Let’s be honest, no one enjoys having difficult conversations.
Whether it’s addressing poor performance, correcting behaviour, or challenging an attitude, these conversations often make leaders uncomfortable. And while avoiding them feels easier in the moment, it always costs more in the long run, in time, trust, and team performance.
If you’ve ever known that something needed to be said but found yourself procrastinating or hoping the issue would “sort itself out,” you’re in good company. Most leaders have been there.
In fact, in my experience, avoiding tough conversations has become an organisational pandemic.
Why Leaders Avoid Difficult Conversations
Leaders often avoid difficult conversations for three reasons:
- Fear of conflict – worrying that emotions will escalate or damage the relationship.
- Lack of confidence – not knowing the right words or approach.
- Avoidance of discomfort – choosing the short-term comfort of silence over the temporary tension of honesty.
Unfortunately, this avoidance can quietly damage your culture. Problems fester, performance declines, and resentment grows, not just with the person involved but across the team.
Sometimes leaders even “solve” the problem by transferring the employee, promoting them out of the way, or hoping someone else will deal with it. But sooner or later, that same problem circles back.
The truth is, having the conversation is the only real solution.
And it doesn’t have to be painful.
Assess the Situation with the D.I.V.E. Criteria
The D.I.V.E. acronym helps you identify whether a conversation needs preparation and planning.
D.I.V.E. stands for:
- D – Divisive: Could this cause tension or disagreement?
- I – Important: Is it critical to team performance or culture?
- V – Vulnerable: Could someone feel exposed or criticised?
- E – Emotive: Might emotions run high?
If any of these apply, you’re about to have a difficult conversation and you’ll need to prepare thoughtfully.
The following four-step process will help you manage that discussion with empathy, clarity, and control.
Step 1 – Set the Context
Before you speak, get clear on what you want to achieve.
Ask yourself:
- Why is this conversation important?
- What outcome am I aiming for?
- What common goals do we share?
Starting with context gives the conversation purpose and balance.
If it’s a performance issue, begin by acknowledging what the person does well before raising what needs improvement. Avoid generalisations like “you’re not doing a good job.” Instead, be specific and factual.
This helps the other person feel respected and less defensive, setting the tone for a more constructive discussion.
Step 2 – Keep It Real
Facts first, opinions second.
The more specific and evidence-based you are, the smoother the conversation will go. Reference observable behaviour, not assumptions or rumours.
If it’s appropriate, acknowledge any ways you may have contributed to the issue. Showing vulnerability builds trust and encourages the same openness in the other person.
This step is about being real, not ruthless. You’re addressing the issue, not attacking the person.
Step 3 – Focus on Outcomes
A difficult conversation shouldn’t end with criticism — it should end with clarity.
Invite the other person into the solution. Ask questions like:
- “What outcome would work best for both of us?”
- “What could we do differently next time?”
Collaborating on the solution turns a defensive situation into a cooperative one. It builds ownership, accountability, and buy-in, all essential for long-term improvement.
Step 4 – Record Your Actions
Finally, document what was agreed upon.
This step ensures accountability and clarity for both sides.
Recording the outcomes also gives you a framework for follow-up, which shows your commitment to supporting their success, not just enforcing compliance.
From Difficult to Constructive
When you follow this structure, tough conversations can transform from awkward and emotional to honest and productive.
By combining context, evidence, shared outcomes, and clear actions, you remove defensiveness and open the door to genuine dialogue.
The result? Better relationships, improved performance, and a stronger culture of trust.
Practice Makes Progress
Of course, even the best structure takes practice. But think of the alternative, avoiding the conversation, tolerating poor performance, or letting frustration simmer.
Preparation is what separates an uncomfortable conversation from a constructive one. And once you master this skill, you’ll find it strengthens your leadership, credibility, and confidence.
Building Confidence in Difficult Conversations
We help leaders develop the confidence and skills to navigate difficult conversations through our leadership and culture development programs.
Our approach combines behavioural science, coaching frameworks, and communication techniques that transform discomfort into constructive dialogue.
If you’d like to explore how to build this capability in your team, get in touch:
📞 1300 551 274
📧 team@teamfocusplus.com
🌐 teamfocusplus.com
Or call me directly: Ross Judd – 0412 490 250
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