BONUS X-Matrix and Obeya: How to Make Strategy Visible and Actionable for Everyone | Jim Benson and Karl Scotland

CTO Series: Navigating Growth, A Playbook for Scaling Engineering Teams With Toni Ala-Piirto   In this BONUS episode, we dive into the journey of Toni Ala-Piirto, a seasoned software leader with 15 years of experience designing and implementing distributed systems. Toni opens up about pivotal lessons from his leadership career, balancing tech strategy with business goals, and the nuances of scaling engineering teams during rapid growth. Whether you’re a CTO, a team lead, or a tech enthusiast, this conversation is packed with practical insights.   The Evolution of a Leader: A Journey, Not a Single Moment   “Leadership isn’t built in a single defining moment but shaped by many experiences.”   Toni recounts a key challenge early in his career involving a major performance issue for a customer. This experience taught him the importance of viewing systems holistically rather than focusing solely on individual contributions. His “boring” leadership style—marked by forward-thinking and crisis prevention—emphasizes preparation and identifying risks without over-engineering solutions.   Aligning Tech and Business: The Power of Collaboration   “Technology vision and business strategy should speak the same language.”   Toni highlights the importance of close collaboration with product managers, sales, and finance to ensure tech strategy aligns with broader business goals. Regular cross-department discussions foster trust and ensure that the product roadmap is both innovative and achievable.   Key Practice: Build relationships with key stakeholders through daily touchpoints to create alignment.   The Roadmap to Success: Vision vs. Execution   “Short-term details drive long-term visions.”   Toni explains their approach to roadmapping, with detailed 6-month plans that address “how” to achieve goals and a broader vision for the longer term. This allows the team to stay agile while keeping future innovations in view.   Pro Tip: Avoid spending excessive time on estimations; use past experience to guide epic-level planning.   “The first six months are about execution—the rest is about imagining what’s possible.”   Scaling Teams During Rapid Growth   “The true challenge of scaling is transferring knowledge while preserving team culture.”   Toni reflects on the growth journey from a small team to a larger organization. As the team grew, onboarding and knowledge transfer became crucial. His solution? Pair testing and collaborative learning to help developers understand the product deeply, not just the code.   Tactical Tips: Implement a “test buddy” system for collaborative testing and learning. Encourage developers to test the product to build domain knowledge and foster cross-functional understanding.   “Your people need to understand the product—not just the code—to scale effectively.”   Maintaining Culture Amid Growth   “Growth changes culture—how you hire and lead defines the next chapter.”   Toni shares how adding new team members can shift team dynamics. The key to sustaining a positive culture is hiring individuals who take ownership and serve as role models. Leaders should seek out those who aim to improve the team, not just perform their tasks.   “The best hires don’t just do their job—they make the whole team better.”   Cross-Functional Insights and Learning the CTO Role   “CTOs operate at the intersection of tech and business—a shift from pure development.”   Toni admits that stepping into the CTO role required him to expand his understanding of business operations, strategic planning, and cross-functional collaboration. He emphasizes that this broadened perspective is essential for impactful decision-making.   “The biggest shift for me was seeing the business as a whole—not just the tech stack.”   Key Influences: The Five Dysfunctions of a Team   “Understanding team dynamics is as crucial as technical expertise.”   Toni cites Patrick Lencioni’s The Five Dysfunctions of a Team as a pivotal read. The book shaped his approach to fostering accountability and ensuring team commitment. Toni underscores that accountability isn’t about blame—it’s about ownership and follow-through.   Scaling with a Talent Strategy in Mind   “Growth requires not just more people but the right investments.”   Toni discusses integrating talent strategy into roadmaps by aligning with business goals, including company size and revenue targets. Strategic hiring and investment in growth ensure that the team remains equipped to deliver on future plans.   About Toni Ala-Piirto   Toni Ala-Piirto is a seasoned software professional with 15 years of experience leading architecture and design for projects of all sizes. He excels in creating practical, fit-for-purpose distributed systems and is known for his hands-on approach and commitment to continuous improvement. Toni consistently delivers solutions that meet specific project needs while aligning with broader business objectives. You can link with Toni Ala-Piirto on LinkedIn.a

