DiscoverSpeak by Design2026 Readiness Day 10 - Difficult Conversations
2026 Readiness Day 10 - Difficult Conversations

2026 Readiness Day 10 - Difficult Conversations

Update: 2025-12-10
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Difficult conversations are coming for you in 2026.

Not “maybe.” Not “if.”

Your team member who keeps missing the mark.

Your leader who wants answers, not excuses.

A client who suddenly sounds disappointed.


In Day 10 of the 12 Days of Readiness, we take those moments off the “dread” list and move them onto your “I’ve got this” list. Discover how to manage the conversation in your own head first, so you stop over-personalizing what is simply about mission, goals, and process. You’ll hear how to set clear expectations without rambling, control your face and body so you don’t look harsher than you feel, and swap dramatic, negative language for values-based, forward-looking phrases that people can actually act on.


You’ll also learn one tiny word that instantly lowers defensiveness: curious. Used with a calm, almost playful tone, it lets you ask the hardest questions without triggering a fight. This is one of our monthly topics inside Speak by Design University, where we’ll go even deeper with role plays and improvisation on your real difficult conversations.


Registration for Speak by Design University 2026 is open at speakbydesign.com/join. If you’d like a sponsorship packet to share with your company, email team@speakbydesign.com and we’ll send you materials to help you get internal approval.


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2026 Readiness Day 10 - Difficult Conversations

2026 Readiness Day 10 - Difficult Conversations

Stephanie Bickel