at Work: When the Going Gets Tough, Get Smart

By Karyn Schoenbart
Published on: June 4, 2021

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Despite our best efforts, “stuff” happens. As the CEO of a global company, I’ve faced my share of tough situations and difficult people – everything from unhappy clients to people who demand the impossible, act like bullies, or play gatekeeper. When faced with a difficult situation or person, from the minute a problem is identified, you need to get through it as quickly and professionally as possible, keeping the issue contained and not letting it blow out of proportion. Here are some strategies to help you. 

Let Them Empty Their Glass – What do you do when someone calls or approaches you and is very upset or angry? Sometimes, even if you give people what they want immediately, what they also need is to have the satisfaction of sharing built-up frustrations and concerns. Imagine a glass completely full of water. If someone is upset or angry, until they can empty out some of that water, there is no room for anything. Until they can get their points off their chest, they won’t be able to hear what you have to say. The best thing you can do in this situation is to listen and then listen more: probing and asking questions until they have completely emptied their glass. During this kind of discussion, I always take copious notes so I can capture everything they said. Then I paraphrase back: “What I heard is…” 

Don’t Immediately Apologize, Say You Want To Resolve The Situation Quickly – In a difficult situation, I don’t rush to apologize until I know all the facts. I might empathize with a comment such as: “I hear how upset you are,” and then add what I’ve found is an extremely powerful statement: “I will do everything I can to help resolve this as quickly as possible.” Note I haven’t promised I will give them what they want—but I have offered my assurance I am committed to a resolution. Another helpful phrase is: “Our relationship/partnership/friendship is very important to me, and I will make this my top priority.” 

Gather Information First – Unless the problem is a simple one that can be solved on the spot, I prefer not to stretch for a resolution during this first conversation. I want to be able to gather all the relevant information and make sure I’m ready to put my best foot forward. And in general, it’s not a good idea to provide too many solutions before someone asks. For example, one of my employees once gave away a lot of free data to make up for a client issue, when the client really wanted a single report. The latter would have cost our company a lot less, if only we’d taken the time to hear her out!

Schedule a Second Interaction – After listening to everything the person has to say, I’ll immediately schedule the next interaction. I do not want to leave this meeting to chance, and I certainly don’t want to try to resolve the situation in email. While text and email are very efficient communication modes for everyday interactions, these are not ideal when faced with a difficult situation. It is important to have a two-way dialogue so you can respond in real time to objections or concerns. You want to be flexible during the discussion with replies that may differ based on the direction of the conversation. Calls should be scheduled with a specific date and time, as in: “I will get back to you tomorrow morning with an update. What time is good for you?” I prefer to be the one making the call as it puts me in control and shows I’m taking charge. If you do not have the answers you need in time for the follow-up call, make the call anyway. You don’t want to make the situation worse by missing opportunities to communicate. Be honest but confident, as in: “Your business/our relationship is important and this issue is complex. I don’t want to give you wrong information. I need more time to gather all the facts. When would be a good time to reach you tomorrow?”

Give Bad News Gracefully – Delivering bad news is never pleasant. Tempting as it is to hold off and wait for a miracle, your best bet is to get it over with quickly. Keep things in perspective. Unless you are a doctor or pilot, it is unlikely that your problem is a matter of life or death. Once I have gathered the facts and brainstormed various options and solutions, I write out what I am going to say so I can communicate it as calmly and succinctly as possible. Part of my script involves being honest about the fact that I feel terrible, as in: “I’m really upset I have to give you this bad news,” or “I was up all night worrying about this.” Humanizing the issue can soften the blow. And to this day, I practice. If I have a colleague with whom I can role play, I do that as well.

Don’t Say “No,” Offer Something – What if someone is asking for the impossible and won’t take no for an answer? In these cases, you must be firm. Educate them as much as possible and give the reasons for your answer. No one likes to hear “no,” so I try to avoid using that word. I love the phrase “What I can do is…” There is always something you can do, even if it is not exactly what the other person wants. Just offering to do something is better than nothing. Imagine you are stuck on an airplane due to a mechanical problem and the flight attendant says there will be a three hour delay. If the airline gives you a choice of getting off the plane or staying in your seat until the issue is fixed, the ball is in your court. While neither option is attractive, at least you feel like you have some control over the situation. If all else fails, maybe you can offer to have your boss call the other person’s boss to let them know the situation wasn’t their fault. While they might not take you up on it, this action proves that you are willing to do what you can to help.

In my experience, most people are reasonable. If someone gets very angry and raises their voice, it is best for you to be as calm and soft-spoken as possible. And if someone is truly abusive, you should not allow the interaction to continue. Tell them you’ll talk more about the issue when they can have a professional discussion, and disengage from the conversation. Whenever I am dealing with a difficult situation, I keep in mind that most people won’t remember the actual issue, but they will remember how it was handled.


Adapted with permission of the publisher, Motivational Press, Inc., from MOM.B.A. Essential Business Advice from One Generation to the Next by Karyn Schoenbart with Alexandra Levit.  Copyright (c) 2017 by Karyn Schoenbart. All rights reserved.

Karyn Schoenbart

Karyn Schoenbart

Karyn is the author of MOM.B.A. and CEO of The NPD Group, a global provider of information and advisory services to many of the world’s leading brands. She has over 30 years of experience in the market research field, with expertise in identifying and developing new business opportunities and client partnerships. Karyn was named one of the Top 25 Most Influential Women of the Mid-Market by the CEO Connection. She is also the recipient of the Long Island Brava Award, which recognizes high-impact female business leaders, and the Legacy Award from Women in Consumer Technology. Karyn is passionate about coaching others to greater levels of achievement. She is a resident of Long Island, NY. To learn more, visit:

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