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Managing Difficult Conversations: A Guide for Project Managers

Managing Difficult Conversations | A Guide for Project Managers

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 conversation 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. This triggers adversarial or defensive reactions that just make things worse.

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 will 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.

PMI Talent Triangle - Leadership

Why Some Conversations are Difficult

Managing Difficult Conversations: A Guide for Project Managers

Managing Difficult Conversations: A Guide for Project Managers

We all know a difficult conversation as soon as it starts.

In fact, we mostly spot it in advance.

And that triggers an adversarial or defensive reaction which does nothing but make the conversation more difficult still.

We need to understand what makes conversations difficult, and find ways to manage them effectively.  As with all things, if you prepare for it and follow a sound process, you give yourself the best chance of success.

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

What is a Difficult Conversation?

Strong emotions are the first thing that comes to mind in making 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 is 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.


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.

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 god orientation is on two sides of a corner.

Also consider somewhere like a hotel lobby or coffee shop. But you do need to consider the implications of this choice within the culture you’re working in.

Preparing for Managing Difficult Conversations


In complicated conversations, what 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
  • 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 dis-respectful 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 and already difficult conversation into a lost cause.


Take the 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 6 years. This will allow you to anticipate short-term problems and set-backs with equanimity.

Anticipate emotional reactions

Over the course of a long project management career, you’ll get them all: 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 tey 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 Step up from a Difficult Conversation

…is Conflict

Are you prepared for it?

How confident are you that you can deal with it well?

Dealing with Conflict in Projects

Learn more about our video training in dealing with conflict in projects by clicking the button.

Get started now!
Find out about conflict mangement training.

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
    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 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

A process is all very well – very useful, in fact. 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


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

And, not But

‘You make a good point, but…’

See how that feels. 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.

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.

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 tips:


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

Pat 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 well 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 is 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 abig impact. That’s why telling ourselves that things are going wrong, or 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 great 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 welcome a break too.

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). Here are just six – 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…”
  • Criticising:
    “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 are impatient”
  • Interpreting:
    “what you really mean is…”
  • Recommending:
    “if I were you”

What Do You Think?

Have you had experience of 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.


Just One Step up from a Difficult Conversation

…is Conflict

Are you prepared for it?

How confident are you that you can deal with it well?

Dealing with Conflict in Projects

Learn more about our video training in dealing with conflict in projects by clicking the button.

Get started now!
Find out about conflict mangement training.

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 13 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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