How Many CTOs Podcast

#How Many CTOs? A Podcast About the Real Work of Engineering Leadership

I co-host a podcast called How Many CTOs? with my longtime friend and fellow technology leader, Scott Porad. We started it as a way to give voice to the conversations we were already having, the candid, sometimes frustrating, often illuminating discussions about the real challenges CTOs face.

Over the course of our careers, we kept encountering the same tough questions:

• How do you measure engineering performance in a meaningful way?
• What does it really take to align product and engineering?
• How do you manage technical debt without burning out your team or the business?
• Why are we still so bad at translating between what stakeholders say they want and what engineers actually build?

We don’t pretend to have the answers, but we believe there’s real value in exploring the questions with honesty and curiosity. That’s what the podcast is: a mix of conversations between the two of us and interviews with other CTOs, engineering leaders, product folks, and founders. We talk about the work behind the work: the leadership, communication, ambiguity, and tradeoffs that don’t always show up in the sprint plan but define whether a team thrives or flails.

The name? It’s part joke, part commentary. In a lot of companies, the CTO role is overloaded, misunderstood, or split across multiple people. “How many CTOs does it take?” became our shorthand for all the ways tech leadership can go sideways, and how we might steer it better.

If you’re interested in the human side of engineering leadership (the messy, strategic, high-stakes part) I hope you’ll give it a listen.