[Ep#216] Handling Challenging Conversations and Building Fear-Resilient Leaders

Handling Challenging Conversations and Building Fear-Resilient Leaders 

My guest today says, “There is no such thing as a fearless leader. But they CAN fear less.”

We are excited to bring you another insightful episode of the Women in Leadership podcast, where we dive deep into the strategies and mindset required to handle challenging conversations and build fear-resilient leaders.

Joining me on today’s show is Nancy Lyons. 

Nancy is an author, a speaker, an entrepreneur/founder and a CEO. Her company, Clockwork is an experience design and technology consultancy. 

We discuss the art of navigating difficult conversations with grace and confidence. Nancy shares her expertise on asking for what you want, setting boundaries, and embracing direct communication. We believe that this episode will empower you to fear less, embrace difficult conversations, and take courageous action in your leadership roles.

On today’s show, Nancy is going to share:  

  1. Learning how to ask for what you want 
  2. Learning how to say no 
  3. Learning how to have difficult conversations 




Jump straight to these golden nuggets:

[00:02:21] Twisty journey towards unexpected career in comedy.

[00:04:17] Various roles, coffee, props, daycare, limited opportunities.

[00:08:30] Star Trek fan envisions evolving tech audience.

[00:12:03] Confident leaders face fear and move forward.

[00:13:58] Confidence and courage: take that one step.

[00:19:59] How did you contribute? Are you clear?

[00:22:23] Supportive assertiveness fosters professional growth, self-awareness key.

[00:25:10] Struggling past, doing things you don't like.

[00:27:50] Conflict in feedback can be constructive.

[00:32:56] Blend respect and likability for effective leadership.


Topic: Importance of difficult conversations and saying no

  • Learn to say no to avoid overwhelm and stay focused
  • Acknowledge the need for difficult conversations in personal and professional contexts

Topic: Skills and strategies for handling difficult conversations

  • Emotional intelligence and active listening
  • Managing emotions and defusing tension
  • Asking for help and turning the other person into a problem-solving partner
  • Tips for creating a safe space and understanding the other person's perspective

Topic: Articulating expectations, asking for what you want, and saying no

  • The importance of clear expectations in relationships
  • Encourage women to be assertive and ask for what they need
  • Criticize societal expectations and embrace assertiveness

Topic: Overcoming fear, self-worth, and the value of saying no

  • The connection between confidence and competence
  • Recognizing the value of saying no and prioritizing what matters most
  • Nancy's personal journey in communication style and embracing directness

Topic: The role of technology in leadership and communication

  • The growth of internet technology and its impact on the workforce
  • Design simplicity in digital products for all generations
  • Overcome self-doubt and fear of judgment to take initiative and solve problems

Topic: Developing confidence and taking ownership

  • Emphasize that confidence and courage can be developed over time
  • Focus on what one can contribute rather than questioning why they are at the table
  • Take ownership of work and being proactive in one's career



Gender Bias in the Film Industry: “I don't think these people are gonna give me an opportunity to really explore the things that I'm interested in.”

— Nancy 00:04:4000:04:46

The Evolution of Technology and the Changing Workforce: ‘The simplicity of design is essential in any digital product, so design for your mom. Except now I am the mom. Right? Like and I know what I'm doing.'”

— Nancy 00:09:0900:09:18

Leadership and Overcoming Fear: “Real leaders, regardless of title, figure out how to move through it, how to move into it and through it in spite of their fear.”

— Nancy 00:12:3100:12:39

Women in the Workplace: “You have to behave to get what you want. You have to act like a nice a nice woman.”

— Nancy 00:18:1400:18:16

The Power of Saying No: “We are all good and valuable simply because we were born.”

— Nancy 00:22:1300:22:16

The Power of Saying No: “The ability to say no comes from the ability to fear less. Right? We don't say no because we're afraid of what will happen if we say no.”

— Nancy 00:22:4900:23:00

The Importance of Setting Limits: “I think that being able to say no is equally as important as saying yes. And having the self-awareness to know your limits and being able to communicate that requires some vulnerability, but also I think it makes you more valuable.”

— Nancy 00:23:4200:23:56

The Importance of Giving Critical Feedback: “I think, you know, one tip that I got from a mentor years ago that I share with everybody…the best way to begin a difficult conversation is instead of being accusatory or coming at it very hot. Ask for help because there's not a human on the planet who doesn't feel inclined to offer assistance when they are asked.”

— Nancy 00:28:3200:28:51

The Impact of Cultural Communication Styles: “If you go to if as a Minnesotan, Minnesotans that go to New York or New Yorkers that moved to Minnesota are always freaked out by how people commute. You hear it from you know, and when you're working with the multinationals, it happens all the time. People move in from other coasts or other countries, and they are completely put off by how people communicate here because it is master's class in avoidance, in avoiding the actual issue and tiptoeing around it. And so, I think for me, I grew up in a family that was very direct.”

— Nancy 00:34:3600:35:06

Connecting with People through Personal Content”: “We put our hearts into the content in that email, and it's not and interestingly enough, for several years, and we very seldomly see people unsubscribe because they've and I see I hear from people every month That they found something useful in the piece.”

— Nancy 00:38:4400:38:50

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