Roadmaps – seperate or together?
In 2026, in a meeting room with a firm’s CEO, CTO and product owner, I looked at two roadmaps.
One was the enterprise roadmap, newly created. The other was a separate map for AI, created a few months earlier.
We brought the AI work into the enterprise roadmap. It opened up a question: in what sequence are these outcomes best to land to deliver the strategy? It highlighted what had to happen before and concurrently to the AI and growth outcomes could be achieved. In this case: capability uplift and data management decisions.
We could see the priorities, the sequence, and whether we had the capacity and capability to deliver. The decisions got sharper.
I’m sharing this because the separate map made AI feel apart from the people, process, technology and data. On one roadmap, it was simply part of getting the outcomes.
Imagine if every strategic outcome, AI included, sat on one roadmap.
“Where are we up to with AI?” is the wrong first question
Mid-tier firms, private wealth, large organisations: they all ask it. I often say that the quality of the questions you ask determines the quality of the answers you get.
The stronger question: what does our strategic pathway look like, and where are the risks, constraints and outcomes?
AI belongs inside that answer, not beside it as a separate technology roadmap. By one roadmap I mean one view of every outcome the strategy needs, the work to deliver it across people, process, data and technology, and the order it happens in. Put everything on it and you see what competes for the same money, people and attention. It shows which decisions need to be made.
Mik Kersten’s Outcome Roadmap works the same way: work sequenced against objectives. AI is part of that sequence, not alongside it. Experienced strategic portfolio managers can build this roadmap quickly.
Curiosity is a key ingredient
AI gives answers quickly. Curiosity decides which questions are worth asking. The “what else?” in that meeting room came from curiosity. It’s a skill you can build, and in a fast-moving portfolio it matters more, not less. Now more than ever, we need to avoid acting on assumptions.
What this means for your PMO, TMO or VMO
Whatever you call the office that runs your portfolio, its service has to keep improving. As strategy shifts, so does the service. It can’t wait for strategy to be settled before it acts.
Its job is to give clarity on:
- the decisions to be made, and when
- how success will be measured
- the constraints, and how to manage them to inform priority and sequence
- the most economical path to an outcome that sticks
- the risks and capabilities needed
Think of the Formula One Pit Wall. When the weather turns or the safety car comes out, it re-plans while the cars are still moving. Your office keeps pace in the same way, with three lenses: where you want to be, where you are today, and what the past has taught you.
Five questions to ask your business this week
- Which strategic outcome does each AI use serve? (An AI use is anywhere AI is used or planned: a chatbot, an automated report, an agent.)
- Does our AI work rank against everything else on the roadmap, or is it running on its own?
- Where are the real constraints? Speed up a step that isn’t the bottleneck and you only move the pile.
- What are the risks, and who owns each one?
- What will we stop doing to make room?
Where is your organisation on the pathway?
Nataliya Shalygina of LeadMark.AI and I have written a free AI question guide for PMO, TMO and VMO leaders, and the executives accountable for them: seven phases, from starting out to banking value, with quality questions for each. The answers help you decide what goes onto your one roadmap, and where.
Download it here: Questions to ask relating to AI from a TMO, PMO, VMO lens
Next week: the operating model of a PMO, TMO or VMO, and the capabilities to build as AI speeds up outputs. Know what informs an operating model. The start point is not your current organisational structure.
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Track first, engine later.
Ferne Eliz King helps executive teams and boards turn strategic complexity into clarity, and clarity into results. Get in touch, or subscribe to the newsletter for more.
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