Dreams with Deadlines

In this episode of Dreams with Deadlines, Jenny Herald welcomes Micaela Arizpe, Chief of Staff at Personio, to discuss the intricate challenges and strategies of scaling Objectives and Key Results (OKRs) in a rapidly growing startup environment.

Key Things Discussed:

• Navigating Growth and Process Evolution: Micaela shares her experience joining Personio at a pivotal growth stage with around 700 employees. She details how existing structures and processes began to show signs of strain under rapid expansion, emphasizing the necessity for process evolution and revamping, especially in communication, alignment, and effectiveness.
• Strategic Implementation and Evolution of OKRs: Delving into the role of OKRs, Micaela discusses their significance in maintaining focus, fostering autonomy, encouraging innovation, and ensuring transparency and alignment within a growing organization. She reveals how Personio adapted its OKR processes, including transitioning from simple tools like Google Sheets to more sophisticated systems, and how executive sponsorship played a vital role in the successful scaling of the OKR program.
• Cultivating a Network of OKR Champions: An intriguing aspect of Personio's journey is the development of an OKR Champion network. Micaela highlights how empowering these champions as subject matter experts and strategic partners in various departments was crucial. She also discusses adapting the OKR processes to remote and hybrid environments, ensuring continuous alignment and collaboration across expanding teams.

Show Notes

• [00:00:06] Challenges of Scaling in a Fast-Growing Startup: Micaela discusses the initial challenges faced by Personio as it scaled, particularly the strain on existing structures and processes. She emphasizes the importance of evolving these elements to maintain efficiency and effectiveness.
• [00:04:16] The Role and Evolution of OKRs. Jenny and Micaela delve into how OKRs were utilized and adapted at Personio. Micaela highlights their role in focusing efforts, fostering innovation, and ensuring transparency and alignment within the growing organization.
• [00:08:09] Adapting OKRs for Remote Work and Collaboration. Jenny and Micaela cover the transition of OKR processes to suit remote and hybrid work environments. Micaela discusses the challenges and innovations in maintaining alignment and collaboration across geographically dispersed teams.
• [00:13:37] Principles Behind the OKR Program. Micaela reflects on whether the underlying principles of Personio's OKR program changed with scaling. She reiterates the consistent focus on core principles like focus, ownership, stretch, innovation, alignment, and transparency.
• [00:17:14] Strategic Priorities and Departmental OKRs. Jenny and Micaela shift to how strategic priorities feed into departmental OKRs at Personio, and the importance of aligning these with operational and financial planning.
• [00:48:00] Quick-Fire Questions for Micaela Arizpe:
  • What is your dream with a deadline? Micaela shares her personal goal of publishing a poetry book, which she achieved by presenting it as a gift to her loved ones.
  • What advice would you give folks who are scaling their OKR program? Micaela emphasizes the importance of executive sponsorship and ensuring collective commitment and involvement in the OKR process.
  • What would you say is the most impactful lesson learned, maybe even failure, if you want to share, insight you've gained from your experience in scaling OKRs at Personio? Micaela advises focusing on training a network of OKR experts rather than creating rigid rules. She highlights the importance of decentralizing expertise to avoid becoming a bottleneck in the process.

Relevant links:

• Masters of Scale Podcast by Reid Hoffman
• Blitzscaling: The Lightning-Fast Path to Building Massively Valuable Companies by Reid Hoffman (Author), Chris Yeh (Author), Bill Gates (Foreword)

About the Guest:
Through years of experience in Customer Success, strategy and business operations, Micaela has worked with C-level executives in B2B SaaS to define and operationalize strategies that drive customer value. In her current role she helped scale Personio’s OKR framework into a robust program suitable to their current size of 1800 employees and beyond.

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In this follow-up episode of Dreams With Deadlines, host Jenny Herald sits down once again with Kenneth Lewis, Co-Founder of OKR International. Building on their previous discussion about performance management and OKRs, they delve into new territories, shedding light on the nuanced application of OKRs in diverse industries.