14 Jan 41min

CTO Series: Sergey’s Leadership Insights—Bridging Innovation and Strategy as CTO of CrateDB   In this BONUS episode, we sit down with Sergey, the forward-thinking CTO of CrateDB, to unpack his journey from Nokia to CrateDB and his leadership philosophy that blends technical expertise with strategic foresight. We dive into the key moments that shaped his career, the challenges of scaling technology in a competitive market, and how Sergey aligns his team’s efforts with broader business goals while staying adaptable in an ever-evolving tech landscape.   The Defining Moment in Sergey’s Leadership Journey   “Being a cheerleader, servant, and strategist for your team creates an environment where innovation can thrive.”   Sergey shares how working at Nokia with an inspiring people manager, Sotiris, influenced his leadership approach. Sotiris embodied servant leadership and made strategic thinking a team-wide responsibility. Sergey reflects on how this mindset helped him approach his current role at CrateDB, emphasizing the importance of not only building great products but ensuring they resonate in the market through thoughtful sales and marketing alignment. “The best leaders help their teams see what’s next—not just solve today’s problems.” Navigating Product-Market Fit for Technical Products “For technical products, adoption is not just about features—it’s about connecting with both developers and decision-makers.”   Sergey breaks down the challenges of achieving product-market fit for developer-centric solutions like CrateDB. He explains the dual approach of engaging both top-down decision-makers, like CTOs, and bottom-up developer communities. By drawing from his startup experience, Sergey underscores the importance of building trust and delivering a developer experience that wins over early adopters.   “The real challenge is bridging the gap between leadership adoption and the developers who use the product every day.”   The Impact of AI on Developer Experience “AI’s true transformation lies in how it enhances the products we already use, often invisibly.”   When asked about AI’s current role, Sergey reflects on the potential of AI-powered tools to transform workflows over the next few years. While not yet life-changing for his daily routine, he anticipates that AI’s influence will soon be felt through the optimization of background processes in everyday tools and databases.   “The future isn’t about flashy AI features—it’s about smarter tools that simplify complex workflows.”   Aligning Tech Strategy with Business Goals “A strong strategy needs to be a story that teams can rally around and imagine themselves in.”   Sergey details CrateDB’s unique approach to strategic planning, inspired by open-source RFCs (Request for Comments). Instead of rigid OKRs, they craft stories that clarify priorities and invite feedback from across the organization. He highlights the importance of quarterly check-ins and building checkpoints to validate assumptions along the way.   Key tips in this segment: Document the assumptions behind the strategy. Break initiatives into steps to test their feasibility. Avoid deadline-driven development; focus on value-driven milestones.   Fostering Collaboration Between Tech and Business Units “Collaboration thrives when both sides understand the trade-offs involved in strategic decisions.”   Sergey explains how collaboration between engineering and business leaders is fostered through transparency and communication. Product managers and engineering leads play key roles in advocating for priorities and ensuring alignment across teams. Sergey emphasizes the value of making trade-offs explicit to avoid silos.   “The best partnerships between tech and business come from mutual understanding—not just of goals, but of constraints.”   Staying Ahead with Strategic Roadmapping   “A good strategy diagnoses the situation, sets guiding policies, and outlines coherent actions.”   Sergey highlights the importance of competitive intelligence in staying ahead of market trends without reacting impulsively. In the world of databases, long adoption cycles offer the advantage of thoughtful strategic planning. He references the book Good Strategy/Bad Strategy and describes how CrateDB maintains an evergreen list of initiatives that can be prioritized when needed.   “Don’t just chase trends—create a strategy that withstands change by focusing on long-term coherence.”   Overcoming the Challenges of the CTO Role   “The CTO role is often ambiguous—define it based on your organization’s needs.”   Sergey candidly discusses the challenge of imposter syndrome and the ambiguity that comes with the CTO title. He outlines two common archetypes: the technical expert versus the team builder and cultural leader. He stresses the importance of adjusting the role to the organization’s maturity and goals.   “Your leadership role isn’t static—adapt your approach to meet your organization where it is.”   Books That Shaped Sergey’s Leadership Approach   “Most tech problems are people problems disguised as engineering issues.”   Sergey shares the books that influenced his leadership style: Peopleware by Tom DeMarco: Reinforces the idea that technical challenges often stem from team dynamics. Drive by Daniel Pink: Highlights the importance of autonomy, mastery, and purpose in motivating teams. Good to Great by Jim Collins: Explores what makes some companies thrive while others stagnate. About Sergey Gerasimenko Sergey is the innovative CTO of CrateDB, leading the charge in real-time analytics and hybrid search. Previously, he was VP of Engineering at MongoDB, shaping the edge device strategy, and at Realm, a leading open-source mobile/embedded database acquired by MongoDB in 2019. With a career spanning groundbreaking roles at Brainly and Nokia, Sergey co-founded two companies and holds a patent. His leadership continues to push the boundaries of tech innovation. You can link with Sergey Gerasimenko on LinkedIn.

