Mastering the Art of Difficult Conversations
AKA: Why the Conversation You’re Avoiding Is Quietly Running Your Team
There are two types of leaders:
Those who engage in difficult conversations
Those who are currently avoiding one
If you’re in the second category, you already know the signs:
You’ve rewritten the opening line in your head six times
You’ve scheduled the meeting… and then moved it to next week
You’ve taken up an inordinate amount of time at the dinner table discussing this person
You’ve told yourself, “Let’s just see if this improves on its own”
It won’t.
What it will do is spread like glitter at a craft table. Subtle at first. Then suddenly everywhere.
Because here’s the truth most leaders learn the hard way: conflict doesn’t disappear when you avoid it. It just becomes less visible and more expensive.
Difficult Conversations vs. Conflict (They’re Not the Same Thing)
Let’s clarify something important:
A difficult conversation is an event.
Conflict is a condition.
You can have a difficult conversation that resolves conflict. Or you can avoid a difficult conversation and allow conflict to quietly embed itself into your team.
Conflict can show up as:
Public agreement in meetings followed by private disagreement in side conversations
Subtle disengagement or creeping apathy
A growing sense that “something’s off,” but no one is naming it; or
Grin F*cking: smiling to your face with absolutely no intention of doing what you’ve said
Then comes the moment when someone says: “Are we ever going to talk about this?”
That moment is not the start of conflict. That’s how we learn that conflict has already been there for a while.
Why Leaders Avoid Conflict (Even Smart, Well-Meaning Ones)
Let’s not pretend this is a skill gap that a LinkedIn Learning course can solve. This is an interpersonal issue, a relational issue, an emotional issue, or a support issue. Avoidance is human.
We avoid conflict because:
We want to preserve relationships
We don’t want to escalate tension
We’re unsure how the conversation will land
We’re hoping the issue will self-correct
In other words: We’re optimizing for short-term comfort over long-term effectiveness.
And look, that’s understandable. But short-term comfort will lead to long-term dysfunction and undermine the team’s respect for its leader.
I’m guilty of this. There was a woman on the team I led – let’s call her Maria (because that’s her name) – who pretended to be a team player only to disregard all the team’s norms and do whatever she wanted. She would try to secretly build a coalition to work against the direction we set. She even bad-mouthed me to other leaders in the organization. And I ignored that behavior out of fear, though I masked that with an outward expression of maturity and superiority. Guess what happened? The rest of the team lost respect for me because I allowed such horrible behavior to go unaddressed. They started to question my ability to lead effectively, and the goals and vision I had set began to unravel.
In other words: I screwed up.
The Cultural Cost of Avoidance
When leaders avoid difficult conversations, teams don’t become more harmonious. They might become more polite – which means less honest, less accountable, or less aligned – but they don’t generally improve their performance. If you look to the Five Dysfunctions of a Team assessment, it will show exactly that: teams that can’t engage in healthy conflict can’t effectively debate ideas, which means they’ll end up with weaker decisions, lower levels of commitment, and a quiet erosion of trust. Oh, and shittier results.
Avoidance doesn’t protect culture. It redefines it, and not in a good way.
Where Assessments Actually Help (And Why They’re Misunderstood)
The real value of leadership assessments, personality assessments, and behavioral assessments is not the label they assign to team members; it’s the conversations they enable team members to have.
They give leaders language to understand:
How people experience conflict
How they react under pressure
What they need to feel in order to engage productively
Tools like the Enneagram are incredibly useful here. The Enneagram can help us understand if we tend to move toward conflict or away from it. It will help us know if we are more likely to get direct, emotional, or withdrawn under stress. It can also reveal why we might be avoiding conflict all together. The value here is not the number or the color, it’s knowing our patterns and our defaults. If we are unaware of our patterns and defaults, we’re not able to choose our response, we’re victims of it.
Similarly, the EQ-i emotional intelligence assessment can help us build the emotional capacity to stay grounded when the situation is elevated, to regulate our reactions when stress is high, to listen without defensiveness. With lower levels of emotional intelligence, difficult conversations tend to go off the rails: they become too aggressive, they stay too vague, or they are washed over with fake niceties, none of which are at all helpful.
Communication breakdowns – a common cause for conflict – can also be better solved for with the understanding that assessments give us. Tools like the DiSC assessment and the Predictive Index can help leaders understand:
Why some people want direct, bottom-line conversations
Why some people need more context and rationale than others
Why some people need relational framing
Why some people rely on data and facts and figures to move forward
If you deliver the same message the same way to everyone, you’re not being consistent, even if you think you are. You’re actually being ineffective. Ineffective at scale.
Engaging in the Hard Conversation
A successful difficult conversation is not about being perfect. In fact, it’s the humanity within the conversation that actually moves people forward.
To engage in a difficult conversation, prioritize four elements:
1. Be Clear. “Here’s what I’m seeing.”
1. Be Specific. “This is the behavior and the impact.”
2. Be Curious. “I’d like to understand your perspective.”
3. Be Direct. “Here’s what needs to change.”
Don’t try to wrap the conversation in five extra layers of politeness, which leads to uncomfortable levels of discomfort. Don’t try to over-explain, which causes more confusion.
In the words of Brene Brown: clear is kind, unclear is unkind. Stay kind.
Now for the bad news: even when you do everything “right,” difficult conversations will still feel, well, difficult. Your voice might get slightly more formal. You might overthink your opening line. You might replay the conversation afterward while making coffee.
All normal. And this means you care. If you care enough to have the conversation, you are signaling to this person that they are important and that the team is important, as well. That is a huge first step in and of itself. Stay human – name it. Saying “this is hard for me, too” is not weakness, it’s humanity. It’s connecting. It’s building the relationship. And the irony is that saying it out loud actually makes it less hard. Weird, I know. Try it.
Because leadership is not about eliminating discomfort. It’s about using it productively. The conversation you’re avoiding is not separate from your leadership. It IS your leadership. Every time you address an issue directly, stay grounded in the conversation, adapt your approach to the person in front of you, or hold people accountable, you’re building a culture where people can speak up, where issues will get resolved, where team members are expected to behave with integrity, and where trust increases. And every time you don’t, you’re building the opposite kind of culture.
So which do you want on your team?