Solo Episode

Don't sleep on Portfolio-level Agility

August 6, 2025 · 00:08:43

When is the right time to introduce portfolio-level agility?

Drawing from more than a decade of experience guiding enterprise transformations, Yuval argues that starting at the portfolio level, early, isn’t just helpful, it’s essential.

He walks listeners through a powerful case study involving a 1000-person delivery organization trapped in a waterfall-heavy, high-coordination setup. By introducing lightweight Portfolio Kanban and visual flow management before fixing the teams, the organization was able to gradually shift to a more outcome-oriented, product-focused structure.

“The best time to start thinking about portfolio-level agility was when you started your agile journey. The second-best time? Now.”

“You don’t need to wait for perfect teams to start fixing the system around them. In fact, doing it the other way around often fails.”

“Portfolio-level practices give leaders massive leverage, they shape the environment teams operate in.”

“Fixing what’s broken requires looking upstream, at how work is shaped, prioritized, and flows through the organization.”

“Leaders who model outcome orientation, empiricism, and agility at the portfolio level create a ripple effect. Everything else becomes easier.”

“Instead of waiting until the trenches are perfect, start by changing the terrain.”


(00:23) The Best (and Worst) Time to Introduce Portfolio Practices

(00:56) Misconceptions: “You Can’t Scale What’s Broken”

(01:46) Case Study: A 1000-Person Delivery Org in Waterfall Hell

(03:53) Visualizing Work and Creating Flow Transparency

(05:04) Reorganizing Around Value and Embracing Change

(05:42) Why Portfolio-Level Agility = Leadership Leverage

(06:16) The Portfolio Agility Trail Map: Yuval’s Free Resource

(08:38) Final Thoughts: Start with the System, Not Just the Teams


🔥 Ready to shift the system, not just the teams? Start with Yuval’s free Portfolio Agility Trail Map.

Yuval Yeret helps leaders maximize outcomes through strategic, nuanced agility. As a Product/Scaling/Agility-focused management consultant, SAFe Fellow, and Professional Scrum Trainer, he specializes in helping organizations evolve beyond agile theater into product-oriented agility.

