On Navigating OKR Check-Ins | Christian Ulstrup, AI Expert & Advisor, GSD @ Work

In this episode, we dive into the world of OKRs (Objectives and Key Results) and explore the critical aspect of OKR check-ins. Our guest, Christian Ulstrup, shares valuable insights and practical advice on making OKR check-ins effective.Key Things Discussed:The Power of Weekly OKR Check-Ins: Discover why having weekly OKR check-in meetings can be a game-changer for your organization. Christian emphasizes the importance of regularity, accountability, and momentum.Balancing Art and Science: Learn how OKR check-ins require a delicate balance of science (quantitative metrics) and art (effective questions and facilitation). Find out how to make sense of confidence scores, set ambitious experiments, and avoid status update pitfalls.Reflecting for Long-Term Success: Christian outlines the significance of end-of-quarter reflections and how they contribute to sustained OKR success. Explore the concepts of "spiritually correct" and "technically correct" key results, as well as the idea of heroic narratives to shape your company culture.Show Notes[00:00:06] Navigating OKR Check-Ins Through Dante's Inferno. Christian Ulstrup discusses the three stages of OKR check-ins inspired by Dante's Inferno and how they can lead from the tedious "Status Update Hell" to the enjoyable "Weekly Sync Heaven."[00:04:16] The Purpose of OKR Meetings and Integration with Existing Practices. Jenny and Christian explore the fundamental question of why organizations should have OKR meetings. They discuss whether OKRs should be integrated into existing practices, and Christian emphasizes the importance of aligning OKRs with the organization's goals and the nature of the work being done.[00:08:09] Overcoming Challenges and Shifting Mindset in OKR Meetings. Christian Ulstrup discusses the size criteria for implementing OKR meetings, emphasizing that OKRs can work at various stages of a company's lifecycle, from startups to larger organizations. He also addresses the challenge of shifting the mindset from dull meetings to engaging, productive ones.[00:13:37] Understanding Confidence Scores and the Role of Stewards in OKRs. Christian Ulstrup explains the concept of confidence scores in the context of OKRs. He describes how confidence scores are used to assess the likelihood of achieving key results and discusses the role of stewards in providing these scores.[00:17:14] Developing Discernment and Leveraging Information Sources for Accurate Scores. Christian Ulstrup discusses the importance of attention, discernment, and decision-making in the context of OKRs, and provides insights into developing discernment and using various sources of information for accurate confidence scores.[00:22:07] Structure and Execution of Weekly OKR Meetings. Christian Ulstrup discusses the structure and execution of weekly OKR meetings. He provides details on the recommended duration, key topics to cover, and the roles of participants, including stewards and facilitators. The discussion also touches on accountability, confidence scores, and how to focus the meeting on making sense of changes and setting ambitious experiments to close gaps.[00:31:25] Success Stories of Engaging Weekly OKR Meetings. Christian Ulstrup shares success stories from organizations that have effectively implemented weekly OKR meetings. He highlights the key indicators of success, including the movement of confidence scores, which indicate that teams are actively pushing boundaries and learning. Christian also emphasizes the importance of novelty and familiarity in making these meetings engaging, drawing a parallel to serialized TV shows. He recounts a pivotal pivot decision made during one meeting and discusses the excitement that arises when team members set ambitious goals and exceed their own expectations.[00:36:36] Check-In Traps to Watch Out For in Weekly OKR Meetings. Christian Ulstrup discusses potential pitfalls and check-in traps that organizations should be aware of in weekly OKR meetings, emphasizing the importance of maintaining accurate confidence scores, avoiding status update-focused meetings, and upholding the commitment to regular meetings.[00:40:54] Sustaining OKRs Beyond Check-Ins. Christian Ulstrup and Jenny Herald explore how organizations can sustain the use of OKRs beyond their weekly check-in meetings by conducting meaningful reflections at the end of each quarter, focusing on the spiritual and technical correctness of key results, and highlighting heroic narratives that reinforce company culture and values.[00:48:00] Quick-Fire Questions for Christian Ulstrup:Dream with a Deadline: Christian shares his dream with a deadline, which involves turning his AI-enhanced code, designed to mine and highlight interesting moments in meetings, into a monetized product. He envisions this product helping organizations extract valuable insights from their recorded meetings.Common OKR Mistake: Christian points out that one common mistake people make when adopting OKRs is becoming overly focused on being objective-driven. While OKRs are powerful, he emphasizes the importance of balancing them with unbounded exploration and exploration outside the scope of objectives and key results.Book That Shaped His Thinking: Christian mentions the book titled "Why Greatness Cannot Be Planned: The Myth of the Objective" by Kenneth Stanley as a significant influence on his thinking. He recommends this book to anyone interested in OKRs as it complements the OKR process by highlighting the importance of unbounded exploration and breakthrough thinking.Relevant links:“The Divine Comedy,” by Dante Alighieri“Dilbert,” American comic strip written and illustrated by Scott Adams“Office Space,”directed by Mike Judge“Radical Focus: Achieving Your Most Important Goals with Objectives and Key Results,” by Christina Wodtke“Succession,” the TV series“Why Greatness Cannot Be Planned: The Myth of the Objective," by Kenneth StanleyAbout the Guest:Christian Ulstrup specializes in OKR implementation for executive teams across industries, from tech startups to healthcare services. He complements OKRs with custom AI integrations, streamlining focus on key objectives and automating tasks. He holds degrees from MIT and Duke.Follow Our Guest:LinkedInFollow Dreams With Deadlines:Host | Company Website | Blog | Instagram | Twitter