Key Things Discussed:

• Failure as a Stepping Stone: Kenneth shares compelling stories from companies that initially struggled with OKR adoption but eventually found success. He emphasizes the importance of learning from failure and approaching OKRs with a change management mindset.
• OKRs in Non-Tech Environments: The conversation pivots to the challenges and unique approaches required when implementing OKRs in non-tech industries. Kenneth discusses the need for context-specific strategies, balancing innovation with traditional business models, and the aspiration of non-tech companies to adopt progressive practices.
• Sustainable Use of OKRs: Addressing the potential for OKRs to become just another management fad, Kenneth argues for a more holistic approach. He advocates for integrating OKRs with organizational rituals, focusing on purpose, and recognizing the importance of conversations and feedback alongside goal setting.

Show Notes

• [00:00:06] The Path of Failure to Success in OKR Adoption. Kenneth Lewis shares real-world stories about companies initially struggling with OKR adoption, reflecting on their failures and learning to eventually succeed in incorporating OKRs into their operational rhythm.
• [00:04:16] Implementing OKRs in Non-Tech Environments. Jenny and Kenneth shift to the challenges and nuances of implementing OKRs in non-tech industries. Kenneth highlights the differences in approach required for knowledge worker-based and labor-intensive non-tech companies.
• [00:08:09] The Endurance of OKRs and Avoiding the Hype Cycle. Kenneth addresses how OKRs can be sustained beyond the initial hype. Kenneth emphasizes the importance of understanding the intent and principles of OKRs, rather than rigidly sticking to frameworks
• [00:13:37] OKRs and Organizational Culture. Kenneth and Jenny delve into how OKRs can shape and influence organizational culture. They discuss the importance of adapting OKRs to align with the company's mission, work processes, and performance goals.
• [00:17:14] Customizing OKRs for Maximum Effectiveness. Jenny and Kenneth explore the customization of OKRs to fit different organizations. Kenneth stresses the need to consider various factors like company size, industry, and culture to effectively implement OKRs.
• [00:22:07] The Future of OKRs in Business. Jenny and Kenneth discuss the future of OKRs in business. Kenneth shares insights on the potential longevity of OKRs, how they can evolve, and the importance of adapting them to an organization's unique needs and aspirations.n making sense of changes and setting ambitious experiments to close gaps.

Relevant links:

• Masters of Scale Podcast by Reid Hoffman
• High Output Management by Andy Grove
• Measure What Matters by John Doerr
• “Switch: How to Change Things When Change Is Hard” by Chip and Dan Heath
• Conscious Business by Fred Kofman

About the Guest:
Kenneth's purpose is to be that eternal flame that ignites passion and performance in others. He is the founder of Atlas Learning, an investor and advisor at Purposetrade, Grassroute, and Docmode, and a consultant with multiple firms. He's also the Co-founder of OKR International, the world’s largest OKR training, coaching and consulting company.

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In this episode of "Dreams With Deadlines," host Jenny Herald welcomes Kenneth Lewis, co-founder of OKR International, to explore the dynamic world of Objectives and Key Results (OKRs) in business. With over two decades of experience and a rich history of working with renowned companies like Colgate, Swift, and Bosch, Kenneth delves deep into the practicalities and philosophies of OKRs.

Key Things Discussed:

• The Journey to OKRs: Kenneth shares his personal and professional journey, revealing how a background in sales, teaching, and organizational development led him to the world of OKRs. His story highlights the transformational potential of OKRs in aligning strategy with execution, focusing on goals, and fostering organizational transparency.
• Integrating OKRs with Performance Management: The conversation delves into the nuances of combining OKRs with performance management systems. Kenneth outlines various approaches, such as the hybrid system where OKRs feed into performance assessments and the impact of this integration on employee engagement and organizational control.
• Real-World Applications and Challenges: Drawing from his extensive experience, Kenneth offers vivid examples from companies like Colgate-Palmolive and discusses the practical challenges and solutions in implementing OKRs. He emphasizes the importance of adapting OKRs to the organization's culture and goals, rather than strictly adhering to predefined frameworks.

