When Difficult Conversations Don’t Go to Plan: Embracing Imperfection in Leadership

As leaders, we’ve all been there – the uncomfortable, critical conversation that’s supposed to set things straight but sometimes takes an unexpected turn.

Managing these moments, especially when things are unplanned, can be critical for SME leaders.

So, what if we started seeing these “failures” as valuable tools for growth for us and our teams?

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Why It’s Okay When Difficult Conversations Go Wrong

Difficult conversations: they’re the words that can make even experienced leaders feel anxious.

Managing people’s emotions, perceptions, and reactions doesn’t follow a formula. It’s natural to feel like you “should have” handled a talk better. But sometimes, these imperfect moments lead to unexpected growth.

?Let’s explore why not having it all figured out during a difficult conversation is okay. Here are a few experiences, lessons, and questions to reflect on as you navigate these challenging moments.

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The Reality of Difficult Conversations

I remember being promoted over someone who’d also applied for the role.

She was frustrated and, as a result, began to push back against nearly everything I did.

One day, the tension came to a head. We sat down for a one-on-one, and it got heated — she raised her voice, and I ended up in tears.

?In that vulnerable moment, I realised that sometimes it’s okay to admit that others can get under your skin.

Instead of sticking to a rigid script, I tried something different:

I asked her openly what she needed to feel valued.

She opened up, and eventually, we built a respectful working relationship.

She even became one of the strongest advocates for our team’s goals.?

This experience taught me that, as leaders, showing a bit of humanity can build trust and lead to positive outcomes, even when the start of the conversation is rocky.

Reflection Question:

When have you shown vulnerability in a conversation, and how did it change the dynamic?

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Lesson 1 - Pausing Before Responding

?When emotions run high, it’s easy to react in ways we might later regret.

The best first step?

Take a breath and allow time to regroup.

An aggressive employee I managed would often dominate meetings, frustrating her teammates.

Instead of responding to her in the moment, I paused, collected my thoughts, and addressed her behaviour directly in a separate one-on-one.

?Taking that pause helped me stay calm and explain the effects of her actions. We even developed a signal for meetings where I would subtly raise my hand if she needed to dial back her tone.

This small step helped her feel understood and gave her a practical cue to adjust her behaviour.

?Reflection Question:

Is there a conversation you’ve rushed into that would have gone better if you’d paused?

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Lesson 2 - Focus on Solutions, Not Blame

?When people feel blamed, they tend to get defensive, which can block productive dialogue.

During another conversation with a team member who was openly critical of a project, I realised I’d been framing the discussion around what they’d done wrong.

Shifting my focus to collaborative solutions changed the tone entirely.

?Instead of dwelling on past errors, we talked about practical steps moving forward.

That conversation transformed them from a critic into a collaborator.

?Reflection Question:

In tough conversations, how often do you focus on “why it went wrong” instead of “how we can fix it”?

?Lesson 3 - Check Your Assumptions at the Door

?Sometimes, our own biases influence how we approach conversations.

Have you already labelled the person you’re speaking to as “difficult” or “aggressive”?

?These assumptions often lead us into the conversation with an emotional charge that the other person may sense.

?One approach that helped me was asking, “What’s the story I’m telling myself about this person?”

By focusing on the facts – specific behaviours rather than personality traits – I was able to stay objective and reduce tension in my approach.

Example - Instead of saying, “You’re always negative about team ideas,” try framing it as “I’ve noticed that you’ve raised concerns in our last few meetings. Could you share what’s motivating that feedback?”

?Reflection Question:

Are there assumptions you carry about people that might be shaping your approach to conversations with them?

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Lesson 4 - Taking Time-Outs Aren’t Weakness

?If you’re mid-conversation and things feel out of control, don’t hesitate to call a time-out.

It’s far better to take a breather than to escalate the situation.

A time-out can help both parties gather their thoughts, calm down, and come back with fresh perspectives.

?During that early difficult one-on-one, I suggested we take a break, which allowed us both to return with clearer minds.

She returned calm and open, and we could move past our tension toward mutual respect.

?Reflection Question:

How comfortable are you with the idea of pausing a tough conversation? Could using this tactic help in future exchanges?

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Key Takeaways for Leaders?

The next time you’re bracing for a tough conversation, remember:

Embrace imperfection – It’s okay if things get heated or emotional. We’re all human.

Plan for flexibility – Prepare and shift gears based on the conversation’s flow.

Let go of “right and wrong – Focus on understanding and problem-solving rather than being “right.”

Reflect and grow – Each difficult conversation offers a chance to refine your approach and grow as a leader.

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Difficult conversations may never be easy, but approaching them with compassion, openness, and a willingness to learn can lead to positive changes for everyone involved. When things don’t go as planned, remember – that’s okay.

In these messy moments, we often find the greatest potential for connection and growth.

?Reflection Question:

After reading this, what will you try differently in your next challenging conversation?

Navigating tough conversations is a skill that grows over time.

Leaders who embrace the unpredictable nature of these talks and learn from each experience are more likely to build honest, resilient teams.

So, the next time you’re gearing up for a difficult conversation, take a breath.

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Nicola Richardson is The People Mentor.

With over 30 years of experience in leadership roles, she helps small employers hold difficult workplace conversations.

Her approach combines practical strategies with emotional intelligence, using tools like her COMPASS? Elite Conversation Model and DiSC assessments.

Nicola understands the challenges of balancing business growth with employee relationships, having faced them herself.

Her mission is to empower employers to handle tough talks confidently, creating stronger teams and healthier work environments.

Through her coaching and training, Nicola guides clients to transform workplace communication, turning potential conflicts into opportunities for growth and understanding.

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