This is a great question – and if you go so far as to identify the right person to lead you on this journey, and set aside the time to have the strategic planning meeting and spend the effort to create the roadmap – you damn sure better have a way of identifying progress. This question is easy to answer, but requires skill to do properly. Each item on the roadmap really should have an in-depth conversation on budget, priority, who it affects. Once that is identified, we should use that as the guide to finding out how the that particular project has succeeded. In order to track total progress, we should only only see our ‘score’ increase – but you should see efficiencies with your eye. Sales takes less time to convert, operations takes less touches to complete, AR comes in faster, etc.