Difficult Conversations Workshops
Work through disagreements with clear, kind conversations you can feel proud of.
Difficult conversations made easier
Difficult conversations are the ones that can tie you up in knots before they’ve even happened.
It’s easy to worry that challenging someone will feel confrontational or damage a good relationship.
We help you handle these conversations with clarity, kindness and confidence.
Difficult Conversations overview
What will I learn?
This workshop is for you if:
- You believe in your people and what they’re capable of
- You’re committed to helping them grow and develop
- You want to improve how your team communicates and works together
- You’re ready to invest in doing things better day to day
You will learn to:
- Listen without interrupting
- Observe without judgement
- Find common ground
- Understand the difference between intent and impact
- Communicate with clarity and kindness
- Ask questions that uncover the truth
The workshop includes:
Pre Workshop:
Pre Thinking
Reflection exercise to consider the quality of your relationships and the honesty of your interaction.
Session 1:
Know yourself to lead yourself
Understand what triggers you and understand how to work with those feelings to facilitate effective conversations.
Session 2:
Creating connection
We need to “Connect before you direct”. Understand how to create connection and trust through curiosity and appropriate vulnerability.
Session 3:
Structuring the conversation
Facilitate the conversation using the 5 step model. Keep your colleague resourceful by demonstrating empathy and share your message in a clear and kind way.
Session 4:
Managing emotional outbursts
Maintain clarity of your objective so that you don’t get railroaded by emotional outburst either from yourself or your colleague.
Session 5:
Practice Sessions
Practice sessions to celebrate what you do brilliantly and should keep repeating and pointers about the couple of things that will lift your performance.
Session 6:
Creating a culture of honest conversations
Ideas on how to make this way of interacting with each other all part of the culture.
Session 7:
Implementing this back in the workplace
What are the smallest changes that will make the biggest impact as you go back into the workplace.
Post Workshop:
Embedding the learning
Behaviour change is about incorporating new habits. A learning platform to support and hold you to account on your new habits.
What changes will you see after the workshop?
Individual changes
Delegates learn to step into difficult conversations with confidence, turning differences into productive dialogue that strengthens relationships and results.
- Make difficult topics easier to talk about
- Create space for open, meaningful conversations
- Approach conversations with curiosity, not judgement
Organisational changes
Teams and organisations perform better when people feel safe to speak openly and work through differences.
- Less groupthink
- Better, faster decisions
- Higher engagement as people feel seen, heard and valued
Difficult Conversations Workshops: FAQs
From avoiding the conversation to having it well
Most managers know that difficult conversations are part of the job. Knowing that doesn’t necessarily make them easier to have.
At Juicing the Lemon, we often find that the challenge isn’t simply knowing what to say. Managers are also managing their own discomfort, anticipating the other person’s reaction and trying to balance being honest with preserving a good working relationship.
Sometimes that means conversations are softened, postponed or avoided altogether. The irony is that what begins as an attempt to be kind can allow a relatively small issue to become a much bigger one.
Our approach is built around Care + Dare.
Managers need enough Care to create connection, listen properly and understand what may be happening for the other person. And they need enough Dare to say what needs to be said, hold appropriate standards and address issues before they grow.
We help managers become more intentional about the conversations they have:
Prepare yourself → Connect before you direct → Get curious → Say what needs to be said → Listen for what you don’t yet know → Agree what happens next → Follow through.
The aim isn’t to make every difficult conversation comfortable.
It’s to help managers create the conditions in which honest conversations can happen well.
Why do managers find difficult conversations so difficult?
Often, it isn’t because managers don’t know what they need to say.
It’s because they’re anticipating what might happen when they say it.
What if the person becomes defensive? What if they get upset? What if they disagree with me? What if I damage the relationship? What if I don’t handle it well?
That anticipation can affect our behaviour before the conversation has even started.
Some managers become more direct and task-focused when they’re uncomfortable. Others soften the message, over-explain, talk too much or put the conversation off altogether.
That’s why we think self-awareness matters.
Before preparing the other person’s message, it can be useful to ask:
What is this conversation bringing up in me?
Am I anxious about conflict? Frustrated by what’s happened? Worried about being disliked? Have I already decided why the person behaved as they did?
Insights Discovery® can provide a useful lens for exploring some of our natural preferences and how they may show up when we’re under pressure. But we wouldn’t use someone’s colour preferences to predict exactly how they will behave.
The important thing is noticing your own starting point and becoming more intentional about what the conversation needs from you.
Before you can manage the conversation, it helps to understand what the conversation is triggering in you.
Does avoiding a difficult conversation actually make you a kinder manager?
Not necessarily.
There are times when choosing not to raise something is absolutely the right judgement. Someone may be under unusual pressure, the issue may genuinely be insignificant, or there may be a better time to talk.
But we encourage managers to ask themselves a more challenging question:
“Am I choosing not to raise this because it’s genuinely the right thing for this person right now—or because having the conversation would make me uncomfortable?”
The distinction matters.
In our workshops, managers often recognise occasions when they have allowed something to go because they believed they were being kind.
