In my book "Social Selling - Techniques to Influence Buyers and Changemakers" I talk about how to get a decision for a digital project signed off at the board.
It's key to understand that all people are different, think differently and have different personal wins. Don't forget, just because you think something is a good idea to expect that everybody thinks the same.
Also you will find that different job roles will want different things. People in Finance tend to be very fact based, Sales people like diagrams and so on. Finance people will look very carefully at any ROI (Return on investment).
Critical for everybody is the business case, what money needs to be invested and what return you will get. The trick here is to under promise and over deliver.
Finally, you need to understand the political capital that people will "burn" to get sign off agreed. Many people are "too scared" to ask management to progress such projects and take the monthly salary, hoping somebody else will do the work.
Let's not forget, Digital Transformation is not about Cloud, SaaS or system change. It's about a new way of doing things and doing them digitally. The largest part of such a project is the change element, which covers the people and the process. How do you not change people minds, but change people's habits.
Thus, monitoring will become crucial once your team has an innovation strategy in place. Digital investment experts at PwC stress establishing "process and governance mechanisms by which [companies] can manage and measure their digital return on investment and innovation," and carrying them across six key areas of the organization: customers, operations, safety and soundness, disruption and innovation, employees, and infrastructure.