Hussein Hallak, serial entrepreneur and author of The Dark Art of Life Mastery, joins Peter Maddison and Dave Sharrock to talk about what really keeps entrepreneurs in the game. It's not resilience or grit, it's clarity about why you're doing this in the first place.

The conversation covers the shift from pre-COVID to post-COVID startup communities, why watching customers do their work beats asking them what they want, and the critical difference between handing off your product and handing off your purpose. Hussein also challenges the wall-poster approach to company values and explains why living your principles matters more than declaring them.

Three Key Takeaways:

• Strategy is becoming - Choose who you want to become as a founder and company, then let your thoughts, words, and actions flow from there. It's about the experience you want to have, not just the exit you want to achieve.
• Hand off the product, never the why - Founders can delegate product development once the team understands the purpose behind it. But stay close to customers. That connection informs everything and keeps you from drifting.
• Live your values, don't announce them - Stop putting principles on posters. Instead, have honest conversations with your team about what matters to them, what's missing, and how you'll work together. Build culture through behavior, not declarations.

Topics Covered:

• Why entrepreneurship is really about your relationship with uncertainty
• The founder's role: stay with the customer, hand off the product
• How 80% of features go unused (and what to do about it)
• Why watching customers work reveals more than asking questions
• Building culture through honest conversations, not corporate values posters

💬 Got feedback? Email us at feedback@definitelymaybeagile.com🌐 Visit definitelymaybeagile.com

🚨 Struggling to implement Agile because you can't get dedicated cross-functional teams? You're not alone.

In this episode, Dave Sharrock and Peter Maddison tackle one of the BIGGEST challenges facing late-adopter organizations: how to increase productivity and deliver value when dedicated teams just aren't in the cards.

In this episode, we explore:

• Why the "dedicated team first" approach often crashes in traditional organizations
• The hidden dysfunctions and perverse incentives that keep teams fragmented (spoiler: it's about promotions and funding)
• The famous "Sock Factory Parable" explains cross-functional alignment perfectly
• How context switching kills productivity with scarce specialists like DBAs
• Three essential steps to make real progress WITHOUT restructuring your entire organization

The Three Critical Steps:

1. Understand WHY dedicated teams work before forcing the structure
2. Get leadership aligned on real prioritization and trade-offs (not everything can be Priority 1)
3. Create genuine work transparency without status report theater

Whether you're an Agile Coach, Scrum Master, Product Manager, or Engineering Leader dealing with organizational resistance, this episode gives you practical strategies to move forward when structural change isn't an option.

Resources Mentioned:

• Peter's LinkedIn Learning Course on Value Stream Management

About Definitely Maybe Agile: Join Peter Maddison (XodiacInc) and Dave Sharrock (IncrementOne) as they discuss the complexities of adopting new ways of working at scale. Real conversations about digital transformation, agile, and DevOps challenges, no sugar-coating, just practical insights.

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Got a question or topic you'd like us to cover? Reach out to us!

In this episode, hosts Peter Maddison and Dave Sharrock sit down with Nick Cawthon to explore how generative AI is revolutionizing the relationship between UX, design, and agile development.

Key Topics:

• Embedding UX research into agile sprints, balancing short-term feedback loops with long-term strategic insights
• The "electric bicycle" analogy: How AI gives teams superpowers but can also accelerate you in the wrong direction
• Why Nick believes he'll never use Figma again, shifting from design tools to code-native prototyping
• Building functional prototypes using company design systems and generative AI tools
• The evolution of team size: From 6-8 person cross-functional teams to powerful 2-3 person teams leveraging AI
• The architect's mindset: Understanding the technical foundation before designing the interface

Three Key Takeaways:

1. What an incredible opportunity we have; it feels like the year 2000 again, with the excitement and disruption ahead
2. Small teams (2-3 people) with diverse perspectives can now move incredibly fast using modern tools
3. Speed is powerful, but you still need feedback loops to ensure you're building the right thing and not racing in the wrong direction

Connect with us: Website: https://definitelymaybeagile.com/ LinkedIn: https://www.linkedin.com/company/definitely-maybe-agile-podcast Email: feedback@definitelymaybeagile.com