Start your journey with his free email course:🎓 Scaling w/ Agility Crash Course

Follow Yuval's insights and conversations on LinkedIn:🔗 Yuval’s LinkedIn

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Help me think through how this episode applies to my situation. Start by asking what I am trying to change. Separate the episode's claims from your suggestions, and say when the notes do not support a claim. Use the transcript to find passages, then check the audio before quoting. Transcript: https://yuvalyeret.com/podcast/episodes/dont-sleep-on-portfolio-level-agility/transcript.md ## Published episode notes When is the right time to introduce portfolio-level agility? Drawing from more than a decade of experience guiding enterprise transformations, Yuval argues that starting at the portfolio level, early, isn’t just helpful, it’s essential. He walks listeners through a powerful case study involving a 1000-person delivery organization trapped in a waterfall-heavy, high-coordination setup. By introducing lightweight Portfolio Kanban and visual flow management before fixing the teams, the organization was able to gradually shift to a more outcome-oriented, product-focused structure. “The best time to start thinking about portfolio-level agility was when you started your agile journey. The second-best time? Now.” “You don’t need to wait for perfect teams to start fixing the system around them. In fact, doing it the other way around often fails.” “Portfolio-level practices give leaders massive leverage, they shape the environment teams operate in.” “Fixing what’s broken requires looking upstream, at how work is shaped, prioritized, and flows through the organization.” “Leaders who model outcome orientation, empiricism, and agility at the portfolio level create a ripple effect. Everything else becomes easier.” “Instead of waiting until the trenches are perfect, start by changing the terrain.” (00:23) The Best (and Worst) Time to Introduce Portfolio Practices (00:56) Misconceptions: “You Can’t Scale What’s Broken” (01:46) Case Study: A 1000-Person Delivery Org in Waterfall Hell (03:53) Visualizing Work and Creating Flow Transparency (05:04) Reorganizing Around Value and Embracing Change (05:42) Why Portfolio-Level Agility = Leadership Leverage (06:16) The Portfolio Agility Trail Map: Yuval’s Free Resource (08:38) Final Thoughts: Start with the System, Not Just the Teams 🔥 Ready to shift the system, not just the teams? Start with Yuval’s free Portfolio Agility Trail Map. Yuval Yeret helps leaders maximize outcomes through strategic, nuanced agility. As a Product/Scaling/Agility-focused management consultant, SAFe Fellow, and Professional Scrum Trainer, he specializes in helping organizations evolve beyond agile theater into product-oriented agility. Start your journey with his free email course:🎓 Scaling w/ Agility Crash Course Follow Yuval's insights and conversations on LinkedIn:🔗 Yuval’s LinkedIn ## Transcript Automatic transcript of the published podcast audio. Recognition errors are possible. Speakers are unlabeled; do not attribute a passage to Yuval or a guest without checking the audio. Episode: https://yuvalyeret.com/scaling-ai-podcast/dont-sleep-on-portfolio-level-agility/ Source RSS GUID: substack:post:169670823 Source: published Riverside RSS audio enclosure Transcription: faster-whisper base.en, English ## Transcript [00:00:02] What's the right timing for using portfolio-level agility? [00:00:07] Either I move all welcome to a skilling with agility, where I talk about [00:00:15] nuanced ways to [00:00:17] bring agility to [00:00:19] your organization at scale. This is a [00:00:24] question that I often get asked. What's the right timing to [00:00:30] introduce portfolio to [00:00:32] your ways of working portfolio perspective? [00:00:34] And the answer is kind of similar to the when to plan wins the best time to plan to treat. [00:00:43] The best time to start talking about portfolio in my view [00:00:48] was, you know, when you started your agile journey, if you already had, then the best timing, no. [00:00:57] Most organizations wait way too long to adopt portfolio-level practices. [00:01:04] They've been told you can't scale what's broken, so they wait until they nail away the team and product group level. [00:01:12] But what I've often seen in my work with organizations is that fixing what's broken requires [00:01:20] focusing on the upstream, that's shaping the work and the context for these teams. Whether you call that portfolio or [00:01:28] just a higher altitude or flight level, I don't really care about that. But [00:01:35] looking upstream and intervening at that level is a [00:01:40] pretty powerful pattern that I've seen work [00:01:44] pretty often. [00:01:45] Let me give you an example. [00:01:47] Back in 2012 or so, I met a senior VP [00:01:52] responsible for a thousand-person delivery organization. It was working in a traditional waterfall. [00:01:57] It was a critical chain optimized waterfall theory of constraints, case study for how to optimize all of the [00:02:06] projects. Over the years, by the way, I met several organizations that all claimed to be [00:02:12] world-class at managing projects and still [00:02:17] something was missing. [00:02:20] And in this case, what they were facing was a lot of component teams. [00:02:26] So a lot of heavy coordination and integration costs across products [00:02:32] and build the takes two weeks to integrate. And whenever they get to the end of a release, a lot of [00:02:39] risk timing scheduling risk around will that really work how long would it take us to stabilize this. [00:02:47] Because