This might be poor timekeeping, a missed commitment, a drop in attention to detail or behaviour that doesn’t quite meet the team’s expectations.
At first, it can feel generous to overlook it.
But if it continues, the manager can inadvertently create a new expectation: this is okay here.
We saw a real penny-drop moment around this with managers at The Best Connection. In discussions about balancing Care and Dare, managers recognised the consequences of allowing standards to slip and how much harder it can then be to bring them back up.
That’s why we talk about Care + Dare.
Care without enough Dare can become avoidance. Dare without enough Care can become confrontation.
Being clear about something that matters isn’t necessarily unkind.
Sometimes clarity is one of the kindest things a manager can offer.
Why is it better to have several small conversations than one big difficult conversation?
Because small issues have an unfortunate habit of growing when nobody talks about them.
Imagine someone is five minutes late.
The manager lets it go.
It happens again. They let it go again.
Perhaps a deadline slips. A commitment isn’t honoured. Attention to detail isn’t quite where it needs to be.
Individually, none of these things feels significant enough to warrant a “difficult conversation”.
So the manager keeps letting them pass.
Eventually, however, they’re no longer responding to one incident. They’re frustrated by a pattern.
Now a bigger conversation happens.
And the employee may quite reasonably be thinking:
“Why are you suddenly making such an issue of this? You’ve never said anything before.”
The manager may feel the employee should have known. The employee may feel the manager has suddenly changed the rules.
Neither is a great starting point for a productive conversation.
This is something managers at The Best Connection explored when considering the impact of too much Care and insufficient Dare. Once standards have been allowed to drift, restoring them can feel much more challenging.
We’d much rather help managers become comfortable having small, respectful conversations early.
Not every piece of feedback needs a meeting room, an agenda and a serious face.
Sometimes it’s simply: “Can I just pick something up from earlier?”
Then deal with it while it’s still small.
Small conversation now. Bigger conversation avoided later.
How do you prepare for a difficult conversation without scripting it?
Preparation matters. But preparing doesn’t mean writing the perfect speech.
In fact, over-scripting can sometimes make things harder because the manager becomes focused on delivering what they’ve rehearsed rather than listening to what actually happens.
At JTL, we’d encourage managers to prepare around four areas.
Me. What am I bringing into this conversation? How am I feeling? What assumptions have I made? What am I worried about? What shadow might I cast?
Them. What might be happening for this person? What do I know—and what am I assuming? What might they need from me to stay engaged in the conversation?
The issue. What have I actually observed? What is the impact? What expectation or standard matters here? What needs to be different?
The conversation. What do I need to understand as well as communicate? What questions might help? What would a useful outcome look like?
That first area is easily overlooked.
In one of our workshops with The Best Connection, a delegate reflected on how relatively small changes in their own management behaviour could affect how a team feels and performs. We used that to explore the shadow of the leader—the helpful and unhelpful impact a manager can have on the people around them.
That shadow comes into difficult conversations too.
If I arrive frustrated, judgemental or determined to prove I’m right, that is likely to influence the conversation.
Preparation therefore isn’t just: “What am I going to say?”
It’s also: “What am I going to bring into the conversation?”
Why do the first few minutes of a difficult conversation matter so much?
Imagine your manager says: “Have you got five minutes? I just need to have a chat with you.”
What happens in your head?
For many people, the internal conversation begins immediately.
What have I done? Is something wrong? Am I in trouble?
The manager may think the difficult conversation hasn’t started yet.
For the other person, it already has.
That’s why we encourage managers to think carefully about the opening few minutes.
At JTL, we talk about connecting before you direct.
That doesn’t mean spending ten minutes making awkward small talk before delivering bad news. And it certainly doesn’t mean disguising the purpose of the conversation.
It means creating enough connection and psychological safety for the other person to remain engaged, listen, think and contribute.
Be clear about why you’re talking. Be human. Check in. Don’t assume you know what has happened before you’ve heard their perspective.
And then listen.
One of the themes that comes through strongly in our workshops is that the quality of our listening can affect the quality of what another person is prepared to tell us.
If someone feels judged from the outset, we may get the safe answer.
If they feel genuinely listened to, we have a better chance of understanding what’s really happening.
That doesn’t mean abandoning the standard or agreeing with everything we hear.
It means creating the conditions for an honest conversation.
The difficult conversation starts before you’ve delivered the difficult message.
How can you be clear and direct without making someone unnecessarily defensive?
Start by separating two things: the standard and the way you communicate it.
The standard doesn’t necessarily need to change from person to person.
If everybody needs to be ready for work at 9am, that’s the expectation. If a particular level of accuracy is required, that’s the expectation. If a commitment has been made, it’s reasonable to expect it to be honoured.
But different people may need different things from the conversation.
This came up very clearly in our work with managers at The Best Connection. One delegate questioned whether adapting how they managed different people meant they were treating them differently. The discussion highlighted an important distinction: expectations can remain consistent while the way we approach conversations varies according to what different people need.
Insights Discovery can help managers become more thoughtful about this.
One person may appreciate getting quickly to the point. Someone else may want more context. Another may need time to think before responding.
