Upcoming events

Menu
Log in


Log in

Say the Hard Thing: A Playbook for High-Stakes Conversations

  • November 18, 2026
  • 8:00 AM - 9:30 PM

Registration


Register


Say the Hard Thing: A Playbook for High-Stakes Conversations

Speaker: Jane Boutelle, Founder & Coach, Conversation Lab

Wednesday, November 18 | 8:00 am - 9:30 am 
WYSO Center

We've all been there: rehearsing a conversation in the shower, drafting the email we never send, or saying "it's fine" when it isn't.

Maybe you need to ask for a raise or promotion. Give hard feedback. Address a conflict with a colleague. Advocate for an idea. Or finally say what you actually want.

The conversations we avoid are often the ones that matter most. And they can have a real impact on our careers.

In this practical, interactive session, Jane Boutelle of Conversation Lab will share a playbook for navigating high-stakes conversations with clarity, confidence, and humanity. You'll learn how to prepare without over-scripting, say what you mean without over-explaining or apologizing, stay grounded when emotions run high, and be both direct and likeable.

Most importantly, you'll have a chance to apply what you learn to a conversation that matters to you—so you can leave ready to have the conversation you've been putting off.

Attendees will walk away from this session having prepared for an important conversation, so they’re ready to face it with confidence.

About Jane Boutelle, Founder of Conversation Lab

Jane has always been the person friends, family, and work colleagues come to for guidance about high-stakes conversations. Her combination of listening skills, empathy, broad work and life experience, and professional training make her ideally suited to help people build self-advocacy skills, resolve conflicts, navigate career moves, ask for raises/promotions, and refine their communication styles to be more clear, compelling, and human. 

A certified Wayfinder Life Coach, Jane founded Conversation Lab to focus on helping professional women close the “influence gap,” where their impact and recognition don’t always keep pace with their competence on the job. She brings to this role a wide-ranging background of professional experience. Most recently, as co-founder of Digsite, a software company, she led all things customer- and culture-related. Previously, she was a team leader and product manager at tech companies such as Intuit and Apple, where she provided guidance to professionals at all stages of their careers. 

Registration: 

TEMPO Madison Members: $30.00 | Attendees: $35.00

Powered by Wild Apricot Membership Software