201: Leaders with Heart Ask the Right Questions

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In this episode, Heather sits down with Misty Guinn, Director of Customer Advocacy at Benefitfocus, a data-driven, cloud-based software solutions for health care and benefits administration. Their mission is to improve lives with benefits that focus on people and culture. Misty believes that leaders can learn exactly what their people need by asking the right questions. After all, it all starts with listening. During her interview with Heather, Misty talks about her leadership journey, why she describes herself as a “recovering perfectionist,” and more. 

Key Takeaways: 

  • Her motivation to lead comes from the desire to help people become the best versions of themselves
  • Becoming a mother and becoming more vulnerable made her a better leader
  • Perfection is not real and it’s not authentic
  • Asking your people the right questions can make a world of a difference
  • Surface level questions will lead to surface level results
  • Benefitfocus is a data-driven, cloud-based software solutions program for health care and benefits administration
I'm a recovering perfectionist. - Misty Guinn  #leadershipwithheart Share on X
Our mission is to improve lives with benefits. - Misty Guinn  #leadershipwithheart Share on X

Misty Guinn’s Bio

Misty Guinn is the director of customer advocacy at Benefitfocus, where she works closely with customers and stakeholders to build relationships and experiences that cannot be replicated anywhere else by designing programs that champion Benefitfocus brand, people and culture. She’s dedicated to designing a culture and environment that allows others’ total well-being to flourish through education, programs, and policies, while also improving employees’ health literacy and consumerism. In her previous role at Benefitfocus, she served as the Director of Benefits & Wellness where she established best practices in benefits engagement, education, and data-driven strategies. Misty is committed to fostering the foundations of a healthier workforce and community by embracing all the different pillars of well-being: physical, mental/emotional, financial, and social/purpose. She has been certified as a worksite wellness specialist with the National Wellness Institute and a Franklin Covey Facilitator in the 7 Habits of Highly Effective People.

Asking the Right Questions

Being aware of what your people need right now and how they want to be engaged are the most important questions to shift from the professional LinkedIn profiles walking around in your hallways to the whole person walking around. It’s important to ask them what’s going on in their life, not just what benefits they want next year, because you’ll get cookie-cutter answers like medical, dental, vision, etc. But instead, if you ask them deeper questions such as “Are you caregiving for anyone in your family right now? Have you purchased a home in the last 12 months?” You will not only connect, but you’ll be able to add real value to them and their benefits options. Asking the right questions is key before you start designing a benefit plan that doesn’t apply or benefit your people.

questions misty guinn leadership with heart

201: Leaders with Heart Ask the Right Questions Share on X
Being able to continue to help others become the best versions of themselves is something that gets me out of bed every morning. - Misty Guinn  #leadershipwithheart Share on X

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Becoming Unshakeable Podcast

With Heather R. Younger

Becoming Unshakable is the podcast for leaders, creators, and changemakers who know TRUE LEADERSHIP starts from within.

Each episode explores what it takes to lead with resilience, compassion, and purpose while staying human through it all.

Through candid conversations with executives, frontline leaders, coaches, and everyday heroes, Heather uncovers the real stories behind growth, compassion, setbacks, and transformation.

From navigating change to creating emotionally safe cultures, Becoming Unshakable reveals what it really takes to create leaders—and organizations—that can’t be shaken.

Hi, I'm Heather

I've been through every type of
ORGANIZATIONAL CHANGE
you can think of.

Layoffs, reorgs, mergers, acquisitions and major technology shifts. More than 20 years leading teams through high-stakes situations where results mattered, people depended on me, and decisions couldn't wait.

Those years taught me how to lead. But they also showed me the hidden cost of always being the one who holds it all together.

During our second reorg in less than a year, I walked out of a meeting with no say in what was happening, just marching orders. When my team asked how the meeting went, I should have said, “Give me 15 minutes to process this.” But I didn't. Instead, I let them absorb every ounce of my frustration.

Then I saw their faces.

The people who looked to me for stability had just watched me unravel. What was that teaching them about their ability to handle the pressure?

That moment changed how I saw my role as a leader. Leading teams isn't only about grit or resilience. It's about how your presence builds the trust your team needs to function when things get hard.

Today, I help organizations build unshakable leaders, teams, and cultures. Because when leaders become the calm teams can count on, organizations don't just survive change, they come out strong enough to handle what’s next.

Heather Sitting
Heather_Younger_The_Cycle_of_Active_Listening_Guide

The Cycle of Active Listening

Create a listening culture that elevates the workplace experience for everyone.

Through this guide, uncover how to ensure those in your care at work feel heard and valued, resulting in increased loyalty and satisfaction.

  • Understand why listening is the key to improved engagement
  • Learn how the Cycle of Active Listening contributes to strong workplace relationships
  • Get a practical framework for creating a listening culture that is bidirectional, responsive, and supportive

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+1 403-398-8488

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Contact Heather Today!
+1 403-398-8488

Contact
Contact

I'm really interested in...

(select all that apply)*

I can be reached at...

Additional Comments