Show Notes

• [00:00:06] Introduction to Kenneth Lewis and OKR International. Jenny Herald introduces Kenneth Lewis, highlighting his extensive experience in business and his role as the co-founder of OKR International, the first OKR consulting company in India and Asia.
• [00:04:16] Kenneth Lewis's Origin Story and Discovery of OKRs. Kenneth shares his journey from being a sales professional and teacher to discovering OKRs, emphasizing his experiences in sales, teaching, and organizational culture that led him to this methodology.
• [00:08:09] Fundamentals and Misconceptions of OKRs. Kenneth discusses the basic principles of OKRs, addressing common misunderstandings and returning to the core ideas behind the methodology, as initially envisioned by Andy Grove and John Doerr.
• [00:13:37] OKRs in Relation to Budgets and Investments. Kenneth explains how OKRs interact with company budgets and investment strategies, using Colgate-Palmolive as a case study to illustrate how businesses can balance budget constraints with aspirational OKRs.
• [00:48:00] Quick-Fire Questions for Kenneth Lewis:
  • Dream with a Deadline: Kenneth aspires to positively impact a million lives during his career and another million post-retirement. Additionally, he has a goal for one of his invested companies to reach $5 million in revenue by 2026.
  • When things start to go sideways in OKR implementations, what advice do you give to turn things around? He emphasizes viewing challenges as learning opportunities and advises not to be too hard on oneself, but to learn from experiences and move forward.
  • What do you believe is the role of the C-level, or the CEO even, in the OKR program? Kenneth believes that C-level executives should have a mix of conviction and hope in the OKR program, actively participate in it, and understand that OKRs are a means to a broader organizational goal, not the end in themselves.
  • What is the single most impactful lesson or insight you've gained from your experience with OKRs and performance management within an organization? He finds that OKRs are fundamentally simple and effective for setting and achieving goals. Their simplicity and holistic approach make them a powerful tool for organizational development.
  • Book That Shaped His Thinking: "Atlas Shrugged" by Ayn Rand has significantly influenced him, teaching him about human potential, the importance of reason, and aiming beyond perceived limitations.

Relevant links:

• "Atlas Shrugged" by Ayn Rand
• "The Fountainhead” by Ayn Rand

About the Guest:
Kenneth's purpose is to be that eternal flame that ignites passion and performance in others. He is the founder of Atlas Learning, an investor and advisor at Purposetrade, Grassroute, and Docmode, and a consultant with multiple firms. He's also the Co-founder of OKR International, the world’s largest OKR training, coaching and consulting company.

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In this episode of "Dreams With Deadlines," Jenny Herald sits down with Aaron Velek, Managing Consultant at Quantive, to delve deep into the world of Objectives and Key Results (OKRs).

Key Things Discussed:

• The Role of OKR Champions: Aaron Velek provides a comprehensive view of what it means to be an OKR champion, emphasizing the importance of being a subject matter expert, a coach to leaders and teams, and a change agent in organizations. He shares insights into the qualities and skills essential for selecting OKR champions, such as problem-solving abilities, strategic thinking, and effective communication across organizational levels.
• Fostering a Community of OKR Champions: The conversation explores strategies for building and sustaining a community of OKR champions. Velek stresses the importance of regular training, meetings, and effective communication channels to ensure a unified understanding and approach to OKRs. He shares practical tips on organizing monthly meetups, developing comprehensive training modules, and using newsletters and technology to keep champions engaged and informed.
• Challenges and Success Stories in OKR Implementation: Velek shares real-world examples and success stories, particularly from his experience at SVB. He discusses how integrating OKRs into existing processes can lead to significant improvements and highlights the role of leadership and steering committees in navigating challenges and steering the OKR program towards success.

