On Crafting Effective OKR Systems


Natalija Hellesoe headshot
Natalija Hellesoe


Episode notes

In this episode of Dreams With Deadlines, host Jenny Herald sits down with Natalija Hellesoe, an Organizational development Coach and OKR expert. Natalija shares her insights and experiences in implementing OKRs, emphasizing the importance of leadership engagement, setting realistic commitments, and making time a priority. 

What you will learn

  • The concept of "eat the frog" days and how they can help teams overcome time constraints
  • The need for education, continuous improvement, and conscious implementation when adopting OKRs
  • She offers guidance on developing a well-designed OKR system that aligns with the organization's goals and addresses the complexity of the business ecosystem
  • The importance of avoiding mainstream implementations and fostering a community that promotes diversity of thought and continuous learning

Show notes

  • [00:00:37] Motivations and Challenges in Implementing OKRs for Business Success: Jenny Herald and Natalija Hellesoe discuss the common motivations and challenges businesses face when implementing OKRs.
  • [00:01:37] Exploring the Pros and Cons of Implementing OKRs for Organizational Success: Jenny and Natalija discuss the advantages and disadvantages of using OKRs for goal-setting and organizational alignment.
  • [00:04:13] Navigating Realism in Company Goal Setting for Effective OKRs: Natalija emphasizes the importance of strategic focus and considering other requirements and stakeholders when setting realistic OKRs.
  • [00:06:51] Navigating Difficult Conversations for Successful OKR Implementation: Natalija discusses the need for difficult conversations in setting priorities and making commitments for successful OKR implementation.
  • [00:07:47] The Importance of Realistic Assessments for Successful OKR Implementation: Natalija highlights the significance of conducting realistic assessments before implementing OKRs.
  • [00:09:44] Balancing Customer Expectations and Delivering Effective Methodologies: Natalija emphasizes understanding customers' needs and meeting expectations while providing what they truly need.
  • [00:10:41] Navigating the Role of Senior Leadership in Successful OKR Implementation: Natalija discusses the challenges and importance of senior leadership involvement in OKR implementation.
  • [00:13:30] The Crucial Role of Senior Leaders in OKR Implementation and Success: Natalija emphasizes the importance of senior leadership's commitment and understanding of OKRs for successful adoption.
  • [00:16:14] Making Time Commitment the First OKR: Natalija explores the concept of making time commitment the first OKR and provides examples of addressing time-related issues.
  • [00:21:20] Fostering Engagement: Natalija discusses the benefits of "eat the frog" days and the challenge of engagement when introducing new initiatives.
  • [00:23:25] Bridging the Gap: Strategies for Engaging Skeptics and Fostering OKR Adoption. Natalija discusses strategies for bridging the gap between OKR believers and skeptics.
  • [00:27:29] Striking the Right Balance: Implementation for Successful OKR Adoption. Natalija emphasizes the importance of finding the right balance in OKR adoption and avoiding micromanagement.
  • [00:29:46] Guidelines for Developing a Well-Designed OKR System. Natalija highlights the importance of understanding the problem, prioritizing focus, and educating oneself about different variations.
  • [00:33:52] The Future of OKRs: Moving Towards Conscious Implementations. Jenny and Natalija discuss the future of OKRs. Natalija urges conscious implementations of OKRs and avoiding the mainstream trap.
  • [00:35:25] Enhancing the OKR Method: Embracing Complexity and Engaging in Conversation. Natalija emphasizes embracing complexity and engaging in conversations to improve the OKR method.
  • [00:37:47] Quick-Fire Questions for Natalija:
    • What’s your Dream With a Deadline: Natalija's dream is to go on an expedition through Greenland before turning 40.
    • What drew Natalija to the OKR method: Natalija's interest in connections and seeing the bigger picture naturally drew her to frameworks and methods that help people understand how things belong together, and OKRs fulfill these aspects for her.
    • Advice for those starting out with OKRs: Natalija advises not to believe everything written about OKRs, but instead to keep digging and talking to people to enrich their understanding and benefit from diverse opinions and perspectives.
    • Where Natalija hopes to be this time next year: Natalija hopes to be in a remote location, reflecting on the past 12 months of working with great customers and finding more organizations that have embraced change in how they work together, driven by enthusiasm to make a difference.
    • Book that shaped Natalija's thinking: The book "Speaking and Being" by Kübra Gümüşay, which explores how language shapes our thinking and determines our politics, shaped Natalija's thinking and emphasized the importance of language, also relevant in the context of OKRs.

Relevant links

About our guest:

Natalija Hellesoe headshot
Natalija Hellesoe


Natalija Hellesoe is a trainer, coach, and chance taker, supporting companies in increasing focus, autonomy, and value creation. She works with organizations at various stages of their OKR journey. Her diverse experiences and global perspective drive her to redefine possibilities.

Additional resources