72: Why OKRs Fail — and What to Use Instead (with Radhika Dutt)

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The CTO Playbook

Adam Horner

77 episodes

3 days ago

Join Adam Horner, a CTO with over 30 years in the tech industry, on The CTO Playbook — the podcast dedicated to helping CTOs excel. Perfect for CTOs and tech leaders navigating the complexities of their roles, each episode offers clear insights, innovative strategies, and practical advice from top leaders in tech. With Adam’s extensive experience mentoring engineers and tech leaders, and over a decade as a CTO, you’ll gain the tools and knowledge to build and refine your own CTO playbook. Whether you're tackling complex projects, fostering innovation, leading teams, or shaping your company's tech strategy, this podcast is your go-to resource. Adam’s journey from engineer to strategic CTO was challenging. He learned through the school of hard knocks, making avoidable mistakes and facing countless challenges. Often out of his comfort zone and wishing for more guidance, he created this podcast to provide the support and advice he once lacked. Tune in for engaging interviews, leadership tips, and the latest in technology strategy. Each episode is designed to help you lead with confidence and level up as a CTO. Listen now to start your journey with The CTO Playbook and build your own playbook to excel in your role.

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72: Why OKRs Fail — and What to Use Instead (with Radhika Dutt)

The CTO Playbook

46 minutes 45 seconds

1 month ago

72: Why OKRs Fail — and What to Use Instead (with Radhika Dutt)

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.