Ep. 489: 6 Tips for Having Difficult Conversations That Produce Results and Preserve Relationships

“Can We Talk?”: How to Have Productive Dialogue during Difficult Conversations

Knowing how to have direct, radically candid conversations that produce desired results while preserving relationships is a skill that can be learned.

“A person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have.”

~ Tim Ferriss, author of The 4-Hour Workweek

If you put two people together for a long enough period, they will inevitably experience conflict—it’s simply a part of the human condition. Tension between employers and employees, loving partners, close siblings, and even the best of friends often stems from misaligned expectations and unspoken assumptions. Egocentric beings that we are, we figure that others should know what we’re thinking and feeling and act accordingly.

When people don’t behave as we expect, we’re confronted with a choice: we can either ignore the problem and hope it goes away (it rarely does and often gets worse), or we can have a conversation to resolve the issue. The latter is typically the better decision, but many people lack the necessary skill to have uncomfortable conversations that eliminate conflict while preserving, perhaps even strengthening, relationships.

In this week’s Silver Dollar episode of Stay Paid, we share six tactics you can implement during difficult conversations that will lead to more beneficial outcomes. Remember that communication is a skill—the more you practice this approach, the easier and more natural it will become.

1. Begin by letting the person know that it’s going to be a difficult conversation.
2. Before proceeding, ask permission to have the conversation.
3. Take responsibility for contributing to the problem.
4. Describe your feelings, identify the behavior that is creating them, and explain the impact if the behavior doesn’t change.
5. Be specific when naming and describing your feelings, their behaviors, and the impact.
6. Engage in active listening while seeking to understand the other person.

We hope you enjoy this episode and act on the advice Luke offers at the end. We’d also appreciate it if you took a moment to leave us a 5-star review and comment on Apple Podcasts. (We read them on air!) Thanks for listening!

Connect | Resources

Radical Candor: Be a Kick-Ass Boss without Losing Your Humanity by Kim Scott

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