Turning Tough Conversations into Opportunities: A Guide for Leaders

Workplaces don’t exist in a vacuum—wherever people gather, conflict inevitably follows. According to one study highlighted in a recent Some Goodness podcast episode, 94% of employees have worked with a toxic individual in the past five years, and 50% of Americans have left a job specifically to get away from their manager. Clearly, organizations can’t afford to brush conflict under the rug. Yet, for many leaders, the idea of sitting down to address a team member’s chronic lateness, negativity, or slipping performance feels daunting.

The good news: You can transform these difficult moments into catalysts for growth. How can leaders address conflict effectively, ultimately creating a healthier team culture and stronger organizational outcomes? 

The High Cost of Avoidance

Human beings are wired to shy away from uncomfortable situations. For new and seasoned leaders alike, this often manifests as delaying—or outright ignoring—tough conversations in hopes that “it’ll get better on its own.” But inaction has a hefty price. Underperformance festers. Small misunderstandings amplify. Morale dips lower each week. Your high performers notice the lack of accountability and may lose faith in leadership. Over time, you risk a culture that tolerates toxicity and confusion, eroding both trust and results.

Leaders who step in early and address conflict head-on send a powerful message: problems won’t linger, and accountability is a top priority. When handled constructively, these interactions can uncover root causes—personal challenges, skill gaps, role misalignment—and enable timely course correction.

The Power of Clarity

Leadership expert Jack Galloway, featured in the Some Goodness podcast, made an important observation: “To be unclear is to be unkind, and to be clear is to be kind.” This boils down to a simple yet frequently overlooked principle: employees can’t fix what they don’t understand.

1. Name the Issue Promptly
   Don’t let a misunderstanding or poor performance linger for days or weeks. Have the conversation as soon as practically possible. By addressing it early, you minimize the chance for resentment or inaccurate assumptions to build.
2. Stick to Observations, Not Accusations
   Instead of confronting someone with “You always interrupt the team,” try, “I’ve noticed you tend to speak over your teammates in meetings. Can we talk about that?” Framing a concern as an observation allows a more open dialogue.
3. Define What “Good” Looks Like
   Want to see higher sales numbers or more collaborative behavior? Let them know exactly what that entails—e.g., “We need an average of X calls per day” or “Please let others finish before adding your insights.” When you outline the path forward clearly, you make success attainable.

Candor and Kindness: The Right Balance

Leaders sometimes confuse honesty with harshness. Simply being “brutally honest” isn’t enough—nor is sugarcoating problems under the guise of “staying positive.” True candor strikes a balance between direct, unflinching honesty and genuine empathy.

•  Be Direct and Respectful
  Acknowledge that you value the person’s contributions, then state exactly what needs to change and why. This combination of clarity and care helps team members understand you’re committed to their success, not just doling out criticism.
•  Listen to Learn
  Galloway points out that venting, when channeled productively, can be a stepping stone toward resolution. Encourage employees to share their side without interruption. Ask open-ended questions to uncover root issues: Is there a skill gap? A personal challenge? A clash with another team member?

Making Time for Crucial Conversations

It’s easy for leaders to say, “I’m too busy for a sit-down meeting—I’ll handle it eventually.” Yet, every day you delay a conversation, you risk further spreading the issue. High-performing organizations schedule regular one-on-one meetings and hold short post-meeting huddles to tackle problems in real time. This proactive approach keeps minor issues from snowballing into team-wide crises.

When pressed for bandwidth, consider whether all existing tasks truly rank higher than addressing people problems. If not, push back on lower-priority items so you can give these conversations the attention they deserve. Productive teams thrive on a stable foundation of clarity and trust, and both emerge from well-handled conflict.

Building a Culture of Constructive Conflict

1. Champion Transparency from the Top

Talk about conflict and healthy resolution in company-wide forums. Encourage managers and employees alike to bring up issues when they see them, reassuring your team that constructive conflict is not just tolerated but valued.

2. Provide Training and Resources

Not every leader intuitively knows how to handle challenging conversations. Workshops or short “lunch and learn” sessions on conflict resolution techniques can equip them with the skills to navigate hard discussions effectively.

3. Celebrate Positive Outcomes

When you see a once-struggling team member flourish after honest feedback, or a difficult conversation leads to a newfound partnership, share those success stories. Reinforce that constructive conflict isn’t a sign of dysfunction, but a hallmark of a mature and forward-moving organization.

Turning Conversations into Opportunity

Hard conversations can yield powerful results. Sometimes, you’ll discover an employee who needs more training or simply sits in the wrong seat for the company’s current direction. In other cases, you’ll find personal crises or outdated processes at the heart of the problem. Addressing these factors head-on paves the way for deep improvements in individual performance, team morale, and, ultimately, organizational success.

Tough conversations, when approached with clarity and empathy, transform from dreaded obligations into valuable opportunities. By having them promptly, listening openly, and following up with actionable steps, leaders foster a culture that prizes trust, accountability, and growth.

Want to learn more, listen to our interview with Jack Galloway on the Some Goodness podcast.