Unlearn Barry O'Reilly

The definition of success can change everything. Properly defined, you have an agile organization where each team member can contribute fully. Poorly defined, you have stagnant teams and users that don’t like the products. In this episode of the Unlearn Podcast, host Barry O'Reilly sits down with Josh Seiden, a sought-after designer, strategy consultant, and coach. Together, they explore the importance of understanding user behavior, how that behavior can be translated into goals, and how company alignment on Outcomes and Key Results can drive business outcomes. 

Josh Seiden has collaborated with top-tier brands such as PayPal, Johnson & Johnson, and 3M. His expertise lies in launching and building innovative products and services, as well as fostering agile and entrepreneurial mindsets within organizations. He is the author of “Outcomes Over Output” and co-author of “Who Does What By How Much,” "Sense and Respond," and "Lean UX," all cementing his reputation as a thought leader in the field of user-centered design and business strategy.

When User Experience Became Design

We know now that understanding how users will experience a product is a critical part of designing a new product, but back in the 90’s when Josh began his career in the industry, it was a radical idea. "A friend told me, 'We’re hiring designers here,' and I laughed, 'Why are you telling me this? I’m not a designer.' But that thing you’re doing here, we call that design," Seiden recalls. This unconventional designation became an entire industry, and his unconventional path to it meant he brought a unique perspective to the field of user experience design. Barry notes that this is a story that gets told again and again on the Unlearn podcast; that the conventional wisdom on how to find or become an expert is often wrong.


Don't Forget Why You’re Building What You’re Building 

Barry points out that companies often measure things like the speed of production, but forget to measure the consumer behavior change that would really demonstrate the value of the project. Josh explains that measurability is important over the life of a project, but keeping the focus on outcomes for actual people is the most important thing to track. This is the key premise of Outcomes over Output that answers the question: what is an outcome? Josh’s definition, “An Outcome is a measurable change in user behavior that creates value.” If you need to identify the outcome you should be measuring for your company, answer three questions: Who?, Does What?, and By How Much?

The Evolution of OKRs in Large Organizations

Design thinking works at the team level very easily, and as the industry developed the question became how to do it at scale? Objectives and Key Results (OKRs) have emerged as a tool for helping  large organizations work in agile ways. Josh explains how OKRs can be used to manage outcomes at scale: “The O is an objective. What's the big audacious goal? And then the KR is the result. How do you measure it? The key result. For most people who look at the system, they understand that [...] you want those Key Results to be outcomes." This way of thinking helps large enterprises maintain focus and drive impactful results by clearly defining and measuring success as it matters to the people using the product.

Read full show notes at BarryO'Reilly.com

Resources
Josh Seiden on the Web, LinkedIn, X, Medium

Accelerator, Incubator, Venture Capital, Venture Studio? There are a lot of ways to get a new startup off the ground. Ben Yoskovitz, founding partner at Highline Beta, joins Barry O'Reilly on this episode of the Unlearn Podcast to talk about exactly that, and Ben shares insights into the world of venture studios, discussing his journey from founding Year One Labs, a venture studio before there were venture studios, to establishing Highline Beta. Ben's expertise in creating and scaling startups provides a unique perspective on the dynamics of venture studios and the strategies for success in the startup ecosystem. 

Trend Towards More StartupsYou always learn the most from failure, and in sharing the difficulties he had with Standout Jobs in the late 2000’s, Ben highlights the importance of building things that people actually want. By applying Lean Startup principles and working with some incredible entrepreneurs, what he was really doing was learning how to build products and companies more effectively.  Failure after failure isn’t fun, but being willing to share what you learn can help you create something incredible. “Founders do need to hear from other founders. you know, sometimes you need a shoulder to lean on,” Ben says, “and that might not be a blog post, or a podcast, that might be actually talking to another human.”