Show Notes

• [00:00:00] Introduction. Jenny Herald introduces Aaron Velek and expresses excitement about having a colleague on the show. This sets the stage for the episode focused on OKRs.
• [00:00:09] Defining the Role of an OKR Champion. Discussion about what an OKR champion is, including their responsibilities and the importance of being a subject matter expert and a coach in the organization.
• [00:00:57] Qualities and Criteria for Selecting OKR Champions. Aaron Velek shares insights on the key qualities and criteria for selecting effective OKR champions, highlighting strategic mindset, organization skills, and the ability to communicate effectively.
• [00:01:37] Backgrounds and Experiences Ideal for OKR Champions. Exploration of the backgrounds and experiences that make someone an ideal candidate for an OKR champion, including roles like chief of staff and project management.
• [00:03:01] The Role of OKR Champions in Organizations. Discussion about the benefits of having in-house OKR champions compared to external OKR coaches, focusing on knowledge, experience, and embedding OKRs into the organization's rhythm.
• [00:03:48] Success Stories of OKR Implementation. Aaron shares success stories from his experience, highlighting the impact of effective OKR implementation and the role of champions in change management.
• [00:04:44] Responsibilities and Challenges for OKR Champions. Jenny and Aaron cover the key responsibilities of OKR champions, including leading workshops, facilitating events, and providing personalized coaching.
• [00:11:00] Building a Community of OKR Champions. Aaron discusses strategies for fostering a community of OKR champions, including training, frequent meetings, and asynchronous communication tools like Slack or Teams.
• [00:14:42] The Importance of Continuous Training and Learning. Detailed exploration of the training process for OKR champions, including fundamental, advanced, and coaching aspects, and the importance of continuous learning.
• [00:17:38] Utilizing Newsletters and Technology in OKR Programs. Discussion on the use of newsletters and technology to keep people engaged in the OKR program, and how these tools support the work of OKR champions.
• [00:23:10] Measuring the Success of an OKR Program. Aaron talks about how to measure the success of an OKR program, including engagement and adoption metrics, and the use of a maturity index.
• [00:24:17] The Role of the Steering Committee. A look into the role and assembly of the steering committee in guiding and supporting the OKR program, including facing obstacles and decision-making.
• [00:26:27] Quick-Fire Questions for Aaron Velek:
  • What is your dream with a deadline? Aaron mentions his commitment to continuous learning without a specific deadline, making it an ongoing journey. On a personal note, he dreams of seeing his children grow up successfully in a good world, which is a constant goal for him.
  • What strong opinions do you have about how OKRs should or should not be used? Aaron emphasizes the importance of focusing on outcomes rather than tasks or projects when using OKRs. He advises keeping the conversation around outcomes and the 'why' of OKRs to avoid turning them into mere task trackers.
  • For an OKR champion lead about to start out, what would you suggest should be the first thing they do? Aaron recommends that new OKR champions should seek out and speak with experienced champions to understand their journey and focus areas for long-term development.
  • What's the value of bringing someone external to help the OKR champions internally with their OKR program? Aaron highlights the value of external OKR coaches, noting that many companies lack dedicated internal resources with extensive experience in launching OKR programs. He suggests that external coaches can help launch or get programs back on track, bringing in-depth experience and knowledge.
  • Book That Shaped Your Thinking:  Aaron cites "Extreme Ownership" by Jocko Willink as influential in shaping his mindset. He appreciates the book's focus on prioritizing critical tasks and not becoming overwhelmed, which has guided his approach to project and program management, as well as OKRs.

Relevant links:

"Extreme Ownership" by Jocko Willink and Leif Babin

About the Guest:
Aaron Velek, Managing Consultant at Quantive, is an expert in OKR methodology with a focus on strategic planning and change management. Known for his work at SVB, he specializes in coaching and developing OKR champions in various organizations.

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In this episode, Eleanor Manley, Co-Founder of Metta Space, delves into the critical issue of workplace misconduct and violence, shedding light on the startling statistics and the profound impact it has on organizations and individuals. Eleanor shares valuable insights into the importance of creating psychologically safe workplaces, the role of technology in preventing and resolving workplace misconduct, and the need for data-driven strategies to address this pervasive problem.

Key Things Discussed:

• Creating Psychologically Safe Workplaces: Eleanor emphasizes the significance of fostering psychologically safe environments where employees can confidently report misconduct.
• Leveraging Technology for Prevention and Resolution: Eleanor explains how Metta Space employs technology, ensuring privacy and advocating for reduced resolution times in addressing workplace misconduct.
• Empowering Employees and Normalizing Reporting: Eleanor underscores the importance of empowering employees to report misconduct while challenging the misconception that fewer reports signify a safe workplace and discussing the complexities of addressing misconduct.

