Squiggly Careers Podcast — Episode Summary

Episode: 3 Hard Work Conversations & How To Handle Each One with Confidence
Hosts: Helen Tupper & Sarah Ellis
Date: December 2, 2025
Featured Experts: Amy Gallo, Celeste Headlee, Dr. Sunita Sah
Episode Theme:
How to handle three of the most challenging types of workplace conversations—conflict in a team, defensiveness in dialogue, and speaking out when something doesn’t feel right—using insights from top experts to help listeners approach each with greater confidence and practical strategies.

1. Overview of Episode Purpose

Helen and Sarah experiment with a new episode structure, curating and discussing the practical wisdom of three experts on different “hard conversations.” Their aim is to break down real-world challenges most professionals face, providing actionable advice to make these difficult dialogues less daunting and more productive.

2. Key Discussion Points & Insights

A. Conflict in a Team with Amy Gallo

[06:40–11:30]

• Why Conflict Matters:

  • Conflict is unavoidable in any workplace. Those who skillfully navigate it and bring out constructive perspectives are often the most successful.
  • Amy Gallo: “There’s no such thing as a conflict-free office... The people who can bring different perspectives together, can advocate for themselves… those are the people who often go far in organizations.” [06:40]

• Normalizing Conflict:

  • Amy Edmondson’s work on psychological safety highlights that tough conversations are a mark of a healthy environment.

• Preempting Pointless Conflict:

  • Reference to HBR article (“How to Preempt Team Conflict”) that suggests proactive team discussions around working styles to minimize needless friction.
  • Sarah Ellis: “If you’re going to have conflict, you want it to build something better… You want it to be helpful, not just annoying.” [05:25]

• Tip: Reframe Irritation into Curiosity:

  • Helen Tupper: “I try to be intrigued over being irritated... flip really quickly to being intrigued and maybe ask some questions.” [08:59]
  • Amy Gallo: “If you can start any difficult conversation with a genuine question… it sets the tone that I’m not going to just, you know, monologue here… I’m going to actually engage.” [09:44]

• Tip: Clarify Your True Goal:

  • Amy Gallo: “What is your goal? What is it you’re actually trying to achieve?... It usually means I have to put down the need to be right.” [10:23]

Memorable Quotes:

• “There’s no such thing as a conflict-free office.” — Amy Gallo [06:40]
• “Be intrigued over being irritated.” — Helen Tupper [08:59]

B. Managing Defensiveness with Celeste Headlee

[12:56–15:30]

• Opening Up Conversations:

  • Start by inviting people to share a recent success, which helps lower defensiveness and creates openness.

  • Celeste Headlee: “If you allow someone to feel a sense of pride at the beginning… it makes it more likely that they will be open, open minded and open to being wrong, open to new information.” [12:56]

• Using Affirmations as Mental Shortcuts:

  • Even when “affirmations” feels like a woo-woo word, science shows they can rewire your response to conflict and feedback.
  • Become aware of your triggers—defensiveness, sensitivity to tone—and create personalized mental affirmations to ground yourself during challenging conversations.
  • “I’m here to listen. I don’t need them to like me, but they may have an insight that will be of use to me.” — Celeste Headlee [14:55]

• Practical Steps:

  • Reflect on what typically triggers your defensiveness.
  • Prepare an affirmation or mental “shortcut” in advance.
  • Take a breath and repeat it to yourself when stress rises.

Memorable Quotes:

• “You can use affirmations to retrain your brain so that when you get negative feedback, you don’t have a defensive response but a productive response.” — Celeste Headlee [13:46]

C. Speaking Out When Something Feels Wrong with Dr. Sunita Sah

[20:14–24:40]

• Redefining Defiance:

  • Defiance isn’t just being loud or combative; it means acting in alignment with your values, especially when there’s pressure to comply.
  • Dr. Sunita Sah: “My definition of defiance is that it’s simply acting in alignment with your values when there is pressure to do otherwise.” [21:29]

• The Five Stages of Defiance:

  1. Tension: Notice internal signals (e.g., stomach tightness, dry mouth) that something’s off.
  2. Acknowledgement: Consciously admit to yourself that you’re uncomfortable.
  3. Vocalization: Share your discomfort or ask clarifying questions to someone else—non-confrontationally.
  4. Asserting Your Boundaries: Calmly state if you don’t feel comfortable moving forward.
  5. Taking Action: Acting in alignment with your values; discomfort dissipates and “feels really good.”
  • Dr. Sunita Sah: “If you can get to stage five of defiance, that tension just melts away. It feels really good to act in alignment with your values.” [24:34]

• Innovation Tie-In:

  • Defiance can spur innovation—by challenging the “way things are,” you can flag inefficiencies and create better processes.
  • Helen Tupper: “Maybe part of defiance is being the person who spots what’s going wrong and is happy to speak up about it.” [17:55]

• Context Matters:

  • Tailor your approach based on trust levels and culture where you work; even small acts of “speaking up” count.

Memorable Quotes:

• “There is a myth that defiance has to be loud, aggressive, violent. But my definition of defiance is that it’s simply acting in alignment with your values when there is pressure to do otherwise.” — Dr. Sunita Sah [21:29]
• “That tension is actually a very useful warning sign for us that something is wrong, and perhaps we do need to defy in this situation.” — Dr. Sunita Sah [21:51]

3. Notable Quotes & Memorable Moments

• “There’s no such thing as a conflict-free office.” — Amy Gallo [06:40]
• “Be intrigued over being irritated.” — Helen Tupper [08:59]
• “You can use affirmations… to shift your brain from retaliation when you are criticized to questioning and curiosity.” — Celeste Headlee [13:46]
• “Defiance is simply acting in alignment with your values when there is pressure to do otherwise.” — Dr. Sunita Sah [21:29]
• “If you can get to stage five of defiance, that tension just melts away. It feels really good to act in alignment with your values.” — Dr. Sunita Sah [24:34]

4. Key Timestamps

• [02:03] — Main theme and episode structure introduced
• [06:40–11:30] — Helen & Amy Gallo: Productive conflict in teams and reframing irritation
• [12:56–15:30] — Sarah & Celeste Headlee: Managing defensiveness and power of affirmations
• [20:14–24:40] — Helen & Dr. Sunita Sah: The five stages of defiance and speaking out with values

5. Episode Takeaways

• Proactive Dialogue: Discuss differences openly and early to transform conflict into creative problem-solving.
• Mindset Matters: Use curiosity and self-reflection (via questions and affirmations) to defuse both irritation and defensiveness.
• Speak Up for Change: “Defiance,” reframed, is a vital skill for personal integrity and organizational innovation—learn to spot, acknowledge, voice, and act on your discomfort.
• Tailor to Context: These techniques work best when adapted to your environment and level of trust.

6. Resources Mentioned

• HBR Article: “How to Preempt Team Conflict”
• Celeste Headlee’s TED Talk: “10 Ways to Have a Better Conversation”
• Books by Amy Gallo and Dr. Sunita Sah (titles discussed/championed during episode)
• For practical tools and weekly inspiration: Squiggly Careers in Action Newsletter

For feedback on this format or additional questions, listeners are invited to email: helenandsarah@squigglycareers.com

This summary captures the heart of the episode—actionable wisdom for tough work conversations, straight from experts, with relatable host perspectives and practical advice.