Mastering difficult conversations

President, Coach


As a Project Manager you have to communicate with such a variety of people on so many levels every day. Some of the conversations you are required to have can be emotional, challenging and sometimes uncomfortable. In this paper we will discuss why we often avoid these conversations and what results we can expect when we do.

Our state of mind going into any encounter will directly affect the outcome. We'll discover how to manage that and put ourselves in control of the situation. Our ability to develop rapport and trust with another individual will prove our most useful tool in working toward a positive outcome. We will learn simple steps to achieve this that are easy and quick! And finally we will explore how important making a plan, focusing on the issue, avoiding the “blame game” and listening are in “Mastering Difficult Conversations”!

Course Content Synopsized

This is a Mind Map outline of the content of the topic “Mastering Difficult Conversations” in a full-day workshop format (see Exhibit 1).

Picture of Mind Map created by Cathy Byrnes in Mindview 4, by Matchware

Exhibit 1 – Picture of Mind Map created by Cathy Byrnes in Mindview 4, by Matchware

Difficult Conversations


What is a difficult conversation? Some examples of conversations that could be challenging or difficult are confrontations, disciplinary action, delivering bad news, delegating tasks or saying NO, to name a few. We tend to avoid difficult conversations. Why do we avoid them and what are the results?

Some common reasons for avoiding Difficult Conversation are:

  1. We don't want to make someone angry.
  2. We wonder if it will really make a difference anyway.
  3. It may open up a “can of worms.”
  4. We could hurt the other person's feelings.
  5. Things might get emotional (angry, sad, upset…even tears).

First, let's address some of those concerns.

  1. Not wanting to make someone angry is a valid concern; however, if the issue at hand is not addressed, someone else might get angry or we might become or remain upset or angry. In almost all cases it is better if we are open and honest about the issue(s) at hand and be prepared for any feelings that might arise. We will talk about some methods for minimizing anger in conversations.
  2. We may have the conversation, give our opinion, or offer our feedback and it just doesn't make a difference in the situation. But if we don't have a conversation at all, will it make any difference?
  3. A “can of worms” may be opened up as a result of the issue being addressed; however, in most cases; the festering can of worms may be much more harmful when it is sealed shut.
  4. Hurting someone's feelings in certain conversations may be unavoidable. Most times people will end up hurt in the long run by a difficult situation that goes unaddressed anyway. It may be easier on all parties if the communication is opened up and dealt with sooner than later. Also, people are usually more hurt and offended when you don't have the conversation and they feel that you deceived them or didn't trust them enough to be honest.
  5. Yes, things might get emotional. Sometimes displays of emotion are unavoidable. We will talk about strategies to lessen the outbursts and control emotions.

What Happens When We Avoid?

Simply put, if we don't address our issues and concerns and avoid having the Difficult Conversations, we continue to get more of the same. So whatever it is that makes us think that we need to have a Difficult Conversation will remain status quo and nothing will change.

I feel it is appropriate at this time to quote the brilliant Albert Einstein. “The definition of stupidity is doing the same thing over and over again and expecting different results.”

State of Mind

Does your state of mind affect the outcomes that you will experience? Many believe so and I am of that mind. If you are in a stressed, agitated, or resourceless state of mind, your outcomes will not be good. You are communicating with the people around you 100% of the time whether you want to or not. People will pick up on your stressful and negative feelings and that will negatively impact the tone of the conversation right at the outset.

Our body and mind are connected and each will affect the other. So, not only are you communicating a negative tone to the other person, you are also inhibiting your own ability to remain calm and to access the part of your brain that is responsible for thinking and reasoning.

We are going to talk about some simple strategies to attain and maintain a state of calm and resourcefulness enabling you to project a positive tone and keep your mental resources available to you so that you can think clearly.


Maintaining good posture is key to feeling calm and confident. Proper posture allows for a natural flow of mental and physical energy. It also allows good circulation enabling the blood to flow to your brain. This promotes clear thought.

In body language, slouching communicates lack of strength and insecurity (Exhibit 2). This posture doesn't give your lungs room to breathe and puts tremendous strain on your neck. The energy, blood, and oxygen in your body cannot flow freely. Not only do you appear to be less powerful, you actually are less powerful! Standing straight says “I am confident! I am in control of my body and my mind.” It also allows your oxygen, blood and energy to flow freely!

“The Ultimate Book of Mind Maps” (Buzan, 2005, p. 150)

Exhibit 2 – “The Ultimate Book of Mind Maps” (Buzan, 2005, p. 150)


When we are stressed we tend to take short, shallow breaths. This is referred to as Chest Breathing. Chest breathing will speed up heart rate and brain waves, tricking the brain into thinking you are in a “flight or fight” situation and inhibiting the blood flow to the “thinking” part of your brain.

