Unlearn

CEO School and The Future of Work with Stephane Kasriel In this episode of the Unlearn Podcast, Barry O'Reilly speaks with Stephane Kasriel, the CEO of Upwork—the world’s largest freelancing platform where businesses and independent professionals connect and collaborate remotely. Upwork is driving the future of work conversation, and discovering what it really means along the way. Creating Capability To Continuously Change Stephane feels one of the most exciting aspects of the tech industry is how quickly it changes— a key competency he believes people must develop is adapting to that change, learning continuously, and unlearning what is no longer useful. He talks through two specific changes Upwork has experienced: the switch from traditional waterfall development to remote agile teams, and sourcing and clarifying Upwork’s values from within. Secrets To Distributed Agility Several years ago, no one believed that agile could work in teams that weren’t co-located, but Upwork—along with other companies like GitHub and Automatic—has demonstrated it can. It takes an open mind, strong culture of feedback and honest personal evaluation to understand if working remotely is a fit for you. Making this clear during hiring is crucial. Not everyone will be passionate about or motivated to work in a distributed manner—and that’s okay. It’s better to discover it as quickly as possible because it means the people who join your organization are aligned with the opportunities and affordances of distributed work. They’re happier, more productive and stay longer. Challenges Transiting To The Top Transitioning from one role to another can be challenging, but the transition to CEO is unique. There’s no CEO school. Stephane shares how he found his way by applying many of the strategies that made him successful as a product and engineering leader. Actively learning from the people around him—wherever they are in the hierarchy—helped guide this approach to lead the company forward. In the tech industry, where so many founders are CEOs, knowing where to step up and step back is key in creating a healthy culture within leadership teams. Stephane shows how he’s tried to let the smart people bring their skills to bear. Unlearning At The Global Level There are a handful of things reshaping the economy: automation technologies, the acceleration of the rate of technological change and innovation, and the geographic mismatch between where jobs are being lost and where they’re being created. Stephane talks about how these forces are causing changes in the labor market and how you need to approach learning to stay current. It’s the people who can be in the habit of doing new things, and consistently adding new small skills who are ultimately going to be successful. Stephane adds that if we can’t embrace change, we’re doomed. We’re part of the future that’s coming; we can be a part of making it happen, or let it happen to us. The Power of Remote Work Upwork is focused on making remote work possible, and that’s not just about profitability. When the cost of living becomes unbearable in the big tech centers, but other towns are dying for a lack of good jobs—the best solution can’t be for everyone to move to expensive cities. Responsible tech leaders need to abandon the idea of having their entire workforce in a single building in a big city. Many jobs do not need to be on-site, and they shouldn’t be. Society as a whole will be better when we start making growth and success inclusive of more people. It’s not a good outcome for the world to have a huge part of the population unemployed or underemployed. One of our most precious resources is the human mind, and we shouldn’t be wasting it.

Barry O’Reilly has had many mentors over the years, and among them, Mary and Tom Poppendieck have been some of the most inspirational. In today’s conversation, they talk about challenges the Agile community faces, debunk the myths of scaling agility, and finally, Mary and Tom reveal how they have stayed relevant for decades as they continue to coach, mentor, and help others. About Mary and Tom Neither Mary nor Tom started with software. Mary was an engineer who worked with problems that had life and death ramifications, and Tom was a physics teacher whose students contact him decades later to say ‘thank you - you made a big difference.’ They’ve written many of the seminal books and contributed much to the Lean and Agile movement and have seen fads and trends come and go. Barry asks them what has been their key insights over the years. When did you discover agile? Agile developed as a reaction to what was happening in the software industry in the late 1990s. Agile has to grow up, to no longer be reactionary when bad things happen, but to determine how to create GOOD software engineering from the start. She draws on her experience as a traditional engineer and shares a lesson about how proxies between engineers and people with problems are a bad idea. It’s a matter of trusting professional judgment. Tom observes that, too often, Agile tries to solve problems with processes. But the problem isn’t usually the process; it’s architectural. He talks about the different structures, from software to the leadership teams, that can lead to dysfunctional situations. If you want to solve a problem, you need to fix the structure. How Agile Can Grow There’s no simple answer to this, Mary points out because it depends on where you’re at. You can understand all the fundamental steps needed but if your team isn’t well-integrated, it will get you nowhere. She shares an experience with a company who had accepted a big contract they weren’t ready for. Mary recommended the ‘sync and stabilize' method and taught them how to use it. It didn’t just save their contract; it changed how they looked at their whole company. Tom highlights the non-technology component of software, the ‘wetware,’ or what happens with people. He points out that money isn’t the issue; it’s the shortage of passionate, creative people - especially in isolated IT departments that are treated as cost centers. Tom believes you should give them challenging problems and get out of their way. Teams Tailored to Problems Mary loves to talk about how organizations such as AWS and T-Mobile handle their organizational structure and customers. When there is a customer problem, a team is brought together to solve it and integrate it into the rest of the services so everything works. That team is given a lot of autonomy, including trading immediate profits for better customer experience AND have accountability to ensure they are also adhering to operational excellence and profitability of their service. Ultimately, better customer experiences drive bigger profits. Tom makes an important point: scaling isn’t possible after a certain point. At some point, complexity dominates future gains and wipes them out, so you have to descale. In other words, you have to do things in ‘little chunks’ that are independent and don’t require strict coordination. Tom uses the example of a city and how it functions. Final Thoughts Part of what helps Tom and Mary stay current is that they are truly agile. Mary points out that she’s never seen anything in technology last two decades and remain current. Agile has been around for about that long, but has it been changing and adapting? Resources https://twitter.com/mpoppendieck http://www.poppendieck.com/