These are possibilities to explore, not rules determined by someone’s colour preference.
So we don’t teach: “This is how you have a difficult conversation with a Fiery Red.”
We’d much rather managers ask:
“What does the person in front of me need from me to hear this clearly?”
Then flex where appropriate without losing the message.
Flex the style. Hold the standard.
How does the “shadow you cast” affect a difficult conversation?
Managers don’t only influence people through the words they use.
They also communicate through tone, pace, facial expression, body language, assumptions, attention and the emotional state they bring into the room.
That’s part of what we mean by the shadow you cast.
The shadow can be helpful.
A manager who is calm, curious, clear and genuinely prepared to listen can create very different conditions from someone who arrives visibly frustrated and already convinced they know what’s happened.
The shadow can also be unhelpful without us realising it.
That’s why preparation should include questions such as:
What am I feeling about this person or situation?
Have I already decided why they behaved this way?
Am I genuinely curious about their perspective?
Am I trying to understand—or simply waiting for my turn to speak?
What might my tone and body language communicate before I’ve even delivered the message?
In our Best Connection workshop, one delegate described how a slight tweak in what they did could affect how their team felt and performed. That led directly into a discussion about the leader’s shadow and how it can be both helpful and unhelpful.
Difficult conversations make that self-awareness particularly important because both people may already be experiencing heightened emotion.
You don’t just bring your message into a difficult conversation. You bring yourself.
What should you do when someone becomes defensive, upset or angry?
First, don’t assume that emotion means the conversation has gone wrong.
Difficult conversations can matter to people.
They may feel embarrassed, disappointed, misunderstood, angry or worried about the implications of what they’re hearing.
Managers sometimes become uncomfortable with that emotion and immediately try to make it disappear.
They soften the message. Talk too much. Rush towards a solution. Reassure before they’ve understood. Or become defensive themselves.
Instead, stay with the conversation.
Pause.
Listen.
Acknowledge what you’re seeing without assuming you know exactly how the person feels.
Ask questions.
“What’s your perspective on this?”
“What am I missing?”
“Talk me through what happened.”
Then listen for what you don’t yet know.
You may discover information that genuinely changes your understanding of the situation.
Or you may understand the situation better while still needing to hold exactly the same standard.
Both are possible.
And sometimes part of our role as a manager is to help someone see an impact they weren’t previously aware of. Feedback can act as a mirror: this is what I’m observing, and this is the effect it is having.
The aim isn’t to win the conversation.
It’s to keep both Care and Dare present: enough Care to listen and understand, and enough Dare to stay with the issue that needs addressing.
You can acknowledge someone’s feelings without losing the message that needs to be heard.
How do you make difficult conversations part of everyday management rather than something managers dread?
Have more conversations while they’re still small.
The more unusual feedback is within a team, the more significant it can feel when a manager suddenly asks for “a chat.”
But when managers regularly talk with people about expectations, commitments, impact, what’s working and what could be better, honest conversations become a more normal part of working together.
That doesn’t mean constantly criticising people.
It means creating a culture where noticing something and talking about it isn’t automatically interpreted as confrontation.
We also encourage managers to practise small behavioural changes rather than waiting to become completely confident.
At JTL, we call this the 5% Flex.
Your 5% Flex might be:
Raise something sooner rather than waiting.
Ask one more question before reaching a conclusion.
Listen for a little longer before responding.
Be clearer about the standard you’re expecting.
Notice when you’re softening a message because you’re uncomfortable.
Check what the other person has understood.
Follow through on what you both agreed.
These are small changes, but practised consistently they can change the quality of everyday management conversations.
And there is a useful paradox here.
The better managers become at having small, honest conversations, the fewer enormous “Difficult Conversations” they may need to have.
The goal isn’t to become brilliant at big difficult conversations. It’s to stop so many conversations becoming big and difficult in the first place.
When is a Difficult Conversations workshop not the right solution?
A Difficult Conversations workshop can help managers become more self-aware, prepare more effectively, listen better, communicate with greater clarity, respond to emotion and practise conversations they may otherwise avoid.
But not every difficult management situation is caused by poor conversation skills.
If roles and expectations are fundamentally unclear, managers lack the authority to act, workloads are unsustainable, organisational processes contradict the behaviour being asked for, or senior leaders routinely tolerate behaviour that other managers are expected to challenge, a conversation-skills workshop won’t remove those problems.
There are also situations involving serious conduct, grievance, safeguarding or formal performance processes where managers need appropriate HR guidance and organisational procedures—not simply a better conversational technique.
And occasionally the issue is simpler.
The manager already knows what conversation they need to have and knows how to have it.
They’re just not having it.
In that situation, the development need may be less about skill and more about confidence, accountability or managerial expectation.
That’s why at JTL we start by understanding what managers are finding difficult, what conversations aren’t happening and what needs to be different afterwards.
Sometimes a workshop is exactly the right intervention. Sometimes practice, coaching or follow-up support needs to sit alongside it. And sometimes the organisation needs to address something else first.
The starting point should be the conversation problem you’re trying to solve, not the workshop you’re trying to buy.