What Karaoke Taught Me About Values (Yes, Really)

It’s good to be back with you in EsquireWell Weekly after a couple weeks of summer break, and I hope you’re having a fabulous summer (how is it almost August?)!

I’ve been traveling a lot the last couple of weeks - recently to Chicago for the Professional Development Consortium (PDC) conference and to Detroit for a client engagement, among other things. I’ve also been navigating some challenging family situations (all is well, but it’s been a lot). And somewhere in the midst of all of that, I celebrated my birthday.

One highlight of the past few weeks was co-presenting a session at PDC titled: “Harnessing the Power of Personal Values to Propel Leadership.” 

And then, something unexpected happened that same night - something that perfectly illustrated what we had just talked about in the session.

I sang karaoke. Here’s why that matters.

I don’t usually sing karaoke. Let’s be honest: my voice is a light, airy soprano - sweet and well-pitched, but better suited for church choirs or Mozart arias than pop songs. (Someone once said I sound like a 10-year-old boy soprano before his voice changes … and they weren’t wrong.)

But that night, a friend of mine had planned to sing “You’ve Got a Friend” with a colleague, and he had to leave unexpectedly. My friend was left standing there - ready to sing, no one to sing with.

So I stepped up. And so did another friend. And the three of us sang that song with full hearts and slightly questionable harmony.

And here’s the thing: I didn’t sing because I’m spontaneous or bold or love the spotlight. In fact, I never sing karaoke, even though I love to sing, so it’s way, way outside my comfort zone. 

But I sang because one of my core values is kindness. And I didn’t want my friend to have to sing “You’ve Got a Friend” alone.

Leading with values

This is exactly what we talked about in our session earlier that day: when you're clear on your values, they can nudge you out of your comfort zone and into meaningful action.

In the legal profession, we’re often trained to lead with intellect. But our values are what help us lead with intention, humanity, and courage. They help us:

• Speak up when something isn’t right
  
• Deliver honest feedback even when it’s uncomfortable
  
• Show compassion in a high-pressure moment
  
• Make hard calls with clarity and conviction
  
• Set boundaries with professionalism and care
  
  

Real-life legal examples of values in action

• If you value kindness, you might give clear, constructive feedback even if it feels awkward because you know that leaving someone in the dark is actually unkind. I learned this during my time as Chief Attorney Development Officer in a large national firm. I had to give difficult feedback often, and the “Minnesota-nice” part of me resisted, not wanting to hurt anyone’s feelings. But I reminded myself: kindness isn’t avoiding discomfort. It’s helping people grow. As Brené Brown says, “Clear is kind.”
  
• If you value respect, you might create space for more junior colleagues to contribute their ideas in meetings, rather than letting louder voices dominate. You also speak up when others are disrespected or marginalized in some way, even when you’re scared to do it.
  
• If you value integrity, you might push back on a questionable client request or billing practice, even when it’s uncomfortable.
  
• If you value inclusion, you might advocate for accessibility in firm events, career development opportunities, or mentorship structures, even if you feel like a “squeaky wheel.”
   

Your values aren’t just personal. They shape how you practice, lead, interact, and build culture in your workplace.

Reflection questions for you or your team

• What are three values that guide you personally and professionally?
  

• What’s one recent situation where a value helped you make a decision or take action?
  

• Which value helps you step up when something feels hard or uncomfortable?
  

• Where might your actions be out of alignment with your values right now—and what shift could bring them back into sync?

These are great questions to reflect on yourself—or to use with your team in a retreat, coaching session, or team meeting.

Want to explore your values?

If you haven’t already, download my free values workbook: “Knowing What Matters”. It’s short, powerful, and designed to help you identify your core values and put them to work in your leadership and life. (Insert link to get the “Knowing Your Values” workbook - do they need to opt-in or can we give a Google link)

Because when we’re grounded in what matters, we show up as the people and professionals we want to be. Even at karaoke.

Recommended Resources

[Podcast] Living Into Our Values | Brené Brown

[Video] Who are you? Unleashing your Core Values | Jennifer Jones | TEDxChathamKent 

[Article] The Importance Of A Workplace That Aligns With Personal Values | Forbes

[Article] The Meaning of Personal Values and How They Guide Your Decisions | BetterUp

Feel free to download, share, and use these quotes to inspire yourself and others!