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Managing Difficult Conversations: Your Guide to How to Get them Right

Managing Difficult Conversations: Your Guide to How to Get them Right

From time to time, every Project Manager will find themselves managing difficult conversations. Because it is an important part of our role. But it’s one we’d rather not have. Then, of course, at the end of a hard day or week at work, you leave work. And again, you will have to face these types of conversations at home, with friends, and in social situations.

We all know a difficult conversation as soon as it gets started.

In fact, we mostly spot it in advance.

And this triggers adversarial or defensive reactions that just make the conversation more difficult still.

In This Article…

There are ways to plan and manage a difficult conversation to vastly increase the chances that it will go well. You want the other person to listen and participate constructively. You also want a good outcome. So, in this guide, I’ll offer you some practical techniques to give you confidence when you are managing difficult conversations.

This is the subject of Chapter 8 of my best-selling book, ‘How to Speak so People Listen’. Here, I offer you:

  1. Why Some Conversations are Difficult
  2. What is a Difficult Conversation?
  3. Time is of the Essence when You are Managing Difficult Conversations
  4. Preparing for Managing Difficult Conversations
  5. A Process for Managing Difficult Conversations
  6. Tips for Managing Difficult Conversations
  7. Keeping Control of Your Emotions, during a Difficult Conversation
  8. BONUS: 15 Attitudes to Avoid

Why Some Conversations are Difficult

Managing Difficult Conversations: Your Guide to How to Get them Right
Managing Difficult Conversations: A Guide for Project Managers

We need to understand what makes conversations difficult, and find ways to manage them effectively. 

There are many facets to this, and we’ll look at them in the next section, on ‘what is a difficult conversation’. But I think the ‘why’ all boils down to one thing…

We really don’t like conflict.


  • don’t like confict with our loved ones and the people who matter most to us
  • feel it is not right, in a professional situation
  • want to avoid alienating colleagues and portential allies
  • believe it is not a productive way to resolve things
  • fear ending up on the losing side

Conflict and Fighting

Please note, by the way, that conflict is not the same as ‘a fight’. Some people like to pick a fight. They do this to either:

  1. prove themselves right (although it doesn’t – it just proves them to be the better fighter)
  2. assert their power (although it doesn’t – it just asserts a greater power in this kind of fight)

I am assuming conflict is about things that matter to the parties. And it can be creative. Respectful conflict can resolve issues and identify alternatives. Most often, these things that matter are things:

  • ideas
  • beliefs
  • principles
  • values

No wonder we feel the stakes are high and fear losing the conflict.

As with all things, if you prepare for conflict and follow a sound process, you give yourself the best chance of success.

What is a Difficult Conversation?

Strong emotions are the first thing that comes to mind in making a conversation difficult.  This is usually because we know that there are important consequences to getting it right or wrong.  As a result, one particularly strong emotion can dominate: fear.

We fear the consequences: succeed or fail.

This also gives us another contributing factor: uncertainty.  The high stakes and emotions of a difficult conversation make it hard to predict what will happen.

And there’s another common factor: baggage.  We pick up emotional and interpretational baggage along our journeys.  These conflict with other people’s baggage.

So, let’s summarize

Here are eight things that can lead to a difficult conversation:

  1. Important Consequences
  2. Complex Issues
  3. Uncertainty
  4. Strong Emotions
  5. Fear
  6. Polarised Disagreement
  7. Emotional Baggage
  8. Interpretational Baggage

Time is of the Essence when You are Managing Difficult Conversations

Difficult conversations go wrong at two specific times:

  1. When you rush to get on with it
    Because you are scared, you are a decisive person of action, or you want it over and done with, or
  2. When you keep putting it off and off
    Because you are scared, you have not prepared, or you hope the problem will go away on its own.

Chose your time carefully

Hold your difficult conversation when:

  • you have prepared,
  • the other person is ready,
  • you can be somewhere you will both feel secure, and
  • you will have plenty of time to do it right.

If you put it off for too long, you could:

  • mislead the other person, by giving the impression that there is no problem
  • deny them the chance to raise the issues they want to address
  • damage the morale or productivity on your project

And choose the right place, too

Your basic turf options are: home, away, or neutral territory. Let’s look at each.


Calling people to your desk, or into your office shifts the balance of power to your side. Often this shift will unbalance the conversation, and make it hard for the other person to relax, and respond productively. Almost certainly, they will feel defensive from the start.


Likewise, going to where the other person is comfortable will make it easy for them. If you have prepared well, and are confident, this can be a very positive gesture. If not, you will feel at a disadvantage.

Neutral Territory

Often, your best approach will be to hold the meeting in a neutral place. The most common option is a meeting room. There, you can sit next to each other without the desk as a barrier. A good orientation is on two sides of a corner.