Understanding the Inflection PointsHow do you make an entrepreneur panic? Tell them they’re locked into a single idea for 25 years. Barry notes that “this idea of pursuing multiple ideas in different domains, but doing it in parallel…” lets the multi-passionate and the multi-skilled create value. Ben talks about the difficulty in working with corporate partners and investors when building startups, because they’re not speaking the same language, and the same challenges keep happening again and again - this was the impetus to find a better way to create new companies. The same challenges kept happening at the same inflection points, which means it can be systematized.

Scaling a Venture StudioBen talks about the challenges and strategies involved in scaling a venture studio, emphasizing the need for effective people management and business model refinement. He reflects on his own experiences and acknowledges the importance of recognizing strengths and weaknesses in leadership roles. Ben discusses the evolution of Highline Beta and the considerations involved in scaling the business, including generating revenue, hiring the right talent, and defining the future direction of the studio. "I think studios are meant to create shortcuts for founders. Not in a bad way, but give me the shortcut tools to validate faster, get to market faster, raise capital faster, recruit a team faster." This can make all the difference for a new startup.

Specialization in Venture StudiosBen and Barry discuss the trend of specialization in venture studios, with Ben highlighting the emergence of more specialized studios focusing on specific industries or markets. He emphasizes the potential benefits of vertical venture studios, where the playbooks are standardized and refined for targeted sectors. Ben envisions a future where studios become experts in niche areas, leveraging their experience to create value and drive better outcomes for startups. The conversation explores the concept of hyper-focused studios and the impact of specialization on the startup ecosystem. Ben makes a prediction: "I think we will see more specialized studios so that the systems that the studio is building and the playbooks are refined and refined and refined."

Resources:
Ben Yoskovitz on LinkedIn
Highline Beta
Lean Analytics

The innovative spirit of startups is one of their strengths, something that seems to disappear as a company matures. Does it have to be that way? In this episode of Unlearn, host Barry O’Reilly is joined by Elliott Parker, CEO of High Alpha Innovation, who is an expert in corporate innovation and entrepreneurship. Together, they explore how corporations can regain the innovative spirit of startups to drive growth and transformation, and it begins with changing how they think about traditional metrics and strategies.

Elliott Parker is a seasoned entrepreneur with a deep-rooted passion for innovation and problem-solving. With a background in working for large corporations and witnessing firsthand the power of entrepreneurship in his family, he brings a unique perspective on the intersection of startups and established companies.

Unlearning to Achieve Big Objectives

In a rapidly evolving business landscape, the ability to unlearn traditional practices and embrace new ways of thinking is crucial for fostering innovation and staying ahead of the curve. Elliott's experience with disruptive events like the collapse of a well-established company highlighted the importance of taking control of fate and exploring alternative paths, even if they involve risks. Elliott seeks to challenge conventional wisdom and to be open to new approaches, so that organizations can adapt to change, drive growth, and seize opportunities that may not have been apparent before.

Nature's Innovation Process vs. Corporate Innovation

What can organizations learn from the Amazon jungle? Resilience and innovation. Elliott shares how companies can draw inspiration from nature to drive creativity and problem-solving. By emulating the decentralized, bottom-up approach to innovation seen in natural ecosystems, businesses can encourage experimentation, embrace uncertainty, and uncover novel solutions to complex challenges. Just as diverse organisms in the jungle adapt and thrive in response to constraints and opportunities, companies can benefit from fostering a culture of exploration and learning at all levels.

Scaling Innovation with Corporations

When startups collaborate with corporations, they have access to resources, expertise, and networks that help them tackle complex issues and bring innovative solutions to the market at a much larger scale. Not only does innovation itself become scalable, it’s also a unique opportunity to address significant societal problems and drive meaningful change. Not only can this approach accelerate the pace of innovation, but it also creates a ripple effect that begins in the company and reaches society as a whole.

Impact of Broadening Insights Portfolio

Thinking of insights as valuable assets, like a diverse investment portfolio, is key to expanding knowledge within a company. By exploring different ideas, trying new things, and questioning the usual way of doing things, businesses can discover fresh opportunities for growth and change. Encouraging a culture of ongoing learning and curiosity while steering clear of strict rules and top-down communication helps companies stay flexible, evolve, and succeed in a constantly shifting business world.


