How to handle difficult conversations

How to handle difficult conversations

When was the last time you had a difficult conversation? For most of us, the answer is today. Difficult conversations are inevitable.   These dreaded conversations happen so frequently, nearly every company we talk to requests skill development in this area. The consequences of having an unprepared response to difficult conversations can be costly for organizations. One poor conversation can cost millions of dollars for a company.   But equally important, is the impact these conversations have on the participants involved. It is a proven fact that stress is the major cause of illness and can strip the joy out of our lives. Since teaming up with Speak So They Listen, there have been many life-changing moments that have empowered me to handle even the most difficult conversations, easing the stress on myself and the other person. This has had many benefits, including better health, better outcomes, better relationships, greater financial rewards, to name just a few. I wanted to share the Top 5 mistakes we see people make when handling difficult conversations and provide an easy to use CPR tool kit to prepare you for your next encounter. Try these 5 tips and experience the positive results.

The Boss Wants To See You NOW!

The players in the following scenario may be different, but the stress and the undesired outcomes are the same no matter who you are. We all have stories that involve a difficult interaction that went wrong. Let’s take a look at a work interaction based on a real-life interaction from one of our recent workshop participants.

We have all had these days. Your work load is increasing, time seems to be shrinking, company goals are getting more aggressive as technology advances….It makes sense, you have faster communication so you should be able to do more, right? Deadlines loom over you as an email comes in from one of your staff members that your best client is not happy with their service this month. The client is one of your companies’ biggest accounts. The client feels that the research and recommendations on a project were not even close to accurate. The staff managing this account dropped the ball, did not do their research for the client, and made incorrect recommendations, costing the client money. For a quick reprieve to decompress, you head to the break room. You see your boss heading your way. You sense that it isn’t good because he looks stern. He asks if you can meet in his office. Your head is swimming with thoughts of the client issue and having to explain how this happened under your direction. There is a sense of responsibility on your shoulders. You know the way you handle this interaction can determine how your boss views your performance and capabilities as a manager. Palms sweaty, you quickly scan your brain for ideas on how to explain the situation, but there is no time to prepare. And let’s not forget, your boss is not the most approachable person. He is direct and seeks direct answers. You are sure this will not go well.

What would you do?

Comply and race into a stress filled conversation? By all means, it is your boss and he wants to see you NOW!

Fumble through excuses on why you cannot meet, making up an appointment with your Dr.?

Prepare to blame it on your staff?

Try to give your best guess without facts to back up your ideas?

Personally, before I learned this first tip, I made this number one mistake. I would head straight into the meeting trying to refocus quickly and come up with my strategy in the hallway on the way to the meeting room. Not good!

This real life situation creates a tremendous amount of stress for you and rarely goes well. Whether it is your boss, a co-worker, spouse, child, family member, friend, difficult conversations taken at the wrong moment do not turn out well.

How can you respond to ease the stress on you and the other person, make better use of time, and come up with positive outcomes?

Tip One: Be Assertive.

The number one mistake people make is taking on a difficult conversation at the wrong time. You do not need to go into a difficult conversation when it is not a good time for you or there is not enough time to cover important information. It is a lose/lose situation. Don’t just assume you need to accept the meeting because the other person is asking. Respect the other person’s time and yourself enough to ask the right questions.  Understanding that timing is everything with difficult conversations has been a game-changer for more positive outcomes.

First, find out what the meeting is about so you have more information. “Do you mind if I ask what the meeting will be about so that I can provide you the information you are looking for?”

Second, if this is truly not a good time for you, your focus is not in the right place or you do not have the information ready, respectfully ask for time to provide the information your boss is asking for and set up a meeting time that is convenient for you both. Be sincere.

Taking a meeting request, or any difficult conversations, that you are not prepared for can be devastating for you personally and professionally. You can lose credibility with others and inhibit positive outcomes. Hint…this works with children as well. If you have teenagers, difficult conversations come at you every minute of the day!

Tip Two: Be Prepared

The 2nd most frequent mistake is moving into a difficult conversation unprepared. In the example above, taking a meeting without having the time to collect your thoughts, be calm and collected, have all the necessary facts, will undermine your credibility and the boss will not get the information he is seeking. Take time to outline and set an agenda for the conversation. Gather all documentation you may need to answer questions and back up the news you are delivering. Consider difficult questions that may be asked and/or negative responses that may occur. Be prepared with answers.