Here is a video on seating positions, from our sister YouTube channel, Management Courses…

Also consider somewhere like a hotel lobby or coffee shop. But you do need to consider the implications of this choice:

  • for privacy and confidentiality
  • within the culture you’re working in

Preparing for Managing Difficult Conversations


In complicated conversations, things that often seem like our priorities should not be. These are things like:

  • being right
  • ‘winning’
  • getting it over with

Take time in your preparation to think about what your priority really is. And keep that at the forefront of your mind throughout your preparation, and then during your difficult conversation. Maybe your priority is:

  • maintaining your relationship
  • being kind
  • finding a solution
  • telling the truth…

Often, in the heat of your difficult conversation, it will be easy to forget just how much the relationship matters. If that happens, you can easily slip into disrespectful language… or worse. And once that has happened, there may be no easy way back.

Know your outcome for the conversation

Before you enter into any difficult conversation, you need to know your range of acceptable outcomes. This should run from your ideal goal, down to your minimum acceptable outcome.

It’s vital to keep your goals realistic. If you set your expectations too high, it will make an already difficult conversation into a lost cause.


Take a long view of the issue you are dealing with. You will find managing difficult conversations easier if you prepare based on a sense of how things need to turn out in 6 months – or maybe even in 6 years. This will allow you to anticipate short-term problems and setbacks with equanimity.

Anticipate emotional reactions

Over the course of a long project management career, you’ll get them all: frustration, bitterness, arguments, blame, denial, tears.

You can’t control the other person’s responses. But you can foresee them, and prepare for them emotionally. That way, when they come, you’ll be able to deal with them effectively. We’ll look at controlling your own emotional responses later in this article.


Just one (sometimes small) step up from a difficult conversation is Conflict.

We have lots of great resources to help you;



And, for Project Managers who want to really get to grips with conflict…

Dealing with Conflict in Projects
Dealing with Conflict in Projects
A Practical Introduction to Conflict Management for Project Managers.

Conflict is an inevitable part of project life.

And it’s not always bad.

But, often, it is. 
It can be stressful, harm productivity, spoil working relationships, and lead to damaging behaviors.

And fixing it is down to you…

A Process for Managing Difficult Conversations

As with every challenging task, you’ll find managing difficult conversations easier if you have a clear process to follow.

This process will help you to:

  • Take responsibility for managing the process, your emotions, and your actions
  • Keep working to ensure you both feel safe enough to speak openly
  • Constantly check mood and progress

The seven step process for a difficult conversation that I describe in ‘How to Speak so People Listen’ is:

  1. Figure out what really matters
    See ‘Priorities’ above.
  2. Create safety
    The other person will feel safe when you show the four Cs:
    •  Confidence
    •  Control
    •  Compassion
    •  Collaboration
  3. Set out the truths of your situation and of what has gone before
    Create a shared narrative of what has led to where you both are. Own up to any mistakes you have made and look for things you can both agree on.
  4. Invite a Deep Dialogue
    Invite the other person to share their perspectives and listen to yours in a process that is honest. You must also both commit to listen to the other person carefully, before commenting.
  5. Story-telling
    Each of you needs to tell your story as you perceive it. And, while you do, the other listens.
  6. Share feelings
    Now, each of you must say what you feel about what you have heard.
  7. Future Thinking
    Have you noticed that when we focus on the past, we get hooked on blame? And when we focus on the present we get hooked on right and wrong? When you focus on the future, your attention turns naturally to options and problem solving – a far more creative mindset.
Managing Difficult Conversations - Process
Managing Difficult Conversations

Tips for Managing Difficult Conversations

Having a process is all very well. In fact, it’s very useful. But for managing difficult conversations, what you also need are some practical tips.


A deep dialogue requires intent listening. Don’t worry about what you will say next – turn over your whole self to hearing what the other person says. If you find your mind wandering from your focus on them, bring it back.

When they stop speaking, you’ll need time to frame your response. Take the time you need. Be comfortable with silence

More resources about listening…

The Power of Listening: Listening Skills 101
The Power of Listening
Communication makes up around 80 percent of the work of any project manager. This is Listening 101.

Communication makes up around 80 percent of the work of any manager and leader.

This makes listening your single most important skill. So in this course, we’ll look at why this is true, and seek to understand what listening really is.

But at the core of this powerful course, we’ll learn something nobody ever teaches at school – despite being so valuable… How to really listen.

And we’ll close by tackling the three main challenges every listener faces.


Adopt an attitude of curiosity. Be keen to learn what they think and how they feel about their own perceptions.

You may not agree with the way they see things, but what is 100 per cent true is that this is their experience. Be respectful of that.