Show Notes

• [00:00:00] Introduction to Workplace Violence and Harassment: Jenny introduces Eleanor Manley, CEO of Metta Space, discussing the complexities of defining workplace violence and harassment.
• [00:01:46] Identifying and Addressing Workplace Misconduct: Jenny and Eleanor explore various forms of workplace misconduct, highlighting its impact and the challenges of identification.
• [00:06:15] The Hidden Costs of Unreported Workplace Misconduct. Jenny and Eleanor discuss the financial consequences of unreported misconduct and the need for data-driven solutions.
• [00:07:56] Understanding the Root Causes of Workplace Misconduct. They delve into reasons behind the persistence of misconduct, including zero-tolerance approaches and cultural factors.
• [00:09:38] Legislation, Rights, and Resolution of Workplace Misconduct. Discussion on laws like POSH and the importance of swift internal resolution.
• [00:12:21] Addressing Workplace Misconduct at the Highest Levels. Jenny and Eleanor discuss Eleanor's invitation to speak at NATO on International Women's Day. They focus on the importance of addressing workplace misconduct to retain and empower women in STEM fields, including the challenges faced by military organizations in reporting misconduct.
• [00:13:47] The Crucial Role of Psychological Safety in Workplace Effectiveness. The role of psychological safety in workplace effectiveness and its impact on team productivity.
• [00:15:22] Leveraging Technology for Safer Work Environments. Eleanor discusses Metta Space and technology's role in prevention, reporting, and resolution.
• [00:20:16] Practical Steps for Creating Safe Work Environments. Jenny and Eleanor discuss practical steps that organizations and leaders can take to create safe work environments. Eleanor explains the importance of implementing clear goals and frameworks, breaking them down into pillars like prevention, reporting, and resolution. She also highlights the value of training to help employees empathize with different situations and understand the nuances of workplace misconduct.
• [00:22:45] Empowering Employees to Speak Up and Measuring Resolution Effectiveness. The importance of empowering employees to speak up and viewing case reporting positively.
• [00:24:27] Understanding the Distinction Between Breach of Code of Conduct and Breach of Law. Jenny and Eleanor discuss the distinction between a breach of a code of conduct and a breach of the law in the context of workplace misconduct. Eleanor explains that the majority of cases are breaches of a code of conduct, which may not necessarily require legal action. She emphasizes the importance of providing evidence gathering tools for individuals reporting misconduct to strengthen their case.
• [00:26:29] Envisioning a Future of Safe and Empowered Workplaces. Eleanor's goal of normalizing safe workplaces with data-driven support.
• [00:28:15] Strategies to Accelerate Resolution Time in Workplace Misconduct Cases. Strategies for organizations to reduce resolution time in misconduct cases.
• [00:33:00] Quick-Fire Questions for Eleanor Manley:
  • What is your dream with a deadline? Normalize creating safe and empowered workplaces within all organizations through prevention, reporting, and resolution of workplace misconduct.
  • What do you appreciate most about your team? Open communication, having each other's backs, and speaking up when something feels true and right.
  • Greatest Challenge as a Leader: Lack of statistics on workplace misconduct and educating organizations about the need for data-driven approaches.
  • Metta Space’s Ideal Customer Profile: Organizations with more than 100 employees, especially those with limited HR resources.
  • Starting with Workplace Misconduct Policies: Have strong policies and employee handbooks but ensure they are living documents with constant reminders.
  • Intrinsic Motivation: Empowering more women in tech and creating safe workplaces where individuals can excel without facing misconduct.
  • Contributing Factors to Exodus from STEM: Poor managerial relationships are a significant reason for people leaving organizations.
  • Book That Shaped Your Thinking:  "Blink" by Malcolm Gladwell, emphasizing trusting instincts and the power of intuition.

Relevant links:

• The U.S. Surgeon General’s Framework for Workplace Mental Health & Well-Being
• The U.S. Surgeon General Workplace Well-Being
• PoSH Act
• International Women's Day 2023: NATO Presents – Innovators and Game Changers: Women in Tech Shaping the Future
• Google’s Project Aristotle
• “Blink: The Power of Thinking Without Thinking,” by Malcolm Gladwel

About the Guest:
Eleanor Manley is the CEO of Metta Space, which helps companies prevent, report & resolve workplace misconduct. Specializing in NLP, she heads up AI, Analytics & RevOps. She has been a guest speaker at NATO and Bosch. Personally, Eleanor advocates for more women and marginalized groups to join tech, both with Metta Space’s mission and mentorship.

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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 Stanley

About 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.

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In this episode of Dreams With Deadlines, we delve into the world of Objectives and Key Results (OKRs) with the expert, Mark Spitzer. Mark is a seasoned coach and consultant who specializes in helping organizations leverage OKRs to drive meaningful change and achieve their goals.

Key Things Discussed:

• OKRs as a Catalyst for Transformation: Learn how OKRs go beyond metrics to inspire innovation and creativity within organizations.
• Balancing Run-the-Business and Change-the-Business Objectives: Find out how OKRs can drive both incremental improvements and groundbreaking change.
• Achieving Alignment and Cross-Functionality: Explore practical strategies for fostering alignment and innovation across teams.