Joe Norena is the Managing Director at HSBC and the Global Markets Americas COO. From corporations to startups to corporate digital, his experience has run the gamut of organization. Joe has led a life of unlearning, and every new thing he learned he has applied to the next situation. In this episode, Joe and Barry talk about the pivotal moments in his career that brought him where he is today. Unlearning Starts Early... From the beginning of his life, Joe has been surrounded by people who modeled the type of behavior that would shape his success. His father, an immigrant who didn’t speak the language, began work in the mailroom of Citibank and retired as the Vice President. His mother always encouraged him to ‘just go and try it.’ Joe shares a funny story about nearly drowning when he tried out for the swim team in grade school. ...And Continues Through Life During his time at Citibank, Joe continued to have powerful role models. First among them was Michael, a senior trade manager. Michael was willing to sit down with the most junior of employees - even graduates - and open his mind to new ways of thinking, doing things, and techniques. He was a true ‘unlearner’ who modeled that behavior for everyone around him. Joe’s time at Bridgewater taught him another very important lesson: having a voice based on principles rather than the desire to be right. Understanding that success might be revealed through another lens, or way of thinking, helps a company grow and remain sustainable. The debate then becomes about what the real issue or problem is, and what is the right thing to do. Unlearning Moments You need to be comfortable with being uncomfortable; it’s the hallmark of a life-long unlearner. Joe experienced this several times during his career. First among those was the huge mind-shift he had to make when moving from being a trader to a COO. A trader knows whether he was an asset to the company at the end of the day; he only needed to look at profit/loss. But when Joe became COO, it wasn’t that obvious. It took 3-6 months before he knew if he was succeeding or not. The second unlearning experience for Joe was at the hedge fund startup. Every day he had to deal with and make decisions about situations he had no experience in. He was also used to having many people to help him, but in the startup, he only had himself. In the end, they had to close the startup, but Joe brought all the new learning with him. Joe’s time at the startup taught him about the need for lean startup principles, and he was able to apply that learning at HSBC. In effect, while leading a team of 30 people on a limited budget Joe looked at an experiment as being successful if it failed because he learned something. From those ‘failures’ came some of the greatest successes. Organizational Learning Learning comes from the bottom up, but if you don’t have support from the top, it becomes very difficult. The message from the top should be ‘we want to change, we want to try this out, and it’s okay.’ This doesn’t mean that C Suite managers need to know exactly how the change will occur or be a daily part of it; the tone they set will be the change maker or breaker. A Principle for Business In any decision that you make, it has to be about building a sustainable business model, which means it goes far beyond your own career. Joe admits it’s not easy, especially when you don’t know if you’re making the right decision for the future. He likens it to raising children. Another is that if you don’t speak, you lose an opportunity for teaching and learning. Joe shares how his office is set up to mirror that belief. Resources LinkedIn

