When you work with stakeholders – or even team members – you sometimes find yourself in difficult conversations you’d really rather not have. You can feel your muscles tensing and sweat rising on your forehead and palms. This won’t be pleasant.
And I’ll own up…
Nothing I can tell you will ever make it so.
But what I can do is give you tips to help you do it well, so your confidence will grow, and you feel more in control. And more importantly, when you face up to difficult conversations and handle them well, they can lead to better relationships with stakeholders, clients, and colleagues.

Broken Relationship: Time to Fix it
The advice I’ll offer you in this article follows the principles I followed when my relationship with a client had seemingly broken down completely. I decided it was worth one last shot.
The result? I managed to trigger the conditions for rebuilding the relationship. I did this by doing two things:
- Confronting the central issues for each of us
- Declaring that I wanted to be as open, honest, and generous as I could be.
So, I will take you through:
- Your Starting Point for Difficult Conversations
- Logistics for Difficult Conversations
- Difficult Conversations come down to Interpersonal Skills
- Moving Forward from Your Difficult Conversation
To begin at the beginning…
Your Starting Point for Difficult Conversations
Always start with the end in mind, and always have a plan. Isn’t that just good project management?
What Matters?
So, before you even start the conversation, ask yourself what matters most to you. Take the 12-month view, rather than how you might feel tomorrow or next week. By the way, why not a 12-year view? Because at that remove, the whole thing may seem wholly pointless!
And here’s a clue to things that won’t matter to you in 12 months. Or, at least, they really should not…
- Scoring points against someone
- Saving a few bucks
- Making someone feel guilty
- Being ‘right’
Instead, you are likely to bring your attention to a stronger relationship, great testimonials (or, at least, a secure reputation), and a long-term operational benefit.
Difficult conversations are times when you often find yourself over-speaking. You say more than you intended to say and complicate things with unnecessary detail. Knowing what matters and also what does not will help you keep the conversation focused. Look for the core of the conversation and decide to exclude anything else.
Have a Plan
Go into your difficult conversation with a plan. But not a script. That would make it impersonal and inflexible. Think about what you need to say and how to say it. Also, think about what you should avoid saying – the recriminations and blame, and also blind alleys that will distract you both from the real issues.
Also consider the process you’ll use. The next steps will help you.
Logistics for Difficult Conversations
When and where you hold your tough conversation are important – more so than the easy, everyday conversations, which can happen anywhere and anytime.
Ends of the Day
The end of the working day tends to be a good time for difficult conversations that can upset the other person – or you. It means you don’t have to return to colleagues afterward, while coping with the mental and emotional processing.
However, some conversations need you both to be at your sharpest. They are not as emotionally challenging, but they are mentally hard. Put these into the morning while you are both still at your most alert, fresh, and resilient.
The time to avoid is the end of the morning, when you are getting hungry. All the evidence suggests that people tend to rush through difficult conversations at this time, and speed over important details. If you care about getting it right, wait until after lunch.
Safe Place
Think about where to hold your difficult conversation. It needs to be a place where you will both feel safe. And as comfortable as possible. Meeting in private is ideal, but these days it pays to be aware of the risks and discomforts either of you may feel. Is there a public-private space?
You have three basic choices:
- home ground for you,
- home ground for them, and
- a neutral place.
All have advantages. The biggest factors to balance are the feeling of:
- Safety and comfort, and
- Psychological advantage
If you are going to initiate the difficult conversation, I would recommend you give up the advantage, and choose a venue that will suit them, or let the other person choose the venue.
Maybe offer to go to them. This will make the difficult conversation a little easier for them. That, in turn, will make it easier for you. If the other person feels at a disadvantage from the outset, they will be wary and defensive. They will be less open to your constructive suggestions.
Difficult Conversations come down to Interpersonal Skills
The content of your difficult conversation is important, but the wrapper is what will either form or break down the barriers to connection between you and them.
Listen Well
At all times, the one secret to hosting a good conversation (difficult or easy, tough or trivial) is your ability to listen well. And your ability to listen to silence or to incoherent struggles for understanding will be at a premium. Commit yourself to focus on the quality of your listening.
The essence of a good conversation is asking questions and listening. If you give the gift of pure attention, two things will happen.
- First, the other person will feel your respect for them, and for their perspective on the issues that have led to your difficult conversation.
- And second, in that silence of your listening, it won’t just be you who hears what they are saying. They will hear themselves, too. And sometimes, this will be for the first time.
Open Body Language
Relaxed, open, non-aggressive body language is best. This means upright, symmetric, and leaning neither too far forward (can appear aggressive) nor too far back (can look like you are dismissive). Good body language shows you are attentive and engaged.
Concentrate on good eye contact when you are delivering difficult messages. But be ready to break eye contact if they look uncomfortable. Note how hard this is. It is pretty easy to keep eye contact when you are listening: far harder when you are speaking.
Give them Time
People need time to process challenging messages. This is true, even if they were expecting them. Allow that time, without filling it with questions, comments, or a defense of what you said. This is the gift of silence.
As a bonus tip, if they ask you a question or make a point that is important to them, do not leap in and respond straight away. The message that gives is:
‘Your question was easy, your point was trivial.’
No one wants to be told that. Instead, pause and think for a couple of seconds. The silence you give, before responding, says:
‘That was a challenging question; your point was a good one, so I need to think about what you said.’
How much more respectful is that response?
Give them Space
Also, give them space to let their emotions out. It’s part of how we deal with difficult conversations. Encourage it, but not in an intrusive or nosy way. Acknowledge the feeling they share, label the feelings you observe, but resist the temptation to dive in and tell your own story:
‘I know how you feel…’
Instead, say:
‘You seem to be feeling…’
Moving Forward from Your Difficult Conversation
As your difficult conversation moves to a close, what are the tips for leaving a platform for a better future relationship?
Future Thinking
Once they have asked their questions and their emotions have cooled, turn the conversation to the future. By the way, this may need to be a second conversation if the emotional temperature gets too high. So, don’t force this.
Future thinking generates solutions. Ask questions like:
- ‘What would you like to have happen as a result of this conversation?’ or
- ‘What do you see as the next step for us?’
You can also introduce your own hopes and aspirations.
Future thinking is far more valuable than present thinking or past thinking. Present thinking focuses on the rights and wrongs of the situation, and mismatches in perceptions. And past thinking tends to focus on blame. None of this is as useful as setting the relationship on track, and working together for your mutual benefit.
Cool Down
After your difficult conversation, take some time to cool down. Never schedule another meeting straight after one of these. You may want to be on your own for a while. Or maybe you have a trusted colleague who can listen to you as you share the non-confidential aspects of what happened.
Follow-up
At the end of the day, or the next morning, make a space to reflect on what happened.
- What went well, and what did not?
- What did you learn, and how would you modify your approach if you had to do it again?
And, perhaps most importantly, what is the follow-up you need to make, to ensure that the hard work you put into your difficult conversation does not go to waste. Remember, strengthening relationships means demonstrating trustworthiness. Now would be the worst of all times to forget a promise or renege on a commitment.
What is Your Experience of Difficult Conversations?
As always, I’d love to hear about your experiences, recommendations, and questions. I’ll respond to every comment.