Show Notes

• [00:00:00] Becoming an Effective Leader through OKRs. Jenny introduces Mark Spitzer, President of Spitzer Coaching, an experienced OKR and leadership expert, discussing effective leadership, creativity, vision, relationships, and motivation as essential leadership elements. They delve into the significance of OKRs as a tool to capture, communicate, and track critical goals.
• [00:02:23] Mark Spitzer's OKR Origin Story. Mark shares his journey, transitioning from software development to Agile coaching, and how he discovered OKRs through Felipe Castro, realizing they provide the missing link for goal alignment and shared purpose in organizations.
• [00:04:16] OKR Champion vs. OKR Coach: Key Differences. Mark distinguishes between the roles of an OKR champion and an OKR coach, highlighting their respective responsibilities in defining strategy and facilitating team success.
• [00:06:13] Seven OKR Coaching Competencies. Mark presents seven vital OKR coaching competencies that empower coaches to facilitate change, ensure accountability, and manage organizational challenges effectively.
• [00:09:12] Transitioning to OKRs. Mark provides guidance on adopting OKRs, emphasizing the importance of understanding individuals, gradual integration, and maintaining a focus on outcomes.
• [00:13:37] Identifying Teams for OKRs. Mark explains how to select teams for OKR implementation, especially in large organizations, highlighting the role of supportive leaders and teams engaged in high-impact projects.
• [00:22:01] OKRs as Dreams with Deadlines. Mark discusses his perspective that OKRs are "dreams with deadlines," emphasizing their role as an inspiration and motivation tool within organizations. He explains how setting ambitious goals with deadlines can spark creativity and innovation among teams, leading to more impactful outcomes.
• [00:24:27] Using OKRs to Improve Existing Metrics. Mark discusses OKRs' versatility, applicable to both visionary and improvement-oriented objectives, underlining the importance of context and balance.
• [00:27:35] Establishing Proof with OKRs: Dreams with Deadlines. Mark explains the concept of "ground shots" and advocates for using confidence scores to set impactful key results and maintain motivation.
• [00:34:24] Tips for Leaders on Achieving Vertical and Horizontal Alignment with OKRs. Mark shares insights into vertical and horizontal alignment, stressing the value of effective communication, active listening, and emotional intelligence.
• [00:41:48] Fostering Alignment Through Common Purpose and Clarity. Mark underscores the importance of finding common purpose through team exercises that connect to higher-level goals, fostering alignment and clarity.
• [00:46:10] The Importance of Strategic Thinking. Mark encourages organizations to make room for strategic thinking, allowing teams to explore innovative solutions and envision a more significant impact.
• [00:47:28] Quick-Fire Questions for Mark Spitzer:
  • Dream with a Deadline: Mark Spitzer's dream with a deadline is to make the biggest impact possible on leaders in organizations for the remainder of his career.
  • Common OKR Mistake: Mark believes that many people, when new to OKRs, tend to focus too much on activity accounting, feeling the need to list everything they're doing rather than aligning their efforts with meaningful objectives and key results.
  • Best Starting Point for OKR Practice: Mark suggests that beginners should start by getting clear on what they do, who they do it for, what success looks like, and identifying opportunities within their space. Additionally, he emphasizes the importance of starting roadmaps to articulate opportunities and select one for an OKR.
  • Future of OKRs: Mark's dream for the future of OKRs is to see them integrated into organizations' regular routines, impactful in helping companies evolve and make customers happy. He hopes that OKRs become a lasting and meaningful practice.
  • Influential Book: One of the books that has significantly influenced Mark Spitzer's thinking is "Dare to Lead" by Brené Brown. He values the book's lessons on vulnerability, authenticity, and taking risks.

Relevant links:

• “Radical Focus: Achieving Your Most Important Goals with Objectives and Key Results,” by Christina Wodtke
• “Dare to Lead: Brave Work. Tough Conversations. Whole Hearts.,” by Brené Brown

About the Guest:
Mark is a highly skilled professional coach (ICF PCC, ORSC-Trained), trainer, and consultant with over 30 years of experience working in technology, agile adoption, and management consulting – including OKRs. He partners with leaders to support their own growth and bring about positive organizational change that helps them achieve their goals.

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In this special episode of "Dreams with Deadlines," Dr. Jennifer Jacobs, a former nuclear physicist and White House fellow, shares her inspiring journey from the world of nuclear counterterrorism to founding Connect Our Kids, a groundbreaking organization dedicated to transforming the foster care system.

