Small Shifts, Big Impact: Transforming Portfolio Management without the Cliff Dive

“If people do not share a common vision, and do not share common mental models about the business reality within which they operate, empowering people will only increase organizational stress and the burden of management to maintain coherence and direction.”

Peter Senge, The Fifth Discipline

Most organizations start their agile journey with a simple experiment: launch a pilot agile team, revolutionize how they work, learn from the pilot, and amplify. The same pattern played out when scaled agility emerged—just at a larger scale. Instead of transforming ten people at a time, we did it for a hundred. The practices remained largely the same, with new collaboration patterns and alignment tools layered on top.

It’s tempting to think of the portfolio as simply another fractal in this scaling pattern—expanding from a hundred people to a thousand. But the portfolio’s role is fundamentally different. It’s not about how we build software; it’s about how we shape, fund, govern, and steer strategy. The stakes are high—hundreds of millions of dollars and the organization’s regulatory reputation are on the line.

When I started discussing portfolio management with clients over a decade ago, the prevailing introduction involved fundamentally changing the investment and funding model. For most organizations, that framing ended the conversation—the first step felt more like a leap off a cliff than an achievable change. The real challenge wasn’t designing a new funding model but creating the conditions where real change could happen.

Consequently, my early portfolio work focused less on transformation and more on helping leaders survive the friction and, at times, the chaos created by agile adoption at the team and team-of-teams levels. I searched for repeatable patterns and had the privilege of working with executives with bold visions for change but struggled to carve out the space to act on them. Every senior executive I coached faced an overwhelming flood of noise, and agile development often added to it. Late-night coaching calls frequently revolved around their frustration: “I can’t clear the space to focus on advancing my vision.”

That realization shifted my approach. Instead of agitating for revolutionary change, I focused on removing pain and friction. My primary goal became creating space and sanity for visionary leaders so they could think and lead effectively. Over time, I saw another clear pattern emerge: the annual investment planning cycle—long viewed as an impediment—was actually an opportunity.

Small, pain-reducing changes built the stability and credibility needed for more significant shifts. The financial year lifecycle provided natural moments to introduce substantial changes without overwhelming the system. The patterns were always there—if we knew where to look.

When we started collaborating in the portfolio space last year, we recognized the same underlying forces. They became the foundation of our approach: “Start where you are. Optimize your current reality with a series of small, evolutionary shifts that prepare you to lift the portfolio into a new reality.”

Instead of chasing a grand redesign, take a moment to assess where incremental improvements could have the most significant impact. What’s one friction point you could eliminate today that would make life easier for your teams or executives? Where could a minor adjustment to existing processes create more clarity or stability? If revolutionary change feels out of reach, focus on the shifts that make evolution inevitable.