“Never be afraid to admit you don’t know something.” – Sheik Meeajaun
Sheik brings a current challenge that goes beyond one team: the gap between Scrum theory and real work when the context changes faster than the playbook. His example is AI. Scrum Masters are now asked to help teams where AI agents contribute to delivery, but no certification course can fully prepare us for that. Sheik’s starting point is humility: say “I don’t know,” learn the domain, run small experiments, and reflect quickly.
In one team, two human developers worked alongside several AI agents. They could not run a normal standup with Claude, so the team created a status report and reviewed it with the human team members. Sheik framed the agents as junior developers: useful, fast, and still requiring clear instructions, review, and guardrails. That framing helped experienced developers see AI collaboration as coaching and oversight, not as magic productivity. The key lesson is practical empiricism: try, inspect, adapt, and keep learning as the work changes.
Self-reflection Question: What new reality is your team facing where the honest Scrum Master answer should start with “I don’t know yet”?
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 Sheik Meeajaun
Sheik is a seasoned product and Agile leader with over 20 years of experience scaling innovative, customer-centric digital solutions. A certified Scrum and Agile expert, he bridges strategy and execution, driving high-performance teams at enterprises like Rabobank and citizenM. As a hands-on builder, Sheik created Scrumling—a free, interactive Agile training platform—and ScrumJobs.net, a niche job board for Agile professionals. His passion lies in transforming theory into impactful, real-world results.
Everybody talks about AI in theory. In this BONUS episode, Dave Westgarth talks about it in practice — the boring, everyday ways a Scrum Master and Agile Coach actually puts AI to work. From t-shirt sizing to sprint reports to a self-coded Monte Carlo forecaster, Dave shares what works, what doesn’t, and the one mindset shift that separates people who get value from AI from those who just generate more noise.
From “Magic Answer Box” to Personalised Partner
“Instead of taking it as a magic answer box, using it as a personalised partner to work through problems, look at your ideas, and really hold them in the cold light of day before proposing things.”
Dave came into agile from a development background, moved through project delivery, and had already worked at AI and ML companies long before ChatGPT made the technology personal and accessible. Like most people, he first met these tools as a “magic answer box” — ask a question, get an answer, run with it.
The real shift came when he stopped optimizing for output and started using AI to drive better outcomes: ping the model, get a response, then interrogate it, refine the thinking, and go around again. The value isn’t the first answer. It’s the conversation that sharpens your own reasoning.
These Tools Aren’t Neutral — So Corner Them Into Being a Critic
“If you ask it to be punishing, negative, and brutal, it gives you a lot more relevant feedback.”
One of Dave’s sharpest points: AI tools are not neutral guides. Because of their system prompts and the incentives baked in by the providers, they’re relentlessly positive — they want to affirm you and keep you around, a little like social media.
That makes them weak for anything where you need honest pushback: personas, user stories, feedback on ideas. Dave’s fix is to flip it on its head. Rather than asking “is this any good?” (which reliably earns an “8 out of 10, but to make it a 10…”), he tells the model to be as harsh and brutal as it can and really try to punish the idea. You don’t want a partner that always agrees with you — you want one that pinpoints the areas you haven’t thought about.
The First Real Time-Saver: Reports, and the Themes You Missed
“Are there any themes that have emerged over the last 4 weeks that I might have missed in this latest deck?”
The first thing that stopped feeling like a party trick was the one we all know: project documentation and reporting — sprint reports, status updates, review decks. Instead of letting AI invent the structure, Dave feeds it his own structure plus Teams recordings, notes, and existing docs, and lets it populate the format he already uses.
The trick that goes a level deeper: after several sprints, feed all the AI-assisted reports back in and ask what themes have emerged across the last four weeks that this latest deck might have missed. Again, it stops being an answer box and becomes a partner and critic.
AI Is Part of the Job Now — Like Spreadsheets Once Were
“The way to get ahead now is figure out how to use it as effectively as you can in your role.”
Dave sees the early resistance movement against AI as a false economy. For delivery professionals — project managers, Scrum Masters, agile coaches — knowing how to use these tools well is fast becoming a core expectation, not a nice-to-have.
Vasco draws the parallel to spreadsheets: once dismissed as too complicated and “not my kind of thing,” until people started building real forecasting and capacity models with them and the work changed. AI is on the same arc — still a little mystical today, genuinely useful tomorrow, and eventually just another tool in the box.
A Week With AI in the Loop
“The power that these prompt-to-product tools give you to create these hyper-personalized tools that make you more effective is, in a lot of ways, magic.”
Dave walked through what his week actually looks like with AI in the loop:
Monday primer: a scheduled ChatGPT task emails him a scene-set every Monday — last week’s plan and top priorities — so he isn’t spending the first half hour reconstructing where things stood.
Priority calls: which items are the toughest, where the quick wins are, where he can get early traction, and where risks might be emerging that he can squash early.
Everyday comms: drafting the bones of emails, pings, and project updates so he spends almost no time formatting.
Prompt-to-product tools: using Base44, Lovable, and Replit to build his own tools — including a Monte Carlo forecaster that takes his team’s sprint throughput and projects the remaining backlog, replacing an ugly spreadsheet with a clean web app. He also builds AI-powered widgets in Miro for retrospectives, mood check-ins, and planning poker.
The theme running through all of it: hyper-personalized tooling, shaped by your team and your own skills, rather than one-size-fits-all software.
The Myth That AI Makes Scrum Masters Worse
“I can’t see any role of a knowledge worker where having an LLM at your disposal makes you less capable, less knowledgeable, less skilled than someone that doesn’t.”
