Build your own CTO Playbook at www.theCTOplaybook.com, the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.

What if goals are the real problem?

In this episode, I’m joined by Radhika Dutt, an engineer who studied electrical engineering at MIT. She wrote Radical Product Thinking and is now working on a new book exploring why goals and OKRs backfire, and what to do instead.

Targets can look great on paper while the foundation quietly erodes beneath them, leaving leaders focused on green dashboards instead of genuine learning. Together we unpack how shifting from goal setting to puzzle setting can unlock motivation, creativity, and alignment, using a simple framework that turns experiments into smarter decisions. By the end, you’ll see why puzzle setting beats targets when progress actually matters.

You’ll Learn:

[00:00] Introduction

[04:12] The story of how chasing perfect targets blinded a company to a crumbling foundation

[05:47] Why leaders often get good news first and the truth too late

[06:32] The hidden reason goal-setting traps teams in the wrong solutions

[07:15] How puzzle thinking rewires teams to stay in the problem space longer

[33:04] What happens when you replace optimization with exploration

[35:41] Why surfacing bad news early helps leaders make smarter choices

[37:18] How one company built real trust by modeling puzzle-solving from the top

[38:21] The three questions that turn metrics into learning loops

Resources Mentioned:

Radical Product Thinking by Radhika Dutt | Book or Audiobook

It’s soul-sucking to chase arbitrary targets. OHLs—Objectives, Hypotheses, and Learnings—shift the focus to learning, experimentation, and real progress. These templates help you break up with OKRs (without a career limiting move) and reclaim meaning at work.

If you want to connect more with Radhika, follow her on Linkedin.

Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company here.