Resources

Elliott Parker on LinkedIn | High Alpha Innovation

What problem are you trying to solve? Is it even the right one? In this episode of Unlearn, host Barry O’Reilly is joined by Renee Hawkins, a skilled technology and transformation practitioner. Together, they discuss problem solving, aligning business strategies with purpose, and how to pivot your organization successfully. With practical tips on networking, market research, and seeking advice, Renee offers a roadmap for anyone looking to make a meaningful impact in the business world.

Renee Hawkins, a technology and transformational practitioner with over 25 years of experience, brings a wealth of knowledge from her time at Thoughtworks and her current role as a fractional COO. Renee's approach of asking for help, networking, and continuous learning serves as an inspiration for aspiring fractional leaders.

The Influence of Thoughtworks and Roy Singham

During his time at Thoughtworks, Roy Singham was a visionary leader who influenced Renee’s entire approach to business. Roy led with purpose and kept social justice and inclusivity top of mind, which made Thoughtworks an incredible organization, internally and externally. When you take time to study the impact of influential leaders like Roy, you can gain insights into creating a culture that drives innovation and fosters a sense of purpose among your team.

Transforming Business Models

To deal with the challenges and leverage the opportunities of changing a business model, you need to ensure that your team, operations, and value stream are consistent with the new goals of your business. When you divide the transformation process into achievable steps and concentrate on urgent needs, you can manage complicated changes and prepare your company for success.

Building Effective Communication Strategies

Communication is essential for keeping teams on the same page and achieving business outcomes. Renee values storytelling, honesty, and frequent updates as ways to keep everyone updated and involved. By using effective communication methods, such as weekly reports or town hall meetings, you can make sure that your team remains in sync, inspired, and oriented towards common objectives.

Embracing Fractional Work and Portfolio Careers

Working fractionally and having a portfolio career can be very advantageous in the changing world of business today. Renee tells us how she went from conventional roles to providing fractional assistance to various companies. By being flexible, learning constantly, and exploring different opportunities, you can use your skills in different projects and sectors while keeping a good balance between work and life.


Resources

Renee Hawkins on LinkedIn

They say those who don’t learn from the past are doomed to repeat it. As true a statement as it is, it’s missing one crucial element. If you never confront the reality of the present and get to the heart of why you are where you are, you won’t be able to unlearn the habits that got you there in the first place. In this episode of Unlearn, Barry O’Reilly talks with Dom Price, Work Futurist at Atlassian, who shares insights on facing the reality of the present, unlearning outdated practices, and embracing new ways of working to drive meaningful change and growth in organizations. 

Dom's early work experience started in London at Deloitte, where he spent three years as an accountant. His job left him unfulfilled and passionless, but that all changed over sushi. Don’s boss at Deloitte offered him the opportunity to work in either New York or Sydney. Despite the allure of New York's size and boldness, Dom chose Sydney for its smaller team environment, where he could have a more hands-on, full-stack experience. This decision marked the beginning of a diverse and interesting career journey that eventually led him to Atlassian.

Embracing Reality and Unlearning Past Practices

Dom highlights the importance of facing the honest reality of the current situation in organizations. When leaders truly acknowledge where they are today, they can pay homage to the past while also identifying areas that need to be unlearned or improved. Not only will this allow those leaders to eliminate what is holding an organization back, it will also shine the light on what is exceptional and should be elevated. Taking this approach will help break away from average practices and strive for continuous improvement.

Collaboration Over Silos

Barry and Dom discuss the significance of breaking down silos within organizations to foster better collaboration and communication. This begins with recognizing that the entire company runs day to day on the hundreds of small tasks that require input from every team member and department. When collaboration and breaking down silos becomes a priority, a company can enhance its efficiency, productivity, and overall effectiveness. Equally as important, this type of culture honors the diverse perspectives they bring.

