A Costly Assumption: Tech Leadership Lessons with Steve Pereira

My guest for Episode #280 of the My Favorite Mistake podcast is Steve Pereira. He has spent over two decades improving the flow of work across organizations. He’s worked through tech support, IT management, platform and infrastructure engineering, product management, and as a founding CTO for enterprise SaaS.

Episode page with video, transcript, and more

He serves as CEO of Visible Consulting, as COO to the Value Stream Management Consortium, Chair of the OASIS VSM Interoperability technical committee, and co-founder of the Flow Collective to bring flow-focused professionals together. Since 2017, he has been developing and facilitating Flow Engineering.

He is the co-author of Flow Engineering: From Value Stream Mapping to Effective Action - his co-author, Andrew Davis, was a guest here recently. Steve and Andrew also joined me for an episode of "Lean Blog Interviews."

In this episode, Steve shares his journey in improving workflows and the lessons learned from his favorite mistake. Steve recounts how, in a previous role as a developer, he assumed that his own needs mirrored those of other developers, leading him to spend significant time creating a solution without gathering proper feedback. This isolated approach resulted in wasted time and an ineffective outcome. Through this mistake, Steve realized the importance of customer validation and iterative development, key principles he now applies in his work.

We also explored the concept of "failure debt," the role of psychological safety in fostering learning from mistakes, and how flow engineering can transform collaborative workflows.

Questions and Topics:

• What would you say is your favorite mistake?
• How did things play out with that mistake in your career?
• How many other developers were you working with on this task?
• When did you realize the project wasn't working, and how did you adjust?
• How did you eventually start to learn from these mistakes?
• When did these lessons become more clear to you in your career?
• Can you elaborate on how sharing mistakes publicly helped lessen the sting over time?
• How would you define 'flow engineering' for someone outside of software development?
• How do you think mistakes, bugs, or defects affect flow? Do speed and quality go hand in hand?
• What are your thoughts on how leaders can foster psychological safety and a learning culture where mistakes are embraced?
• What is 'failure debt' and how can organizations address it?
• Did the writing process for Flow Engineering reflect some of these lessons on customer feedback and iteration?

Key Topics:

• Steve's favorite mistake of assuming his own needs were the same as other developers, leading to wasted time.
• Importance of customer feedback and validation in technical projects.
• The Abilene Paradox and how it relates to satisfying multiple stakeholders poorly.
• Learning from mistakes over time, especially in leadership roles like CTO.
• The impact of public accountability in lessening the sting of failure.
• Definition and application of flow engineering to improve collaborative workflows.
• The relationship between mistakes and flow, and how speed and quality work together.
• The role of psychological safety in creating a learning organization.
• Concept of failure debt and how unaddressed failures can accumulate, leading to bigger issues.
• How Flow Engineering was written iteratively, applying lessons learned from Steve’s career.