Wasim Osman: How Agile Teams Can Start Adopting AI in Software Development

“It’s like my own software has a voice now. It’s telling me—okay, you’re going to build me like this? Have you considered this?” – Wasim Osman

Wasim’s biggest current challenge is one nearly every team shares: how AI is reshaping software development. He sees a clear split—developers rapidly adopting AI-driven development, and others “not downright rejecting it, but still taking their time.” His warning is blunt: even when AI hallucinates and generates garbage code, it lets you deliver an order of magnitude faster, and the quality is only going to improve.

The early adopters are heading somewhere the late adopters won’t be able to reach. In practice, the resistance shows up as questions no one can answer: if I used to get every requirement nailed down before writing code by hand, what do I do with AI—just ask it for a one-liner and hope? Leadership often can’t help, because they lack AI experience themselves. At Orkestra SCS, the head of engineering did holistic research into how companies (like AWS, with its AI-Driven Development Lifecycle) are reshaping the process, documented it, and shared it with every team.

Feedback sessions and hands-on experiments followed, until they built a tailored version that fit how they actually work. The mindset shift that unlocked it: treat AI as a partner. Wasim describes his software “having a voice”—asking it questions he’d never think of, the way a pair-programming partner would, so the team explores the solution space instead of guessing at it.

Self-reflection Question: Is your team treating AI as a threat to write around, or as a pair-programming partner that surfaces the blind spots you’d never find alone?

Transform Your Agile Teams with Hard-Earned Lessons from Super-Experienced Scrum Masters

Do you wish you had decades of experience? Learn from the Best Scrum Masters In The World, Today! The Tips from the Trenches – Scrum Master edition audiobook includes hours of audio interviews with SM’s that have decades of experience: from Mike Cohn to Linda Rising, Christopher Avery, and many more. Super-experienced Scrum Masters share their hard-earned lessons with you. Learn those today, make your teams awesome!

About Wasim Osman

Wasim OsmanWasim Osman is a seasoned Agile Coach and a Product Owner at Orkestra SCS. He launched his agile career at a Silicon Valley startup based in New York, then spent years coaching teams across Canada, helping organizations transform how they deliver value. Wasim brings a rare blend of agile discipline and product thinking. He’s passionate about building technology that drives real business impact.

You can link with Wasim Osman on LinkedIn.

Havva Sevay: AI vs. Real People—Helping Teams Avoid Information Overload

“It’s still a tool. It can make mistakes, it can hallucinate. People don’t really question it—and that’s the danger.” – Havva Sevay

This week’s coaching conversation tackles a challenge Havva—and many Scrum Masters—are living right now: AI vs. real people. For some, AI is a useful tool; for others, it’s a magic oracle that solves everything and makes people replaceable. Havva sees the real risk in teams that accept AI’s confident answers without double-checking, and in leaders who use AI to generate massive documents and dump them on teams as finished decisions.

Vasco pushes the conversation into the practical: when a flood of AI-generated information, requirements, and tool changes lands on a busy team, how do you help them cope?

Havva’s answer is to step back and ask the human questions first—what is the epic? what does the stakeholder actually want? what do we really need right now? Then she pulls out a deliberately low-tech move: forget AI for one second. Her team uses the Eisenhower matrix manually to separate what’s important now from what can wait. AI is a great tool—but the filtering of what matters is still human work.

Self-reflection Question: When AI floods your team with information and options, what is your practice for helping them separate what matters now from the noise?

Transform Your Agile Teams with Hard-Earned Lessons from Super-Experienced Scrum Masters

Do you wish you had decades of experience? Learn from the Best Scrum Masters In The World, Today! The Tips from the Trenches – Scrum Master edition audiobook includes hours of audio interviews with SM’s that have decades of experience: from Mike Cohn to Linda Rising, Christopher Avery, and many more. Super-experienced Scrum Masters share their hard-earned lessons with you. Learn those today, make your teams awesome!

About Havva Sevay

Havva SevayHavva is a people-focused organizational development expert with a Master’s in Business Administration and certification as a Scrum Master. She empowers teams and leaders through agile methodologies, modern leadership, and a strong feedback culture, fostering psychological safety and collaboration. Passionate about HR initiatives, Havva shapes people strategies, enhances employee experience, and drives inclusive, high-performing workplaces built on trust and engagement.

You can link with Havva Sevay on LinkedIn.

Danil Chernyshev: Coaching the Outsider In—Helping a Distrustful Team Through Transformation

“Developers and QAs know each other very well, but they don’t trust anybody else.” – Danil Chernyshev

This week’s coaching conversation starts with a hard situation. A subcontractor’s developers—people who had always worked isolated from the business, with no plans and no communication—were brought back inside the “mother firm” as part of a digital transformation. Overnight they faced new teams, Scrum, SDLC, CI/CD, and full transparency.

The developers and QAs trusted each other completely and trusted no one else: not the Scrum Master, not the Product Owner, not the BAs. Forced to estimate with story points, every story came back as a 3 or a 5, with no conversation. When Danil asked why, the answer was always “we’ll discuss internally and tell you tomorrow”—he suspected a second, hidden daily Scrum without him. As he and Vasco unpack it, the real issue is transparency itself: a team used to hiding now feels exposed and doesn’t know the consequences of being open.

