Navigating difficult conversations: A leadership skill you can master
Every great leader knows that difficult conversations aren’t optional—they’re essential.
Whether it’s addressing performance issues, giving constructive feedback, or managing conflict, your ability to navigate tough discussions directly impacts your team’s success.
But let’s be real—these conversations can feel uncomfortable (even for seasoned managers). The good news? You can get better at them. Here are four simple strategies to help make tough conversations smoother—for you and your team.
- Prepare—Set yourself up for success.
Before you even sit down, get clear on your goals, motivations, and emotional state. Shift judgment to curiosity—this helps you uncover root causes that may not be obvious. - Set the Stage—Create a productive environment.
Invite the person to talk, set expectations, and establish a shared goal. And please—don’t ambush them. Springing a tough conversation on someone who’s already stressed? That’s a recipe for disaster. - Foster Two-Way Communication.
Check your assumptions at the door, use “I” statements, and remember—this isn’t about winning. You’re working toward a solution, not keeping score. - End with a Resolution.
Identify next steps, thank the other person, and stay open to feedback. Leaving things vague? That’s just asking for another awkward conversation later.
The bottom line? Tough conversations don’t just solve problems—they build trust, strengthen relationships, and set the stage for long-term success.
Leadership and Management Certificate Program
5-Day Virtual Program (9:30am – 3:30pm CT): April 7-11
5-Day In-Person Program (9:30am – 3:30pm Local): June 2-6 (Calgary); August 18-22 (Halifax)
Your managers set the tone for your workplace. They’re the ones handling difficult conversations, motivating teams, and making decisions that shape your organization’s culture.
Here’s the challenge: 70% of HR leaders say they aren’t effectively developing their leaders. So, the question is—do your managers have the training they need?
The Leadership and Management Certificate Program equips them with practical, real-world leadership skills.
5 days of game-changing leadership training
Confidence to lead tough conversations & workplace challenges
A stronger, more engaged team
Give your managers the tools they need to lead with confidence.
Leadership Retreat
Two-Day In-Person Workshop (3:30am – 3:30pm MT): July 16-17 (Canmore)
Learn alongside a community of leaders in the breathtaking Canadian Rockies. ACHIEVE’s founder, Randy Grieser, is back to share insights from his leadership journey and help you grow in ways you didn’t expect.
Using lessons from his books—The Ordinary Leader, The Culture Question, and Don’t Blame the Lettuce—Randy will challenge you to think differently about leadership.
Curious? Come for the insights, stay for the mountain views.
The Culture Question – How to Create a Workplace Where People Like to Work
How does your organization’s culture impact how much people like where they work? And more importantly—how can you make it better? This book dives into practical ways to build a culture where people want to stay.
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Workplace Cultural Health Assessment
In 2–5 minutes, get a personalized 8-page report evaluating your workplace culture. Curious about what it means? Reach out—we’d love to connect you with one of our workplace culture guides.
4 Questions to Evaluate Your Own Leadership
A quick self-check to reflect on your leadership approach and see where you can grow.
ACHIEVE Centre for Leadership
Phone (Toll Free): 877-270-9776
training@achievecentre.com
Posted: February 13, 2025