84 episodes

These are real stories of trials and victories in business. We'll talk about aligning teams and organizations around a common purpose, the ups-and-downs of goal management using Objectives and Key Results (OKRs), and everything in-between.

Dreams with Deadlines Quantive

    • Business
    • 5.0 • 11 Ratings

These are real stories of trials and victories in business. We'll talk about aligning teams and organizations around a common purpose, the ups-and-downs of goal management using Objectives and Key Results (OKRs), and everything in-between.

    On Scaling OKRs in a Fast-Growing Startup | Micaela Arizpe, Chief of Staff to the COO at Personio

    On Scaling OKRs in a Fast-Growing Startup | Micaela Arizpe, Chief of Staff to the COO at Personio

    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 oper

    • 42 min
    On Tailoring Strategies for Every Industry | Kenneth Lewis, Co-Founder at OKR International

    On Tailoring Strategies for Every Industry | Kenneth Lewis, Co-Founder at OKR International

    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.

    Follow Our Guest:
    LinkedIn | Atlas Learning | Purposetrade | Grassroute | Docmode | OKR International
     
    Follow Dreams With Deadlines:
    Host | Company Website | Blog | Instagram | Twitter

    • 57 min
    On Transforming Performance | Kenneth Lewis, Co-Founder at OKR International

    On Transforming Performance | Kenneth Lewis, Co-Founder at OKR International

    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 pur

    • 1 hr 7 min
    On Building a Champion Community | Aaron Velek, Managing Consultant (VP) - Americas at Quantive

    On Building a Champion Community | Aaron Velek, Managing Consultant (VP) - Americas at Quantive

    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 gu

    • 31 min
    On Creating Psychologically Safe Workplaces | Eleanor Manley, CEO and Co-Founder at Metta Space

    On Creating Psychologically Safe Workplaces | Eleanor Manley, CEO and Co-Founder at Metta Space

    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 work

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

    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 meetin

    • 55 min

Customer Reviews

5.0 out of 5
11 Ratings

11 Ratings

MR. HARRIVAN ,

Insightful, and Entertaining

If you're looking for a business podcast that delivers actionable insights and thought-provoking discussions, look no further than then Dreams with Deadlines, hosted by Jenny Herald, Chief Evangelist at Quantive. Each episode features a well-respected business leader who share their expertise and experiences in a conversational and engaging format. Jenny's questions are always on point and keep the conversation flowing smoothly. I've found that after listening to each episode, I come away with at least one new idea or insight that I can apply to my own work. Overall, I highly recommend this podcast to anyone looking to drive better business outcomes

7MCB7 ,

Actionable content

What I like most about the Dreams with Deadlines show is how it provides context for the topic then follows up with actionable steps. This is helpful, especially for those who are newer to implementing OKR’s in their organization. Keep up the great content!

i lovee ny ,

Amazingly insightful

What an excellent podcast and so happy I found it. Thanks for the notes which are summarized and time boxed so I can go to what I want to listen to in case I want a repeat or quick reminder.

This is like a mini MS in OKRs. Count me in as a supporter and follower!

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