Acknowledge what you have heard, and also their courage in speaking their truth. Too often conflict escalates for the simple reason that we don’t think the other person has heard and valued what we have been saying.

Perhaps the most important need for a human being is to be heard.

And, not But

‘You make a good point, but…’

See how that feels.

The ‘but’ pretty much negates everything you’ve just said. Instead, try:

‘You make a good point, and…’

Blame is for God and Small Children’

This quote – taken from the film Papillon – is one of my favorites. It’s a crucial thing to remember during a difficult conversation.

Blame is for God and Small Children
Blame is for God and Small Children

Give bad news quickly

Bad news doesn’t keep. Don’t pretend you can diminish its impact with small talk. Get on and say what you need to say. Be clear and precise, without being blunt and brutal.

For many people, giving feedback is a Difficult Conversation

But, giving feedback is a crucial part of your leadership role, as a Project Manager. As a result, we have valuable resources for you:

Keeping Control of Your Emotions, during a Difficult Conversation

The hardest thing for most of us is nonetheless crucial: you need to stay in control of your emotional state.

So, a particular valuable area of study for project managers is that of Emotional Intelligence.

We also have a more in-depth article: Emotional Intelligence: The Secret to Being an Excellent Project Manager.

If you need to, ask for breaks

This is not about hiding your feelings; it is about being able to follow the process, to play your part fully, and stay respectful to the other person.

Here are some more tips:


If you start noticing yourself getting nervous, tense, or angry, try to focus on your breathing.

Pay attention to the air going into and out of your lungs. Feel it pass through your nose and down into your chest. Concentrate on breathing deeply, from your abdomen. This will distract your attention from the physical signs of emotion. So, it will help keep you calm and centered.


When you sit still, emotions get pent up, making you agitated. You start to fidget, and so betray a lack of confidence, annoyance, or upset.

Stand up. And walk around. Any movement will help to calm your emotional responses and activate the thinking part of your brain.

If you are sitting at a table, you may worry about suddenly standing up. So, you might say something like:

‘I need a bit of a stretch some. Do you mind if I get up and walk abound a bit?’


Remind yourself that the discomfort you are feeling, and any lack of confidence are temporary. Or maybe that your uncertainty can be countered by certainty in your preparation and competence.

Repeating some simple phrases in your head can have a big impact. That’s why telling yourself that things are going wrong, or that we are useless, can create such a big dip in your confidence.

Instead, try phrases like:

  • ‘This is a stage. It’ll be over soon.’
  • ‘I’ve prepared well. I’m ready for the set-backs.’
  • ‘I have lot of experience. I can handle this.’
  • ‘This isn’t about me. I’m the professional messenger.’


One way to dissipate a strong emotion is to analyze it. Give it a name. Think about what triggered it. Recognize it as a temporary guest.


If all else fails, suggest taking a break. If you are getting emotional, there’s a good chance the other person is too. So, they will probably also welcome a break.

If you need to, ask for a comfort break, or suggest getting a drink.

15 Attitudes to Avoid

If I am absolutely honest (and why wouldn’t I be?) these attitudes to avoid reflect a difficult conversation from my past that went badly.

I came up with a list of fifteen things (and memory is not what it used to be). And these are probably just the ones that rang most true when I sat down to write this!

  • Exaggerating:
    ‘always’, ‘every’, ‘never’ or ‘none’
  • Using dangerous words like:
    ‘why’ and ‘but’
  • Prejudging:
    ‘you are going to say…’
  • Assuming:
    ‘what you meant was…’
  • Judging:
    ‘you should have…’
  • Blaming:
    ‘this was your fault’
  • Accusing:
    ‘It was you who…’
  • Criticizing:
    ‘you are over-reacting’
  • Over-reacting:
    ‘we’ll never be able to get past this’
  • Digging up dead bodies:
    ‘this is just like last time’
  • Threatening:
    ‘if you don’t…’
  • Sarcasm:
    ‘that’s just the way to impress me’
  • Name-calling:
    ‘you’re impatient’
  • Interpreting:
    ‘what you really mean is…’
  • Recommending:
    ‘if I were you…’

What Do You Think?

Have you had experience managing difficult conversations? If you have, please share your thoughts with our community, below. We love hearing from you and will reply to every comment.

More Resurces

Most of these come under the category of ‘miscellaneous, but related’:

About the Author Mike Clayton

Dr Mike Clayton is one of the most successful and in-demand project management trainers in the UK. He is author of 14 best-selling books, including four about project management. He is also a prolific blogger and contributor to and Project, the journal of the Association for Project Management. Between 1990 and 2002, Mike was a successful project manager, leading large project teams and delivering complex projects. In 2016, Mike launched OnlinePMCourses.

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