🗺️ Helpful? - Roadmaps as Expectation Anchors

Ever provided a “draft” roadmap and now it’s written in “stone”?

I learnt very early on that no matter how many “caveats” I put on a roadmap presentation, it became what I was measured against from then on.

I once found an interesting statement, “Roadmaps don’t just show what’s coming. They shape what people believe is possible.”

A roadmap is one of the most useful tools digital leaders have in their “quiver”, but it can cause the most controversy if it is not communicated clearly, like:

• Assumptions made in creating the roadmap

• Dependencies for the execution to succeed

• Who supported the timeline and milestones, and who didn’t

I have found it strange how a simple picture of a possible “future” can create expectations, sometimes hopeful and sometimes unrealistic. It is one of the most difficult conversations to manage in any digital transformation execution.

A roadmap is, above everything else, an expectation contract; even if we don’t agree.

So how do we, as leaders, manage and communicate this difficult, complex conversation?

Here’s how I now lead that conversation:

🔹 Build from real capacity, not aspiration

🔹 Leave space for “oh ....” things went wrong

🔹 Need to make choices, Name the trade-offs explicitly

🔹 Anchor dates to decisions, not optimism

🔹 Review the roadmap as a leadership team, not just a delivery team

🔹 Revisit it often enough that it stays honest

🔹 Report weekly or as often as required to keep stakeholders informed

A roadmap is a great tool to communicate our aspirations, but it must be anchored in the “real world”.

So here’s my reflection for you this week: Where might your roadmap currently be anchoring the wrong expectations?

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