Have you ever felt boxed in based on your job description? Join us today as Katri Harra-Salonen, the Chief Digital Officer of Finnair Oyj, shares what she’s learned and unlearned throughout her career of mixing industries, mixing roles, and being comfortable with being uncomfortable. The Un-comfort Zone: By design, Katri actively puts herself in situations where she has to grow, and calls this being in the Un-comfort Zone. When you put yourself in a place that challenges you, you become energized, you’re able to be curious and explore, and you learn new things, not just about the situation, but about yourself as well. Katri has gone from the consultancy world into the airline world, which has meant a lot of discomfort, learning, and unlearning. But there is so much that the two worlds - consultancy and airline - can learn from the other, so she believes in building bridges between different kinds of companies and different kinds of thinking. That’s where creativity stems from. Inspiration: Working with other countries is strategic. But for Katri, there are intangible benefits as well. For example, they work with a lot of exciting Asian companies, which gives them insight into how mobile services are developing, what’s happening in the digital world, and how they can possibly incorporate this into a European country. For example, many cities in Asia are cashless societies, whereas Europe has been slow to adapt to digital money. But studying Asia, you can see how people behave and what it means, and insights like these can help embrace development. Best of both worlds: Katri is a third-generation engineer, and at one point in her career, she worked for a design company. How did she bring those two worlds together? Don’t put people in boxes. “Boxes are for dead people.” You need to be able to change perspectives in order to be creative, so don’t limit yourself to the box that’s been given to you. Just because you’re an engineer by profession, that’s not all you are and all you can do. Thinking you’re locked in does nothing to help you move forward. Katri believes in lifelong learning and unlearning. You want that exchange of disciplines and perspectives. Collaboration and building bridges: Katri shares about an experiment they conducted where the employees themselves designed their office space instead of hiring a design firm. It was done in five batches, and the teams were a mix of people from different departments. People collaborated, learned about how different teams work, and were learning and unlearning at the same time. Structures: Structure follows strategy. And when the strategy changes — as it does, because it needs to be agile — it’s so important that the structures are alive as well. Be aware of the structures you create, and think of them when you think of serving your talent best. For example: how can you build collaboration into the structure of your organization? Many departments are siloed from one another, but to innovate and move things forward, people need to be able to work together across disciplines. The future of technology: Technology is everywhere, and Katri is looking forward to it solving the big issues today. What do we need to do so we can create a setting where technology is working for the benefit of the world? Resources: Katri Harra-Salonen (LinkedIn)| https://twitter.com/KinStockholm

How do you figure out what works? On this episode, we have Gibson Biddle, a speaker, advisor, and teacher who is the former Vice President of Product Management at Netflix. He’s been involved with many startup companies to help them develop products, and today we’re talking about consumer science, metrics, and experimenting our way through work and life. Data and consumer science: “I don’t care what they said, I don’t care what it looks like, I just want to see the data.” These were a former boss’s words to Gibson and a moment of great insight for him. Consumer science is about forming hypotheses quickly, putting them into A/B tests to see which ones move the metrics, and then create a system where you can test and discover what consumers love. And though he worked for people who said they didn’t care what a focus group said (“launch it, get it out there, and see if it moves the metrics or not”), speaking to people was still important for Gibson because it gave him great ideas. It kept the voice of the customer top of mind when he generated new hypotheses. Top line metrics and proxy metrics: Being able to measure whether you’re successful are critical. At Netflix, Gibson’s top line metric was to improve retention. But the key thing is to also develop proxy metrics to help you achieve your top line metric. One of their proxy metrics was the percentage of members who watched at least 15 minutes in a month. These proxy metrics work on a local level to impact your top line metric and define success. They also help build in a system of accountability — that ties in with freedom and responsibility — for people on the front lines. Context not control: Inventing the future is really hard, and to build and teams that can figure things out for themselves, the idea is context, not control. Success relies on testing and the willingness to experiment with ideas to discover what works. Strategy meetings would discuss hypotheses to hit proxy metrics, and while there is a certain discipline to all that, it wasn’t about telling people what to do. Things to think about: One of the most effective tactics Gibson has for learning new things is to teach. For years, he would teach a topic of the week on Friday mornings, and having to codify his thoughts and share them with others was an amazing way for him to learn. Another nugget: building a career is a lot like building a product. You have theories, hypotheses, and metrics, and you can test and learn and experiment your way to discover what works. Gibson also has a personal Board of Directors: a collection of peers, people he’s worked with, and mentors, who care about him and give him insight about the things he’s trying to explore — while being candid and giving him the hard truth when he needs it. “Treat me like I’m stupid” is one of Gibson’s catchprases. It’s simply daring to acknowledge that you’re at the beginning of your learning curve, and that there are no stupid questions. Resources Gibson Biddle (LinkedIn)