of those risks, they were working very hard to try and control change. [00:02:55] They recognized that in order to successfully release, they need to control change. [00:03:00] They cannot really access future requests from their customers during this. [00:03:05] And this was a successful and profitable shop, but Tricky, who was the leader for that team, [00:03:14] was looking for ways to make it better. [00:03:17] She didn't really like [00:03:20] the fact that she was saying no, that the team was saying no to customers. [00:03:24] We cannot do your things right now. [00:03:26] We'll do it in the next cycle. [00:03:31] What they realized was that in order to [00:03:34] welcome change for their customers, they often had to accept change out of cycle. [00:03:39] They started to do that because they were focused on profitably and this created the constant fire. [00:03:46] So that was the beginning of the conversation and we started to discuss options. [00:03:51] The option that the team, like the most, was starting with visualizing, understanding and managing flow [00:04:00] across this delivery organization. [00:04:02] You might call it the portfolio of deliveries. [00:04:05] This organization was driving again. [00:04:07] It was a thousand people strong delivery organization with a lot of component teams. [00:04:13] Several development groups focused on different aspects of the solution. [00:04:19] This visualization board, we got it going within weeks. [00:04:23] This team was very experienced, highly motivated, operationally focused. [00:04:28] So it didn't take long to start to see work flowing or not flowing. [00:04:34] And once the team started to see what's going on on this conman board, [00:04:40] they started making changes. [00:04:43] They started thinking about how could we integrate more often? [00:04:48] How could we have conversations about pulling work in more often? [00:04:54] They started to see the effect of the waterfall and they started to break through it at their level. [00:05:03] We've seen how much cross product work this portfolio delivered. [00:05:09] Then we started to explain ways to reorganize around value. [00:05:13] We started introducing more and more agility principles and practices. [00:05:19] Like continuous integration, like breaking the work to smaller pieces [00:05:24] and feeding it into the cycle rather than waiting for, we were just batch sizes. [00:05:30] Eventually they did reorganize to stream-aligned cross product groups, [00:05:34] focused on the real product from the eyes of the customers and leveraged team level edge [00:05:39] of working, but that took time. [00:05:42] The thing that I've noticed in this case and in other situations where we've used that approach [00:05:49] is that starting at this altitude, what you might call the portfolio level, [00:05:54] gives you as a leader tons of leverage to make an impact on the agility [00:06:00] and product orientation of your organization. [00:06:04] By tackling the systemic constraints to product thinking, flow, empiricism, [00:06:09] and allowing you as a leader to learn and model the behaviors you expect from your team. [00:06:15] If you're interested to learn a bit more about how to go through this cycle [00:06:21] to use this portfolio agility intervention, [00:06:25] I wrote this portfolio agility trail map, which is a free email course [00:06:30] based on the lightweight common first approach I described above, [00:06:34] combined with modern concepts such as the product operating model evidence based name. [00:06:40] This is kind of the playbook that I use with enterprise level organizations [00:06:46] that I'm helping today and in some cases also for smaller businesses [00:06:51] where we use this approach for bringing agility to the whole organization. [00:06:57] Delivery projects or features or product initiatives, [00:07:02] it's actually all of our company bets, bets that could be related to our products, [00:07:08] they could be related to internal capabilities. [00:07:11] And before we go and implement edgel in the trenches, [00:07:17] let's start with organizing and thinking about the flow and the outcome orientation [00:07:25] and steering with evidence for our biggest initiatives. [00:07:30] What I like about this is a management consultant is that this provides the surface area [00:07:36] to have exactly the sort of conversations that are moving the needle for how leaders think [00:07:42] about their operating system. [00:07:45] And once we have these conversations, once you start to see the VP starting to ask their people [00:07:51] about stop starting, start finishing or the COO asking people to describe outcomes [00:07:59] when they talk about the initiatives rather than what's the actual work. [00:08:03] When that starts happening, it's like a tree tag for the organization. [00:08:09] When these leaders become the heroes of the agility journey in the organization, [00:08:17] everything else becomes much easier. [00:08:21] A lot of the time the constraint for organizations is the system around the teams. [00:08:27] So instead of waiting to work on the system around the teams until the teams are working great, [00:08:34] why not tackle this system? [00:08:37] Thank you for listening to this episode of Scaling With Agility. ## Source boundary These are the published show notes from the podcast feed. They are a starting point for discussion, not a verbatim record of the conversation. The transcript is machine-generated and may contain errors or unlabeled speakers. Check the audio before quoting anyone.
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