13 Jan 44min

BONUS: Building Agile Startups with Nick Hughes of Founders Live   Welcome, Agile friends! In this episode, I had the pleasure of sitting down with Nick Hughes, the founder of Founders Live, a global startup community now operating in more than 100 cities and 50 countries. Our conversation explored what it really takes to build a business and how the principles of agility can help entrepreneurs adapt, iterate, and thrive.   If you’ve ever wondered how to sharpen your message, build resilience in the face of setbacks, and foster meaningful connections in the startup world, this episode is for you!   The Birth of Founders Live “Test, learn, iterate, and grow. That’s how I built Founders Live.”   Nick’s story began over 10 years ago when he noticed something missing in the entrepreneurial world—a supportive community where early-stage founders could connect, learn, and grow together. As a founder himself, he knew firsthand how isolating the startup journey could be.   He decided to experiment with an idea, and it worked. Founders Live has since become a thriving global movement where entrepreneurs pitch their ideas, connect with like-minded people, and celebrate innovation in an engaging, fun atmosphere.   Each Founders Live event follows a simple but powerful format: five founders deliver 99-second pitches, followed by four minutes of audience Q&A. Then, the crowd votes on the winner. Add some networking, food, and drinks, and you’ve got a recipe for an unforgettable experience!   The takeaway here? Test small, see what works, and refine from there.   The Power of a 99-Second Pitch “It’s not easy to create your 99-second pitch. But that time frame forces founders to really think: What is my message?”   Nick’s 99-second pitch format is more than a clever gimmick—it’s a forcing function for founders to get crystal clear about their message. In a short window of time, founders must distill their big idea into something precise, engaging, and impactful.   Many founders tell Nick that while it’s nerve-wracking at first, they walk away feeling more confident and impressed with their own ability to communicate under pressure. It’s not just about pitching—it’s about building communication agility and clarity of purpose.   Why Networking and Mentorship Matter “If you figure out ways to help people and open doors for them, it comes back to you tenfold.”   One of the most valuable aspects of Founders Live is its emphasis on connection. Nick shared that many of the most successful founders he knows have built networks by being generous—by “opening doors” for others. Whether it’s offering advice, making introductions, or helping someone troubleshoot a challenge, those who give tend to receive tenfold in return.   His advice for founders? Show up, participate, and look for ways to add value to your community. Authenticity and generosity go a long way in building strong relationships that will support your growth.   Embracing Agility and Resilience “Agility is looking at things as experiments—identify what works, keep that, and stop what isn’t working.”   We also dove into the mindset that helps founders bounce back from setbacks. For Nick, agility means viewing everything as an experiment. When things don’t go as planned, the question isn’t “Why did this happen to me?” but rather “What can I learn from this, and how can I adjust?”   Successful founders are constantly iterating—testing, learning, and evolving. The entrepreneurial journey isn’t a straight line; it’s a cycle of experimentation and improvement. Agility doesn’t just happen in the product—it starts with how you frame your challenges and your willingness to pivot when needed.   Common Misconceptions About Entrepreneurship “We all want creators in the world, but it’s a tough road. You need to build something that adds value before pitching it.”   According to Nick, many first-time founders enter the startup world with unrealistic expectations. Building a business isn’t just about pitching your idea to investors—it’s about creating something valuable, getting traction, and proving adoption first. If you don’t have traction or proof points, you’re burning bridges by pitching too early.   His advice? Focus on solving real problems and showing early growth before you seek funding. When you walk into the room with evidence that people love your product, your pitch becomes much stronger—and much harder to ignore.   Intrapreneurship: Innovating Inside Larger Companies   Not every entrepreneur is working outside the corporate world—some are internal innovators looking to make a difference within their organizations. For those intrapreneurs, Nick had some great advice: define your opportunity clearly, understand your company’s risk tolerance, and align your goals with measurable outcomes.   If you want to pitch new ideas inside a company, start by identifying what success would look like and communicating that vision effectively. Intrapreneurship thrives when there’s clarity around expectations and potential rewards.   Nick’s Resource Recommendation   When I asked Nick for a resource recommendation, he shared the book “The Second Mountain: The Quest for a Moral Life” by David Brooks. It’s an inspiring read about finding purpose and meaning by building something bigger than yourself—a fitting message for entrepreneurs seeking to create meaningful impact.   We closed with Nick’s final piece of advice: “Test, learn, iterate, and grow. That’s how I built Founders Live.”   This simple but powerful mantra reminds us that agility isn’t just a process—it’s a mindset. Whether you’re launching your own startup or driving innovation within a larger organization, success comes from being open to experimentation and continuous improvement. About Nick Hughes Nick Hughes is the founder of Founders Live, a global community and event platform for entrepreneurs, now active in over 100 cities across 50 countries. With a background in founding companies, Nick created Founders Live to foster connection, mentorship, and growth for startups worldwide.  To learn more about Nick and Founders Live, visit FoundersLive.com or connect with Nick Hughes on LinkedIn.

