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In this episode of Definitely Maybe Agile, hosts Peter Maddison and David Sharrock tackle an often overlooked but critical topic: career progression for Scrum Masters and Product Owners. They explore how organizations initiate these crucial Agile roles but frequently fail to consider their long-term evolution within the company structure.

The discussion contrasts the divergent career trajectories of these two roles. For Product Owners, a clearer path exists from managing individual products to becoming Chief Product Owners and potentially Line of Business managers, though challenges arise when the role lacks proper autonomy or is treated as a part-time responsibility. Meanwhile, Scrum Masters face a more ambiguous journey, with traditional progression into Agile coaching roles becoming increasingly limited in many organizations despite the valuable skills they develop.

Peter and Dave highlight the critical importance of demonstrating value and making contributions visible, particularly for Scrum Masters whose impact often remains behind the scenes. They also discuss how understanding financial aspects of the business becomes increasingly crucial as professionals advance in either career path.

Key Takeaways:

• Product Owners have clearer progression paths toward leadership positions, but organizations must properly position and empower the role from the beginning to enable this growth.
• Scrum Masters develop highly valuable skills in facilitating delivery and optimizing organizational flow, but need to actively demonstrate their impact to create career advancement opportunities.
• Both roles require increasingly strategic thinking about business value and financial outcomes to progress into higher leadership positions within organizations.

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In this episode of Definitely Maybe Agile, hosts Peter Maddison and David Sharrock dive into the world of Objectives and Key Results (OKRs). They explore how this increasingly popular framework helps organizations create alignment, measure progress, and foster autonomy while moving away from traditional KPIs. From the origins at Intel in the 70s to widespread adoption by tech giants like Google, Peter and David discuss the nuances of implementing OKRs effectively and why they're particularly well-suited for organizations operating in rapidly changing environments.

This week´s takeaways:

• Unlike KPIs which measure performance, OKRs measure progress and alignment to strategy. They should never be tied to individual performance metrics as this undermines their exploratory nature.
• Successful OKR implementation requires ongoing conversations, regular reviews, and a cultural shift. Many organizations underestimate the effort needed to maintain OKRs effectively.
• Effective OKRs should be limited in number (3-5 objectives with 3-5 key results each), represent stretch goals beyond business-as-usual, and serve as a prioritization mechanism for the organization.

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When was the last time raising risk in your organization led to anything other than slowing down? Join hosts Peter Maddison and David Sharrock as they challenge conventional thinking about risk management in the age of rapid technological change. This episode reveals why traditional approaches might be putting your organization in greater danger.

Drawing from their battle-tested experience working with financial and technology organizations, Peter and David crack open the uncomfortable truth: many companies still treat risk management as a checkbox exercise rather than a competitive advantage. They reveal how the explosion of data analytics capabilities has rendered old "rule of thumb" approaches obsolete while simultaneously creating entirely new risk landscapes that most organizations are woefully unprepared to navigate.

This week's takeaways :

1. Risk management begins with identifying vulnerabilities, understanding potential impacts, and making informed decisions about how to handle them—whether through acceptance, avoidance, transfer, or reduction.
2. Effective risk management isn't just about frameworks and committees—it requires a cultural environment of psychological safety where risks can be openly discussed without fear.
3. The most effective approaches position oversight functions like architecture as service providers rather than gatekeepers, helping teams move forward safely rather than simply blocking progress.

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