Key Things Discussed:

• The Foster Care Landscape: Dr. Jacobs delves into the staggering statistics surrounding foster care in the United States, shedding light on the number of children in foster care, the challenges they face, and the financial implications of the current system. She emphasizes the critical importance of permanent, loving families for these children.
• Empowering Social Workers with Data-Driven Tools: Discover how technology is revolutionizing the foster care system. Dr. Jacobs introduces Connect Our Kids' innovative software, "Family Connections," which empowers social workers to efficiently connect foster children with their families and support networks. The software's success stories, like that of Abby, highlight its transformative impact.
• An Audacious Goal for the Future: Dr. Jacobs reveals Connect Our Kids' audacious goal for the next decade: to ensure that every child and family affected by foster care or at risk of foster care is connected with their people, their relationships. The organization envisions a future where social workers prioritize maintaining children's connections with their families and loved ones, ultimately changing the landscape of foster care.

Show Notes

• [00:00:00] Introduction. Dr. Jennifer Jacobs, a former nuclear physicist and White House fellow, discusses her transition from nuclear counterterrorism to founding Connect Our Kids, inspired by reading a Time Magazine article about foster care.
• [00:04:10] The Foster Care Landscape: Statistics and Costs. Dr. Jacobs shares staggering statistics about foster care, including the number of children, their age when aging out, and the dire consequences faced by those who do. She also explores the financial implications of the current foster care system.
• [00:09:39] Transforming Social Work: Shifting Focus from Beds to Families. Dr. Jacobs highlights the challenges faced by social workers within the foster care system and the need to shift focus from finding beds for children to placing them with their own families and trusted individuals.
• [00:12:12] Empowering Social Workers with Data-Driven Tools and Transforming Lives. Dr. Jacobs discusses the pivotal role of technology in empowering social workers to connect foster children with their families and support networks. Dr. Jennifer Jacobs introduces the Connect Our Kids software, Family Connections, and explains how it mimics intelligence-style software to efficiently organize and search for crucial data. The discussion emphasizes the collaborative nature of the software and its potential to streamline social work processes, ultimately benefiting both social workers and the children they serve. The segment concludes with a heartwarming success story about Abby, illustrating the profound impact of reconnecting children with their families.
• [00:19:25] The Quantitative Impact: Transforming Lives and Society. Dr. Jacobs focuses on the financial costs associated with youth aging out of foster care without support and the substantial return on investment (ROI) achievable by redirecting resources to support these youth. The estimated ROI is over 20,000%.
• [00:31:15] An Audacious Goal: Connecting Children with Their People. Dr. Jacobs reveals Connect Our Kids' audacious goal to ensure that every child and family affected by foster care or at risk of foster care is connected with their people, their relationships. The organization envisions a future where social workers prioritize maintaining children's connections with their families and loved ones.
• [00:35:12] Quick-Fire Questions for Dr. Jennifer Jacobs:
  • What are the current challenges that you think are potentially roadblocks or obstacles to getting to that 10-year-goal? The main challenge is the resistance to change inherent in established systems, which tends to reinforce itself, making change difficult.
  • What Keeps You Going? The stories of individuals like Abby, whose lives have been positively impacted by Connect our Kids' work, serve as powerful motivation, despite bureaucratic challenges and setbacks.
  • Books or Articles That Shaped Thinking. Dr. Jennifer Jacobs mentioned the book "Foster Girl" by Georgia Todd, a team member who shared her brutally honest experiences in foster care, as well as other books and articles that offer detailed accounts of why children end up in challenging situations within the child welfare system and how bureaucracy and decisions can contribute to these issues.

Relevant links:

• “Foster Girl, a Memoir,” by Georgette Todd
• “Being Too Fierce,” by Lisa Cohen

About the Guest:
Dr. Jennifer Jacobs - CEO and co-founder of Connect Our Kids, a non-profit that helps connect foster kids with their families. Jennifer was working as a nuclear counter-terrorism expert when she noticed similarities with the foster care space. Connect Our Kids software now helps keep kids in care connected with their families.

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In this episode of Dreams with Deadlines, host Jenny Herald dives deep into the world of product management with guest Itamar Gilad, author of the newest book, "Evidence-Guided: Creating High-Impact Products in the Face of Uncertainty."