11 Jan 28min

Ellen Grove: The Messenger Anti-Pattern, When Product Owners Lack Authority Read the full Show Notes and search through the world’s largest audio library on Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. The Great Product Owner: Building Shared Understanding, The Collaborative Product Owner Pattern Ellen describes an exemplary Product Owner (PO) who actively engaged with customers, often bringing the team along to meet users. This practice fostered a shared understanding of customer needs and amplified creativity within the team. A great PO promotes collaboration and ensures that the team is aligned with the product vision, enabling innovative solutions and meaningful outcomes. The Bad Product Owner: The Messenger Anti-Pattern, When Product Owners Lack Authority A poor PO, Ellen explains, is one who lacks decision-making authority. In one case, a PO served merely as a messenger for the CEO, repeatedly deferring to higher-ups for answers. This lack of empowerment hindered team progress and frustrated the development process. Ellen underscores that Scrum Masters play a crucial role in supporting POs to ensure they can fulfill their responsibilities effectively. Self-reflection Question: How can you support Product Owners to strengthen their ability to make informed decisions? [The Scrum Master Toolbox Podcast Recommends] 🔥In the ruthless world of fintech, success isn’t just about innovation—it’s about coaching!🔥 Angela thought she was just there to coach a team. But now, she’s caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn’t just about the product—it’s about the people. 🚨 Will Angela’s coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue. Buy Now on Amazon [The Scrum Master Toolbox Podcast Recommends] About Ellen Grove Ellen is a skilled business agility coach, trainer, and facilitator, helping teams and leaders foster collaboration, productivity, and meaningful change. With expertise in Agile, Scrum, Lean, and systems coaching, she partners with diverse organizations—from startups to global enterprises—to navigate complex challenges, build resilience, and drive impactful organizational transformations across all departments. You can link with Ellen Grove on LinkedIn.

10 Jan 16min

Ellen Grove: The Power of "Why", Modeling Coaching Behavior for Agile Teams Read the full Show Notes and search through the world’s largest audio library on Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Ellen defines success for Scrum Masters as the team developing a stronger sense of agency and self-sufficiency. When teams begin asking better questions and demonstrate ownership of their processes, it indicates growth and maturity. Scrum Masters must model this behavior by being thoughtful, curious, and consistently asking "why" to encourage a coaching mindset. This approach enables teams to think critically and solve problems collaboratively. Self-reflection Question: How can you model the behavior you want to see in your team during retrospectives and beyond? Featured Retrospective Format for the Week: Retromat Ellen recommends using Retromat, a versatile online tool that provides a variety of retrospective formats to match the specific needs of your team. Ellen values mixing up retrospective formats to keep sessions engaging and contextually relevant. She stresses the importance of paying attention to all steps of a retrospective process, ensuring teams reflect, ideate, and act effectively. [The Scrum Master Toolbox Podcast Recommends] 🔥In the ruthless world of fintech, success isn’t just about innovation—it’s about coaching!🔥 Angela thought she was just there to coach a team. But now, she’s caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn’t just about the product—it’s about the people. 🚨 Will Angela’s coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue. Buy Now on Amazon [The Scrum Master Toolbox Podcast Recommends] About Ellen Grove Ellen is a skilled business agility coach, trainer, and facilitator, helping teams and leaders foster collaboration, productivity, and meaningful change. With expertise in Agile, Scrum, Lean, and systems coaching, she partners with diverse organizations—from startups to global enterprises—to navigate complex challenges, build resilience, and drive impactful organizational transformations across all departments. You can link with Ellen Grove on LinkedIn.

