Great Leaders Let You Make Mistakes, but Don’t Let You Quit – Podcast Interview with Anne Steiner

Anne Steiner, VP of Product Agility at Cprime is at the forefront of Agile expansion across industries and disciplines. She acts primarily as a highly respected and experienced coach and trainer for product managers and agile teams, but she’s also often called upon to share her unique view and insights as part of the larger conversation around Agile. Anne was recently interviewed on the Minneapolis-based podcast, Women in Tech (WIT) Twin Cities, where cohosts Jessica Meyer and Anna Bliss engaged her in a discussion about her early days in tech and how the sometimes unconventional path she’s followed has led her to where she is today.

We encourage you to check out the full podcast when you have half an hour to invest, because there are more golden nuggets than we can highlight here. The full episode is embedded below:



Here are a few highlights from the conversation you can enjoy right now.

Why Anne Never Pursued Paleontology

It’s always fascinating to hear how professionals weaved through the thousands of choices that culminate in a successful career because no two people ever wind up with the same story.

At the age of 5, Anne was absolutely certain she was going to be a paleontologist. “From that point to now,” she says, “there hasn’t really been a lot of clarity.”

She goes on to relate that she had a passion for math and for some of the sciences. In high school, she decided to pursue math, but knew she didn’t have an interest in teaching. Although some people insisted that teaching was the only career path available for someone with a math degree, Anne pushed forward anyway.

“Luckily some folks at the University of Wisconsin told me that was really stupid advice,” she recalls, “so I went up there and went to school as an applied math and computer science major.”

Building off that degree, Anne started out as a front-end developer and identified her love of software design, both on the architectural and UI sides. But, she also enjoyed talking to people and solving problems in that way. Eventually, she recognized, “I don’t know if I want to sit at my desk and code the rest of my life.”

As a result, she migrated into product management. Fortuitously, this move came at the same time that the company she worked for was beginning to embrace Agile methodologies, so this strongly influenced her entire perspective on product management and product ownership.

After a few years of successfully climbing the product management ladder, she admits, “I got really burnt out on that.” She sought out a new application of her dual engineering/communication skill sets, and settled on a new trajectory. “So at that point in time, I had a really cool opportunity to come here to DevJam and to begin coaching.”

Since then, Anne has evolved in her role at DevJam and, later, Cprime, but she’s never lost her passion for coaching. “I really enjoy getting out there on the street and helping all the good product managers and product owners out there with their jobs. I think it’s a really tough job and it’s a job I respect a tremendous amount.”

The Dual Superpowers: Making Mistakes but Never Quitting

Later in the interview, Anne makes an important point regarding one of the key lessons she’s internalized from a career working largely around Agile software development:

“Hey, you’re not going to always be right the first time, and from failure actually comes success. So, if life is a series of experiments, like a great product design and delivery is, then it’s okay to be wrong. Because that’s going to make us better later. So, I try to go a little easier on myself with respect to that.”

This led naturally into an insightful conversation on the female perspective on failure and the benefits of making mistakes, and some fond memories about mentors and leaders that provided space to learn: “Like everyone, I’ve had good leaders and bad leaders, but I had good leaders at the right times. And that was important because those good leaders will let you fail but then not let you quit.”

Other highlights we’re sure you’ll enjoy:

  • The important role communication skills play in the success of a Product Manager
  • The power of confidence in professional development and how to instill it in others
  • Advice from an NCAA soccer coach on internalizing commendation and criticism
  • The dangers posed by Imposter Syndrome
  • What all of us can do to encourage women to pursue and persevere in STEM careers
  • … and more!

We’re sure you’ll enjoy the full interview. Click here to listen now or download it for your ride home.

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Cassidy Knight
Cassidy Knight
Agile Coach, Cprime