Dave sees the same adoption spectrum among developers and Scrum Masters — from “I’ll never touch it” to “I’ll never write code by hand again.” And he pushes back hard on an emerging prejudice that echoes the old “technical Scrum Masters are worse” debate: the idea that Scrum Masters who use AI are somehow weaker.
Used well, AI lets you elevate your strengths and cover your gaps — a people-centered Scrum Master can become far more technical, and a technical one far more people-centered, each with a trusted teaching guide right there. The key competency isn’t avoidance; it’s discernment about when to reach for the tool and when not to.
From More Output to Better Outcomes
“The bottleneck has never really been typing code. The bottleneck has been understanding the problems and the customers well enough to define a solution that fixes them.”
Dave’s clearest reframe: AI is driving the price of output down. When volume is easy — more features, more emails, more documents on demand — churning out more of it stops being a differentiator, because everyone can do it. What matters is deciding which problems are worth solving and finding the most effective solution.
Experienced agile professionals have always known the real bottleneck was understanding the customer well enough to define the right solution, not the typing. AI just exposes that in a much starker way: there’s nowhere left to hide behind sheer volume.
What to Pay Attention To — and a Monday Experiment
“It can do a lot of that manual, low-thinking, high-effort work to free you up to do more of the really impactful stuff.”
For Scrum Masters being told to “adopt AI,” Dave’s advice is to let it take the joyless work — the end-of-sprint collateral, the Jira monitoring, the reports and charts — so you can spend your time on the coaching, the strategic thinking, and the organizational-level impact that’s harder to reach when you’re buried in tactical chores.
His concrete Monday-morning experiment: take the two or three prioritized actions from your next retrospective, bring them to ChatGPT or Claude, and ask, “which of these could you really help me with, and how could you help me move the needle?” Start a conversation. You don’t have to accept its answers — the point is to sharpen your own thinking about where you can add the most value next sprint.
Developing “Taste” With AI
“One element of taste is being able to judge it fairly harshly — getting through the beige as quickly as you can to find the little nuggets and gems.”
Both Dave and Vasco land on the same skill for the year ahead: taste. These tools produce a lot of text, and not all of it is useful. Vasco shares his own aha moment — asking for ideas, getting the obvious ones, then repeating “give me more, don’t repeat any” until the model finally surfaced something genuinely unexpected. That simple move turns AI into an engine for exploring the solution space until something clicks. The competency to build is the ability to move through the beige quickly and recognize the gems that materially change what you do next.
Recommended Resources
In this episode, Dave has the following recommendations for those wanting to learn, and take advantage of AI at work:
Dave Westgarth is a product and Agile practitioner exploring how AI transforms product development, experimentation, and team workflows. He shares practical insights on leveraging tools to accelerate value delivery and innovation.
“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 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.
“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 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.
“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 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.
Enter e-mail to download a clickable PO Cheat Sheet
This handy Coach Your PO cheat-sheet includes questions to help you define the problem, and links to handy, easy techniques to help you coach your Product Owner
Enter e-mail to download a clickable PO Cheat Sheet
This handy Coach Your PO cheat-sheet includes questions to help you define the problem, and links to handy, easy techniques to help you coach your Product Owner
Enter e-mail to download a checklist to help your PO manage their time
This simple checklist and calendar handout, with a coaching article will help you define the minimum enagement your PO must have with the team
Enter e-mail to download a checklist to help your PO manage their time
This simple checklist and calendar handout, with a coaching article will help you define the minimum enagement your PO must have with the team
Internal Conference
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Internal Conference
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Download a detailed How-To to help measure success for your team
Motivate your team with the right metrics, and the right way to visualize and track them. Marcus presents a detailed How-To document based on his experience at The Bungsu Hospital
Download a detailed How-To to help measure success for your team
Read about Visualization and
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A moving story of how work at the Bungsu Hospital was transformed by a simple tool that you can use to help your team.
Read about Visualization and
TRANSFORM
The way your team works
Overcome Team Resistance and Gain Leadership Buy-In
Discover practical, real-world solutions from leading Agile practitioners. Download three free chapters from 'Tips from the Trenches Scrum Master Edition' and start transforming your Agile practices today!
Overcome Team Resistance and Gain Leadership Buy-In
Discover practical, real-world solutions from leading Agile practitioners. Access three free chapters from 'Tips from the Trenches Scrum Master Edition' and start transforming your Agile practices today!
Overcome Team Resistance and Gain Leadership Buy-In
Discover practical, real-world solutions from leading Agile practitioners.
Download three free chapters from 'Tips from the Trenches Scrum Master Edition' and start transforming your Agile practices today!
FREE! Audiobook Chapters: Overcome Team Resistance and Gain Leadership Buy-In
Download three free chapters from 'Tips from the Trenches Scrum Master Edition' and start transforming your Agile practices today!
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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!
Sheik is a seasoned product and Agile leader with over 20 years of experience scaling innovative, customer-centric digital solutions. A certified Scrum and Agile expert, he bridges strategy and execution, driving high-performance teams at enterprises like Rabobank and citizenM. As a hands-on builder, Sheik created Scrumling—a free, interactive Agile training platform—and ScrumJobs.net, a niche job board for Agile professionals. His passion lies in transforming theory into impactful, real-world results.
Dave Westgarth is a product and Agile practitioner exploring how AI transforms product development, experimentation, and team workflows. He shares practical insights on leveraging tools to accelerate value delivery and innovation.
Wasim 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.
Havva 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.
Alf 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.