Tip Three: Set the tone for the encounter

The third frequent mistake is not setting the right tone that will bring about positive outcomes. It comes down to the old saying “treat others as you would want to be treated”. Put yourself in the other persons seat for a moment. In addition, begin with the end in mind. If you want a mutually beneficial outcome there needs to be two things present. Discovery and Dignity. This means we take the time to ask the right questions, listening, and respectfully providing feedback/information that leaves the other person feeling respected. It is about considering what the other participant may be seeking from the conversation.

Tip Four: Relocate the bad news

What do you do when your difficult conversation revolves around you delivering bad news or difficult information. In sports, when we train our bodies, muscles respond to the activity like they are memorizing the motion. Just like muscles have memory, the space where news is delivered generates a memory connecting the news with the location it was delivered. Therefore, there are a couple things that can help separate the news from you personally. Place the news on a piece of paper. When you discuss the news, you point and direct your eyes and hands to the paper. This naturally brings the other person’s attention to the document and not you personally. This technique can help promote a more positive relationship for solutions to be discussed.

Tip Five: Check your breathing

Did you know that you can impact another person’s breathing by the way you breathe? Our breathing is an important body language signal that goes out to the other person. This can have a positive or negative impact on the conversation. Some of the more obvious signals we send with our body language are facial expressions, gestures, and posture. However, we may never notice how our breathing impacts a message. But it does. For example, if we become nervous in a difficult conversation, our breathing will become more rapid and upper body muscles naturally tense, causing us to look nervous. Breathing becomes noticeable to the eye, as well as heard over a phone call. This may have a couple different results on the other person. They may also become nervous (especially if you are delivering difficult information to a client, patient, subordinate). Similarly, their breathing will increase and they become tense as well. This is called mirroring. We do it without even realizing it. This makes problem solving more difficult. Our brains are not getting the adequate oxygen it needs to think clearly and calm our reactions. Solutions become more difficult in these situations.

On the flip side, we can have a calm and reassuring effect on the other person. A healthy breathing pattern is one that originates from the abdomen. Quiet breathing is best through the nose and not with our mouths hanging open (with the exception of when you are speaking). This actually allows for better listening as well.   This creates trust, reassurance, and provides a more approachable environment for others to communicate their thoughts and ideas. Identifying what type of breathing pattern you have is covered in our Speak So They Listen, Signature Workshop.

I encourage you to try one or more of these techniques and see how subtle changes can make a big impact. Once you put these tips into practice, contact us and let us know how they have worked in your life!

You can learn more about these techniques and more at our Speak So They Listen, Signature Workshop.

Schedule a free discovery session to discuss how to:

Equip yourself with simple vital skills that are

  • Easy to learn and implement
  • Build confidence and empower you to respond with credible solutions
  • Make a difference in how you are perceived by others
  • Bring about positive change

What is in your communication CPR kit look like currently?

Do you feel confident in how you deliver a difficult message?

Are you experiencing stress on the job?

Do you have a set of simple techniques that can be pulled out when the need arises?

Do you have resources at your fingertips that you can rely on quickly to remind you and prepare for these difficult situations?

Is your tool kit disjointed, lacks effective implementation, never makes it into practice?


These simple communication tips today are consistent with our methodology on training. We believe that igniting respectful communication within organizations transforms how people perform in their 1:1 conversations, meetings, and presentations. We do this by delivering powerful training:

Effective: Short digestible chunks In an energizing and unique format. Your audience must be engaged in what you are saying. So we want to engage you during your skill building.   We practice what we preach. Your training will be fun and engaging.

Useful: Targeting only the most useful skills: We want you to go home having mastered simple, concrete skills that last a lifetime. Nothing is added for fluff. Time is money and we won’t waste yours.

Lasting: Practice is the king: leaving our workshops mastering the skills and ready to use as you walk out the door.

Mobile reinforcement on the go. Have valuable resources when you need it. No need to get to the office to look at your notes. Your training app is there for you loaded with helpful resources.