In order to allow proper blood flow, slow down our breathing, heart rate and brain waves, we need to take three deep breaths. Breathe in so that your tummy rises, like a baby's does when they breathe. I recommend a count of 10. Make sure that you also exhale fully, again for a count of 10 (Exhibit 3).

Self Talk

Whenever we are preparing for an encounter of any sort, we are using our internal voice. What is important here is that the things you are saying to yourself are positive, present tense. This convinces your brain that you are confident, self-assured and will help to ensure a positive outcome (Exhibit 4). What percentage of self-talk do you think is negative on average in North America today? Studies show that 87% of self-talk is negative. So we need to recognize the negative things that we're saying to ourselves and replace it with present tense, positive statements expressing our self-love, confidence, and optimistic attitude.

Cycle of Self-Talk, Self-Worth, Performance, Results and Self-Acceptance

Exhibit 4 – Cycle of Self-Talk, Self-Worth, Performance, Results and Self-Acceptance


Before you enter into any encounter, especially one that you think will be difficult or emotional, plan what you will say and practice. Do so with a trusted friend who will give you honest feedback or even with a mirror. This way, you will find out what non-verbal message you are sending. If you practice over and over, even if you get stressed and can't easily access the thinking part of your brain, you will remember what you need to say.


In every encounter there are two things that need to be considered. One is the substance, meaning the issue, matter or product, and the other is the relationship. The most important thing to consider, out of the two, is the relationship. The relationship will trump every time. If you have or build a good relationship with the other person, you will always have more success. So how do we achieve that good relationship?

Rapport and Trust

The Boothman Bit

First of all, in my training I like to use a training film called “How to Connect in Business in 90 Seconds or Less” by Nicholas Boothman (Exhibit 5). He also has a book of the same name. Boothman talks about some simple ways to build rapport and trust. I have added my own experience into the mix and will talk about a few simple strategies you can follow.

“How to Connect in Business in 90 Seconds or Less” by Nicholas Boothman

Exhibit 5 – “How to Connect in Business in 90 Seconds or Less” by Nicholas Boothman

Boothman talks about choosing your attitude. Do you believe that you can choose your own attitude? I do. We can allow ourselves to be victims of our surroundings and experiences or we can use strategies to choose our own attitude and overcome our circumstances. One such strategy is creating an anchor word to illicit a smile, laugh, and good attitude whenever we need it. Boothman chooses “GREAT!” You can choose any word you like. You just look in the mirror say it over and over again until you laugh your head off. If you do this a few times you will create an anchor in your brain. Then, when you are experiencing a negative mood or attitude, you can say this word inside your head and it will make you smile. When you smile, good hormones are released in your brain that makes you feel great! This is the first step toward choosing your own attitude and attaining a positive state of mind and body before you enter into your Difficult Conversation.

Next, look them in the eye and smile. Make sure you have open body language, point your heart toward the other person, give a firm handshake, make eye contact and give them a genuine smile. You must be genuine or people will see through you. All of this takes only a couple of seconds and it goes a long way toward building rapport and trust. If you develop trust with the other person they are more likely to have an open mind toward what you need to say to them and less likely to be negative and emotional.

Let the other person know that you are truly empathetic and care about their position. The most important thing to the other person is that you care. More potentially explosive situations are defused because the person in question feels listened to! People want to know that somebody really gives a darn about their problem, takes the time to listen and understands their situation. Ask them questions first to help them to open up and again, be genuine, show authentic interest.

Listen Actively

Do you know what it means to listen? I mean ... really listen. We think that we're listening when the other person talks, but are we really thinking of our next question, the next comment we want to make or maybe even our “to-do list”? In North America we are notoriously bad listeners. We are all in such a hurry to get on to the next thing. We have deadlines, appointments, projects and we are constantly multi-tasking.

How do we really listen actively? And why is it important?

First of all, listening is important for a number of reasons. We miss so much information by not listening actively. This could be information that would help us to solve the problem, deliver the message, address the conflict and/or lessen the stress. If we are not truly listening we are not showing the other person that we care. Even if they don't know that they know, people do know when you are not truly giving them your attention. In this case you will not develop rapport and trust. This puts the relationship at risk which makes the task of having the Difficult Conversation that much more difficult! You are not respecting the other person when you do not listen actively. When it is your turn to speak, would you like them to give you all of their attention? Of course you would. This is mutual respect. It also speaks to the deep seeded human law of reciprocity. If you respect the other person, give them their chance to talk and listen actively, when it is your turn to talk they will feel both willing and obligated to do the same.

Chinese characters depicting words are often made up of a grouping of other characters representing other words. Take a look at the Chinese character for LISTEN (Exhibit 6).

