The Challenges and Complexities of Implementing OKRs

In this episode of Dreams With Deadlines, host Jenny Herald interviews Tim Herbig, a seasoned expert on Objectives and Key Results (OKRs). They unpack the deeper facets of this management tool that's taking the corporate world by storm:

Key Things Discussed:

• Journey with Tim as he retraces his formative years with OKRs, shedding light on the challenges of top-down implementations. Emphasizing utility over form, he makes a case for the importance of day-to-day applicability of OKRs in organizations.
• Delve into the resistance faced by product teams towards OKRs, especially when established strategies are in place. Tim’s pragmatic approach champions the integration of OKRs with current team practices, ensuring they bring tangible value to daily operations.
• Navigate the intricate relationship between OKRs and product strategy. With a spotlight on the essence of strategy, Tim guides listeners on making strategic choices that can be tracked effectively with OKRs, bridging the gap between grand visions and actionable metrics.

Show Notes

• [00:00:31] Discovering OKRs: A Personal and Professional Evolution. Tim Herbig's journey with OKRs began at XING, evolving through challenges and insights. He underlines the issue of top-down OKRs without clarity and stresses their day-to-day utility.
• [00:02:37] Bridging the Gap: Ensuring OKRs Reflect Everyday Utility and Purpose. Tim Herbig dissects the outcomes vs. outputs debate, emphasizing OKRs' bridge role between mission and daily tasks. OKRs should be flexible tools, reflecting real team tasks and challenges.
• [00:05:44] Marrying OKRs with Established Practices: Pragmatism Over Dogma. Jenny and Tim explore why product teams resist OKRs. Tim advocates for intertwining OKRs with current practices like sprint planning, emphasizing their practical day-to-day value.
• [00:08:56] Making Pragmatic Choices: How OKRs Bridge Product Strategy to Everyday Work. The dialogue between Jenny Herald and Tim Herbig delves deep into the intersection of OKRs and product strategy. Tim highlights recognizing strategy's essence, making impactful choices, and then tracking progress with OKRs.
• [00:14:06] Marrying OKRs with Product Discovery: From Outcomes to Behaviors. Jenny and Tim discuss tracking team/user behaviors and predicting product success using OKRs.
• [00:20:54] Embracing 'Better' Practices in OKRs Over 'Best' Practices. Jenny Herald and Tim Herbig delve into the nuances of better practices (adaptive and relative methods) as opposed to rigid best practices, highlighting five critical 'better practices' for effective and practical application of OKRs.
• [00:24:11] Aligning OKRs with Organizational Capabilities and Structures. Jenny Herald prompts Tim Herbig to share insights on the challenges faced by organizations when their desired objectives do not align with their current capabilities or structures. Tim elaborates with stories that exemplify the discrepancies between organizational structures and the application of OKRs.
• [00:28:52] Aligning the Cadence of Product Delivery with Outcomes. Jenny Herald and Tim Herbig discuss the challenge of synchronizing the cadence of product delivery with the desired outcomes. They ponder on the nuances of how teams should approach measuring meaningful progress, especially when direct results may not be immediately evident.
• [00:30:07] The Art of Developing Leading Indicators in Product Delivery. Jenny Herald and Tim Herbig delve deeper into the concept of leading and lagging indicators in relation to key results. They discuss the challenges, conceptual considerations, and the dynamism of creating proxies and leading indicators.
• [00:35:37] Quick-Fire Questions for Tim:
  • What is your dream with a deadline? Tim's dream with a deadline is to do a solo travel to Tel Aviv in the next two years.
  • When someone says they failed with OKRs previously and want to try again, what's your advice? Tim advises them to first clarify why they want to use OKRs in the first place.
  • What's a good reason for using OKRs? The ideal reason is to enable team autonomy and outcome thinking. A more pragmatic reason is to ensure people work on the right things and maintain strategic focus.
  • Which book largely shaped how you think? Both in general and related to OKRs. For general thinking, "Radical Acceptance" by Tara Brach influenced him the most. Regarding OKRs, he credits "Radical Focus" by Christina Wodtke and "OKRs at the Center" co-written by Natalija and Sonja.

Relevant links:

• “Radical Acceptance,” book by Tara Brach
• “The Courage to Be Disliked: How to Free Yourself, Change your Life and Achieve Real Happiness,” book by Ichiro Kishimi and Fumitake Koga
• “Radical Focus,” book by Christina Wodtke, American businessperson and specialist in the area of design thinking, information architecture and Management Science (specializing in objectives and key results (OKR) and team productivity.)
• “OKRs At The Center: How to use goals to drive ongoing change and create the organization you want,” by Natalija Hellesoe and Sonja Mewes
• Linked Better Practices over Stacked Best Practices

About the Guest:
Tim Herbig is a seasoned Product Management Coach and Consultant. He is passionate about helping product teams develop better practices to measure the progress of their decisions. Tim masterfully connects Strategy, OKRs, and Product Discovery. Tim has worked on solving hard business problems and driving user behaviors in diverse product contexts.

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