What the board and C-Suite want to see in a Transformation Roadmap

When you first present a transformation roadmap to a board or C-suite audience, you're not just laying out a plan, you are also telling a story and (hopefully) inviting trust. It’s a unique fusion of strategic communication, marketing finesse, and rigorous programme planning. Yes, the facts matter: timelines, milestones, financial projections, and dependencies, but I also find that senior leaders also look for and sense the feeling the roadmap evokes.

A well-crafted roadmap should radiate ambition. It should signal that the organisation is no longer playing it safe - that the shackles are off. It should show that risks are being taken, but they’re calculated and purposeful, not reckless. If there are some big swings in there that might be more innovative than guaranteed, they should be called out as more specultative, and balanced off against those initiatives with more ‘known’ outcomes.

It should feel different, bold, and energising. This is a moment to prove that transformation isn’t just a process to get through - it’s a living, breathing effort being led with clarity, courage, and conviction.

At its best, a transformation roadmap becomes a point of evidence: that the work is happening, that it’s being considered from the right angles, and that the people leading it are not only capable but visionary.

Here are some practical points to consider when drafting communication material for a Board or C-suite audience.

1. Clear Strategic Intent

• What is the endgame? (e.g., £7m EBITDA uplift—what does that mean in terms of top-level business considerations like market position, valuation, exit options?)

• Why now? (What’s changed that makes this ambition necessary, credible or timely?)

• What’s the transformation thesis? (What are the levers—growth, efficiency, innovation, market expansion?)

2. Evidence of Boldness and Differentiation

• Show what you’re doing differently (new markets, new operating models, digital transformation, partnerships, etc.)

• Highlight calculated risks (e.g., investing in capabilities, entering new segments, rethinking pricing)

• Demonstrate that “the shackles are off”—you’re no longer constrained by legacy thinking or incrementalism

3. A Structured, Phased Roadmap

They almost always expect a timeline-based view that shows:

• Different initiatives

• Key delivery phases

• Milestones and value inflection points

• Dependencies and critical enablers (e.g., talent, systems, funding)

My personal top tip here is to be sure to show that you know the difference between the initiatives that deliver high value back to the business, and the activities that are strategic enablers - you will and should have a mix of both - show you know the difference between the two.

It can be useful to be able to show this knowledge of prioritisation within the timeline.

4. Bridge doings to outcomes - financial and goal translation

• How each initiative contributes to each goal - be realistic, not fictitious

5. Benefits realisation roadmap

When and how value (not projects) will be delivered — early wins, mid-term gains, long-term impact.

Benefits are most often realised after a project has concluded.

6. Governance and Accountability

• A clear owner for each initiative

• Defined KPIs and success metrics

• A cadence of reporting and escalation

What else they may expect you’ve considered

This will depend on how mature your roadmap is. These things are possibly not expected in V1 of the roadmap, or when you’re in a early phase of delivering those easy quick wins which won’t kick up any kind of fuss.

• Market dynamics - Have you factored in external trends, competitor moves, and customer shifts?

• Organisational readiness - Do you have the people, culture, and capabilities to execute?

• Change management - How will you bring the organisation along?

• Risk appetite: What risks are you taking, and how are they being managed?

• Investment needs: What’s the total required spend (CapEx/OpEx), and what’s the ROI? *note - this may not be needed at this stage, if instead this is considered at the project level, which it often is. Very possibly needed further down the line though.