If you run a technology organization, you are caught between a rock and two hard places when it comes to when and how to do IT planning. Development teams: Agile, Waterfall, hybrid approaches. If you run a large technology team and there isn’t a battle for development planning models you probably aren’t just aren’t aware of them. Finance: When you walk into the room with the finance team, they have never wavered from looking at quarterly and yearly finance planning and budgeting rhythms. Customers: When you talk to customers (or investors, CEO, Board of directors for that matter), they want to understand the roadmap they are buying into. This is especially important in the SaaS business. 

Imperfect visibility is not an excuse for no visibility.

With all these legitimate needs, when is the right time to plan technology? The short answer is now. Whether you are running a software product organization or the IT division of a company, the pressures are similar. You will always have to have a longer term technology roadmap for a variety of constituents. Large software projects require integration points that different teams and work towards and plan around. Budgeting, to manage to external investors or internal cash flow goals, requires a view of the future that with headlights that illuminate at least quarters at the right level. This doesn’t have to lock out agility to meet rapid business need changes. Imperfect visibility is not an excuse for no visibility. You will still be forced to make decisions, even if you don’t know everything – how many staff will be full-time vs. contractors, how long will you sign a lease or contract for, will you direct the development team to code for flexibility or optimize for certainty?

 

Keeping the best of both worlds

Keeping your organization (and constituents, customers) aligned to both the long-term direction and near-term realities and details is possible if you are intentional. It requires a frequent rhythm (monthly or quarterly) of updates to both the near-term plans (development sprints, budget forecasts, execution decisions) and longer-term roadmaps (3/6/12/24 month roadmaps). Doing both requires being clear with your team on the granularity and accuracy of both. Defining your low beams (detailed near term) and high beams (rough long term) levels of accuracy helps everyone stay on the same page and align decisions. One of the most common disconnects is between engineering and finance. Both need to plan, and having different accuracy tolerances can make for poor decisions and mistrust down the road. Common definitions, expectations, and common or integrated planning tools go a long way to making this work.

Defining your low beam (detailed near term) and high beam (rough long term) levels of accuracy helps everyone stay on the same page and align decisions.

Running an agile organization does not preclude you from having both near-term and long-term visibility. Your current sprint and prioritized backlog provide the near-term detail. And product/organizational strategy and development velocity can be used to provide directional guidance longer term. In an agile world, the conversation for working with finance and customers can move from the 'what' to 'is the strategy and velocity adequate for the business'.

In many large technology organizations, the planning and budgeting cycle can consume months of your life you never get back. Having a regularly updated long-term plan makes the 'what should we be doing' part of the process a series of manageable chunks of work instead of one effort too big to tackle efficiently. Organizations who do this well also develop frameworks and metrics for making decisions with all, some, or only little amounts of the total data you would ideally have. For instance, in the short term, you can work off exact budgets and detailed technology schedules. In the mid-term, you can work off estimated work and budgets, with acknowledged movement (say month-level or quarter-level accuracy). And when you’re planning at your ‘high beam’ level, directional technology commitments and budgeting at the metrics level can still produce reasonable plans. You always have time to refine as projects and plans move into the ‘low beam’ range. Your customers, finance partners, and technology organization will all benefit from a clear and shared view of the future at the right level of detail.

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