Key Things Discussed:

• Evidence-Guided Product Management: Itamar emphasizes the importance of making evidence-based decisions in product management. He shares how to set clear goals and align them with company objectives, enabling teams to focus on what truly matters.
• The AFTER Model: Itamar introduces the AFTER model—a comprehensive framework that covers Assessment, Fact-finding, Tests, Experiments, and Release Results. This model guides product managers in evaluating and testing ideas effectively, leading to better decision-making.
• Common Mistakes with OKRs: Itamar addresses misconceptions about Objectives and Key Results (OKRs), emphasizing the need for outcome-based OKRs rather than focusing on output. He also warns against the common mistake of creating too many OKRs, which can hinder commitment and trust within teams.

Show Notes

• [00:00:07] Introduction to "Evidence-Guided: Creating High Impact Products in the Face of Uncertainty. Jenny Herald introduces the newest book "Evidence-Guided: Creating High Impact Products in the Face of Uncertainty" by Itamar Gilad. Itamar shares the opening story of Google+ and why it was chosen to lead the book.
• [00:03:43] The Pitfalls of Planning Waterfall in Product Development. Jenny and Itamar discuss the concept of the planning waterfall and why it's not an effective approach in product development.
• [00:06:36] Understanding Evidence-Guided Development. Jenny and Itamar delve into the concept of evidence-guided development and explore why Itamar is so passionate about sharing this approach with the world.
• [00:08:21] The GIST Model: A Framework for Evidence-Guided Development. Jenny and Itamar discuss the GIST model, a foundational framework in evidence-guided development, and its importance in helping organizations embrace change and innovation.
• [00:11:22] From Idea to Reality: The Tabbed Inbox and Evidence-Based Development. Jenny and Itamar discuss the development of Gmail's tabbed inbox as an example of evidence-based development within the GIST model framework.
• [00:18:10] Prioritizing Ideas with the Confidence Meter. Jenny and Itamar discuss the confidence level meter, a framework for prioritizing ideas based on evidence and confidence. Itamar explains how this tool helps product teams avoid investing in ideas with low confidence and guides them towards incremental development.
• [00:24:55] Setting Evidence-Guided Goals. Jenny and Itamar discuss the importance of setting evidence-guided goals and how to choose the most important outcomes. Itamar explains why goals are crucial, regardless of whether you use OKRs or other frameworks, and emphasizes the need for both qualitative and quantitative aspects in goal setting.
• [00:31:22] Balancing Local Optimization with a Bigger Picture. Jenny and Itamar delve into the challenge of avoiding local optimization while setting evidence-guided goals. They discuss the importance of aligning team goals with the company's overarching strategy and how metrics and impact assessments can play a role in achieving this alignment.
• [00:37:03] Using the AFTER Model for Effective Idea Validation. Jenny and Itamar explore the AFTER model, a framework Itamar developed to help teams define steps for idea validation. The AFTER model stands for Assessment, Fact-Finding, Test Experiments, and Release Results. Itamar explains how each stage in the model contributes to the validation process, from initial idea assessment to controlled experiments and gradual product releases.
• [00:43:58] Quick-Fire Questions for Itamar:
  • What is your dream with a deadline? Itamar's dream with a deadline is to help product people bring evidence-guided thinking into their product development process, ultimately leading to better products, higher value, and greater job satisfaction for everyone involved.
  • What do people get wrong about OKRs? People often make two common mistakes with OKRs: using them to capture a plan (output OKRs) instead of focusing on outcomes, and creating too many OKRs, which leads to lack of commitment and trust in the process.
  • When can we expect your book to be released? The target release date for Itamar's book is September 20th, with a possibility of it being released a few days later or by the end of September.
  • What would you say is the book that largely shaped how you think?  Two books have significantly shaped Itamar's thinking: "INSPIRED" by Marty Cagan, which is highly influential in the product management field, and "The Lean Startup" by Eric Ries, which introduced the concept of evidence-guided development and the interplay between business and product development.

Relevant links:

• “Evidence-Guided: Creating High-Impact Products in the Face of Uncertainty,” by Itamar Gilad
• GIST Framework
• ICE and The Confidence Meter
• Wizard of Oz tests
• Andy Grove
• The Four Big Risks by Marty Cagan
• “INSPIRED," by Marty Cagan
• Idea Validation Methods
• David J. Bland
• "The Lean Startup" by Eric Ries

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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