Seeking Growth and Avoiding Plateaus

Over time, companies trend toward mediocrity and status quo, but Dom stands firmly against the plateaus that seem inevitable. There is always a place for growth and improvement, and it requires each person involved to challenge themselves, step out of comfort zones, and actively seek new opportunities. Instead of complacency, a mindset of continuous learning, adaptation, and growth will ensure excellence and innovation.

Practical Change Initiatives Over Theoretical Transformations

Dom discusses the pitfalls of theoretical transformations, such as Agile transformations, that lack a clear understanding of the underlying goals and realities of the organization. Instead, he advocates for practical, action-oriented change initiatives that address specific needs and challenges within the organization. By focusing on tangible outcomes and being honest about real issues, companies can drive sustainable change and meaningful progress.

Balancing Heritage and Innovation

Not all of a company’s past should be unlearned, nor should its achievements be forgotten. There is a balance to strike between an organization’s rich heritage and the need for innovation and adaptation. Dom shares how companies can find a balance between honoring the past and embracing innovation, and companies can leverage their heritage while staying relevant and competitive in a rapidly changing environment.

Resources

Dominic Price on LinkedIn | Atlassian

How well would you fare in the high-stakes world of blockchain and cryptocurrency? Could you navigate the complexities of decentralized technology and its potential to revolutionize society? In this episode of Unlearn, Barry O'Reilly sits down with Anne Connelly, a blockchain expert passionate about leveraging technology to transform lives in emerging economies.

As a faculty member at Singularity University and Boston University, who has also lectured at Oxford University, Anne teaches about how blockchain can enable us to redesign the foundations of society . She is also the author of "Bitcoin and the Future Fundraising," a guide that guides charities on how to accept crypto donations. Anne shares her journey from the nonprofit sector to the world of crypto, highlighting the importance of risk-taking and unlearning traditional structures to embrace innovation.

Embracing Risk and Making Tough Decisions

Anne's journey into the blockchain space began with a pivotal decision to forgo a promotion in the nonprofit sector for a career in an emerging industry. She reflects on the momentous choice she made, stating, "I would rather try and fail than never have tried at all." Even in the face of extreme uncertainty, there are times to take a risk and be open to new opportunities. Anne's story serves as a reminder that sometimes the path less traveled can lead to unexpected and fulfilling outcomes. As she navigated the decision-making process, Anne's willingness to embrace uncertainty and step outside her comfort zone ultimately propelled her toward a path of innovation and growth.

Transformational Experiences at Singularity University

Anne's experience at Singularity University's Global Solutions Program marked a turning point in her understanding of the potential of technology to address global challenges. She discusses the fusion of her passion for social impact with the innovative solutions offered by technology. Anne believes in rethinking the traditional approaches to problem-solving, stating, "We could make this a little bit better, but why? If we completely transformed it, we could make such a difference." Anne is a champion for using the power of technology to drive meaningful change on a global scale through a holistic and impactful approach to addressing societal issues.

Decentralized Autonomous Organizations (DAOs)

Decentralized Autonomous Organizations have an incredible disruptive potential in reshaping how we govern ourselves as a society. Anne explains how DAOs enable groups to collaborate without traditional hierarchies, leveraging blockchain technology for transparent decision-making processes. She highlights a real-world example of Constitution DAO, where a collective effort raised funds to purchase a copy of the US Constitution. These decentralized systems offer unique possibilities by democratizing decision-making, which allows for meaningful innovation in traditional governance models.

Onboarding and Adoption of Crypto Technology

Anne shares the challenges of onboarding newcomers into the crypto and blockchain space, especially when it comes to accessible entry points. She shares a story about introducing a group of skeptics to Bitcoin. Their resistance held firm until they had a true, hands-on experience, which shifted their perceptions entirely. There’s a disparity in crypto adoption rates across different groups and regions, and Anne highlights how crypto often resonates with populations facing financial instability or limited access to traditional banking. If we want to encourage broader participation in the crypto ecosystem, we must focus on creating more inclusive strategies.

Read full show notes at BarryO'Reilly.com

Resources

Anne Connelly on the Web | LinkedIn | X(Twitter)