5. Lindsay Verstegen - Unlocking Exponential Potential In Each Other

Listen to this episode on your favorite platform!

Key Takeaways

Culture of vulnerability

  • The easiest way to build this is to come from a CEO that is human
  • Lindsay felt like she could have candid conversations with the CEO and COO of Braintree when she was there.
  • We all need buddies on the vulnerability journey - it’s tough to be authentic every day. You need someone to help bring you along on the days you don’t feel like being real and honest.

People dynamics

  • You need to understand your personal accountability within any relationship dynamic
  • If it goes awry, you need to self reflect on what went wrong: are you withholding? Are you sitting back on judgement? Are you acting inappropriately?

Common traits of good leaders

  • None were ever rubbed the wrong way when asked a simple question. A humility to make sure you are bringing people along the journey and ensuring everyone understands their role to play.
  • The ability to be honest when you’ve failed - getting up in front of people and being open about being wrong. This is incredibly important to set a model for a learning mindset.
  • Being an ally - they show up, do the work and admit when they are wrong.
  • Not being insecure when they say, “I don’t know"

Managing hypergrowth in an organization

  • Fight the urge to constantly be reacting 
  • The biggest problem is not making space to reflect on when frameworks and processes that aren’t working

What is culture?

  • It’s who you hire, fire and promote.
  • Who you promote are the heroes in your story. Who you don’t promote are unsung heroes.
  • But there’s also so many other dynamics - there’s the history of the organization and the vision for what leaders want it to be that also drive culture.
  • The People team’s role is to play that of a guide or sherpa to drive culture.

The role of social justice and political issues in the workplace

  • Lindsay believes we are here to build businesses that allow people to thrive.
  • The question you have to ask is - who are we doing this for? If it’s for shareholders, it’s 100% capital returns. If it’s stakeholders, it’s about employees as well.
  • If you view the issues as moral and not political, it allows you to charter a course on what your authentic and meaningful/thoughtful response will be to the issues.

Show Notes

My guest today is Lindsay Verstegen, the Chief People Officer at Shoprunner. Pretty quickly it’ll become clear to you that Lindsay’s career leading Human Resources and People teams has allowed her to think deeply about people dynamics - she could probably teach a class on behavioral psychology. Some topics we discussed were vulnerability, the role of personal accountability and common traits in great leaders.

My respect for Lindsay only grew after this conversation and it’s reaffirmed my perspective that a strong People leader is crucial for all organizations. I hope you enjoy this one!

Lindsay’s LinkedIn



Show Highlights

(1:31) - How her passion for the arts prepared her for a career leading People functions

(5:27) - Where does a culture of vulnerability come from?

(10:18) - Understanding your personal accountability in a relationship dynamic

(11:39) - Common traits in good leaders

(15:24) - Managing hypergrowth within an organization

(19:02) - What is culture?

(24:01) - Social justice / political issues in the workplace

(30:21) - The future of building teams


For more episodes and access to our bi-weekly newsletter with key takeaways, subscribe for free at reorgpod.com or follow me on Twitter @itsdanwu

Episode Transcript