9 Jan 16min

Ellen Grove: The Dual Work of Agile, Managing Projects and Change Simultaneously Read the full Show Notes and search through the world’s largest audio library on Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Ellen shares her insights on managing organizational change effectively. She explains how Scrum and Lean Change Management offer tools to make the "change work" visible alongside project work. By putting infrastructure in place to support this dual focus, stakeholders and teams can gain transparency and clarity. Ellen emphasizes that lasting change requires collaboration and visibility, not isolation. Self-reflection Question: How can you make the "change work" more visible in your organization? [The Scrum Master Toolbox Podcast Recommends] 🔥In the ruthless world of fintech, success isn’t just about innovation—it’s about coaching!🔥 Angela thought she was just there to coach a team. But now, she’s caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn’t just about the product—it’s about the people. 🚨 Will Angela’s coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue. Buy Now on Amazon [The Scrum Master Toolbox Podcast Recommends] About Ellen Grove Ellen is a skilled business agility coach, trainer, and facilitator, helping teams and leaders foster collaboration, productivity, and meaningful change. With expertise in Agile, Scrum, Lean, and systems coaching, she partners with diverse organizations—from startups to global enterprises—to navigate complex challenges, build resilience, and drive impactful organizational transformations across all departments. You can link with Ellen Grove on LinkedIn.

8 Jan 15min

Ellen Grove: Why Feedback Loops Are Essential for Agile Teams Read the full Show Notes and search through the world’s largest audio library on Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Ellen shares a story about coaching a team in a public sector enterprise working on a website project. Despite their commitment to Agile, the team’s disconnect from user feedback led them to build features that missed critical functionality. This stealthy anti-pattern—assuming "what should be done and why" without user input—resulted in wasted effort and budget. Ellen emphasizes the importance of direct feedback loops with real users, even for internal products. Self-reflection Question: How can you ensure your team receives continuous feedback from real users to avoid building the wrong product? Featured Book of the Week: Humble Inquiry by Edgar Schein Ellen highlights "Humble Inquiry," a transformative book that stresses the importance of relationships over tasks in solving problems. The book encourages leaders to build trust and respect through better questioning techniques. It challenges readers to rethink their interactions and adopt a stance of curiosity, fostering collaboration and understanding. [The Scrum Master Toolbox Podcast Recommends] 🔥In the ruthless world of fintech, success isn’t just about innovation—it’s about coaching!🔥 Angela thought she was just there to coach a team. But now, she’s caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn’t just about the product—it’s about the people. 🚨 Will Angela’s coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue. Buy Now on Amazon [The Scrum Master Toolbox Podcast Recommends] About Ellen Grove Ellen is a skilled business agility coach, trainer, and facilitator, helping teams and leaders foster collaboration, productivity, and meaningful change. With expertise in Agile, Scrum, Lean, and systems coaching, she partners with diverse organizations—from startups to global enterprises—to navigate complex challenges, build resilience, and drive impactful organizational transformations across all departments. You can link with Ellen Grove on LinkedIn.

7 Jan 14min

Ellen Grove: Managing Change in Complex Organizational Cultures Read the full Show Notes and search through the world’s largest audio library on Scrum directly on the Scrum Master Toolbox Podcast website: http://bit.ly/SMTP_ShowNotes. Ellen reflects on her early experiences as a Scrum Master, facing challenges in an environment that resisted the introduction of Scrum. She shares valuable lessons about handling external resistance, managing personal expectations, and avoiding emotional burnout when navigating organizational change. Ellen emphasizes the importance of focusing on what can be influenced and detaching from outcomes beyond one’s control. Self-reflection Question: How do you maintain focus and resilience when dealing with resistance to Scrum in your organization? [The Scrum Master Toolbox Podcast Recommends] 🔥In the ruthless world of fintech, success isn’t just about innovation—it’s about coaching!🔥 Angela thought she was just there to coach a team. But now, she’s caught in the middle of a corporate espionage drama that could make or break the future of digital banking. Can she help the team regain their mojo and outwit their rivals, or will the competition crush their ambitions? As alliances shift and the pressure builds, one thing becomes clear: this isn’t just about the product—it’s about the people. 🚨 Will Angela’s coaching be enough? Find out in Shift: From Product to People—the gripping story of high-stakes innovation and corporate intrigue. Buy Now on Amazon [The Scrum Master Toolbox Podcast Recommends] About Ellen Grove Ellen is a skilled business agility coach, trainer, and facilitator, helping teams and leaders foster collaboration, productivity, and meaningful change. With expertise in Agile, Scrum, Lean, and systems coaching, she partners with diverse organizations—from startups to global enterprises—to navigate complex challenges, build resilience, and drive impactful organizational transformations across all departments. You can link with Ellen Grove on LinkedIn.

6 Jan 14min