Why the Organizing Portfolios Toolkit Isn't Just Another Workshop

“You’re making a big withdrawal from the transformation credit bank to get that many senior executives into a room for two days, aren’t you?” – Mark

Introduction

What justifies pulling senior leaders away for two days of portfolio work? In this episode, Mark, Ali, and Niko dig deep into the newly released Organizing Portfolios for Strategic Agility toolkit. The discussion is honest and pragmatic—tempered by real use, not just theory—but above all, it’s focused on how the toolkit can prompt meaningful insight and concrete movement inside organizations that rarely pause to re-examine their boundaries and assumptions.

Mark reflects on the toolkit’s progression from rough concept to proven tool. Ali enters as a “workshop skeptic,” bringing fresh eyes and healthy questioning from the LPM classroom. Niko connects the dots between early pilots and live delivery, sharing where even experienced hands needed to adjust. Together, the team underscores real value: the toolkit creates space for leaders to surface trade-offs and stuck patterns that often go unaddressed.

This one’s for coaches, VMOs, and change agents weighing not just “will this work here?” but “how do we make real progress with our stakeholders?”

Actionable Insights

Here’s what the Unleashed crew surface—explicitly or between the lines—about navigating portfolio structure and workshop facilitation:

- Workshops demand deep preparation, not a plug-and-play approach: Effective portfolio sessions rely on understanding the unique context, stakeholder views, and organizational politics ahead of time. “If this workshop would take us two days, I’m probably going to spend a full two weeks or more preparing for this workshop,” Ali notes.

- Strategic use of the two-part design is critical: The Overview builds shared language and a safe space to test boundaries, before executives confront trade-offs in the subsequent Workshop. This separation helps surface and derisk sensitive topics before action is taken.

- Language matters: frame conversations commercially: The toolkit’s focus on commercial criteria—regulatory, regional, business unit, innovation—allows executives to show up as decision-makers, not as process students. This turns frameworks into relevant strategy conversations.

- Drive momentum with phased, tangible action: Close sessions with clear next steps—now, next week, next month. Appreciation and clarity matter as much as insight; don’t end on a vague list.

Highlights

Why This Toolkit Demands Real Facilitation Skill

Mark and Niko make it clear: facilitating at this level is a distinct skill, fraught with political nuance and heightened stakes. It’s about more than managing group process—executives expect relevance and rigor. The enablement videos—especially Rebecca’s walkthroughs—surprise even seasoned coaches, who admit to slowing down and watching rather than skimming.

“You have to be good in facilitating high-ranked people or people who are doing strategic things, and that’s different from a workshop you are with teams, with developers.” – Niko

Who Is This Really For? Boundary Friction and Target Audience

Ali presses on audience fit: “To whom is this workshop, specifically designed?” The consensus: readiness is more about mindset and context than about scale. Whether facing a complex multi-portfolio landscape or just a single portfolio, the process uncovers where leaders are stuck or blind to key trade-offs.

“Some of the most profound insights and aha moments seem to come for the people who only had one portfolio, because it could help you think about what was inside your portfolio.” – Mark

Action, Not Just Awareness: Generating Real Change

Ali points to the challenge of translating group insight into organizational movement—especially around funding and governance. The conversation veers into the reality that a high-energy workshop can expose risk just as quickly as it exposes opportunity.

“A workshop like this can become quite a snake pit...if the workshop has participants that are very eager to do something, this workshop can really make or break your push to agility.”

Mark’s advice: aim for a charter you can realistically deliver on, and build your workshop flow to support that momentum.

Facilitation Patterns: Building the Team and Owning the Room

The team highlights running the Overview as a preparatory exercise for facilitators as much as for participants. Get your team aligned and immersed before you go live; it makes the Workshop delivery more resilient and adaptive.

Niko, usually quick to customize workshops, finds the toolkit robust right out of the box—an unusual endorsement, underscoring the quality and structure of the supporting materials.

The ASPC Requirement: Paywall or Professionalism?

The exclusive hosting requirement for Advanced SPCs (ASPC) evokes no debate about barriers. Instead, the team emphasizes the level of craft and preparation required to make the workshop safe and valuable for executive participants.

“If you have to be an ASPC or not, at least, what I expect is you have to know the article. You have to have done the overview yourself...experience on this level is not really high, even for the coaches.” – Niko

Conclusion

If you’re considering a portfolio structure workshop, resist the urge to treat the kit as an off-the-shelf solution. Its real power lies in providing structure to the necessary, often messy dialogue—helping leaders move past inertia, see the real trade-offs, and sketch a more actionable path forward. As Mark points out, “You could do the full workshop, change nothing, and still be better off for it—if you emerge with a clearer sense of your map and your mileposts.”

Don’t start with the stickies. Start with the purpose, the politics, and the prep.