Avoiding the awkward: Getting leaders to have that conversation that counts

Leaders will go to extraordinary lengths to avoid necessary conversations.

I recently delivered training on having kind but firm difficult conversations for an intact team. As the sessions unfolded, I realised something telling — the manager had brought me in because of one particular person whose communications were poisoning the team atmosphere.

People avoid difficult conversations because they’re afraid of conflict

Let's call her Martha. She'd been in the team for years but had recently been passed over for a team leader role. Ever since then, she'd been corroding team morale through both verbal and non-verbal behaviours.

Verbally, she was constantly arguing back, resisting others' ideas, and making snarky comments like "that won't work" or the classic "we did that before." Non-verbally, she was even more disruptive — sighing loudly when others spoke, rolling her eyes, crossing her arms, and fidgeting or looking away during discussions.

What really astonished me was her complete inability to listen — something I experienced firsthand during our sessions.

Here's the kicker: rather than addressing Martha's behaviours directly, the team leader organised communication training for the entire group. Everyone benefited and improved their communication skills, but it got me thinking — why wasn't the leader willing to have that conversation directly with the main cause of the issue?

Why leaders avoid hard conversations

1. Dodging Drama: Why Leaders Would Rather Wrestle a Bear Than Talk About Real Issues

2. The Art of Awkward Avoidance: How Leaders Perfect the ‘Let’s Circle Back’ Move

3. Silence Speaks Volumes: Why Tough Talks Terrify Even the Boldest Bosses

This scenario highlights something I see all the time. Leaders will:

• Create new policies

• Reorganise teams

• Bring in external training

• Hope the problem magically resolves

...all to avoid having one honest conversation.

How to help your leaders have those necessary conversations

If you've got leaders avoiding important conversations, here are practical steps to help them build that skill:

1. Help them identify the real conversation they're avoiding
   Many leaders aren't even aware they're sidestepping the issue. Ask them: "If you could wave a magic wand and have one conversation go perfectly, what would it be about, and with whom?"

2. Normalise their discomfort
   Let them know that everyone finds these conversations challenging. The discomfort isn't a sign they shouldn't have the conversation — it's just part of being human.

3. Break down the fear
   Have them articulate exactly what they're afraid might happen. Often, when spoken aloud, these fears ("They might cry" or "They might quit") become more manageable.

4. Reframe the conversation as an act of respect
   Not having the conversation is actually disrespectful — it assumes the other person can't handle honest feedback or isn't worth the effort of growth. Remember: clear is kind. Withholding feedback denies someone the opportunity to grow.

5. Give them a simple structure
   I teach the "DEARCC" framework:

• Describe the behaviour specifically

• Express the effect on the team/work

• Align by asking for their perspective

• Reaffirm their worth and your confidence

• Change: co-create the path forward

• Consequences: clarify what's at stake

DEARCC Framework

1. Role play it
   Practice makes progress. Have them practice the conversation with you or a trusted colleague before having it for real.

2. Focus on one specific behaviour
   In Martha's case, addressing eye-rolling is much more specific than "your whole attitude". Specific is good and "unarguable" — a key theme in my training. When you mention observable behaviours, they're simply harder to dispute.

3. Set them up for success
   Help them plan the right time, place and opening statement. The first 30 seconds often determine how the whole conversation will go.

4. Prepare them for reactions
   People commonly respond with denial, anger, tears, or silence. Having strategies ready for each reaction helps leaders stay calm.

5. Debrief afterwards
   Schedule time to discuss how it went. What worked? What would they do differently next time?

Remember that for most leaders, the anticipation of these conversations is far worse than the reality. Once they've had one or two successful difficult conversations, their confidence grows dramatically.

What I've noticed is that the best leaders eventually come to see these conversations not as "difficult," but as necessary moments of truth that build stronger teams and better relationships.

What difficult conversation is your leader avoiding right now? And which of these steps might help them finally have it?

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