Melissa Perri is a champion for product management who’s built her business around helping others understand it. She now teaches product thinking for product management to all types of companies and excels at experimenting small and fast for big results. Unlearning Business Analysis and relearning Product Management. Starting out, Melissa had no idea what she wanted to do but she knew she wanted to work with people, code and design together. After passing on Wall Street and developer jobs, Melissa found her first gig as a business analyst at Capital IQ. After numerous roles trailing developing and business analyst, Melissa landed at Open Sky, which served as a pivotal moment in her professional life. She discovered the term that truly represented what she was doing—product management. Melissa’s manager at Open Sky pushed her into teaching her personal type of product management thinking. This led to successful talks and workshops, and eventually, consulting. However, the employees she worked with weren’t allowed to execute what she was teaching, so she taught her way up to the C Suite, innovating product management into product transformation. Recognizing and solving problems. One skill that sets Melissa apart is her natural ability to recognize, address, and fix problems within organizations. Her mantra is ‘what’s the bigger problem?’ and she follows it to the source. Melissa shares a story about working at a startup and how she had to unlearn everything that had made her successful before. It started with karaoke in Nashville and ended up with Scrum. Melissa’s next unlearning moment came after she and her product team found major success working together to figure out how to ship products sooner. They were more productive than ever before, but that came to a screeching halt when no one used a product she and her team developed. After a weekend conference for startups, Melissa was inspired and began to experiment more freely. She shares the story of how she overcame her fear of failure that enabled her to breakthrough. How Melissa experiments. One of the keys to Melissa’s experimentation strategies is to implement small changes that can be iterated quickly. It all comes down to this: How do I learn a little more about what works and what doesn’t? She reveals a huge mistake that many organizations make when they consider an experiment ‘one and done.’ Instead, she recommends starting with the vision and the outcome, taking the next small step that will lead you to your vision, and the importance of learning as you go. This strategy isn’t fiction, as Melissa shows how she used it to launch her own rapid scaling business of today. Innovating the product management industry. The product management field as a whole is still quite immature and Melissa believes there is much that can be learned. She speaks in terms of two types of companies: those who have scaled through people growth, and those that scale using software. For both types, the cycle of unlearning must begin in the C Suite. Melissa explains why product thinking is the critical component that ties everything together. And the question these companies need to ask is “How do we evolve our businesses to embrace product thinking for scaling product management?” Resources for Melissa Website | LinkedIn | Product Institute | Escaping The Build Trap: How Effective Product Management Creates Real Value

Kent Beck, creator of Extreme Programming and pioneer of Agile Manifesto, shares insights on unlearning, creating a safe work environment, and the power of small experiments. He discusses the importance of trying new experiences, rearranging furniture to foster collaboration, and using Twitter for idea testing. Beck also talks about leveraging technology for customer feedback, critiquing traditional decision-making methods, and embracing fast experimentation in programming to drive innovation.

Over 2,000 years ago, the Roman Empire rose to heights previously unseen, occupying more than 2 million square miles and ruling 20 percent of the world's population. Was that success due to visionary leaders? The prime location of the Tiber River? Engineering feats of roads and aqueducts? Maybe the laws of governance? The truth is, it was none of those. The Roman Empire's tactic of abandoning old practices in favor of new ones that worked better, often taken from those they conquered, is what gave them the flexibility to scale to such a massive level. My inspiration to create the Unlearn podcast came from what I frequently find to be a significant inhibitor when helping high-performance individuals get better—not the ability to learn new things but the inability to unlearn mindsets, behaviors, and methods that were once effective but now limit their success. In this podcast, we’ll dig deep into the practice of unlearning—what it is, why you should adopt it, and how you can leverage its tremendous power for yourself, your teams, and your organization. If you already feel you’ve unlearned before, great—I’ll teach you how to do it intentionally. If not, I’ll teach you to practice it deliberately. I’ll show you how to think big but start small, and why choosing courage over comfort can take you to places you never imagined possible.