Podcast Episode Transcript

Transcript: Don't sleep on Portfolio-level Agility

August 6, 2025 · 00:08:43 · ← Episode overview & show notes

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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, 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 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.

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