Like any strategy, there are more ways to find pitfalls than success. The first step in planning is to clearly articulate the overall strategy in a way that is easy to understand at all levels of the organization.
The second step is to break the strategy into S.M.A.R.T. goals -- goals that are Specific, Measurable, Achievable, Realistic, and Time-based. The best digital strategy that is poorly executed will fail. A mediocre digital strategy that is well-executed is more likely to succeed.
We highly recommend outside facilitation with your leadership in planning your digital strategy. Getting out of the office and into a facilitated environment improves both organization and efficiency. Outside facilitators can sometimes see things your team can’t see and can often bring fresh perspectives by seeing the forest and not the trees.