When implementing agile portfolio management, leaders’ first—and often most daunting—question is: “Where do we start?”

I’ve taught my share of frameworks. In some cases, a comprehensive blueprint or roadmap makes sense. They feel safer to people from traditional project/program management – who ARE often the exact people leading the move towards agile ways of working, especially at the portfolio level.

But this sense of safety and predictability is often misplaced. It comes with the baggage of requiring people involved with the change to grasp a lot, plan in depth, and, most importantly, commit to comprehensive change.

What often works better is a more straightforward, iterative, evolutionary approach.

Think Trail Map rather than a blueprint.

It highlights the trails but gives you options for approaching them.

What does that look like when pursuing Portfolio-level agility?

• Visualize Your Portfolio Flow: Start by laying out all your initiatives on a transparent board. This isn’t about micromanaging every task—it’s about seeing the big picture.
• Manage and Shape Flow: Once you have visibility, look for opportunities to reduce overcommitment. Fewer, better‑funded initiatives lead to a more empowered, outcome‑focused team.
• Organize in ways that accelerate Flow: Experiment with ways to organize in a more streamlined fashion. Try these approaches on specific examples, see what works, inspect, and adapt.
• Use Evidence-Based Management To Improve Outcomes: Orient your most significant initiatives towards outcome-oriented goals and steer based on feedback loops.
• Evolve: Use evidence‑based management to see what works and let that learning inform future decisions.

By thinking of your portfolio as a living, evolving entity—and using a trail map to guide your early steps—you can gradually build a product‑oriented, agile portfolio without overwhelming your teams or leadership.

As a side benefit, leadership will see, learn, and model the behaviors and culture needed for organizational agility…

How are you thinking about bringing agility to your company/portfolio? What’s one first trail you can explore?

PS The Portfolio Agility Trail Map is an email course where I share what I’ve learned about using this approach. Similarly, the Mastering Organizational Traction Trail Map applies this concept to improve organizational traction for growing companies.

​Read From Blueprints To Trail Maps On Your Browser​

Yours,

Yuval