Vasco offers an experiment—build a “trio” of the Product Owner, the Scrum Master, and one friendly insider from the team to prepare refinements together. The Product Owner is always the outsider; pairing them with a trusted insider lets ideas and experiments spread faster. Before you can improve the Scrum, you first have to bring the outsiders in.

Self-reflection Question: Where on your team is trust the real bottleneck—and who is the “insider” who could help an outsider earn it?

Transform Your Agile Teams with Hard-Earned Lessons from Super-Experienced Scrum Masters

Do you wish you had decades of experience? Learn from the Best Scrum Masters In The World, Today! The Tips from the Trenches – Scrum Master edition audiobook includes hours of audio interviews with SM’s that have decades of experience: from Mike Cohn to Linda Rising, Christopher Avery, and many more. Super-experienced Scrum Masters share their hard-earned lessons with you. Learn those today, make your teams awesome!

About Danil Chernyshev

Danil ChernyshevDanil is a results-driven Scrum Master and Delivery Manager passionate about optimizing SDLC processes and unlocking development teams’ potential. With a keen interest in AI, he empowers organizations to innovate and excel, bridging agile practices with cutting-edge technology for impactful results.

You can link with Danil Chernyshev on LinkedIn.

Alf Dobbert-Baums: When Management Writes a Book — AI, Strict Process, and the Missing Court System

“They don’t really know — do I need to follow these rules, or are they at my goodwill?” – Alf Dobbert-Baums

The developers and AI are on good terms. Then management decided to extend AI into product management — and the way to do that, of course, was stricter process. Same JIRA boards. Same columns. Same quality gates. Across every product.

Management wrote a book and called it “how we develop.” Then, in the next breath, said: “but it’s not meant to be that strict — you have flexibility.” Two messages, opposite directions.

The result, Alf describes, is confusion and psychological-safety problems. The teams don’t know whether they’re playing by the rules or breaking them. They experiment with how far they can bend the book. They fall back on “common sense” and quietly skip what makes no sense. They’ve collected feedback — structured, organized — but feel they aren’t heard. In the conversation, Vasco’s framing of the legal system (every set of rules needs a court system to interpret them) led Alf to a real experiment: take the negative rules and reframe them as positive goals.

Not “fewer meetings” — “meaningful meetings.” Then match feedback to the goal, not the rule. It’s an idea Alf came up with mid-conversation, and it’s the kind of small frame-shift that can crack open a stuck dialogue with management.

Self-reflection Question: Where in your organization is management asking people to follow rules they haven’t defined the goal for — and what would change if you reframed those rules as goals?

Transform Your Agile Teams with Hard-Earned Lessons from Super-Experienced Scrum Masters

Do you wish you had decades of experience? Learn from the Best Scrum Masters In The World, Today! The Tips from the Trenches – Scrum Master edition audiobook includes hours of audio interviews with SM’s that have decades of experience: from Mike Cohn to Linda Rising, Christopher Avery, and many more. Super-experienced Scrum Masters share their hard-earned lessons with you. Learn those today, make your teams awesome!

About Alf Dobbert-Baums

Alf Dobbert-BaumsAlf lives in Berlin. He studied Theater/Religion at the Freie University Berlin. He is a Systemic Organizational Consultant, a Scrum Master and Agile Coach. He has also been a freelancer for Usability and Requirements Engineering for car manufacturers. At “Verti” he led the agile transformation.

You can link with Alf Dobbert-Baums on LinkedIn.

Mirco Gerling: Two Teams, One Sprint Cadence — The Hidden Cost of Synchronization

“The teams need to understand the advantage of the synchronization — but will they?” – Mirco Gerling

Two of Mirco’s teams just got merged into one — and the brand-new, fused team is now part of a 10+ team organization trying to move from loose-coupled chaos to a standard process. Different sprint lengths. Different estimation methods. Different ticketing tools. The plan: align everyone to 4-week sprints, hold a global planning week every three months, and synchronize start and end dates across all teams.

Mirco voted for 2-week sprints. The majority went with 4. And then the side effects started. Sprint reviews stack up on the same days, making it impossible for Scrum Masters to facilitate them all.

Teams synchronize on paper, but interact organically across the four weeks anyway, so the cadence advantage doesn’t materialize. And the merged team itself? Pushed back through Tuckman’s stages by the merge — the Tuckman model reminded Mirco that “adjourning” is real, and a high-performing team starts over when its membership changes.

Mirco’s experiment: let faster-moving teams run two 2-week sprints inside the 4-week window, keeping organizational sync while restoring their own learning rhythm.

Self-reflection Question: Where in your organization is process standardization being mistaken for actual alignment — and what would it cost you to separate the two?

Transform Your Agile Teams with Hard-Earned Lessons from Super-Experienced Scrum Masters

Do you wish you had decades of experience? Learn from the Best Scrum Masters In The World, Today! The Tips from the Trenches – Scrum Master edition audiobook includes hours of audio interviews with SM’s that have decades of experience: from Mike Cohn to Linda Rising, Christopher Avery, and many more. Super-experienced Scrum Masters share their hard-earned lessons with you. Learn those today, make your teams awesome!

About Mirco Gerling

Mirco GerlingMirco is an experienced Scrum Master in the public sector. With a strong IT background, he has spent 25 years developing software and driving agile transformations. Passionate about innovation and teamwork, Mirco brings expertise and dedication to every project.

You can link with Mirco Gerling on LinkedIn.

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