Estimating knowledge work is always more unwieldy, and in this context you are often working towards outcomes which ultimately have no precedent (although they

Estimating knowledge work is always more unwieldy, and in this context you are often working towards outcomes which ultimately have no precedent (although they may be made up of known components). It is also more difficult to initially assess the skills fit of candidates for knowledge based work, especially those that require creative problem solving, and unlike other engineering disciplines past outputs are opaque and hard to rely on as simple markers of past performance. For a project, in order to produce a good estimate you need to understand scope, then align it with precedent, adjust for your resources and productivity profile and then view all of that through a risk lens to set probable outcome ranges. For a programme, in order to produce a good estimate you need to understand and manage the risks, constraints and dependencies across all your projects and ensure that the projected benefits (both hard and soft) are still net positive, meaning the investment makes sense. From my observations at least it doesn't look like the idea of development as "investment" in a product or service is very common. I'm assuming because time to market is often the ultimate driver rather than cost, in which case, congratulations, you should increase your costs on more numerous and productive resources whilst aligning your strategy and risks to iterate on smaller scopes faster so that dead ends can be quickly parked. The problem isn't so much the estimation process as it is more generally poor portfolio/programme governance and management practices and more specifically a lack of risk management and understanding of contingency at those levels. I find IT, and Software Development more particularly, to be some of the worst offenders, but that is because the risk profiles of such projects are vastly different to the risk profiles of other types of work. The productivity of your resources is difficult to discern and a lack of precedent for similar-enough projects and knowing what their variables were, all meaning you really can't produce a reliable estimate with incomplete information.