What are the common pitfalls and challenges of creating and executing an IT roadmap?

IT strategy is plan that match current and future business plan. It is also a bench for IT department. IT strategy plan can clarify many misunderstanding of IT department and other departments that get influenced by IT solutions provided.

The IT department exists to make the organization successful. Any IT Strategy document must start with the organization's strategy. We must write it in the organization's language, not in the language of IT. The audience is the organization's leadership, not the IT department. Starting with each point in the organization's strategy, the IT Strategy must explain what IT will do to support each point. Most strategies contain changes the organization wants to make. Each of those changes will probably require changes to IT systems, either directly or indirectly. The IT Strategy covers, at a high level, what IT is committing to do to support the organization's strategy.

Your IT Strategy should align with your organizational strategy and allow you to clearly articulate how IT services and resources support the success of the organizational goals.

IT is about people, and people are the building block of any and very business. A proper IT Strategy needs to revolve around how we will empower staff and help them accomplish the organization’s goals and plans. Never forget that IT is about helping the business grow and do the job.

Key measurable results should be outlined to help better understanding the tangible impact of the implementation of technology. A wider sense of meaning can be established by capturing those and a better perspective on the alignment with the company's mission, workplace culture and commercial purpose could be achieved.

We communicate the IT Strategy to the IT staff using the IT Roadmap. Projects, priorities, and IT department changes go here. We have to integrate IT internal changes like server upgrades, new backup systems, integration of cloud, etc. Everything in the IT roadmap should connect to the IT Strategy. Everything in the IT strategy should map into the IT Roadmap. A special note about day-to-day activities like help desk, cyber-security, etc. These activities should connect to the roadmap and strategy. It may be a vague connection, but some of those activities may need to take a backseat to strategy/roadmap items and documenting how IT should make those trade-odds is important. Too often, individuals make these tradeoffs on an ad hoc basis.

Simply if there is no IT Roadmap, then there should not be a budget for IT. Having IT Roadmap and sharing it with management can help IT to get further support and get other departments ready for IT and excited about it

In short, the IT Roadmap is the tactical action plan to achieve your IT Strategy, which in turn should support the organization achieving its' overall goals.

An IT Roadmap should incorporate a Risk Register, as well as the respective Mitigation or Remediation Plans at least for the most critical Risks identified.

The IT Strategy guides "what" you will do from a broad perspective. Your Roadmap indicates "how" you will accomplish it. When goals, strategies, resources, etc change, the Roadmap and/or Strategy may also need to change as well.

The IT Strategy document is a commitment to the organization's success. The IT Roadmap provides direction for the IT team to meet those commitments. Those are two very different goals and require different documents and communications.

IT should be built according to company business strategy. Focuses should be core solutions first and rest can be built according to technical requirements of core solutions and business requirements. Building IT strategy should include exit strategy too for each step

One challenge that many businesses face, is lacking clear insight and transparency as to exactly what technology has been deployed within the organisation. If you don't understand what you have then how can you ensure that (1) it remains fit for purpose, is (2) secure and (3) won't be impacted by any change put forward in your roadmap.

Company Culture, Consensus and some experience within IT are most common pitfalls causing IT failures. Building consensus is most challenging issues for IT. Once there is consensus, rest can be achievable.

Some challenges are: - The org's leaders don't understand the IT Strategy. Focus on connecting to the organization's goals and communicating it well to the organization's leaders. The more we use the leaders' language, the easier the adoption will be. If they don't understand it, we haven't done a good job of communicating. - The IT team doesn't internalize the IT Roadmap. Every IT employee needs to draw a straight line between what we do on a day-to-day basis and how the organization succeeds. The Roadmap becomes the foundation for decisions and allows everyone in IT to stay focused. - We don't refer to the documents frequently. They need to always be front of mind. - We don't update the documents frequently.

One of the biggest challenges in strategic planning, and the execution of that plan, are the unkowns. Consider the plans you had going into the 2019-2020 calendar year and how quickly (and frequently) they changed that year? While some aspects of the pandemic only required a change it tactics (i.e. supporting working from home as much as possible), others may have required a complete change in strategy (supply chain issues, lock downs, etc). Also consider those who managed to leverage the pandemic to accelerate their strategic goals (remote meeting vendors for example). The key is to be flexibly with the tactics of executing the plan, and to be able to identify risks that may require changes to the strategic vision as well.

Always keep your stakeholders in mind when creating your strategy and roadmap. While it seems obvious that a departmental plan must align with the organizational plan, it is sometimes easy to lose track of the "boots on the ground" when brainstorming abstractly with an executive team. Also, encourage your team to be willing to ask probing questions and play "devil's advocate" when needed.