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Scaling w/ Agility

A newsletter for leaders on how to think through scaling challenges and develop/grow organizations using product and agility principles and practices.

Are You Struggling to Scale Your Organization ? Need agility but dubious of process BS/dogma? I share reflective, pragmatic, principled takes on how to approach scaling your organization leveraging the essence (rather than theater) of product operating models, agile practices and frameworks, and business operating systems such as EOS and OKRs.

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Featured Post

What would an Agility Guarantee look like?

Hey Reader, I have a question for you. Let's say you're in the market for some agility improvement service. What kind of guarantee would help you differentiate between services that are likely to end up in agile theater vs ones that will guide you to improved outcomes? Here's the thing - We've been buying (and selling) Agile "Features" for way too long: Training (you're guaranteed to get a certificate of completion. Some even guarantee you'll pass the exam...) Mechanics (You're guaranteed to...

1 day ago • 1 min read

Ever get the feeling you’re the “agile person” in the room—brought in to run ceremonies, fix Jira boards, or play Scrum cop, but never actually invited to shape real strategy? If that hits close to home, you’ll want to listen in on my latest conversation with Michael Gerharz. Michael’s a computer scientist by training, but these days he’s known for helping leaders and teams find the right words so their ideas land, rather than getting tossed in the trash. We dug into why so many agilists get...

2 days ago • 1 min read

Hey Reader, Most days, it feels like mentioning Agile anywhere in your online presence is like the GenAI Emdash. A troll magnet. That makes it harder (maybe even unsafe) to have a real conversation. share nuanced opinions. (And its even less safe to talk about SAFe...) If you're a leader working on improving your organization, should you only listen to people that DON'T talk about Agile? That don't have any SAFe association? Does not mentioning their Agile association immediately mean that...

12 days ago • 2 min read

Picture this: you've a breakthrough strategic initiative tied to one of your company-level goals that impacts 10 teams across two product groups, as well as your GTM organization. These are all busy, overloaded teams. Those same 10 teams are also juggling five other initiatives. And the business-as-usual whirlwind. You pull this work into the backlogs and roadmaps for all these teams. Fractional slices of people across the teams will work on this. Which means it will take a while. Leaders...

13 days ago • 1 min read

Please don’t write your OKRs using AI. OKRs should reflect YOUR strategy. Your choices. Your strong opinion. Your tradeoffs. What you CAN do is use AI to fix your OKRs. Here are some ways you could go about doing that: Collaborate with AI to create a prompt that reflects your perspective on what makes great OKRs Point AI at an OKR expert you’re following and tell it to create a prompt based on that expert’s advice. (Your OKR Hot Seat with that expert) Point AI at a set of OKR experts and ask...

14 days ago • 1 min read

Hey, You probably noticed that I rarely promote/launch offerings around here. Today is the exception. I’m starting a small peer group (up to 10 people) for product/tech leaders who are working on evolving/ transforming their organizations. This Mastermind was born through conversations with leaders like you who expressed a desire for an intimate peer group with a high signal-to-noise ratio, where they can go beyond theory and dogma and have thoughtful, nuanced conversations about the journey...

15 days ago • 1 min read

Do you ever have nightmares of underpant gnomes running your transformation? Process Theater happens when people focus on following the process instead of connecting it to outcomes and impact. It's like the South Park underpants gnomes, who never managed to figure out the connection between stealing underpants and world domination. So, how can we break the downward spiral caused by process theater and switch to a positive transformational flywheel? Outcome Mapping can help us clarify the real...

16 days ago • 1 min read

Hi there, After years of listening to podcasts, guest appearances, and co-hosting, I’m finally launching my own show: the Scaling w/ Agility Podcast! . Why? I've heard from leaders and practitioners like you that podcasts and audiobooks are where you escape from your inbox and social feed to find nuance, insight, and inspiration. The Scaling w/ Agility podcast is for people like you—leaders and practitioners who are building empowered, scalable organizations - who want to learn from others...

20 days ago • 1 min read

Hi Reader, Are you a Head of Product, Engineering, Technology, or Transformation? Are you working to evolve your organization from a Product Theater / Feature Factory towards becoming more scalable, outcome-oriented, empowered, and evidence-driven? If that sounds familiar, you’re exactly who I want to hear from. I’m building a new masterclass for leaders like you- those navigating the messy, high-stakes shift from project/feature delivery to true product operating models, often in founder-led...

27 days ago • 1 min read

I talk quite a bit about the notion of "Developing your company like a product". One of the obstacles I see in the adoption of this concept is that's hard without having the "Developers" and "Product" people that consider the company their product... What I've seen in companies I work with is that there are MANY Ops teams - RevOps, EngOps, ProdOps, DevOps, PeopleOps. Too often these teams are too focused on the respective tools. Worse than that, they are often siloed - optimizing locally for...

28 days ago • 1 min read