The benefits in economic growth, productivity, competitiveness, social inclusion, good government that the power of information and communications technology (ICT) could create are demanding high policy initiatives (Digital Agendas or Digital Strategies) to increase the adoption of ICT and network connectivity.In order to remain competitive developed and developing countries around the world that understand the benefits of ICT are looking on ways to outperforms its peers and get closer to their respective inspirational peers on broadband penetration and ICT sector contribution to GDP.Many governments such as New Zealand and Chile have recognized these objectives as strategic goals to create a digital future for all their citizens. New Zealand and Chile captured these initiatives around the countries’ digital strategies. A Digital Strategy is a comprehensive government lead plan that outlines the goals, stakeholders, process, budget, and monitoring mechanisms to make a country’s digital future a reality. Here I present some of the challenges to consider when developing a digital strategy.1- Understand the Pillars Digital strategy/agenda does not mean telecommunications policy and should not be limited to infrastructure. A digital strategy relates to an ecosystem where public citizens and communities, local and federal government, and small and large enterprises (the three agents) take advantage of the country’s ICT infrastructure, skills, and content (the three enablers) to increase economic welfare.It is a delicate environment where demand and supply factors across all elements interact looking to reach equilibrium. However, the existing ICT ecosystem (business climate, quality of ICT regulations, ICT market competition) and ICT infrastructure (telecommunications networks infrastructure) in many countries could lead to an inferior equilibrium where the ICT sector would growth at a slow slope, perhaps just a few points above the country’s GDP growth.A digital strategy is necessary to find the ICT ecosystem and infrastructure market failures that are limiting growth in order to identify enablers’ accelerators that can quickly move the country exponentially to the digital future.2- Use an Analytical FrameworkUse an analytical framework to understand the country’s current position on the ICT ecosystem and infrastructure relative to best-practice ICT environments. Understanding where a country’s position is with respect to these factors would help identify ICT policy initiatives.3- Define the Enablers’ Goals Content should be diverse, high quality and valuable. Producers and consumers need to have the skills to understand the benefits of ICT and the confidence to use it in a safe environment. The infrastructure should be based in a competitive market that guarantees fast, affordable access that is available everywhere.4- Fourth Challenge: LeadershipTraditionally all topics related to ICT have been automatically delegated to the Secretary of Communications and the Telecommunications regulator. However, the Digital Strategy challenge requires actions across the entire country’s ecosystem. Support and participation from federal, state and local governments, as well as business and communities is an essential prerequisite. Therefore in order to have a Digital Strategy in top of the governments’ agenda, a Digital Strategy requires total executive support -ideally it should be a key presidential initiative- and the institutional structure that reflects the challenges of the political process.A key success factor is the appointment of a high level leader that understands the government process, technology and markets that has the leadership skills to build support to the initiatives. Independent boards of advisors and multidisciplinary counsels could bring another set of skills and vision to help the design and strategy execution.There are different approaches among these lines. In some countries like Chile, the Digital Strategy is responsibility of four ministries including Economy, Treasure, Educations and Communications, an Executive Secretary responsible for the execution, and a number of advisors representing all segments of society. 5- How to do it1) Set Specific Goals in all Work streams: Governments should set clear, specific and quantifiable targets at all levels within the ecosystem. It is fundamental to develop initiatives in all three work streams so the market can reach an optimum equilibrium. 2) Allocate Budget: The government also needs to allocate sufficient resources to support the initiatives. 3) Build coalition within the government: so local municipalities support the projects and become key stakeholders4) Build Public Private Partnerships: invite private companies to join the initiative. Not only bringing their technologies, products and services, but also their human capital. 5) Measure, Evaluate and Adjust or Replicate: Governments should not be afraid of experimentation, as it could lead to great opportunities. Transparency is also a must. Therefore, monitor closely the different initiatives, evaluate and depending on the results; call off, adjust or replicate.