We need to listen with our ears, keeping our mouths closed while we do this. Listen with our eyes by making eye contact and watching the other person's body language to get their entire message. Listen by giving them our undivided attention. Don't be distracted by your smart phone, writing notes or by your next thought. And most importantly, listen with your heart or your empathy. Show them that you really care about what they are saying by truly caring.

Remember, when you listen actively you are more likely to be listened to!

Read People and Adapt

People communicate in different ways. If you want to be a successful communicator and problem solver you will be most effective if you do your best to adapt to the other person's style.

Some are more primarily visual communicators and would like to look at diagrams and pictures or map out the problem. These people would like it if you show them the problem and ask them to look at it with you and visualize solutions. You will see this thing through together. When communicating with the visual person you will want to use visual words that have to do with seeing. Visual communicators usually speak more quickly and like to sculpt or draw their ideas in space by using their hands. Try to adapt this style and do the same. It is also handy if you give them paper and pencil to jot down ideas and map out their thoughts.

Then there are the people who prefer the auditory communication mode. These people like to listen carefully to your words and their own. For this reason they usually speak more slowly and do not have distracting hand movements or sculpting. You should tell them the problem and ask them to hear you out and talk about solutions. You should be their sounding board and hear them out. For this person you should try to be more still and speak more slowly and listen carefully.

The third primary communication mode is kinesthetic. These communicators FEEL everything. They will speak very slowly if they are thinking about how they feel about the conversation or speak very quickly if they are excited. Their hand movements are usually more inward toward their hearts or bodies. It is important to them to be comfortable in the setting you choose for your conversation. You should ask how they interpret the problem and ask them to examine the pros and cons, brainstorm solutions and use their intuition to anticipate how all parties will react to the situation. Always consider and mention how they feel about things and how others will feel. Make them as comfortable as possible.

Focus on the Problem


The number one law of negotiation is to disentangle the person from the problem. We need to focus ourselves and others on the issue at hand and not on the people. Especially in an emotional situation, it is very difficult to not take things personally and to get others to do the same, but this is number 1, the most crucial! Map out and diagnose the problem, conflict, news…..whatever the substance of the Difficult Conversation is. Focus on the components of the problem, the impact of the situation, the motivations and the end results. People's egos and personalities must be kept aside as much as possible.


Simply put, if we are spending time worrying about and discussing who is to blame, we are not spending our time, energy and attention on a solution. Put aside the issue of blame and focus everyone involved on a WIN-WIN solution.


Before you tackle your Difficult Conversation you need to be very sure of what you want to achieve. What are your own motivations and what are the motivations of the other parties involved. Make a list of all of your “wants” and then highlight and segregate your needs. What does your ideal situation look like and what would be the ideal outcome of the other people involved. Determine your “bottom line” or your final position. What do you really need to achieve, where are you willing to compromise, what are you comfortable with giving up? Invent options that you can suggest when your preferred solution is not acceptable to others.


Find out everything you can about everyone involved before you decide to go ahead with the Difficult Conversation. Explore the other person's motivations, desires, needs, situation and feelings. Learn as much as you can about them and their specific predicament or circumstances. Be prepared to be empathetic and open minded as much as possible.

Listen from the inside out. Shift from “I know” to “Help me Understand.”


Make a plan and plan to stick to it. Lay out your problem, all influencing factors and people, your ideal outcome, your options or alternatives, possible problems you think you may encounter, potential objections and your answers or solutions to them. Make your plan and practice.


In conclusion, it is my belief that the relationship is the most important part of any encounter, but even more so when the encounter you are about to have is one that you believe will involve a Difficult Conversation. Most conflicts or disagreements are compounded because we get so worried or stressed about what might happen and how people may react, that we go into the encounter with a negative attitude and the expectation of an unpleasant result. Self-fulfilling prophecy kicks in and we get what we envision.

So, manage your state of mind and body, respect the relationship, focus on the issue, and do NOT avoid the Difficult Conversation! Because after all, we don't want to do the same thing over and over again and get the same undesirable result. Let's shake things up and change the way we do things and go forward with an optimistic attitude and an expectation of positive results. Master your ability to approach and triumph over the challenge of a Difficult Conversation.

Boothman, Nicholas. (2002). How to connect in business in 90 seconds or less. New York: Workman Publishing Company.

Stone, D., Patton, B., & Heen, S. (2010). Difficult conversations: How to discuss what matters most. New York: Penguin Books.

Ury, William. (1993). Getting past no. New York: Bantam.

© 2013, Cathy Byrnes
Originally published as a part of 2013 PMI Global Congress Proceedings – New Orleans, Louisiana



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